Home Vacation Condo Rentals By Owner In Key West, FL

Showing 300 Of 527 Vacation Rentals
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Exceptional(19)

$195.7

/ Nightly
Condo

Sweet Sunshine Garden Flat – Downtown Key West - 2 Blocks Off Duval w Pool Access

Key West, Florida, United States

Ever dream of vacationing in a sun-kissed Caribbean Cottage-style flat close to the beach, nestled behind a white picket fence in a landscaped tropical garden Sweet Sunshine Garden Flat can make that dream come true. Set in the beautiful Key West Truman Annex Shipyard condominium complex, flowers and palm trees frame the front entrance like a pretty picture. Pale pink wood-slat siding, a faint-blue front porch ceiling, and a nautical octagon window epitomize Key West nouveau architecture and welcome you to your own slice of paradise.brbrSweet Sunshine Flat is a synonym with Key West luxury, every direction you look is idyllic in this luxury neighborhood. And here you are perfectly situated for a week near the beach, and just as close to downtown Old Town Key West.brbrLooking north from the front porch, facing town, you’re less than two blocks from Duval Street. Looking south you’re less than two blocks from the Truman Waterfront Park and Key West Amphitheater. You’re also at the gateway to the iconic pre-Civil war Fort Zachary Taylor, and just a ten-minute walk to the water`s-edge of the beach. But before we explore more of the surrounding grounds, let’s step inside the flat and focus on the layout and amenities, and peek at the covered back porch and courtyard garden.brbrInterior Layout:brbrLet’s start at the front door entrance, The entry hall makes good use of space by providing a hidden laundry closet to the left, equipped with a washer / dryer. Take a few more steps, and you find the fully equipped U-shape kitchen. Set into blonde wooden cabinets, the appliances include a full-sized refrigerator, with top freezer, electric glass stove top with full size oven, and space-saver microwave over the stove. The sink is on the bar counter opposite the appliances facing toward the living room and back deck – a perfect place to brew a pot of coffee or spin a cocktail. Recessed lighting over both counters, provides plenty of light for cooking and serving.brbrThe dining and living room area are on the other side of the bar counter, set with a round table and four chairs, an artistic garden rose chandelier adds a touch of elegance over the glass table.brbrThe living room grouping is next, providing comfortable seating with a wicker sofa, easy chair and ottoman, and nesting coffee tables. For movie night and games, a flat-screen TV is placed on a rustic wood carved stand. Let’s go to the other side of the flat, and see the two bedrooms and the bathroom.brbrThe architectural transition from the living room side of the flat to the bedroom / bathroom side, incorporates a pass-through window and open entry leading into the bedroom hall. This design makes the entire flat feel more spacious. Straight through the hall entrance is the bathroom, which provides a tiled shower with glass door, vanity with single sink, and commode. brbrThe bedrooms are on opposite sides of the bathroom. Both bedrooms provide wall mounted flat screen TV’s, ceiling fans, and plenty of closet space. The master bedroom, which provides a queen size bed, is to the right of the bathroom, as you enter the bedroom hall. brbrThe second bedroom, which provides two twin beds, is to the left of the bathroom. The beds can be pushed together and made up as a king size bed upon request. brbrThroughout the interior of the entire flat, floors are finished with large light grey tiles. Adding an element of casual elegance, windows throughout are nicely appointed with plantation shutters.brbrPorch and Grounds:brbrOne of the nicest features of this garden flat, is the generous covered back porch, that creates an enviable spot for the famous Key West indoor-outdoor lifestyle. Access this outdoor room through the single-pane French doors off the living room. Here you find an outside dining set and plenty of extra chairs. Just beyond the porch, is a bricked courtyard, set with chaise lounges for horizontal relaxation. The view from your courtyard is landscaped grounds, steps from the shared swimming pool and cabana.brbrWhen you’re ready for a dip in the pool, you only need to walk twenty meters (65 feet). The pool deck is furnished with chaise lounges and sun umbrellas. A Caribbean style cabana offers shade from the sun and creates a nice tropical ambience.brbrParking: A free private designated parking space located in the parking lot. If you do bring a car, plan to park and forget about it. Parking is limited and expensive throughout Old Town. Enjoy walking or biking everywhere you`ll see more that way. brbrRestrictions: Smoke Free House. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. The property is in a private gated residential complex in a secured neighborhood and is not suitable for staging loud parties.brPARKING: There is one free parking space which is located in the parking area and labeled 106-6 on the parking block (please see map). You will need a parking pass to park your car in the designated spot. The parking pass form you will find in the unit. Please fill it out and place it on the dashboard of your vehicle. brbrPLEASE NOTE: Per the HOA, vehicles over 18` long or 80` wide are not allowed on property. No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked within the Truman Annex. For more informatio on parking please refer to the HOA Rules and Regulations document provided in the Welcome Packet under `Additional Documents`.brbr**Bike Parking**brbrIf you are bringing your own bikes with you will need to get a temporary yellow tag from the office at Truman Annex. Please call the office at 305-296-0556 ahead of time so they can prepare the yellow tags and arrange for pick up. Guests are not allowed to leave bicycles, whether personal or rental, on the front porches but must be put in the bike racks that are found throughout the community. Any bikes found in violation of this policy are subject to removal.
Bed 2

