Home Vacation Condo Rentals By Owner In Key West, FL

Showing 320 Of 527 Vacation Rentals
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Exceptional(1)

$236.12

/ Nightly
Condo

Ahoy Mate! with Compass Realty at the Truman Annex in Key West

Key West, Florida, United States

Completely updated condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled with flair and detail. Open design with new flooring, coastal hues and furnishings -feels spacious and decadent. The kitchen boasts new stainless appliances, and a show-stopping chandelier. After a day of frolicking, slip into the new bed featuring cozy organic bedding. The double French doors lead to a huge deck- perfect for morning coffee, or happy hour entertainment. The Shipyard includes a heated pool, assigned parking, security, and tree shrouded walking paths. The condo is perfectly placed in the very desirable Truman Annex offering a tranquil neighborhood, yet so close to the newly developed Truman Waterfront Park, Fort Jefferson State Park and its popular beaches, and the excitement of Duval St.brPlease note: The minimum rental period is 27 nights
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$518.3

/ Nightly
Condo

1800 ATLANTIC 2-bedroom condo with Particle Ocean view in Key West Florida

Key West, Florida, United States

Your Key West adventure begins at this 2-bedroom condo. Inside, guests find two king beds that promise restful nights The condo features two bathrooms, each equipped with a hair dryer for added convenience. Stay comfortable with air conditioning throughout the unit, and keep up with your routine in the fitness room just steps away. Beautiful swimming pool on property. 4 adult max , no children , no pets of any kind owner has serious allergie.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(41)

$1528.9

/ Nightly
Condo

Waterfront Dock Pool Penthouse Near Duval St

Key West, Florida, United States

Summary:brbrRelax in this spacious 2,000 sq ft waterfront penthouse in downtown Key West, featuring dual balconies with marina and sunset views. This 4BR/4BA plus loft sleeps up to 16 and is ideal for group getaways and special occasions. Dockage included with a fish cleaning station and ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, the Historic Seaport, restaurants, and nightlife, with a heated pool, tiki area, BBQ grills, parking, and elevator access.brbrbrbrThe Space:brbrWELCOME TO ST. KITTS YOUR WATERFRONT PENTHOUSE RETREAT IN KEY WESTbrbrbrbrWake up to marina views and unwind with sunset skies from this spacious two-story waterfront penthouse in downtown Key West. Designed for large groups and memorable stays, this 4 bedroom plus loft home offers approximately 2,000 sq ft of indoor and outdoor living space, ideal for families, group getaways, and multi-generational trips.brbrbrbrLocated in the Pelican Landing waterfront community, this top-floor residence features dual balconies, open living areas, and comfortable accommodations for up to 16 guests, all just about 1 mile from Duval Street, the Historic Seaport, and Key West’s best dining and nightlife.brbrbrbr DUAL BALCONIES WITH WATER AND CITY VIEWSbrbr• Enjoy sunrise over the marina and sunset views over Old Townbrbr• Outdoor seating for dining, relaxing, and taking in the breezebrbr• Watch boats pass through Garrison Bight belowbrbrbrbr ️ SPACIOUS AND COMFORTABLE LIVINGbrbr• Bright living area with floor-to-ceiling glass and waterfront viewsbrbr• Fully equipped kitchen with granite countertops and essentialsbrbr• Full-size washer and dryerbrbr• High-speed WiFi and flat-screen TVs throughoutbrbr• Loft area provides additional space for relaxing or kidsbrbrbrbr ️ SLEEPING ARRANGEMENTSbrbrUPPER LEVEL:brbr• Bedroom with two Queen beds, ensuite bath, and balcony accessbrbr• Bedroom with two Queen beds, ensuite bath, and city viewsbrbr• Loft with two Twin bedsbrbrbrbrLOWER LEVEL:brbr• Marina-view primary suite with King bed and ensuite bathbrbr• Bedroom with two Queen beds and ensuite bathbrbrComfortably sleeps up to 16 guestsbrbrbrbr DOCKAGE INCLUDEDbrbrA private boat slip is available for your stay, complete with water and a covered fish cleaning station. An ice maker is available on-site, perfect for boating, fishing, and easy days on the water.brbrbrbr ️ EXTRAS AND AMENITIESbrbrPet-friendlybrbrFree on-site parking for up to two vehiclesbrbrHigh-speed WiFibrbrSecure building elevator accessbrbrbrbr COMMUNITY AMENITIES PELICAN LANDINGbrbr Heated poolbrbr Waterfront setting on Garrison Bight, located near Charter Row where many captains offer pickup directly from the dockbrbr Fish cleaning stationbrbr Private dock access for guests and ownersbrbr Tiki area and BBQ grillsbrbrbrbr LOCATION HIGHLIGHTSbrbr Bayview Park is adjacent with tennis courts and open green spacebrbr Fausto’s Food Palace 0.4 miles and Publix grocery store 1.4 milesbrbr ️ Higgs Beach 1.2 miles, Smathers Beach 1.5 miles, Fort Zachary Taylor Beach 2 milesbrbr✈️ Key West Airport about 10 minutesbrbrbrbr INSIDER TIPSbrbr Mac’s Place is right next door, a local favorite for casual food and drinksbrbr☕ Sandy’s Cafe 0.3 miles, known for Cuban coffee and breakfastbrbr Charter fishing, sandbars, and sunset cruises depart nearby from Garrison Bightbrbr Easy access to downtown, Duval Street, and the Historic Seaport, about 1 mile awaybrbrbrbrGuest Access:brbrGuests have full access to the entire 2,000 sq ft penthouse condo, including an oversized private balcony with water views, perfect for enjoying sunrise and watching boats pass through the marina. Inside, the home features a fully equipped kitchen, two spacious living areas, and four bedrooms, each with its own en-suite bathroom. Guests may also enjoy the shared amenities, including a heated pool, tiki area with BBQ grills, and dock access. Boating guests will appreciate the on-site commercial ice maker and fish cleaning station. The unit is accessed by a secure building elevator, with stair access always available. Parking is included on-site for two vehicles. The adjacent park with tennis courts is also available for guest use.brbrbrbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.brbrbrbrThe Neighborhood:brbrLocated in the downtown area of Key West, this waterfront condo offers easy access to everything the island is known for, while still providing a more relaxed setting just outside the busiest streets. Duval Street, the Historic Seaport, restaurants, bars, and nightlife are all about 1 mile away.brbrbrbrKey West is famous for its vibrant atmosphere, with live music, over 200 restaurants and bars, and nightly sunset celebrations. From beaches and boating to historic landmarks like the Hemingway House and Southernmost Point, everything is within easy reach. Bayview Park is right next door with tennis courts and open green space.brbrbrbrThe property overlooks Garrison Bight Marina, a hub for boating, fishing, and charter excursions. Located near Charter Row, many captains offer convenient pickup directly from the dock, making it an ideal location for guests planning time on the water.brbrbrbrGetting Around:brbrOur location is ideal for exploring Key West by foot or bicycle—everything is close by! Many guests also enjoy renting electric carts, which are widely available on the island, and we can accommodate plug-in access if needed. You really won’t need a car unless you're driving down Route 1 from mainland Florida. Lyft and Uber are also readily available throughout the area for added convenience.brbrbrbrOther Things to Note:brbr⏰ CHECK-IN AND CHECK-OUTbrbrCheck-in is 4:00 PM and check-out is 10:00 AM. The base rate includes up to 10 registered guests. Guests 11 and above are $100 per person per night and must be included on the reservation prior to arrival.brbrbrbr PETSbrbrOne dog up to 25 lbs is welcome with a $200 non-refundable pet fee.brbrbrbr PARKINGbrbrFree on-site parking is guaranteed for two vehicles or golf carts.brbrbrbr DOCKAGE DETAILSbrbrMaximum boat length 40 ft, maximum beam 13 ft, with an 18 ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted.brbrbrbr PENTHOUSE ACCESSbrbrThis top-floor unit is accessed by elevator, with stair access always available. As with many island properties, occasional elevator downtime may occur, though service is managed and addressed by the building.brbrbrbr AGE REQUIREMENTbrbrAll guests must be at least 25 years of age unless accompanied by a parent. Please reach out with any questions.brbrbrbr TROPICAL ENVIRONMENTbrbrOur home is treated regularly by professional pest control. Due to the tropical climate, occasional insects may be present. If needed, we will promptly arrange service during your stay. Access must be permitted for service.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrCheck-in is simple with keyless entry. You will receive access codes for the building at least 24 hours prior to arrival and your condo access code on the day of arrival.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.
Bed 4

Bed

Bath 4

Bath

Sleep 16

Sleeps
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Exceptional(45)

