Vacation Rentals By Owner In Key West, FL

$225.7

The Tipsy Mermaid at Key West Golf Club

Key West, Florida, United States

Welcome to Tipsy Mermaid, your tropical retreat in the heart of the Key West Golf Club community. This stylish two-story townhome sits right on the fairway, just minutes from the island’s famous beaches, dining, and nightlife.brbrStart your day with coffee on the front porch rocking chairs, enjoy a shaded afternoon on the wraparound screened-in veranda, or savor sunset dinners on the garden patio surrounded by lush palms and lake views. With three private outdoor spaces, there’s a perfect spot for every mood.brbrInside, the home is freshly updated with coastal-chic décor, elegant furnishings, and modern touches throughout — from quartz countertops and stainless-steel appliances to luxurious glass-enclosed rain showers. The open-concept living area is perfect for gathering, cooking, or simply unwinding after a day in the sun.brbrStep across the street to take a dip in one of two resort-style community pools or squeeze in a workout at the clubhouse gym. Stroll the scenic walking paths, tee off at the golf course, or hop on a bike for a quick ride into Old Town.brbrDog friendly (1 allowed - no other types of pets allowed)brbrPlease let us know if there are any specific dates you would like or to tailor your stay- simply send us a message through the channel ! Open to off season longer terms stays or booking next season in advance as well! Come enjoy the laid back sunshine and all Key West has to offer! If you would like suggestions of things to do while you are here or to book any excursions we are happy to help!

3

Bed

2

Bath

6

Sleeps

$422.13

/ Nightly

Private Vacation Home

**WATERFRONT WHISPERS @ GULFVIEW** Waterfront Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrWATERFRONT WHISPERS captures the essence of island living within a private gated community situated on the water where you can’t hear a whisper. This 4 bedroom premium waterfront home blends total tranquility with easy access to the waters of the Florida Keys via a private boat dock. Spend your days relaxing in the pool or out on the boat, and your evenings taking in the Key West sunset from the dock. The sleek interior provides an open and airy layout, perfect for entertaining a large group. Combined with Last Key Realty's Five-Star Guest Services & In-house Concierge, your month at WATERFRONT WHISPERS will be filled with cherished memories.brbrTHE LIVING AREA & KITCHEN…brbrSteeped in natural light, the spacious, open-concept first floor immediately captures your attention with breathtaking water views framed by oversized sliding glass doors. The inviting living area serves as the perfect central hub, offering comfortable seating arranged around a large flat-screen TV. Steps away, the chef's kitchen is fully-equipped with stainless steel appliances and every culinary tool required to whip up gourmet meals. Guests can gather at the large dining table that comfortably seats eight or grab one of the three barstools at the kitchen bar for a quick bite.brbrDesigned with versatility in mind, the first floor also hosts a private den/home office. This dedicated workspace ensures a quiet retreat for those needing to catch up on remote work, while the plush Queen-sized sleeper sofa will comfortably accommodate extra guests. A convenient half bathroom is located just off the living area.brbrTHE BACKYARD, POOL & DOCK…brbrAs impressive as the interior is, the real showstopper of WATERFRONT WHISPERS is the outdoor space. Featuring an in-ground heated pool that overlooks the Gulf, it’s easy to see why this will be a primary gathering space for your group. The pool can be heated or chilled to your preferred temperature ensuring a comfortable swim year-round. For the sun worshipers, there are plenty of chaise lounges for laying out on the spacious pool deck. When you’ve had enough sun, retreat to the covered back porch with comfortable seating options. brbrThe most unique feature of this home is the private boat dock that stretches out from the back of the property. The dock is perfect for keeping your boat or boat rental right in your back yard during your vacation. The size of the boat being docked here is restricted to a shallow draft, 21-foot maximum length. The boat dock includes a fish cleaning station, power, and water. The outdoor shower is perfect for rinsing off after the pool or a day on the boat.brbrTHE LOCATION…brbrAll of this splendor in a centralized mid-island location, within the quiet residential gated community of Gulfview. You’ll be away from the hustle & bustle of Duval St, yet only be a short 10 minute drive or Uber ride down to the heart of the action. There’s one dedicated covered parking space included.brbrTHE ACCOMMODATIONS…brbr** Master Bedroom: King bed, flat screen TV, closet, private balcony with water view and en-suite bathroom.brbr** Second Bedroom: Queen bed, flat screen TV, closet, private balcony, and access to the hall bathroom.brbr** Third Bedroom: Queen bed, flat screen TV, closet and access to the hall bathroom.brbr** Fourth Bedroom: Queen bed, flat screen TV, closet and access to the hall bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE: brbr** Washer and Dryer br** Central Heat and A/C br** Ceiling Fans Throughoutbr** Flat Screen Cable TVs in Living Room & Bedrooms br** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels provided br** Wireless high-speed Internet access and full cable is included br** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list: brbr** Flex Room/Home Officebr** Boat Dock (max length of 21 ft)br** Fish Cleaning Stationbr** Propane BBQ Grillbr** Private Heated/Chilled Poolbr** Outdoor Showerbr** Covered Parking Space for 1 VehiclebrbrOther notes: brbr** Interim housekeeping provided upon request br** This property will accommodate up to 10 adultsbr** Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