Bed

Bath 1

Bath

Sleep 4

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$1216.39

/ Nightly
Condo

Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites - CLEANING FEE INCLUDED

Key West, Florida, United States

Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale Bayfront Suites.brbrNorth Bayview is the place to stay if you are looking for lodging where you and your guests can fully unwind in a coastal chic, home in Key West overlooking the water! The comfortable design and luxurious amenities are second to none in Key West and are sure to make your stay, a memorable one. brbrNear the stairs, and upon entering this four-bedroom four-bathroom suite via our secure electronic lock system, one will first notice the tall ceilings and the high-end interior design the vacation home has to offer. This four-bedroom condo has been delicately crafted with high end furnishings, detailed moldings, and modern amenities. Plush couches with strategic accent pillows, a combination of single king and double-twin bedroom options, coupled with luxurious sheets along with a kitchen that’s fully equipped with stainless steel appliances, dishwasher, disposal and all the culinary tools needed to create the finest cuisine. brbrThis vacation home offers the most necessary amenity for a stay in the Florida Keys, a private covered porch with access to the ground floor, which leads to the water’s edge. Like a local, take a seat and lean back on your private porch to enjoy your morning coffee or take an afternoon break to read your favorite book. In North Bayview, guests can find their expansive views of Garrison Bight, from the property’s dock as well as the pool. brbrBeyond visual accommodations, Bayfront Suites also offers all the creature comforts one would need in their home away from home. Parking is provided for the vacation homes, and for the electric traveler, a car charging station is provided on the property. There is also complimentary wireless internet throughout the property, including the pool and tiki hut. Other amenities such as luxurious high thread count sheets, Virtual Concierges through Alexa, wireless thermostat and just in case you don’t get to the store in time, we provide your first morning’s coffee. The best part about these amenities, are that they align with Key West’s lifestyle to do good to Mother Earth. Bayfront Suites is a certified green building and LEED Certified, which means that a stay at Bayfront Suites is a step in reducing one’s carbon footprint. brbrOur unique pool design is perfect for any traveler including families. There is a dip area for shallow water enjoyment that kids love and designed for even the smallest of guests in mind. There are several ledges along the pool’s edge for relaxation. Situated on the water’s edge, enjoy the view while you soak. Plenty of lounge chairs and tables line the pool deck.brbrA rooftop deck was designed into the building of this fabulous small resort for guest’s enjoyment as well as to aid in providing a special area for which guests can have memorable events. We encourage guests to enjoy the panorama view from this rooftop deck overlooking Garrison Bight. brbrWe can accommodate one vessel up to 11' beam per reservation at no additional charge.brbrIn conclusion, Bayfront Suites and Marina is the place to have an enjoyable, comfortable and memorable retreat while in Key West and we hope to have you as our guest.
Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps

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$1147.73

/ Nightly
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4-Bed, 4.5 Bath Condo & Bayfront Suites-non waterfront CLEANING FEE INCLUDED