$687.33

/ Nightly
Condo

Waterfront Dock Pool Condo Near Duval St Pet OK

Key West, Florida, United States

Summary:brbrBring friends and family to this spacious 1,350 sq ft waterfront corner condo in historic downtown Key West. Enjoy a full kitchen, open living space, and a private balcony with marina and pool views. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, the Historic Seaport, and Hemingway House. Amenities include a heated pool, tiki area, BBQ grills, parking, elevator, and secure entry.brbrbrbrThe Space:brbrWELCOME TO FLORIDA YOUR CORNER WATERFRONT RETREAT IN KEY WESTbrbrbrbrLocated in the desirable Pelican Landing waterfront community, Florida is a bright and updated 2 bedroom, 2 bath corner condo situated on the third floor, offering added privacy, more natural light, and open marina views. Ideal for families, couples, or small groups, this home comfortably sleeps up to 6 guests, with a maximum occupancy of 8.brbrbrbrDesigned for relaxed coastal living, the condo features a spacious layout, comfortable furnishings, and a private balcony overlooking Garrison Bight Marina and the pool. Thoughtful touches, including quality bedding and an inviting interior, create a comfortable and easygoing Key West stay, whether you are here for boating, exploring downtown, or simply unwinding by the water.brbrbrbr✨ THE SPACEbrbr Primary Suite: King bed, marina views, private balcony access, ensuite bathroom, walk-in closet, and flat-screen TVbrbr ️ Second Bedroom: Two Queen beds, ensuite bathroom, and flat-screen TVbrbr ️ Living and Dining Area: Spacious open layout with comfortable seating, perfect for relaxing, dining, or gathering after a day on the waterbrbr ️ Kitchen: Fully stocked with cookware and essentials, ready for meals at homebrbr Laundry: Full-size washer and dryer for added conveniencebrbr Balcony: Large private balcony with open views of Garrison Bight Marina and the pool, ideal for morning coffee, boat watching, or sunset drinks.brbrbrbr DOCKAGE INCLUDEDbrbrA private boat slip is available for your stay, complete with water and a covered fish cleaning station. A commercial ice maker is available on-site, perfect for boating, fishing, and easy days on the water.brbrbrbr ️ EXTRAS AND AMENITIESbrbrPet-friendlybrbrFree on-site parkingbrbrHigh-speed WiFibrbrPrivate building elevatorbrbrbrbr COMMUNITY AMENITIES PELICAN LANDINGbrbr Heated poolbrbr Waterfront setting on Garrison Bight. Located near Charter Row at Garrison Bight, many captains offer pickup directly from the dockbrbr Fish cleaning stationbrbr Private dock access for guests and ownersbrbr Tiki area and BBQ grillsbrbrbrbr LOCATION HIGHLIGHTSbrbr Bayview Park is adjacent with tennis courts and open green spacebrbr Fausto’s Food Palace 0.4 miles & Publix grocery store 1.4 milesbrbr ️ Higgs Beach 1.2 miles, Smathers Beach 1.5 miles, Fort Zachary Taylor Beach 2 milesbrbr✈️ Key West Airport about 10 minutesbrbrbrbr INSIDER TIPSbrbr Mac’s Place is right next door, enjoy a local favorite restaurant with live music, craft beerbrbr☕ Sandy’s Cafe 0.3 miles, known for Cuban coffee and breakfastbrbr Charter fishing, sandbars, and sunset cruises depart nearby from Garrison Bightbrbr Easy access to downtown, Duval Street, and the Historic Seaport, about 1 mile awaybrbrbrbrGuest Access:brbrGuests have full, private access to the entire 1,350 sq ft condo, including both bedrooms, two bathrooms, a fully equipped kitchen, and open living and dining areas. Enjoy the private balcony overlooking the marina and heated pool, along with direct access to the pool and dock area. You will also have access to the heated pool, tiki area, BBQ grills, and a private boat slip reserved for your stay. Free on-site parking is included, and a private building elevator provides easy access to the unit. Guests may also enjoy the adjacent park with tennis courts.brbrbrbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.brbrbrbrThe Neighborhood:brbrLocated in the downtown area of Key West, this waterfront condo offers easy access to everything the island is known for, while still providing a more relaxed setting just outside the busiest streets. Duval Street, the Historic Seaport, restaurants, bars, and nightlife are all about 1 mile away.brbrbrbrKey West is famous for its vibrant atmosphere, with live music, over 200 restaurants and bars, and nightly sunset celebrations. From beaches and boating to historic landmarks like the Hemingway House and Southernmost Point, everything is within easy reach. Bayview Park is right next door with tennis courts and open green space.brbrbrbrThe property overlooks Garrison Bight Marina, a hub for boating, fishing, and charter excursions. Located near Charter Row, many captains offer convenient pickup directly from the dock, making it an ideal location for guests planning time on the water.brbrbrbrGetting Around:brbrOur location is ideal for exploring Key West by foot or bicycle—everything is close by! Many guests also enjoy renting electric carts, which are widely available on the island, and we can accommodate plug-in access if needed. You really won’t need a car unless you're driving down Route 1 from mainland Florida. Lyft and Uber are also readily available throughout the area for added convenience.brbrbrbrOther Things to Note:brbr⏰ CHECK-IN AND CHECK-OUTbrbrCheck-in is 4 PM and check-out is 10 AM. The base rate includes up to 6 guests, with a maximum occupancy of 8. Guests 7 and 8 are $100 per person per night and must be included on the reservation prior to arrival.brbrbrbr PETSbrbrOne dog up to 25 lbs is welcome with a $200 non-refundable pet fee.brbrbrbr PARKINGbrbrFree on-site parking is available for one vehicle or golf cart.brbrbrbr DOCKAGE DETAILSbrbrMaximum boat length 40 ft, maximum beam 13 ft, with an 18 ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted.brbrbrbr AGE REQUIREMENTbrbrAll guests must be at least 25 years of age unless accompanied by a parent. Please reach out with any questions.brbrbrbr TROPICAL ENVIRONMENTbrbrOur home is treated regularly by professional pest control. Due to the tropical climate, occasional insects may be present. If needed, we will promptly arrange service during your stay.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrCheck-in is simple with keyless entry. You will receive access codes for the building at least 24 hours prior to arrival and your condo access code on the day of arrival.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.
Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(37)

$687.82

/ Nightly
Condo

Waterfront Condo | Pool, Dock, Parking, Sleeps 8

Key West, Florida, United States

Summary:brbrRelax and unwind in this spacious 1,200 sq ft waterfront condo in downtown Key West. Perfect for families and groups, enjoy a full kitchen, open living space, and a private balcony overlooking the marina. Dockage available with a fish cleaning station and ice maker, ideal for boating & fishing. Located about 1 mile from Duval Street, restaurants, and nightlife, and just 10 minutes from EYW airport. Amenities include a heated pool, tiki area, BBQ grills, free parking, elevator, and secure entry.brbrbrbrThe Space:brbrWELCOME TO CURACAO YOUR WATERFRONT GETAWAY IN KEY WESTbrbrbrbrLocated in the Pelican Landing waterfront community, Curacao is a spacious and updated 2 bedroom, 2 bath condo designed for comfort and relaxation. With over 1,200 sq ft of living space, this home features a bright, open layout, comfortable furnishings, and a private balcony overlooking the marina and pool.brbrbrbrThoughtful touches like quality bedding, a fully equipped kitchen, and generous living space make it easy to settle in and enjoy your time in Key West, whether you are here for boating, exploring downtown, or simply unwinding by the water. Comfortably sleeps up to 6 guests, with a maximum occupancy of 8.brbrbrbr✨ THE SPACEbrbr Primary Suite: King bed, marina views, private balcony access, ensuite bathroom, walk-in closet, and flat-screen TVbrbr ️ Second Bedroom: Two Queen beds, ensuite bathroom, and flat-screen TVbrbr ️ Living and Dining Area: Spacious open layout with comfortable seating, perfect for relaxing, dining, or gathering after a day on the waterbrbr ️ Kitchen: Fully stocked with cookware and essentials, ready for meals at homebrbr Laundry: Full-size washer and dryer for added conveniencebrbr Balcony: Large private balcony overlooking Garrison Bight Marina and the pool, ideal for morning coffee, boat watching, or sunset drinks. Includes direct stair access to the pool and docksbrbrbrbr DOCKAGE INCLUDEDbrbrA private boat slip is available for your stay, complete with water and a covered fish cleaning station. A commercial ice maker is available on-site, perfect for boating, fishing, and easy days on the water.brbrbrbr ️ EXTRAS AND AMENITIESbrbrPet-friendlybrbrFree on-site parkingbrbrHigh-speed WiFibrbrPrivate building elevatorbrbrbrbr COMMUNITY AMENITIES PELICAN LANDINGbrbr Heated poolbrbr Waterfront setting on Garrison Bight, located near Charter Row where many captains offer pickup directly from the dockbrbr Fish cleaning stationbrbr Private dock access for guests and ownersbrbr Tiki area and BBQ grillsbrbrbrbr LOCATION HIGHLIGHTSbrbr Bayview Park is adjacent with tennis courts and open green spacebrbr Fausto’s Food Palace 0.4 miles and Publix grocery store 1.4 milesbrbr ️ Higgs Beach 1.2 miles, Smathers Beach 1.5 miles, Fort Zachary Taylor Beach 2 milesbrbr✈️ Key West Airport about 10 minutesbrbrbrbr INSIDER TIPSbrbr Mac’s Place is right next door, a local favorite for casual food and drinksbrbr☕ Sandy’s Cafe 0.3 miles, known for Cuban coffee and breakfastbrbr Charter fishing, sandbars, and sunset cruises depart nearby from Garrison Bightbrbr Easy access to downtown, Duval Street, and the Historic Seaport, about 1 mile awaybrbrbrbrGuest Access:brbrGuests have full, private access to the entire 1,200 sq ft condo, including both bedrooms, two bathrooms, a fully equipped kitchen, and open living and dining areas. Enjoy the private balcony overlooking the marina and heated pool, along with direct access to the pool and dock area. You will also have access to the heated pool, tiki area, BBQ grills, and a private boat slip reserved for your stay. Free on-site parking is included, and a private building elevator provides easy access to the unit. Guests may also enjoy the adjacent park with tennis courts.brbrbrbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.brbrbrbrThe Neighborhood:brbrKey West is where the tropics meet southern charm—a vibrant island at the southernmost tip of the U.S., known for its colorful sunsets, quirky characters, rich history, and laid-back lifestyle. It's a place where roosters roam freely, everyone travels by bike or scooter, and every hour feels like happy hour. Surrounded by crystal-clear waters, the island is a haven for boating, fishing, snorkeling, and diving. But there’s just as much to explore on land: historic homes, world-famous landmarks like the Hemingway House and Southernmost Point, and lively streets filled with art, music, and culture. Despite being just 4 miles long, Key West is packed with over 200 restaurants and bars, from toes-in-the-sand beach bars to upscale waterfront dining. The sunsets are a nightly celebration, and the community is known for its warmth, creativity, and come-as-you-are attitude. Whether you’re here to unwind or explore, Key West has a way of making you slow down, breathe in the salty air, and enjoy every moment.brbrbrbrGetting Around:brbrOur location is ideal for exploring Key West by foot or bicycle—everything is close by! Many guests also enjoy renting electric carts, which are widely available on the island, and we can accommodate plug-in access if needed. You really won’t need a car unless you're driving down Route 1 from mainland Florida. Lyft and Uber are also readily available throughout the area for added convenience.brbrbrbrOther Things to Note:brbr⏰ CHECK-IN AND CHECK-OUTbrbrCheck-in is 4 PM and check-out is 10 AM. The base rate includes up to 6 guests, with a maximum occupancy of 8. Guests 7 and 8 are $100 per person per night and must be included on the reservation prior to arrival.brbrbrbr PETSbrbrOne dog up to 25 lbs is welcome with a $200 non-refundable pet fee.brbrbrbr PARKINGbrbrFree on-site parking is available for one vehicle or golf cart.brbrbrbr DOCKAGE DETAILSbrbrMaximum boat length 40 ft, maximum beam 13 ft, with an 18 ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted.brbrbrbr AGE REQUIREMENTbrbrAll guests must be at least 25 years of age unless accompanied by a parent. Please reach out with any questions.brbrbrbr TROPICAL ENVIRONMENTbrbrOur home is treated regularly by professional pest control. Due to the tropical climate, occasional insects may be present. If needed, we will promptly arrange service during your stay.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrCheck-in is simple with keyless entry. You will receive access codes for the building at least 24 hours prior to arrival and your condo access code on the day of arrival.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(32)