4

Bed

2

Bath

10

Sleeps

$985.47

/ Nightly

Hotel

Newport Getaway! Pool, Spa, Onsite Dining, & Easy Access to Attractions!

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 322 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

1

Bed

1

Bath

4

Sleeps

$985.47

/ Nightly

Hotel

Pet-Friendly Ocean View Stay! Pool, Spa, Historic Sights Nearby!

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 322 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

1

Bed

1

Bath

4

Sleeps

$1151.96

/ Nightly

Hotel

Pet-Friendly Stay, Pool, Spa, Fitness Center! Historic Sights Nearby

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

Bed

Bath

Sleeps

$410.63

/ Nightly

Hotel

Spacious Lanai Suite! Pool, Marina Access, Walk to Dining Spots & Museums

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 344 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

1

Bed

1

Bath

2

Sleeps

$1137.38

/ Nightly

Hotel

Spacious Oceanfront Stay! Spa, Fitness, & Steps to the Beach!

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

1

Bed

1

Bath

2

Sleeps

$1137.38

/ Nightly

Hotel

Stylish Suite w/ Oceanfront View, Pool, Spa, & Steps to Historic Newport

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

1

Bed

1

Bath

2

Sleeps

$401.58

/ Nightly

Hotel

Pet-Friendly Waterfront Escape w/ Pool, Near Cliff Walk & Newport Fun

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 322 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

1

Bed

1

Bath

3

Sleeps

$401.58

/ Nightly

Hotel

Lux Waterfront Suite w/ Pool, Spa, & Walk to Newport Marina & Attractions

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 322 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 24 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool available all year.brbr✦ Paid parking lot – 1 space(s), available for $40.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $62.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00. Only one dog under 20 pounds is allowed per roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ The property requires a damage deposit of 1-night rate + tax on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.