Key West, Florida, United States

Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale Bayfront Suites.brbrUpper Sunset North (not waterfront) is the place to stay if you are looking for lodging where you and your guests can fully unwind in a coastal chic, home in Key West. The comfortable design and luxurious amenities are second to none in Key West and are sure to make your stay, a memorable one. brbrUpon entering this four-bedroom four-and-a-half-bathroom suite via our secure electronic lock system, one will first notice the high-end interior design the vacation home has to offer. This four-bedroom condo has been delicately crafted with high end furnishings, detailed moldings, and modern amenities. Plush couches with strategic accent pillows, a combination of single king and double-twin bedroom options, coupled with luxurious sheets along with a kitchen that’s fully equipped with stainless steel appliances, dishwasher, disposal and all the culinary tools needed to create the finest cuisine. brbrThis vacation home offers the most necessary amenity for a stay in the Florida Keys, a private and rather large, covered porch. Like a local, take a seat and lean back on your private porch to enjoy your morning coffee or take an afternoon break to read your favorite book. In Upper Sunset North, guests can find their view of nearby neighborhood rooftops and natural foliage of the “Meadows”, a local term for the surrounding area. brbrBeyond visual accommodations, Bayfront Suites also offers all the creature comforts one would need in their home away from home. Parking is provided for the vacation homes, and for the electric traveler, a car charging station is provided on the property. There is also complimentary wireless internet throughout the property, including the pool and tiki hut. Other amenities such as luxurious high thread count sheets, Virtual Concierges through Alexa, wireless thermostat and just in case you don’t get to the store in time, we provide your first morning’s coffee. The best part about these amenities, are that they align with Key West’s lifestyle to do good to Mother Earth. Bayfront Suites is a certified green building and LEED Certified, which means that a stay at Bayfront Suites is a step in reducing one’s carbon footprint. brbrOur unique pool design is perfect for any traveler including families. There is a dip area for shallow water enjoyment that kids love and designed for even the smallest of guests in mind. There are several ledges along the pool’s edge for relaxation. Situated on the water’s edge, enjoy the view while you soak. Plenty of lounge chairs and tables line the pool deck.brbrA rooftop deck was designed into the building of this fabulous small resort for guest’s enjoyment as well as to aid in providing a special area for which guests can have memorable events. We encourage guests to enjoy the panorama view from this rooftop deck overlooking Garrison Bight. brbrWe can accommodate one vessel up to 11' beam per reservation at no additional charge.brbrIn conclusion, Bayfront Suites and Marina is the place to have an enjoyable, comfortable and memorable retreat while in Key West and we hope to have you as our guest.
Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps

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$1063.17

/ Nightly
Condo

4-Bed 4.5 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED Non-Waterfront

Key West, Florida, United States

Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale Bayfront Suites.brbrNorth Sunset (not waterfront) is the place to stay if you are looking for lodging where you and your guests can fully unwind in a coastal chic, home in Key West. The comfortable design and luxurious amenities are second to none in Key West and are sure to make your stay, a memorable one. brbrClose to the stairs, and upon entering this four-bedroom four-and-a-half-bathroom suite via our secure electronic lock system, one will first notice the high-end interior design the vacation home has to offer. This four-bedroom condo has been delicately crafted with high end furnishings, detailed moldings, and modern amenities. Plush couches with strategic accent pillows, a combination of single king and double-twin bedroom options, coupled with luxurious sheets along with a kitchen that’s fully equipped with stainless steel appliances, dishwasher, disposal and all the culinary tools needed to create the finest cuisine. brbrThis vacation home offers the most necessary amenity for a stay in the Florida Keys, a private and rather large, covered porch. Like a local, take a seat and lean back on your private porch to enjoy your morning coffee or take an afternoon break to read your favorite book. In North Sunset, guests can find their view of nearby neighborhood and natural foliage of the “Meadows”, a local term for the surrounding area. brbrBeyond visual accommodations, Bayfront Suites also offers all the creature comforts one would need in their home away from home. Parking is provided for the vacation homes, and for the electric traveler, a car charging station is provided on the property. There is also complimentary wireless internet throughout the property, including the pool and tiki hut. Other amenities such as luxurious high thread count sheets, Virtual Concierges through Alexa, wireless thermostat and just in case you don’t get to the store in time, we provide your first morning’s coffee. The best part about these amenities, are that they align with Key West’s lifestyle to do good to Mother Earth. Bayfront Suites is a certified green building and LEED Certified, which means that a stay at Bayfront Suites is a step in reducing one’s carbon footprint. brbrOur unique pool design is perfect for any traveler including families. There is a dip area for shallow water enjoyment that kids love and designed for even the smallest of guests in mind. There are several ledges along the pool’s edge for relaxation. Situated on the water’s edge, enjoy the view while you soak. Plenty of lounge chairs and tables line the pool deck.brbrA rooftop deck was designed into the building of this fabulous small resort for guest’s enjoyment as well as to aid in providing a special area for which guests can have memorable events. We encourage guests to enjoy the panorama view from this rooftop deck overlooking Garrison Bight. brbrWe can accommodate one vessel up to 11' beam per reservation at no additional charge.brbrIn conclusion, Bayfront Suites and Marina is the place to have an enjoyable, comfortable and memorable retreat while in Key West and we hope to have you as our guest.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 4