$1626.38

/ Nightly
Condo

Waterfront Dock Pool Near Duval St Penthouse

Key West, Florida, United States

Summary:brbrBring your group to this spacious waterfront penthouse in downtown Key West, featuring dual balconies, marina and sunset views, and a flexible layout with loft space for everyone to spread out. This 4BR/4BA plus loft sleeps up to 15 and is ideal for families and group getaways. Dockage included, perfect for boating and fishing. Located about 1 mile from Duval Street, the Historic Seaport, restaurants, and nightlife, with a heated pool, tiki area, BBQ grills, parking, and elevator access.brbrbrbrThe Space:brbrWELCOME TO ST. CROIX YOUR WATERFRONT PENTHOUSE RETREAT IN KEY WESTbrbrbrbrWake up to marina views and unwind with sunset skies from this spacious two-story waterfront penthouse in downtown Key West. Designed for both relaxation and group gatherings, this 4 bedroom plus loft home offers a flexible layout, dual balconies, and room to comfortably host up to 15 guests.brbrbrbrLocated in the Pelican Landing waterfront community, this top-floor residence features open living spaces, multiple areas to gather, and easy access to everything downtown Key West has to offer, just about 1 mile from Duval Street, the Historic Seaport, and the island’s best dining and nightlife.brbrbrbr DUAL BALCONIES WITH WATER AND SUNSET VIEWSbrbr• Oversized rear balcony overlooking Garrison Bight Marina, perfect for morning coffee and boat watchingbrbr• Private upstairs balcony with sunset views over Old Townbrbr• Outdoor seating for relaxing, dining, and enjoying the breezebrbrbrbr ️ SPACIOUS AND FLEXIBLE LIVINGbrbr• Open-concept living area with floor-to-ceiling waterfront viewsbrbr• Fully equipped kitchen with granite countertops and essentialsbrbr• Full-size washer and dryerbrbr• High-speed WiFi and flat-screen TVs throughoutbrbr• Loft-style second living area, ideal for games, kids, or additional sleeping spacebrbrbrbr ️ SLEEPING ARRANGEMENTSbrbrMAIN LEVEL:brbr• Primary suite with King bed, water views, balcony access, and ensuite bathbrbr• Bedroom with two Queen beds and ensuite bathbrbrbrbrUPPER LEVEL:brbr• Second primary suite with private balcony, city views, and ensuite bathbrbr• Bedroom with two Queen beds and ensuite bathbrbr• Loft with three Twin beds, perfect for flexible group setupsbrbrComfortably sleeps up to 15 guestsbrbrbrbr DOCKAGE INCLUDEDbrbrA private boat slip is available for your stay, complete with water and a covered fish cleaning station. An ice maker is available on-site, perfect for boating, fishing, and easy days on the water.brbrbrbr ️ EXTRAS AND AMENITIESbrbrPet-friendlybrbrFree on-site parking for up to two vehiclesbrbrHigh-speed WiFibrbrSecure building elevator accessbrbrbrbr COMMUNITY AMENITIES PELICAN LANDINGbrbr Heated poolbrbr Waterfront setting on Garrison Bight, located near Charter Row where many captains offer pickup directly from the dockbrbr Fish cleaning stationbrbr Private dock access for guests and ownersbrbr Tiki area and BBQ grillsbrbrbrbr LOCATION HIGHLIGHTSbrbr Bayview Park is adjacent with tennis courts and open green spacebrbr Fausto’s Food Palace 0.4 miles and Publix grocery store 1.4 milesbrbr ️ Higgs Beach 1.2 miles, Smathers Beach 1.5 miles, Fort Zachary Taylor Beach 2 milesbrbr✈️ Key West Airport about 10 minutesbrbrbrbr INSIDER TIPSbrbr Mac’s Place is right next door, a local favorite for casual food and drinksbrbr☕ Sandy’s Cafe 0.3 miles, known for Cuban coffee and breakfastbrbr Charter fishing, sandbars, and sunset cruises depart nearby from Garrison Bightbrbr Easy access to downtown, Duval Street, and the Historic Seaport, about 1 mile awaybrbrbrbrGuest Access:brbrGuests have full access to the entire 2,400 sq ft penthouse condo, including an oversized private balcony with water views, perfect for enjoying sunrise and watching boats pass through the marina. Inside, the home features a fully equipped kitchen, two spacious living areas, and four bedrooms, each with its own en-suite bathroom.brbrbrbrGuests may also enjoy the shared amenities, including a heated pool, tiki area with BBQ grills, and dock access. Boating guests will appreciate the on-site commercial ice maker and fish cleaning station.brbrbrbrThe unit is accessed by a secure building elevator, with stair access always available. Parking is included on-site for two vehicles. The adjacent park with tennis courts is also available for guest use.brbrbrbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.brbrbrbrThe Neighborhood:brbrLocated in the downtown area of Key West, this waterfront condo offers easy access to everything the island is known for, while still providing a more relaxed setting just outside the busiest streets. Duval Street, the Historic Seaport, restaurants, bars, and nightlife are all about 1 mile away.brbrbrbrKey West is famous for its vibrant atmosphere, with live music, over 200 restaurants and bars, and nightly sunset celebrations. From beaches and boating to historic landmarks like the Hemingway House and Southernmost Point, everything is within easy reach. Bayview Park is right next door with tennis courts and open green space.brbrbrbrThe property overlooks Garrison Bight Marina, a hub for boating, fishing, and charter excursions. Located near Charter Row, many captains offer convenient pickup directly from the dock, making it an ideal location for guests planning time on the water.brbrbrbrGetting Around:brbrOur location is ideal for exploring Key West by foot or bicycle—everything is close by! Many guests also enjoy renting electric carts, which are widely available on the island, and we can accommodate plug-in access if needed. You really won’t need a car unless you're driving down Route 1 from mainland Florida. Lyft and Uber are also readily available throughout the area for added convenience.brbrbrbrOther Things to Note:brbr⏰ CHECK-IN AND CHECK-OUTbrbrCheck-in is 4:00 PM and check-out is 10:00 AM. The base rate includes up to 10 registered guests. Guests 11 and above are $100 per person per night and must be included on the reservation prior to arrival.brbrbrbr PETSbrbrOne dog up to 25 lbs is welcome with a $200 non-refundable pet fee.brbrbrbr PARKINGbrbrFree on-site parking is guaranteed for two vehicles or golf carts.brbrbrbr DOCKAGE DETAILSbrbrMaximum boat length 40 ft, maximum beam 13 ft, with an 18 ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted.brbrbrbr PENTHOUSE ACCESSbrbrThis top-floor unit is accessed by elevator, with stair access always available. As with many island properties, occasional elevator downtime may occur, though service is managed and addressed by the building.brbrbrbr AGE REQUIREMENTbrbrAll guests must be at least 25 years of age unless accompanied by a parent. Please reach out with any questions.brbrbrbr TROPICAL ENVIRONMENTbrbrOur home is treated regularly by professional pest control. Due to the tropical climate, occasional insects may be present. If needed, we will promptly arrange service during your stay. Access must be permitted for service.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrCheck-in is simple with keyless entry. You will receive access codes for the building at least 24 hours prior to arrival and your condo access code on the day of arrival.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.
Bed 4