Bed

Bath

Sleeps

$283.18

/ Nightly

Private Vacation Home

Blue Duval walking distance to Duval St

Key West, Florida, United States

Welcome to Blue Duval a downtown Key West Home just Steps to Duval Street & Hemingway House!brbrPROFESSIONAL Monthly rental ONLY: We specialize in 30-day stays. To ensure calendar continuity, we require all residencies to align with the 1st of the month. Stays not starting on the 1st must be approved by management prior to bookingbrbrBackyard is off limits and glass sliding door to remain closedbrbrThis brand-new 1,460 sq ft modern conch cottage fuses timeless Key West architecture with sleek luxury amenities.brbrNestled in the heart of Old Town, 176 yards (under 3-minute stroll) to Duval Street`s iconic bars, restaurants, galleries and more—plus, the legendary Ernest Hemingway Home & Museum is just .2 miles away (a quick 5-minute walk).brbrBEDROOM CONFIGURATIONbrBedroom 1 - King bed with ensuite bathroombrBedroom 2 - 2 Twin XL with ensuite bathroombrbrAdditional bedding: Pull of Queen size Sofa bed (60x72)brbrHIGHLIGHTSbr- Newly Constructed in quiet neighborhoodbr- Key West Style Housebr- Dedicated 1 parking space (rarity in Key West)br- Walking distance to downtown Duval St, bars and restaurants.br-Fully equipped kitchen: drip coffee, electric kettle, all pots/pans/silverware/dishwarebrbrAMENITIESbr- 5-star amenities and furnishingsbr- Modern finishes and luxury appliances throughoutbr- 2 bedrooms & 2.5 bathroomsbr- Fully stocked kitchenbr- Wall-to-wall floor-to-ceiling retractable glass doors in the living room (Currently off limits and not for use)br- Dining Roombr- Designated dedicated parking spot (Not suitable for large SUV or truck)(Right side facing houses)br- Fast Wi-Fi internet 400-600 mbsbr-75 inch Smart TVbr- In-unit washer & dryerbr- Room-darkening shades in all roomsbr- Central A/C + ceiling fans throughoutbr-Starter Set for monthly staybrbrMove-in ready—everything is brand new and pristinebrNo car required. This unbeatable spot on quiet Amelia St puts Hemingway`s world and Duval`s energy right at your doorstep.brbrMonthly rental | Fully furnished | No pets | Non-smokingbrContact for rates and specials and secure your 2025-built Key West escape!brbrMin 29 nightsbrbrOur villa is only for responsible guest who will respect and not damage the villa and property. Guest booking must be 21 years or older. No Pets. No parties or events. No Smoking or Drug use on property. No fireworks allowed.brbrEVENTS & COMMERCIAL PHOTOSHOOTS: Are not permitted brbrA refundable security deposit is collected upon booking can be used to cover any damage that occurs during the stay. Automatically refund after 7 days after stay if no damages occur. Rental agreement must be signed and security deposit provided prior to check in.

2

Bed

2

Bath

6

Sleeps

$1370.24

/ Nightly

Private Vacation Home

Waterfront 4 Bed 4 Bath Home in Key Cove Landings

Key West, Florida, United States

Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Sailor's Son. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on private driveways leading to the house.brbrUNIQUE FEATURES:br2 EnSuite bedrooms, both facing the water with porch access. br4 Full Baths.brbrThis home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with a couch around a large HD flat screen Smart TV. There is a dining table with seating for up to 8 diners, with additional seating for 6 at the kitchen bar. brThe master bedroom has a King sized bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has a King sized bed, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is also on the 2nd floor with twin beds, flat screen TV, and also with balcony access. On the main floor there is a fourth bedroom with twins bed. There is a full bath down the hall for convenience.brOut back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. brAMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. This property will accommodate 8 adults.brbrDockage is not available at this home's development.brbrRATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

Bed

Bath

Sleeps

$227.73

/ Nightly

Apartment

Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

Key West, Florida, United States

Truman @ Duval - Unit E | Cozy Getaway in the Heart of Key WestbrbrDuval Studio is your perfect launchpad for an unforgettable Key West adventure! Situated near the vibrant intersection of Truman Ave. and Duval St., wonderful studio offers a prime location just steps from some of the island's top attractions. Whether you're visiting the Ernest Hemingway Home and Museum around the corner or indulging in Duval Street's lively nightlife, you'll find everything you need just moments away from your door.brbrThe Ambiance:brThis quaint studio is designed for ultimate convenience and comfort. The open floor plan features a cozy sleeping area with everything you need to relax after a day of island exploration. A mini-fridge, coffee station, and microwave make it easy to enjoy a morning coffee or a quick snack between adventures. With free WiFi, cable TV, and AC , you'll have everything you need to relax after a day of exploring.brbrGuest Perks:brEnjoy a seamless, contactless check-in process with a personalized code. The studio is equipped with free WiFi for staying connected and planning your next outing. You'll also find plenty of local dining options within walking distance, ensuring you never run out of things to try!brbrNeighborhood Highlights:brThe studio places you right at the heart of Key West. From here, you can easily walk to the iconic Ernest Hemingway Home and Museum, just steps away, or visit the Key West Lighthouse, only a block from your front door. For a truly Key West experience, stroll down the lively Duval Street, where you'll find renowned bars, local restaurants, and all the excitement that makes this island so famous.brbrTransportation Tips:brPlease note that there is no designated parking on-site. However, paid parking is available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- This studio is located on the second floor.br- For your safety, there are two cameras monitoring the exterior entrances.br- There is no parking available on-site, but we can provide recommendations for nearby parking options.br- Guests must be 25 years of age or older to reserve this property.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrThis inviting studio offers the perfect balance of comfort and convenience for your Key West getaway. Don't miss out on this prime spot—plan your stay today!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Bed

Bath

Sleeps

$295.71

/ Nightly

Apartment

Welcome Matt's - Truman @ Duval | Perfect Hideaway!