Bed

Bath 4

Bath

Sleep 8

Sleeps

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Exceptional(79)

$835.67

/ Nightly
Condo

3 Bed 3 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED (Non-Waterfront)

Key West, Florida, United States

Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale Bayfront Suites.brbrUpper Sunset South (not waterfront) is the place to stay if you are looking for lodging where you and your guests can fully unwind in a coastal chic, home in Key West. The comfortable design and luxurious amenities are second to none in Key West and are sure to make your stay, a memorable one. brbrNear the elevator and upon entering this three-bedroom three-bathroom suite via our secure electronic lock system, one will first notice the high-end interior design the vacation home has to offer. This three-bedroom condo has been delicately crafted with high end furnishings, detailed moldings, and modern amenities. Plush couches with strategic accent pillows, a combination of single king and double-twin bedroom options, coupled with luxurious sheets along with a kitchen that’s fully equipped with stainless steel appliances, dishwasher, disposal and all the culinary tools needed to create the finest cuisine. brbrThis vacation home offers the most necessary amenity for a stay in the Florida Keys, a private and rather large, covered porch. Like a local, take a seat and lean back on your private porch to enjoy your morning coffee or take an afternoon break to read your favorite book. In Upper Sunset South, guests can find their view of nearby neighborhood rooftops and natural foliage of the “Meadows”, a local term for the surrounding area. brbrBeyond visual accommodations, Bayfront Suites also offers all the creature comforts one would need in their home away from home. Parking is provided for the vacation homes, and for the electric traveler, a car charging station is provided on the property. There is also complimentary wireless internet throughout the property, including the pool and tiki hut. Other amenities such as luxurious high thread count sheets, Virtual Concierges through Alexa, wireless thermostat and just in case you don’t get to the store in time, we provide your first morning’s coffee. The best part about these amenities, are that they align with Key West’s lifestyle to do good to Mother Earth. Bayfront Suites is a certified green building and LEED Certified, which means that a stay at Bayfront Suites is a step in reducing one’s carbon footprint. brbrOur unique pool design is perfect for any traveler including families. There is a dip area for shallow water enjoyment that kids love and designed for even the smallest of guests in mind. There are several ledges along the pool’s edge for relaxation. Situated on the water’s edge, enjoy the view while you soak. Plenty of lounge chairs and tables line the pool deck.brbrA rooftop deck was designed into the building of this fabulous small resort for guest’s enjoyment as well as to aid in providing a special area for which guests can have memorable events. We encourage guests to enjoy the panorama view from this rooftop deck overlooking Garrison Bight. brbrWe can accommodate one vessel up to 11' beam per reservation at no additional charge.brbrIn conclusion, Bayfront Suites and Marina is the place to have an enjoyable, comfortable and memorable retreat while in Key West and we hope to have you as our guest.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 3

Bed

Bath 3

Bath

Sleep 6

Sleeps

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Exceptional(95)