Bed

Bath 4

Bath

Sleep 15

Sleeps
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Exceptional(30)

$1637.96

/ Nightly
Condo

Waterfront Dock Pool Pet Friendly Near Duval St

Key West, Florida, United States

Summary:brbrRelax in this 2,400 sq ft waterfront penthouse in downtown Key West. This 4BR/4BA plus loft sleeps up to 16 and features expansive water views, dual balconies, and space for your entire group. Ideal for group getaways and special occasions. Dockage included with a fish cleaning station and ice maker, perfect for boating and fishing. Located less than 1 mile from Duval Street, the Historic Seaport, restaurants, and nightlife, with a heated pool, tiki area, BBQ, parking, and elevator access.brbrbrbrThe Space:brbrWELCOME TO THE ST. THOMAS PENTHOUSE YOUR TWO-STORY WATERFRONT RETREAT IN KEY WESTbrbrbrbrWake up to marina views and end your day with sweeping sunset skies from this expansive two-story penthouse in downtown Key West. Designed for gathering, relaxing, and enjoying the water, this 4 bedroom plus loft home offers over 2,400 sq ft of indoor and outdoor living space, ideal for families, group getaways, and multi-generational stays.brbrbrbrLocated in the Pelican Landing waterfront community, this top-floor residence features dual balconies, open living areas, and room to comfortably host up to 16 guests, all just about 1 mile from Duval Street, the Historic Seaport, and Key West’s best dining and nightlife.brbrbrbr DUAL BALCONIES WITH WATER AND SUNSET VIEWSbrbr• Oversized rear balcony overlooking Garrison Bight Marina, perfect for morning coffee and watching boats come and gobrbr• Private upstairs balcony with panoramic sunset views over Old Townbrbrbrbr PRIME DOWNTOWN LOCATIONbrbrLess than 1 mile to Duval Street, the Historic Seaport, and the Hemingway House—walk or bike to the best of downtown Key West.brbrbrbr ️ SPACIOUS AND COMFORTABLE LIVINGbrbr• Main living room with floor-to-ceiling glass and water views, ideal for gathering as a groupbrbr• Fully equipped kitchen with quartz countertopsbrbr• Full-size washer and dryerbrbr• Second living area in the loft, perfect for kids or additional lounging spacebrbr• High-speed WiFi and flat-screen TVs throughoutbrbrbrbr ️ SLEEPING ARRANGEMENTSbrbr• Primary suite with King bed, balcony access, and ensuite bathroombrbr• Two guest bedrooms with two Queen beds and private ensuite bathroomsbrbr• One guest bedroom with two King beds and private ensuite bathroombrbr• Loft area with bunk beds and two Twin beds, ideal for kids or flexible sleepingbrbr✔ Comfortably sleeps up to 16 guests brbrbrbr DOCKAGE INCLUDEDbrbrA private boat slip is available for your stay, complete with water and a covered fish cleaning station. A commercial ice maker is available on-site, perfect for boating, fishing, and easy days on the water.brbrbrbr ️ EXTRAS AND AMENITIESbrbrPet-friendlybrbrFree on-site parking for up to two vehiclesbrbrHigh-speed WiFibrbrSecure building elevator accessbrbrbrbr COMMUNITY AMENITIES PELICAN LANDINGbrbr Heated poolbrbr Waterfront setting on Garrison Bight, located near Charter Row where many captains offer pickup directly from the dockbrbr Fish cleaning stationbrbr Private dock access for guests and ownersbrbr Tiki area and BBQ grillsbrbrbrbr LOCATION HIGHLIGHTSbrbr Bayview Park is adjacent with tennis courts and open green spacebrbr Fausto’s Food Palace 0.4 miles and Publix grocery store 1.4 milesbrbr ️ Higgs Beach 1.2 miles, Smathers Beach 1.5 miles, Fort Zachary Taylor Beach 2 milesbrbr✈️ Key West Airport about 10 minutesbrbrbrbr INSIDER TIPSbrbr Mac’s Place is right next door, a local favorite for casual food and drinksbrbr☕ Sandy’s Cafe 0.3 miles, known for Cuban coffee and breakfastbrbr Charter fishing, sandbars, and sunset cruises depart nearby from Garrison Bightbrbr Easy access to downtown, Duval Street, and the Historic Seaport, about 1 mile awaybrbrbrbrGuest Access:brbrGuests have full access to the entire 2,400 sq ft penthouse condo, including an oversized private balcony with water views, perfect for enjoying sunrise and watching boats pass through the marina. Inside, the home features a fully equipped kitchen, two spacious living areas, and four bedrooms, each with its own en-suite bathroom. Guests may also enjoy the shared amenities, including a heated pool, tiki area with BBQ grills, and dock access. Boating guests will appreciate the on-site commercial ice maker and fish cleaning station. The unit is accessed by a secure building elevator, with stair access always available. Parking is included on-site for two vehicles. The adjacent park with tennis courts is also available for guest use.brbrbrbr This home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.brbrbrbrThe Neighborhood:brbrLocated in the downtown area of Key West, this waterfront condo offers easy access to everything the island is known for, while still providing a more relaxed setting just outside the busiest streets. Duval Street, the Historic Seaport, restaurants, bars, and nightlife are all about 1 mile away.brbrbrbrKey West is famous for its vibrant atmosphere, with live music, over 200 restaurants and bars, and nightly sunset celebrations. From beaches and boating to historic landmarks like the Hemingway House and Southernmost Point, everything is within easy reach. Bayview Park is right next door with tennis courts and open green space.brbrbrbrThe property overlooks Garrison Bight Marina, a hub for boating, fishing, and charter excursions. Located near Charter Row, many captains offer convenient pickup directly from the dock, making it an ideal location for guests planning time on the water.brbrbrbrGetting Around:brbrOur location is ideal for exploring Key West by foot or bicycle—everything is close by! Many guests also enjoy renting electric carts, which are widely available on the island, and we can accommodate plug-in access if needed. You really won’t need a car unless you're driving down Route 1 from mainland Florida. Lyft and Uber are also readily available throughout the area for added convenience.brbrbrbrOther Things to Note:brbr⏰ CHECK-IN AND CHECK-OUTbrbrCheck-in is 4:00 PM and check-out is 10:00 AM. The base rate includes up to 10 registered guests. Guests 11 and above are $100 per person per night and must be included on the reservation prior to arrival.brbrbrbr PETSbrbrOne dog up to 25 lbs is welcome with a $200 non-refundable pet fee.brbrbrbr PARKINGbrbrFree on-site parking is guaranteed for two vehicles or golf carts.brbrbrbr DOCKAGE DETAILSbrbrMaximum boat length 40 ft, maximum beam 13 ft, with an 18 ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted.brbrbrbr PENTHOUSE ACCESSbrbrThis top-floor unit is accessed by elevator, with stair access always available. As with many island properties, occasional elevator downtime may occur, though service is managed and addressed by the building.brbrbrbr AGE REQUIREMENTbrbrAll guests must be at least 25 years of age unless accompanied by a parent. Please reach out with any questions.brbrbrbr TROPICAL ENVIRONMENTbrbrOur home is treated regularly by professional pest control. Due to the tropical climate, occasional insects may be present. If needed, we will promptly arrange service during your stay. Access must be permitted for service.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrCheck-in is simple with keyless entry. You will receive access codes for the building at least 24 hours prior to arrival and your condo access code on the day of arrival.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.
Bed 4

Bed

Bath 4

Bath

Sleep 16

Sleeps
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Exceptional(35)