Key West, Florida, United States

Truman @ Duval Unit B | Ideal One-Bedroom Retreat for CouplesbrbrEscape to a charming one-bedroom apartment in the heart of Key West, the perfect spot for a romantic retreat or a weekend getaway. Recently remodeled with comfort and style in mind, this apartment offers all the essentials for a relaxing and memorable stay. Whether you're here to explore the vibrant culture, lounge on the beach, or enjoy a romantic evening, this apartment puts you right in the middle of it all.brbrThe Ambiance:brThis newly remodeled apartment is designed to offer a cozy, intimate space for couples. Featuring a comfortable bedroom, modern décor, and thoughtful touches throughout, it's the perfect place to unwind after a day of island adventures. The apartment comes with a well-equipped kitchen, including a fridge and coffee maker to start your mornings right. Beach towels are provided for your convenience, so you can easily head to one of the nearby beaches or enjoy a day in the sun.brbrGuest Perks:brEnjoy the convenience of free WiFi and a digital lock for easy, contactless check-in. The apartment also comes with essential amenities to ensure your stay is as comfortable as possible. Whether you're exploring the city, relaxing indoors, or taking in the island breeze, this apartment provides a perfect home base during your time in Key West.brbrNeighborhood Highlights:brLocated just steps from Duval Street, this apartment offers an unbeatable location to experience the best of Key West. Walk to local attractions such as the Southernmost Point, Hemingway House, and the Key West Lighthouse. For nature lovers, the Key West Butterfly and Nature Conservatory is just a short stroll away, and if you're seeking outdoor adventure, be sure to visit Fort Zachary Taylor State Park or relax at one of the beautiful local beaches. With a variety of restaurants, shops, and entertainment options nearby, you'll never run out of things to do.brbrTransportation Tips:brPlease note that there is no designated parking on-site. However, paid parking is available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dog with a $20/per dog per night fee.br- This studio is located on the first floor.br- For your safety, there are two cameras monitoring the entrances.br- There is no parking available on-site, but we can provide recommendations for nearby parking options.br- Guests must be 25 years of age or older to reserve this property.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrThis charming one-bedroom apartment in downtown Key West is the perfect choice for couples looking to enjoy a romantic and convenient stay in paradise. Book your getaway today and experience the magic of Key West!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Bed

Bath

Sleeps

$227.68

/ Nightly

Apartment

Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Key West, Florida, United States

Truman @ Duval Unit A | Perfect for a Getaway in Key WestbrbrEscape to this cozy, vibrant cottage in the heart of downtown Key West, where adventure and relaxation await just outside your door. Ideal for couples or solo travelers, this charming retreat offers the perfect spot to enjoy all that Key West has to offer, from historic landmarks to lively nightlife.brbrThe Ambiance:brThis quaint cottage is bursting with character and laid-back island vibes. While it doesn't feature a full kitchen, you'll have a mini-fridge to store your favorite snacks and drinks, perfect for keeping cool after a day exploring. With partial A/C, cable TV, and free WiFi, you'll have all the modern comforts while soaking in the island atmosphere.brbrGuest Perks:brEnjoy a hassle-free, contactless check-in with your personal entry code, and settle in to enjoy everything this vibrant area has to offer. With cable TV, free WiFi, and air conditioning, this cozy retreat ensures you'll always have a comfortable place to unwind after a day of island adventures.brbrNeighborhood Highlights:brLocated just steps from the intersection of Truman Avenue and Whitehead Street, this cottage puts the best of Key West at your fingertips. Take a short walk to the iconic Southernmost Point, visit the Ernest Hemingway Home, or grab a bite at one of the many local restaurants. Whether you're exploring the lively downtown area or catching a sunset on the water, this location is ideal for experiencing the essence of Key West.brbrTransportation Tips:brPlease note that there is no designated parking on-site. However, paid parking is available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- There is no parking available on-site, but we can provide recommendations for nearby parking options.br- The studio is located on the first floor for easy access.br- For your peace of mind, there are two security cameras monitoring the exterior entrances.br- Guests must be 25 years or older to book this property.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Bed