$817.56

/ Nightly
Condo

Waterfront 3-Bedroom Condo at Bayfront Suites & Marina- CLEANING FEE INCLUDED

Key West, Florida, United States

Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale Bayfront Suites.brbrMiddle Bayview is the place to stay if you are looking for lodging where you and your guests can fully unwind in a coastal chic, home in Key West overlooking the water! The comfortable design and luxurious amenities are second to none in Key West and are sure to make your stay, a memorable one. brbrUpon entering this three-bedroom two-bathroom suite via our secure electronic lock system, one will first notice the tall ceilings and the high-end interior design the vacation home has to offer. This three-bedroom condo has been delicately crafted with high end furnishings, detailed moldings, and modern amenities. Plush couches with strategic accent pillows, a combination of single king and double-twin bedroom options, coupled with luxurious sheets along with a kitchen that’s fully equipped with stainless steel appliances, dishwasher, disposal and all the culinary tools needed to create the finest cuisine. brbrThis vacation home offers the most necessary amenity for a stay in the Florida Keys, a private covered porch with access to the ground level, which leads to the water’s edge and pool area. Like a local, take a seat and lean back on your private porch to enjoy your morning coffee or take an afternoon break to read your favorite book. In Middle Bayview, guests can find their expansive views of Garrison Bight, from the property’s dock as well as the pool. brbrBeyond visual accommodations, Bayfront Suites also offers all the creature comforts one would need in their home away from home. Parking is provided for the vacation homes, and for the electric traveler, a car charging station is provided on the property. There is also complimentary wireless internet throughout the property, including the pool and tiki hut. Other amenities such as luxurious high thread count sheets, Virtual Concierges through Alexa, wireless thermostat and just in case you don’t get to the store in time, we provide your first morning’s coffee. The best part about these amenities, are that they align with Key West’s lifestyle to do good to Mother Earth. Bayfront Suites is a certified green building and LEED Certified, which means that a stay at Bayfront Suites is a step in reducing one’s carbon footprint. brbrOur unique pool design is perfect for any traveler including families. There is a dip area for shallow water enjoyment that kids love and designed for even the smallest of guests in mind. There are several ledges along the pool’s edge for relaxation. Situated on the water’s edge, enjoy the view while you soak. Plenty of lounge chairs and tables line the pool deck. brbrA rooftop deck was designed into the building of this fabulous small resort for guest’s enjoyment as well as to aid in providing a special area for which guests can have memorable events. We encourage guests to enjoy the panorama view from this rooftop deck overlooking Garrison Bight. brbrWe can accommodate one vessel up to 11' beam per reservation at no additional charge.brbrIn conclusion, Bayfront Suites and Marina is the place to have an enjoyable, comfortable and memorable retreat while in Key West and we hope to have you as our guest.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 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

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Exceptional(82)

$968.23

/ Nightly
Condo

3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED

Key West, Florida, United States

Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific property, take advantage of the multitude of amenities offered to make a vacation in the Florida Keys the perfect one. Guests can take in all the island has to offer, from the comfort of their own vacation rental at the new and upscale Bayfront Suites.brbrMiddle Sunset (not waterfront) is the place to stay if you are looking for lodging where you and your guests can fully unwind in a coastal chic, home in Key West. The comfortable design and luxurious amenities are second to none in Key West and are sure to make your stay, a memorable one. brbrNear the elevator and upon entering this three-bedroom 3-bathroom suite via our secure electronic lock system, one will first notice the high-end interior design the vacation home has to offer. This three-bedroom condo has been delicately crafted with high end furnishings, detailed moldings, and modern amenities. Plush couches with strategic accent pillows, a combination of single king and double-twin bedroom options, coupled with luxurious sheets along with a kitchen that’s fully equipped with stainless steel appliances, dishwasher, disposal and all the culinary tools needed to create the finest cuisine. brbrThis vacation home offers the most necessary amenity for a stay in the Florida Keys, a private and rather large, covered porch. Like a local, take a seat and lean back on your private porch to enjoy your morning coffee or take an afternoon break to read your favorite book. In Middle Sunset, guests can find their view of nearby neighborhood and natural foliage of the “Meadows”, a local term for the surrounding area. brbrBeyond visual accommodations, Bayfront Suites also offers all the creature comforts one would need in their home away from home. Parking is provided for the vacation homes, and for the electric traveler, a car charging station is provided on the property. There is also complimentary wireless internet throughout the property, including the pool and tiki hut. Other amenities such as luxurious high thread count sheets, Virtual Concierges through Alexa, wireless thermostat and just in case you don’t get to the store in time, we provide your first morning’s coffee. The best part about these amenities, are that they align with Key West’s lifestyle to do good to Mother Earth. Bayfront Suites is a certified green building and LEED Certified, which means that a stay at Bayfront Suites is a step in reducing one’s carbon footprint. brbrOur unique pool design is perfect for any traveler including families. There is a dip area for shallow water enjoyment that kids love and designed for even the smallest of guests in mind. There are several ledges along the pool’s edge for relaxation. Situated on the water’s edge, enjoy the view while you soak. Plenty of lounge chairs and tables line the pool deck.brbrA rooftop deck was designed into the building of this fabulous small resort for guest’s enjoyment as well as to aid in providing a special area for which guests can have memorable events. We encourage guests to enjoy the panorama view from this rooftop deck overlooking Garrison Bight. brbrWe can accommodate one vessel up to 11' beam per reservation at no additional charge.brbrIn conclusion, Bayfront Suites and Marina is the place to have an enjoyable, comfortable and memorable retreat while in Key West and we hope to have you as our guest.
Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps

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Exceptional(4)

$329.06

/ Nightly
Condo

Seaside Serenity-2BD 2BA condo w/ pool, parking, tennis courts, near beaches

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 EXCEPTIONSbrbrThis property is a 30 night minimum.br brFEATURES:brBedrooms: 2 (1 king, 2 twins)brBathrooms: 2 brLocation: Salt Ponds CondosbrSquare Feet: 772brParking: There is a 2 car MAXIMUM policy.brAmenities: Wifi, TVs, in-unit laundry, shared pool (not-heated), tennis courts, close to the beachesbrbrTHINGS 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.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

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Exceptional(9)

$785.2

/ Nightly
Condo

Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Key West, Florida, United States

Your Treetop Condo awaits. The welcoming garden atmosphere of this adorable tropical property is perfect for a tranquil getaway. We are located in the heart of historic Old Town. Relax and refresh with ocean breezes on your treetop balcony. For your security and peaceful enjoyment, this property is surrounded by a bamboo privacy fence. This desirable property is highly recommended and reasonably priced. No resort or parking fees.brbrLocationbrOur Treehouse Condo is situated in a prime island location on the southern side of Key West in the prestigious residential Casa Marina neighborhood surrounded by majestic and luxurious homes with beautiful tropical gardens, perfect for pleasant walks any time of day. We are only a 3 minute stroll to Higgs Beach, Salute's Restaurant and West Martelo Tower, a Civil War Fort which is now home to the Key West Garden Club and walkable tropical gardens. We are a 13 minute walk to the Southernmost Point and a 12 minute walk to the Butterfly House. We are also close to several excellent restaurants and only a 9 minute drive from the airport.brbrOther Nearby Restaurants and AttractionsbrNearby access to the free Duval Loop Bus, provides access to the Historic Seaport, aquarium, Sloppy Joes, Truman Waterfront Park, Southernmost Point, Butterfly House and Nature Conservatory, Mel Fisher and Sails to Rails museums, art galleries and other attractions. Walking minutes to several nearby restaurants include: Dorada's (2min), Ana's Cafe and Southernmost Grocery Store (8min), El Siboney Cuban (8min), Oasis Mediterranean (7min), White Street Pizza (7min) and famous Sandy's Cafe for authentic Cuban coffee and sandwiches (5min).brbrBeach, Pool and Outdoor LivingbrJust steps from the beach, your condo is surrounded by lush gardens and palm trees. You can lounge on your treehouse style private balcony, 10 feet above the garden floor, among the treetops overlooking the common area complete with hammock swings and a dining table for six guests under our mango, a shared grilling area and a putting green. During your stay, relax and refresh in our intimate Cocktail Spa Style Pool, which is veiled by a wall of flowering vines and located immediately at the base of your staircase or escape to Higgs Beach just down the street. Higgs Beach is also ideal for romantic evening walks for stargazers.brbrFurnishingsbrOur decor reflects a true Key West vibe. The dining table in the open concept livingroom seats four, a day bed couch and the balcony includes two comfortable lounge chairs for relaxing in the treetops under the stars. The kitchen is complete with a two burner cook top, microwave, drip coffee maker, toaster, Cuisinart Griddler Grill/Panini Press, silverware, pots/pans, sink, refrigerator and a dishwasher. The full bathroom is complete with a shower and shelves for your toiletries. Bodywash, shampoo, conditioner, extra toilet paper, large bath sheet towels and a hair dryer are provided. Our bedrooms are equipped with cozy Tommy Bahama comforters. There are 3 televisions complete with cable channels and free WiFi for your entertainment and convenience.brbrSleeping ArrangementsbrYour condo sleeps up to six guests and includes 4 beds, a primary California King bedroom, a queen bedroom and two twin beds in your livingroom, perfectly arranged for families or couples with friends. The balcony lounge chairs are perfect