$1640.3

/ Nightly
Condo

Penthouse Waterfront Dock Pool Condo Near Duval St

Key West, Florida, United States

Summary:brbrBring the whole crew to this spacious 2,200 sq ft waterfront penthouse in downtown Key West, perfect for families and large groups. This 4BR/4BA plus loft sleeps up to 16 and features marina views, dual balconies, and multiple living areas to spread out and relax. Dockage included with a fish cleaning station and ice maker. Located about 1 mile from Duval Street, the Historic Seaport, restaurants, and nightlife, with a heated pool, tiki area, BBQ grills, parking, and elevator access.brbrbrbrThe Space:brbrWELCOME TO THE ST. JOHNS PENTHOUSE YOUR WATERFRONT GROUP RETREAT IN KEY WESTbrbrbrbrWake up to marina views and end your day with sunset skies from this expansive two-story waterfront penthouse in downtown Key West. Designed for group comfort and connection, this 4 bedroom plus loft home offers approximately 2,200 sq ft of indoor and outdoor living space, ideal for family vacations, group getaways, and multi-generational stays.brbrbrbrLocated in the Pelican Landing waterfront community, this top-floor residence features dual balconies, multiple living areas, and room to comfortably host up to 16 guests, all just about 1 mile from Duval Street, the Historic Seaport, and Key West’s best dining and nightlife.brbrbrbr DUAL BALCONIES WITH WATER AND SUNSET VIEWSbrbr• Oversized rear balcony overlooking Garrison Bight Marina, perfect for morning coffee and boat watchingbrbr• Private front balcony with sunset views over Old Townbrbr• Outdoor space ideal for relaxing, dining, and enjoying the breezebrbrbrbr ️ DESIGNED FOR GROUP LIVINGbrbr• Bright main living area with floor-to-ceiling windows and waterfront viewsbrbr• Fully equipped kitchen with quartz countertops and essentialsbrbr• Loft-style second living area, ideal for kids, games, or additional hangout spacebrbr• Full-size washer and dryerbrbr• High-speed WiFi and flat-screen TVs throughoutbrbrbrbr ️ SLEEPING ARRANGEMENTSbrbr• Primary King suite with balcony access and ensuite bathbrbr• Upstairs Queen suite with private balcony and ensuite bathbrbr• Two additional bedrooms, each with two Queen beds and private ensuite bathsbrbr• Loft area with bunk bed and two Twin beds, perfect for flexible group setupsbrbrComfortably sleeps up to 16 guestsbrbrbrbr DOCKAGE INCLUDEDbrbrA private boat slip is available for your stay, complete with water and a covered fish cleaning station. An ice maker is available on-site, perfect for boating, fishing, and easy days on the water.brbrbrbr ️ EXTRAS AND AMENITIESbrbrPet-friendlybrbrFree on-site parking for up to two vehiclesbrbrHigh-speed WiFibrbrSecure building elevator accessbrbrbrbr COMMUNITY AMENITIES PELICAN LANDINGbrbr Heated poolbrbr Waterfront setting on Garrison Bight, located near Charter Row where many captains offer pickup directly from the dockbrbr Fish cleaning stationbrbr Private dock access for guests and ownersbrbr Tiki area and BBQ grillsbrbrbrbr LOCATION HIGHLIGHTSbrbr Bayview Park is adjacent with tennis courts and open green spacebrbr Fausto’s Food Palace 0.4 miles and Publix grocery store 1.4 milesbrbr ️ Higgs Beach 1.2 miles, Smathers Beach 1.5 miles, Fort Zachary Taylor Beach 2 milesbrbr✈️ Key West Airport about 10 minutesbrbrbrbr INSIDER TIPSbrbr Mac’s Place is right next door, a local favorite for casual food and drinksbrbr☕ Sandy’s Cafe 0.3 miles, known for Cuban coffee and breakfastbrbr Charter fishing, sandbars, and sunset cruises depart nearby from Garrison Bightbrbr Easy access to downtown, Duval Street, and the Historic Seaport, about 1 mile awaybrbrbrbrGuest Access:brbrGuests have full access to the entire 2,000 sq ft penthouse condo, including an oversized private balcony with water views, perfect for enjoying sunrise and watching boats pass through the marina. Inside, the home features a fully equipped kitchen, two spacious living areas, and four bedrooms, each with its own en-suite bathroom. Guests may also enjoy the shared amenities, including a heated pool, tiki area with BBQ grills, and dock access. Boating guests will appreciate the on-site commercial ice maker and fish cleaning station. The unit is accessed by a secure building elevator, with stair access always available. Parking is included on-site for two vehicles. The adjacent park with tennis courts is also available for guest use.brbrbrbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.brbrbrbrThe Neighborhood:brbrLocated in the downtown area of Key West, this waterfront condo offers easy access to everything the island is known for, while still providing a more relaxed setting just outside the busiest streets. Duval Street, the Historic Seaport, restaurants, bars, and nightlife are all about 1 mile away.brbrbrbrKey West is famous for its vibrant atmosphere, with live music, over 200 restaurants and bars, and nightly sunset celebrations. From beaches and boating to historic landmarks like the Hemingway House and Southernmost Point, everything is within easy reach. Bayview Park is right next door with tennis courts and open green space.brbrbrbrThe property overlooks Garrison Bight Marina, a hub for boating, fishing, and charter excursions. Located near Charter Row, many captains offer convenient pickup directly from the dock, making it an ideal location for guests planning time on the water.brbrbrbrGetting Around:brbrOur location is ideal for exploring Key West by foot or bicycle—everything is close by! Many guests also enjoy renting electric carts, which are widely available on the island, and we can accommodate plug-in access if needed. You really won’t need a car unless you're driving down Route 1 from mainland Florida. Lyft and Uber are also readily available throughout the area for added convenience.brbrbrbrOther Things to Note:brbr⏰ CHECK-IN AND CHECK-OUTbrbrCheck-in is 4:00 PM and check-out is 10:00 AM. The base rate includes up to 10 registered guests. Guests 11 and above are $100 per person per night and must be included on the reservation prior to arrival.brbrbrbr PETSbrbrOne dog up to 25 lbs is welcome with a $200 non-refundable pet fee.brbrbrbr PARKINGbrbrFree on-site parking is guaranteed for two vehicles or golf carts.brbrbrbr DOCKAGE DETAILSbrbrMaximum boat length 40 ft, maximum beam 13 ft, with an 18 ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted.brbrbrbr PENTHOUSE ACCESSbrbrThis top-floor unit is accessed by elevator, with stair access always available. As with many island properties, occasional elevator downtime may occur, though service is managed and addressed by the building.brbrbrbr AGE REQUIREMENTbrbrAll guests must be at least 25 years of age unless accompanied by a parent. Please reach out with any questions.brbrbrbr TROPICAL ENVIRONMENTbrbrOur home is treated regularly by professional pest control. Due to the tropical climate, occasional insects may be present. If needed, we will promptly arrange service during your stay. Access must be permitted for service.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrCheck-in is simple with keyless entry. You will receive access codes for the building at least 24 hours prior to arrival and your condo access code on the day of arrival.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.
Bed 4

Bed

Bath 4

Bath

Sleep 16

Sleeps
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Exceptional(19)

$657.57

/ Nightly
Condo

Waterfront Condo with Dock, Pool, Downtown Key West Near Duval

Key West, Florida, United States

Summary:brbrEnjoy true space in Key West in this spacious 1,200 sq ft waterfront condo overlooking Garrison Bight Marina. The home features a full kitchen, dining area, living room, two bedrooms, and a private balcony with marina and pool views, offering far more space than a typical hotel stay.brbrbrbrGuests have access to a private boat slip with water and a fish cleaning station, making it ideal for boating and fishing. Relax by the heated pool, enjoy the tiki area and BBQ grills, or explore downtown Key West just 1 mile away, including Duval Street, the Historic Seaport, restaurants, and nightlife.brbrbrbrPet-friendly with free on-site parking, elevator access, and located about 10 minutes from Key West Airport.brbrbrbrThe Space:brbrWELCOME TO ARUBA YOUR WATERFRONT ESCAPE IN KEY WEST brbrLocated in the desirable Pelican Landing waterfront community, Aruba is a spacious, updated 2 bedroom, 2 bath condo offering over 1,200 sq ft of living space, perfect for families, couples, or small groups. Comfortably sleeps up to 6 guests, with a maximum occupancy of 8. brbrbrbr✨ THE SPACEbrbr Primary Suite: King bed, water views, private balcony access, ensuite bathroom, walk-in closet, and flat-screen TV brbr ️ Second Bedroom: Two Queen beds, ensuite bathroom, and flat-screen TV brbr ️ Living and Dining Area: Bright, open layout with plenty of space to relax, play games, or dine together brbr ️ Kitchen: Fully stocked with cookware and utensils, just bring your favorite spices and oil brbr Laundry: Full-size washer and dryer for added convenience brbr Balcony: Oversized and private with views of Garrison Bight Marina and the pool, ideal for morning coffee, boat watching, or sunset drinks. Includes direct stair access to the pool and docks brbrbrbrDOCKAGE INCLUDED A private boat slip is available for your stay, complete with water and a covered fish cleaning station. A commercial ice maker is available on-site, perfect for boating, fishing, and easy days on the water. brbrbrbrEXTRAS AND AMENITIES brbrPet-friendly brbrFree on-site parking brbrHigh-speed WiFi brbrPrivate building elevator brbrbrbrCOMMUNITY AMENITIES PELICAN LANDING brbr Heated pool brbr Waterfront setting on Garrison Bight. Located near Charter Row at Garrison Bight, many captains offer pickup directly from the dock brbr Fish cleaning station brbr Private dock access for guests and owners brbr Tiki area and BBQ grills brbrbrbrLOCATION HIGHLIGHTS brbr Bayview Park is adjacent with tennis courts and open green space brbr Fausto’s Food Palace 0.4 miles & Publix grocery store 1.4 miles brbr ️ Higgs Beach 1.2 miles, Smathers Beach 1.5 miles, Fort Zachary Taylor Beach 2 miles brbr✈️ Key West Airport about 10 minutes brbrbrbr INSIDER TIPS brbr Mac’s Place is right next door, a local favorite for casual food and drinks brbr☕ Sandy’s Cafe 0.3 miles, known for Cuban coffee and breakfast brbr Charter fishing, sandbars, and sunset cruises depart nearby from Garrison Bight brbr Easy access to downtown, Duval Street, and the Historic Seaport, about 1 mile awaybrbrbrbrGuest Access:brbrGuests have full, private access to the entire 1,200 sq ft condo, including both bedrooms, two bathrooms, a fully equipped kitchen, and open living and dining areas. Enjoy the private balcony overlooking the marina and heated pool, along with direct access to the pool and dock area. You will also have access to the heated pool, tiki area, BBQ grills, and a private boat slip reserved for your stay. Free on-site parking is included, and a private building elevator provides easy access to the unit. Guests may also enjoy the adjacent park with tennis courts.brbrbrbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.brbrbrbrThe Neighborhood:brbrLocated in the downtown area of Key West, this waterfront condo offers easy access to everything the island is known for, while still providing a more relaxed setting just outside the busiest streets. Duval Street, the Historic Seaport, restaurants, bars, and nightlife are all about 1 mile away.brbrbrbrKey West is famous for its vibrant atmosphere, with live music, over 200 restaurants and bars, and nightly sunset celebrations. From beaches and boating to historic landmarks like the Hemingway House and Southernmost Point, everything is within easy reach. Bayview Park is right next door with tennis courts and open green space.brbrbrbrThe property overlooks Garrison Bight Marina, a hub for boating, fishing, and charter excursions. Located near Charter Row, many captains offer convenient pickup directly from the dock, making it an ideal location for guests planning time on the water.brbrbrbrGetting Around:brbrOur location is ideal for exploring Key West by foot or bicycle—everything is close by! Many guests also enjoy renting electric carts, which are widely available on the island, and we can accommodate plug-in access if needed. You really won’t need a car unless you're driving down Route 1 from mainland Florida. Lyft and Uber are also readily available throughout the area for added convenience.brbrbrbrOther Things to Note:brbr⏰ CHECK-IN AND CHECK-OUT: Check-in is 4 PM and check-out is 10 AM. The base rate includes up to 6 guests, with a maximum occupancy of 8. Guests 7 and 8 are $100 per person per night and must be included on the reservation prior to arrivalbrbr PETS: We welcome one dog up to 25 lbs with a $200 non-refundable pet fee.brbr PARKING: Free on-site parking is guaranteed for one vehicle or golf cart.brbr DOCKAGE DETAILS (OUTSIDE CONSTRUCTION PERIODS): Maximum boat length 40 ft, maximum beam 13 ft, with an 18-ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted.brbr AGE REQUIREMENT: Primary renter must be 25+ unless approvedbrbr TROPICAL ENVIRONMENT REMINDER: Our home is treated monthly by professional pest control; however, in Key West’s climate, occasional insect sightings are possible. If needed, we will promptly arrange professional inspection and treatment. Access must be permitted for service.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed. Check-in is simple with keyless entry. You will receive access codes for the building at least 24 hours prior to arrival and your condo access code on the day of arrival. Our team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(29)