Bath

Sleeps

$230.23

/ Nightly

Apartment

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Key West, Florida, United States

Scott's Cottage - Truman @ Duval F | Perfect Location! Ideal for Solos & CouplesbrbrLooking for a relaxing retreat in the heart of the Florida Keys This charming studio offers the ideal blend of comfort and convenience for your tropical getaway. Whether you're here to explore Key West's rich history, lounge by the beach, or soak up the vibrant culture, this vacation rental is the perfect base for your island adventures.brbrThe Ambiance:brThis charming studio is thoughtfully designed to maximize space and comfort. Equipped with a fully stocked kitchen featuring stainless steel appliances—fridge, stove, oven, microwave, blender, coffee maker, and toaster—you'll feel right at home while preparing meals. Enjoy your morning coffee or dine al fresco on your private patio, complete with an outdoor dining table. With free WiFi, cable TV, and AC , you'll have everything you need to relax after a day of exploring.brbrGuest Perks:brYour stay includes a contactless check-in for your convenience. Access your studio with a personalized code that ensures a secure and seamless arrival. Stay connected with free WiFi, cool off with air conditioning, and enjoy your favorite shows on the cable TV after a fun day out in Key West.brbrNeighborhood Highlights:brLocated just steps from downtown Key West, this studio places you right where the action is! Explore iconic landmarks like the Key West Lighthouse and the Hemingway Home and Museum, all within walking distance. Indulge in the island's cuisine, visit local shops, or enjoy the local nightlife—everything is just a short stroll away.brbrTransportation Tips:brPlease note that there is no designated parking on-site. However, paid parking is available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- This studio is located on the first floor.br- For your safety, there are two cameras monitoring the exterior entrances.br- There is no parking available on-site, but we can provide recommendations for nearby parking options.br- Guests must be 25 years of age or older to reserve this property.brbrCheck-in time: 3:00 PMbrCheck-out time: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrWhether you're here for a romantic getaway, a solo adventure, or to enjoy all the sights and sounds of Key West, this tropical studio offers the perfect spot to call home during your stay! brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

1

Bed

1

Bath

2

Sleeps

$343.54

/ Nightly

Apartment

Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!

Key West, Florida, United States

Truman @ Duval - Unit D | Two-Bedroom with Full Kitchen & Prime LocationbrbrWelcome to your perfect family getaway in the heart of Key West! This charming two-bedroom, one-bathroom offers a wonderful combination of comfort, convenience, and prime location for your next vacation. Just a half block from the lively Duval Street, you'll be steps away from iconic attractions, restaurants, and the best of Key West's vibrant downtown scene.brbrThe Ambiance:brThis cozy home offers the ideal retreat for families looking to relax and enjoy the island life. With a spacious, air-conditioned living area, you'll have plenty of room to unwind. The fully equipped kitchen makes it easy to cook meals together, and the flatscreen TV provides entertainment for everyone after a day of exploring. The two bedrooms provide a peaceful, restful setting, ensuring you wake up refreshed and ready for another fun day.brbrGuest Perks:brThe property comes with a private parking space, ensuring you never have to worry about finding a spot. With free WiFi, you can easily plan your next outing, book tickets for local tours, or just stay connected. Whether you're preparing a homemade breakfast or enjoying a quiet evening in, this home has everything you need for a stress-free stay.brbrNeighborhood Highlights:brLocated just steps from Duval Street, you'll find yourself in the heart of Key West's action. Walk to Southernmost Point, explore the famous Mallory Square Sunset Celebration, or take a dolphin tour to experience the island's natural beauty. There are a variety of restaurants, bars, and cafes nearby, so whether you're craving fresh seafood or a casual bite, you'll find plenty of options. Plus, the nearby beaches provide easy access to sun and sand for a relaxing day by the water.brbrTransportation Tips:brPlease note that there is one designated parking spot on-site. Paid parking is also available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- The cottage is located on the first floor for easy access.br- For your peace of mind, there are two security cameras monitoring the exterior entrances.br- Guests must be 25 years or older to book this property.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrBook your stay at this cozy Key West home today and enjoy a fun-filled, relaxing family vacation in one of the world's most beloved destinations!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Bed

Bath

Sleeps

$264.23

/ Nightly

Apartment

Jerry's Escape - Truman @ Duval | Cozy Studio, Perfect Location!