$676.34

/ Nightly
Condo

Waterfront Condo Dock Pool Downtown Near Duval

Key West, Florida, United States

Summary:brbrTime to relax and vacation in this spacious 1,350 sq ft waterfront corner condo in downtown Key West. Bring your family and friends and enjoy a private balcony with marina views, full kitchen, and open living space. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Amenities include a heated pool, tiki area, BBQ grills, free parking, elevator access, and secure entry. Located about 1 mile from Duval Street and 10 minutes from EYW airport.brbrbrbrThe Space:brbrWELCOME TO ABACO YOUR SPACIOUS WATERFRONT RETREAT IN KEY WESTbrbrbrbrLocated in the desirable Pelican Landing waterfront community, Abaco is a beautifully updated 2 bedroom, 2 bath corner condo offering 1,350 sq ft of living space, ideal for families, couples, or small groups. Comfortably sleeps up to 8 guests, with room to spread out and relax.brbrbrbr✨ THE SPACEbrbr Primary Suite: King bed, marina views, private balcony access, ensuite bathroom, walk-in closet, and flat-screen TVbrbr ️ Second Bedroom: Two Queen beds, ensuite bathroom, and flat-screen TVbrbr ️ Living and Dining Area: Spacious open layout with comfortable seating, perfect for relaxing, dining, or gathering after a day on the waterbrbr ️ Kitchen: Fully stocked with cookware and essentials, ready for meals at homebrbr Laundry: Full-size washer and dryer for added conveniencebrbr Balcony: Large private balcony overlooking Garrison Bight Marina and the pool, ideal for morning coffee, boat watching, or sunset drinks. Includes direct stair access to the pool and docksbrbrbrbr DOCKAGE INCLUDEDbrbrA private boat slip is available for your stay, complete with water and a covered fish cleaning station. A commercial ice maker is available on-site, perfect for boating, fishing, and easy days on the water.brbrbrbr ️ EXTRAS AND AMENITIESbrbrPet-friendlybrbrFree on-site parkingbrbrHigh-speed WiFibrbrPrivate building elevatorbrbrbrbr LOCAL TIPbrbrRight next door, enjoy a local favorite restaurant with live music, craft beer, and sunset tiki cruises, a perfect Key West evening.brbrbrbr COMMUNITY AMENITIES PELICAN LANDINGbrbr Heated poolbrbr Waterfront setting on Garrison Bight. Located near Charter Row at Garrison Bight, many captains offer pickup directly from the dockbrbr Fish cleaning stationbrbr Private dock access for guests and ownersbrbr Tiki area and BBQ grillsbrbrbrbr LOCATION HIGHLIGHTSbrbr Bayview Park is adjacent with tennis courts and open green spacebrbr Fausto’s Food Palace 0.4 miles & Publix grocery store 1.4 milesbrbr ️ Higgs Beach 1.2 miles, Smathers Beach 1.5 miles, Fort Zachary Taylor Beach 2 milesbrbr✈️ Key West Airport about 10 minutesbrbrbrbr INSIDER TIPSbrbr Mac’s Place is right next door, a local favorite for casual food and drinksbrbr☕ Sandy’s Cafe 0.3 miles, known for Cuban coffee and breakfastbrbr Charter fishing, sandbars, and sunset cruises depart nearby from Garrison Bightbrbr Easy access to downtown, Duval Street, and the Historic Seaport, about 1 mile awaybrbrbrbrGuest Access:brbrGuests have full, private access to the entire 1,350 sq ft condo, including both bedrooms, two bathrooms, a fully equipped kitchen, and open living and dining areas. Enjoy the private balcony overlooking the marina and heated pool, along with direct access to the pool and dock area. You will also have access to the heated pool, tiki area, BBQ grills, and a private boat slip reserved for your stay. Free on-site parking is included, and a private building elevator provides easy access to the unit. Guests may also enjoy the adjacent park with tennis courts.brbrbrbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.brbrbrbrThe Neighborhood:brbrLocated in the downtown area of Key West, this waterfront condo offers easy access to everything the island is known for, while still providing a more relaxed setting just outside the busiest streets. Duval Street, the Historic Seaport, restaurants, bars, and nightlife are all about 1 mile away.brbrbrbrKey West is famous for its vibrant atmosphere, with live music, over 200 restaurants and bars, and nightly sunset celebrations. From beaches and boating to historic landmarks like the Hemingway House and Southernmost Point, everything is within easy reach. Bayview Park is right next door with tennis courts and open green space.brbrbrbrThe property overlooks Garrison Bight Marina, a hub for boating, fishing, and charter excursions. Located near Charter Row, many captains offer convenient pickup directly from the dock, making it an ideal location for guests planning time on the water.brbrbrbrGetting Around:brbrOur location is ideal for exploring Key West by foot or bicycle—everything is close by! Many guests also enjoy renting electric carts, which are widely available on the island, and we can accommodate plug-in access if needed. You really won’t need a car unless you're driving down Route 1 from mainland Florida. Lyft and Uber are also readily available throughout the area for added convenience.brbrbrbrProfessionally managed by the family-owned team at KeysTime Vacation Rentals.brbrbrbrOther Things to Note:brbr⏰ CHECK-IN AND CHECK-OUTbrbrCheck-in is 4 PM and check-out is 10 AM. The base rate includes up to 6 guests, with a maximum occupancy of 8. Guests 7 and 8 are $100 per person per night and must be included on the reservation prior to arrival.brbrbrbr PETSbrbrOne dog up to 25 lbs is welcome with a $200 non-refundable pet fee.brbrbrbr PARKINGbrbrFree on-site parking is available for one vehicle or golf cart.brbrbrbr DOCKAGE DETAILSbrbrMaximum boat length 40 ft, maximum beam 13 ft, with an 18 ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted.brbrbrbr AGE REQUIREMENTbrbrAll guests must be at least 25 years of age unless accompanied by a parent. Please reach out with any questions.brbrbrbr TROPICAL ENVIRONMENTbrbrOur home is treated regularly by professional pest control. Due to the tropical climate, occasional insects may be present. If needed, we will promptly arrange service during your stay.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrCheck-in is simple with keyless entry. You will receive access codes for the building at least 24 hours prior to arrival and your condo access code on the day of arrival.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.
Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(34)