Key West, Florida, United States

Truman @ Duval - Unit C | Cozy Studio Perfect for CouplesbrbrExperience your perfect romantic retreat, offering a charming and vibrant atmosphere right in the heart of downtown Key West! Whether you're here for the local culture, waterfront activities, or a peaceful island escape, this cozy condo is the ideal home base to experience it all.brbrThe Ambiance:brThis uniquely decorated one-bedroom condo is perfect for couples seeking a quiet getaway with easy access to the best of Key West. Located just off Truman Avenue, the condo boasts a bright and inviting living area, where you can unwind with free WiFi, cable TV, or simply enjoy the island's breeze through your windows. The cozy kitchen allows you to prepare your favorite meals, and the private patio is a perfect place for a romantic dinner under the stars or a delightful place to soak up the sun!brbrGuest Perks:brThis condo offers seamless, contactless check-in with a personalized entry code, ensuring your arrival is smooth and secure. Free WiFi and cable TV are provided for your convenience, and you'll enjoy the comfort of air conditioning as you relax in this intimate space.brbrNeighborhood Highlights:brLocated just a short walk from iconic Key West attractions, Key West Bliss places you steps away from the Ernest Hemingway Home and Museum and Key West Lighthouse. Stroll down the street to explore local shops, bars, and restaurants, or take a quick drive to Fort Zachary Taylor State Park and the Key West Tropical Forest and Botanical Garden for a day of outdoor adventures. Whether you're interested in history, nature, or just soaking in the island charm, you're right in the middle of it all.brbrGetting Around: Key West is incredibly walkable, so you'll have no problem exploring nearby attractions on foot. You can also rent bikes, scooters, or golf carts to explore the island at your leisure. While there is no parking available at the condo, public parking options are nearby, and we're happy to recommend convenient spots.brbrTransportation Tips:brPlease note that there is no designated parking on-site. However, paid parking is available in the surrounding area. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- The studio is located on the second floor.br- For your peace of mind, there are two security cameras monitoring the exterior entrances.br- Guests must be 25 years or older to book this property.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrBook your stay at Key West Bliss today and treat yourself to a memorable romantic escape in the heart of one of the most beautiful destinations in the world!brbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Bed

Bath

Sleeps

$133.45

/ Nightly

Apartment

Beautiful Waterfront Studio- Dock your boat here! - 15 mi to Key West.

Key West, Florida, United States

What a VIEW!! Enjoy breathtaking sunsets right from home in this well-appointed, clean and modern studio. Picture yourself waking up in a king-size bed and enjoying a gorgeous view of the ocean every morning. Drink your morning coffee or juice outside on the private deck overlooking the water. Take advantage of our available paddle board, kayaks, noodles, and snorkel gear to get out there and explore or just jump in the water to beat the heat. Retreat to the shade of the deck or inside the air-conditioned comfort of your room. Enjoy the best of both worlds during your stay in the Keys. Only a 15 -20 min drive so you can enjoy everything Key West has to offer: excellent restaurants, exciting nightlife, shopping, museums, live music, etc (don't worry our guests will get a list of recommendations we know there are lots of tourist traps out there too). Then at the end of your day or night you get to leave all that Key West noise behind when you come back to the peace and tranquility of the bay. brbr*King-size bed has a memory foam mattress with high-quality linens. There is a small kitchenette inside with an apartment-size refrigerator/freezer, microwave, coffee maker, Nespresso maker, toaster oven, and all of the kitchen basics. Outside on the deck is a propane grill with 4 burners plus one separate burner on the side for use with a pot or pan (2 propane tanks are provided). There is also a kitchen sink with a good amount of countertop and storage out on the deck. The bathroom has 2 sinks, a large bathtub, a very romantic double shower, and an amazing view. There is a 32-inch smart TV in the sitting area so you may log into your own Netflix or other online streaming account. The unit has a small apartment-size washing machine for small loads of laundry. There is NO DRYER for your clothing. There is a clothesline and drying rack with clothespins (just like my grandma used to use. Works just fine)! There is parking for one vehicle. 28-night minimum stay.

Bed

Bath

Sleeps

Select Dates for Price

Private Vacation Home

**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrResembling a French Plantation, PLANTATION TROPICALE is an impressive island estate that occupies an entire corner block of the desirable Casa East neighborhood of Key West. This expansive property features nearly 3,000 square feet of indoor living space, a separate Guest House, beautifully maintained gardens, and a large private pool and cabana – all of which are hidden amongst dense tropical foliage to provide ultimate privacy for your group. Speaking of privacy, each bedroom in this impressive home is designed as a private Suite, with an en-suite bathroom and access to a private covered porch. It’s easy to see why PLANTATION TROPICALE is the perfect vacation setting for those looking for a secluded tropical oasis. brbrTHE LIVING AREA & KITCHEN... brbrThe main living area of PLANTATION TROPICALE has two sets of French doors that open to the gardens and fill the space with natural light. A large SMART TV hangs on the wall in front of the plush sectional sofa, which pulls out to a Queen sleeper to accommodate extra guests. The indoor dining table sits just beyond the living room and seats six comfortably. Follow the hallway from the living area to the airy galley-style kitchen. This fully equipped kitchen with multiple sets of French doors offers all of the appliances and tools needed to prepare meals from home.brbrTHE POOL AREA.... brbrThe 28 x 14 private pool is available heated, and is large enough for everyone in your group to swim around in both the sun and shade. The spacious pool deck has chaises for lounging in the sun and a four-top dining table when you want to enjoy a poolside meal. Then, there’s the covered cabana with additional chaises for relaxing in the shade. Finally, there's a propane gas grill and outdoor dining set situated within the gardens when you want to enjoy a BBQ. brbrTHE LOCATION…brbrThe Casa Marina East district of Key West is a quiet, mostly residential neighborhood on the southern side of the island. Just a quick three block walk from the start of Higgs Beach at White Street, and just down the street from Smathers Beach, PLANTATION TROPICALE is a dream for beach-lovers who prefer to pack their coolers and towels and walk down to the sand and water. Watch the sunset from Smathers Beach or the White Street pier just around the corner. Take the short stroll to Salute Ristorante for a beach-side meal, or ride bikes down to Duval Street or the Historic Seaport for the most popular Key West attractions.brbrTHE ACCOMMODATIONS... brbrThis sprawling estate features four bedrooms in the main house and a detached guest house. Each bedroom in PLANTATION TROPICALE has an en-suite bathroom, flat screen TV, closet, and a private covered porch. Spread out in the following accommodations:brbrFirst Floorbrbr** Bedroom #1: Two Twins OR One King. En-suite bathroom has double sinks and a shower and tub combo.brbr** Bedroom #2: Queen bed En-suite bathroom has a walk-in shower.brbr** Guest House: Queen bed. En-suite bathroom has a walk-in shower.brbrSecond Floorbrbr** Master Bedroom: King bed. En-suite bathroom has double sinks and an oversized shower.brbr** Bedroom #5: Queen bed. En-suite bathroom has a walk-in shower.brbrbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced and Lushly Landscaped Private Yard br** Private Pool with available Pool Heatbr** Off-Street Parkingbr** Propane BBQ GrillbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 12 adultsbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

6

Bed

5

Bath

12

Sleeps

Vacation Rentals By Owner In Key West, FL

$225.7

$422.13

$985.47

$985.47

$1151.96

$410.63

$1137.38

$1137.38

$401.58

$401.58

$283.18

$1370.24

$227.73

$295.71

$227.68

$230.23

$343.54

$264.23

$133.45

Rent a place that suits your needs

Most popular vacation rentals in Key West

$2653.01

$2168.85

$2179.76

$2193.75

$2377.08

$2433.36

$2489.04

$2519.19

$2606.88

$4253.21

Most Popular Cities in Florida