$677.23

/ Nightly
Condo

Waterfront Dock Pool Key West Near Duval

Key West, Florida, United States

Summary:brbrRelax in this bright 2nd-floor corner waterfront condo in downtown Key West, offering extra natural light and unobstructed marina and pool views. Enjoy a spacious layout, full kitchen, and private balcony. Dockage available with a fish cleaning station and ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, restaurants, and nightlife, and 10 minutes from EYW airport. Amenities include a heated pool, tiki area, BBQ grills, free parking, elevator, and secure entry.brbrbrbrThe Space:brbrWELCOME TO ELEUTHERA YOUR CORNER WATERFRONT RETREAT IN KEY WESTbrbrbrbrLocated in the desirable Pelican Landing waterfront community, Eleuthera is a bright and updated 2 bedroom, 2 bath corner condo offering additional natural light and open views from its second-floor location. Ideal for families, couples, or small groups, this home comfortably sleeps up to 6 guests, with a maximum occupancy of 8.brbrbrbrPositioned as a corner unit, the condo features a spacious layout and a private balcony with unobstructed views of Garrison Bight Marina and the pool. Whether you are here for boating, exploring downtown Key West, or simply relaxing by the water, this is an ideal place to settle in and enjoy your stay.brbrbrbr✨ THE SPACEbrbr Primary Suite: King bed, marina views, private balcony access, ensuite bathroom, walk-in closet, and flat-screen TVbrbr ️ Second Bedroom: Two Queen beds, ensuite bathroom, and flat-screen TVbrbr ️ Living and Dining Area: Spacious open layout with comfortable seating, perfect for relaxing, dining, or gathering after a day on the waterbrbr ️ Kitchen: Fully stocked with cookware and essentials, ready for meals at homebrbr Laundry: Full-size washer and dryer for added conveniencebrbr Balcony: Large private balcony overlooking Garrison Bight Marina and the pool, ideal for morning coffee, boat watching, or sunset drinks. Includes direct stair access to the pool and docksbrbrbrbr DOCKAGE INCLUDEDbrbrA private boat slip is available for your stay, complete with water and a covered fish cleaning station. A commercial ice maker is available on-site, perfect for boating, fishing, and easy days on the water.brbrbrbr ️ EXTRAS AND AMENITIESbrbrPet-friendlybrbrFree on-site parkingbrbrHigh-speed WiFibrbrPrivate building elevatorbrbrbrbr COMMUNITY AMENITIES PELICAN LANDINGbrbr Heated poolbrbr Waterfront setting on Garrison Bight. Located near Charter Row at Garrison Bight, many captains offer pickup directly from the dockbrbr Fish cleaning stationbrbr Private dock access for guests and ownersbrbr Tiki area and BBQ grillsbrbrbrbr LOCATION HIGHLIGHTSbrbr Bayview Park is adjacent with tennis courts and open green spacebrbr Fausto’s Food Palace 0.4 miles & Publix grocery store 1.4 milesbrbr ️ Higgs Beach 1.2 miles, Smathers Beach 1.5 miles, Fort Zachary Taylor Beach 2 milesbrbr✈️ Key West Airport about 10 minutesbrbrbrbr INSIDER TIPSbrbr Mac’s Place is right next door, enjoy a local favorite restaurant with live music, craft beerbrbr☕ Sandy’s Cafe 0.3 miles, known for Cuban coffee and breakfastbrbr Charter fishing, sandbars, and sunset cruises depart nearby from Garrison Bightbrbr Easy access to downtown, Duval Street, and the Historic Seaport, about 1 mile awaybrbrbrbrGuest Access:brbrEnjoy access to all areas of this waterfront condo, including the fully renovated 2-bedroom unit with a private balcony offering direct access to the pool and docks. Guests can utilize the on-site boat slips, heated pool, tiki bar, BBQ grills, and fish cleaning station. A commercial ice machine is also available. The property features a private elevator and secure keyless entry. Guests will also have access to high-speed WiFi. The condo is located near a fantastic waterfront restaurant.brbrbrbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.brbrbrbrThe Neighborhood:brbrLocated in the downtown area of Key West, this waterfront condo offers easy access to everything the island is known for, while still providing a more relaxed setting just outside the busiest streets. Duval Street, the Historic Seaport, restaurants, bars, and nightlife are all about 1 mile away.brbrbrbrKey West is famous for its vibrant atmosphere, with live music, over 200 restaurants and bars, and nightly sunset celebrations. From beaches and boating to historic landmarks like the Hemingway House and Southernmost Point, everything is within easy reach. Bayview Park is right next door with tennis courts and open green space.brbrbrbrThe property overlooks Garrison Bight Marina, a hub for boating, fishing, and charter excursions. Located near Charter Row, many captains offer convenient pickup directly from the dock, making it an ideal location for guests planning time on the water.brbrbrbrGetting Around:brbrOur location is ideal for exploring Key West by foot or bicycle—everything is close by! Many guests also enjoy renting electric carts, which are widely available on the island, and we can accommodate plug-in access if needed. You really won’t need a car unless you're driving down Route 1 from mainland Florida. Lyft and Uber are also readily available throughout the area for added convenience.brbrbrbrOther Things to Note:brbr⏰ CHECK-IN AND CHECK-OUTbrbrCheck-in is 4 PM and check-out is 10 AM. The base rate includes up to 6 guests, with a maximum occupancy of 8. Guests 7 and 8 are $100 per person per night and must be included on the reservation prior to arrival.brbrbrbr PETSbrbrOne dog up to 25 lbs is welcome with a $200 non-refundable pet fee.brbrbrbr PARKINGbrbrFree on-site parking is available for one vehicle or golf cart.brbrbrbr DOCKAGE DETAILSbrbrMaximum boat length 40 ft, maximum beam 13 ft, with an 18 ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted.brbrbrbr AGE REQUIREMENTbrbrAll guests must be at least 25 years of age unless accompanied by a parent. Please reach out with any questions.brbrbrbr TROPICAL ENVIRONMENTbrbrOur home is treated regularly by professional pest control. Due to the tropical climate, occasional insects may be present. If needed, we will promptly arrange service during your stay.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrCheck-in is simple with keyless entry. You will receive access codes for the building at least 24 hours prior to arrival and your condo access code on the day of arrival.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.
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Exceptional(5)

$534.38

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Condo

Penthouse in Paradise!

Key West, Florida, United States

Coconut Mallory is a waterfront private community that provides resort-style amenities, including two large pools, Jacuzzi, BBQ grills, picnic tables and much more. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use. Community asks that master tub in master not be used due to neighbors having leaks in the past.brbrThis unit is a two bedroom two bath. It also features two off street parking spaces included.howrver shower is allowed.
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$804.38

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Stunning Views at The Galleon Resort in Beautiful Key West! Charming 2 Bed!

Key West, Florida, United States

Concierge Realty is proud to present luxury villas at The Galleon Resort!brbr**Reservations are available in weekly (7 night) increments with arrivals and departures on Saturdays only.brbr**All bookings are time sensitive and availability can change at any time. Send us a message to confirm exact availability prior to making a booking request. brbrOverlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends at the Tiki Bar, or relax in the swimming pool. The observation deck guarantees stunning views, sunrise to sunset, star gazing. Rent a boat for a private viewing of the Keys or take a jet ski for a spin right from the marina. Work up a sweat at the on site gym and afterwards, relax your body & mind in the sauna.brbrTwo-bedroom suites sleep up to six, and include a full kitchen, dining area, and decked out living area. Each is lovingly furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West.brbrThe second bedroom will have either a Queen size bed or two twin beds. brWe offer many activities on site at the Galleon Resort and Marina. From fishing charters to sunset cruises, snorkel adventures, boat and jet ski rentals, parasailing to live music.brbrA resort fee of approximately $75/week (subject to change) or $20/day (for stays shorter than one week) will be collected by the resort at time of check-inbr brThe Vrbo calendar helps provide availability and estimated price quote. Always inquire with the agent and do not reserve airfare until your confirmation has been received.brbrAny issues with resort service, accommodations, physical plant, amenities, etc. are the direct responsibility of the developer and must be handled through the resort, not Concierge Realty.  Photos are thought to be truly representative of the resort and accommodations.  Any variation from the photo and actual property are unintentional, so guests are encouraged to do their own due diligence prior to reserving. Any variance or disruption including but not limited to renovation, unavailable amenity, change in decor, etc. during the stay, whether announced prior to reservation, occurring during the stay or announced after confirmation, is a matter strictly between the guest and resort, are not deceptive advertising, breach of contract or the responsibility of Concierge Realty.brbrNote that the images are representative of this villa and that a specific view type is not implied nor promised by virtue of the images. A specific view category must be addressed with rental agent. Concierge Realty reserved the right to reserve any view category unless one has been agreed upon in writing.  The resort confirmation will show the view designation and the villa will be placed within that view category unless, in a rare instance the view will be noted as not guaranteed in which case the resort reserves the right to place the guest anywhere within the property.  Issues regarding view within the guaranteed view category are to be addressed with the resort management as Concierge Realty is not responsible for villa placement.brbrPlease be advised that if a non-domestic credit card is used to reserve a vacation rental, additional fees may be incurred.brbrAll details are accurate to the best of our knowledge.  Any questions with regard to view, amenities, bedding configuration, decor or other details should be addressed with Concierge Realty, Winter Garden, FL.brbrGuests are encouraged to do their own due diligence to assure that the resort and villa will meet their expectations.
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Exceptional(1)

$154.57

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Condo

NEWTON'S NEST ~ Adult Only, 1st Floor 1 Bedroom, 1 Bath Condo w/ Shared Pool!

Key West, Florida, United States

SIMPLISTIC ELEGANCE...brEnjoy easy tropical living in this quiet refuge located within Old Town where you can roost and immerse yourself in island joy.  A charming adult only hideaway located tucked in serene surroundings with the opportunity to fully live like a local! This one bedroom condo has been lovingly restored to envelop you in all its simple charm.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brCome unwind in this cozy layout on the first floor with delightful accents and vintage Dade County walls throughout. Large windows attract incredible natural lighting in this cheery space with comfortable furnishings and a flat screen TV for lazy afternoons. Perch the doors open to a light filled sunroom to get lost in your favorite novel. A fully equipped kitchen allows for all your meal prep and cocktail crafting.brbrSLEEPING ARRANGEMENTS…brA queen guest room features a comfy canopy bed and plush bedding with a TV for a perfect night's sleep. A very stylish en suite bathroom will wash your cares away which offers a shower. This unit also has its own private washer and dryer.brbrOUTDOOR LIVING…brA second entrance from the kitchen area takes you out to your outdoor tropical oasis. Steps away you will find a friendly community pool (not heated) with plenty of loungers to soak up the island rays and seating to dine al fresco. Park your bike on the side of the building and stroll in town to meet old friends and new. brbrPETS...brPets are not considered at this home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrPARKING...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood.  Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last).  We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more.  They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). brbrAUTHENTIC KEY WEST...
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Exceptional(11)

$175.08

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Come escape to Island Time Hideaway - Wonderful monthly renovated rental

Key West, Florida, United States

Beautifully Renovated 2BR/2BA Condo at Exclusive 1800 AtlanticbrbrExperience comfort and elegance in this beautifully renovated 2-bedroom, 2-bath condo located in the prestigious 1800 Atlantic community. Each bedroom features a king-size bed, generous closet space, and direct access to a private balcony overlooking a serene nature preserve—offering a quiet, tranquil setting within the property.brbrThe spacious master suite boasts a large walk-in closet and a stunning, custom-designed bathroom with a walk-in shower. The full-size, fully equipped kitchen makes dining in easy, and a full-size washer and dryer add convenience. Ample storage throughout the unit ensures a clutter-free stay.brbrLocated just across from the elevator, this unit offers easy access and includes one assigned covered parking space in a secure garage.brbrResort-Style Amenities Include:brbr Olympic-sized heated poolbr 20-person jacuzzibr Three tennis courts (including a clay court)br Small fitness centerbr Lush tropical landscaping and a peaceful settingbrbrThis is island living at its best—perfect for a relaxing vacation or an extended stay in Key West.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.
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$223.68

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Sea Haven Delight A delight in Key West Open March 2026 - Great

Key West, Florida, United States

This top-floor condominium features 3 bedrooms and 2 bathrooms, situated in the beautiful La Brisa Complex. It is conveniently located directly across the street from Smathers Beach and just a 10-minute bike ride from downtown Key West. The master suite includes a king-sized bed and an en-suite bathroom, while both guest bedrooms are equipped with queen-sized beds. For entertainment, there are Smart TVs in both the master bedroom and the living room. The dining area comfortably seats six, and the full-sized, fully equipped kitchen includes a washer and dryer for your convenience. La Brisa offers a peaceful atmosphere, overlooking the salt ponds. The unit comes with one designated parking space. Residents and guests can enjoy the lovely amenities of the community, which include a tennis court, BBQ grills for communal use, and a heated outdoor swimming pool.
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Exceptional(27)

$287.73

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Condo

Sunrise 307-2BR/2BA condo near beaches with pool, parking, balcony

Key West, Florida, United States

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrFEATURES:brBedrooms: 2 (1 king, 1 queen, sofa sleeper recommended for children ONLY)brBathrooms: 2 brLocation: Sunrise SuitesbrSquare Feet: 798brParking: 2 parking spaces includedbrAmenities: Wifi, TVs, in-unit laundry, shared pool, close to beaches, private balconybrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.
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$457.01

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Key West Hen

Key West, Florida, United States

brGive me a call if you have any questions!br702-232-3750. Welcome to your home away from home and enter through the canopy of trees to the secure, patrolled Shipyard Condominium's in the desirable Truman Annex Complex. Professionally designed to maximize relaxation and encourage adventure. BeautifulbrRelax on the balcony with your glass of wine or hang out on the reading porch with a cup of coffee and a great book. Fort Zachary Taylor State Beach is a 2 minute bike ride away. This wonderful home has been newly decorated with a conch farm theme, comfortable outdoor furniture, professionally designed bedrooms with new queen beds in each room , fully stocked kitchen, living room, washer/dryer. Some of the amenities include WIFI, SMART TV's, and an assigned parking spot . Steps from the world famous Duval Street, sunset celebration and all the downtown action one desires. You are only one block down from The Green Parrot, rated the 3rd best bar in America. The Shipyard is the closest residential location to Fort Zachary State Park and Beach. You are in the heart of Old Town, Mallory Square (sunset celebration) and on the grounds of Harry Truman's Little White House located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million dollar homes that are landscaped with 30’ palms and exotic flowering plants. It is just a short stroll to the Historic “Little White House” where President Truman called home whenever he could. You are close by the warm tropical waters of the Gulf of Mexico where you can hop on a fishing boat for flats or deep sea fishing, take the Ferry to Sunset Key for lunch or dinner, go parasailing, snorkeling, diving, shopping, dining or wherever your dreams might take you. Just another short stroll takes you to Mallory Square where the world renowned “Sunset Celebration” occurs every day! This event is a “don’t miss” of things to do in Key West.brbrWe provide all of your kitchen necessities, just bring the cook & the food! Spacious living room where the living room doors open up into the private deck making your vacation a true Tropical experience. brbrWhat is provided:brbrWe provide 4 towels, wash cloths for each reservation as well as 2 bath robes and beach towels.brbrWe provide 2 rolls of toilet paper and 1 roll of paper towels per reservation. Please bring extra if this is not enough.brbrDaily maid service is not provided.
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Exceptional(24)

$193.08

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THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!

Key West, Florida, United States

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCUTE CONDO IN STEPS FROM IT ALL…brThis 2 bedroom, 1 bath ground level flat is located in The Shipyard, a neighborhood of the coveted Truman Annex in the heart of Old Town Key West! You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! Throw your cares to the wind as you unwind in this charming, tree-shrouded neighborhood with walking paths and lanes. This cozy downstairs unit has everything you'll need for your stay in paradise!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEnter through the white picket fence and you are greeted by a lovely front porch with sitting area where you can sip coffee and plan your island adventures for the day. The flowing floor plan offers a spacious and lovely living and dining area that offer rest and relaxation after a day in the sultry sun and balmy breezes of the island. Whip up your favorite recipes in the fully equipped and stocked kitchen that overlooks the living area. A dining table for 4 sits next to the kitchen where you can enjoy cozy meals with your loved ones. A comfy couch, plush cushioned chairs and smart tv in the living area provide the perfect resting spot for bingeing on your latest shows and movies. A stacked laundry closet sits just off the living area for your convenience. Open the French Doors to your sweet backyard oasis.brbrSLEEPING ARRANGEMENTS…brThe first queen bedroom is on the left as you enter the home. It offers a spacious hanging closet, smart tv, and a clothing dresser for your belongings. The primary bedroom also has a queen bed, smart tv, large hanging closet and clothing dresser, and is adjacent to the full bathroom, where you can wash off the day in the shower/tub combination. brbrOUTDOOR LIVING…brThe Shipyard offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun. Open the French door in the living area to the delightful private deck, a shaded retreat outfitted for unwinding and refreshment.br brPARKING...brThis home does offer parking for one vehicle (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community.brbrPETS...brThis is a pet friendly home with a required pet fee. Please include the size and breed when inquiring. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet Fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrYOUR SWEET RETREAT...
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Exceptional(10)

$466.88

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Condo

Craig & Cindy Key West Truman Annex Shipyard Condo w/ balcony at Mile Marker 0!

Key West, Florida, United States

Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes:brbr2 bedrooms 2 full bath {queen and king bedrooms} plus a sleeper sofa in the living room.brbrFully equipped kitchen with upgraded appliances and cooking accessories.brWasher & dryer with iron & ironing board.brAll towels and linens, including beach towels.brCentral air & ceiling fans.brSecond floor condo with outdoor balcony.brLarge shared Shipyard pool located just steps away.br3 Smart TV's and Amazon Echo (just tell Alexa to play some Jimmy Buffett!)brHigh speed fiber optic internet with Wi-Fi.brAssigned parking spot for 1 car.brbrLocated in prestigious Truman Annex at Mile Marker 0 - location, location, location. Shipyard Condos are right at the entrance to Ft. Zachary Beach and next to Mallory Square and those famous nightly Sunset Festivals and just two blocks from Duval Street and all of the shops, restaurants, night clubs and museums. While we provide a parking spot, you will not need a car! brbrExcept for festivals such as Fantasy Fest, Meeting of the Minds, and Powerboat Races, we generally require Saturday-Saturday rentals so if your dates are not Saturday-Saturday please email us with your dates prior to booking so that we can check our calendar to see if an exception is possible. brbrWe have many other Key West Truman Annex vacation rental listings that can be accessed via VRBO. Let us know if you have a particular interest or property size in mind.
Bed 2

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