for an outdoor nap any time of day or night.brbrDetails and AmenitiesbrYour second-floor Treetop Condo is 514 sqft. A shared Cocktail Spa Style Pool, bike rentals, washer/dryer service are all available on our property. We are family and pet friendly. Wrapped breakfast bars, nuts, fruit snacks, gourmet meatsticks, cheese and crackers, mini muffins, coffee/teas are provided in the condo along with fresh Florida oranges and grapefruits in our common area. Higgs Beach city park is nearby, complete with tennis, pickleball, sand volleyball, professional bocce courts, two playgrounds for children, White St. fishing and observation piers, an oceanside restaurant and a dog park. The White Street Pier is a quarter mile over the ocean with spectacular views of sunrise and sunset and excellent fishing.brbrConcierge ServicesbrEnjoy our concierge service to assist you before or during your stay with planning activities with the very best of Key West. From bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset sails, sandbar excursions, scuba diving, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. We can also arrange licensed massage therapy for you and your party, in our gardens or in your suite and have your condo stocked with groceries, adult beverages and all the necessities in advance of your arrival.brbrParkingbrFree off-street parking in front of and around the condo.brbrYou Need To KnowbrOur property is equipped with fire extinguishers and smoke detectors.brOnsite parties, weddings and other events can be scheduled with prior approval by property owner.brGovernment issued photo ID and a credit or debit card or cash deposit may be required at check-in for incidential chargesbrExtra person charges may apply per the property's policies.brReport any damages prior to check out.brKey West Quiet Time may apply after 10pm on weekdays and 11pm on weekends through 8am in the morning. Thank you for supporting our efforts to be a good neighbor. Please note that your condo is located in a noise sensitive area. When you return from the parties, celebrations and live music on Duval street you will have a quiet, tranquil and restful sleep.brbrMake marvelous memories that will last for a lifetime while staying at our condo in paradise.
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Exceptional(2)

$240.09

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Tropical Condo • Shared Pool + Near Duval St | Month-Long Stays | A Siesta Bay

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrPLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests. *The rates for the month of August have already been discounted to reflect the loss of the amenity.*brbrA Siesta Bay brings easy Key West living to one of the island’s most loved locations: Truman Annex. Bright, breezy, and surrounded by tropical palms, this two-bedroom condo is made for guests who want a relaxed retreat with the best of Old Town close enough to explore on foot or by bike.brbrInside, the home feels light and coastal, with soft blue tones, island-inspired details, and a comfortable living area that opens to the balcony. Start the morning with coffee outside, come back for a quiet afternoon break, or wind down with a drink while the palms sway around you. The updated kitchen is fully equipped for easy meals at home, and the dining area seats four for casual breakfasts, snacks, or dinner after a day out in town.brbrJust steps away, the shared community pool offers a refreshing place to cool off between adventures. Lounge in the sun, take a swim, or enjoy a slow afternoon in the shade before heading back out to experience Key West.brbrA Siesta Bay sleeps up to four guests across two bedrooms. The primary bedroom features a queen bed, while the second bedroom includes two twin beds, making the layout ideal for couples, small families, or friends traveling together. A full bathroom sits conveniently between the bedrooms, and in-home laundry adds extra ease for longer stays.brbrSet in Truman Annex, the location is one of the biggest highlights. You’ll be close to Duval Street, Mallory Square, Fort Zachary Taylor State Park, local restaurants, shops, nightlife, and some of Key West’s most iconic sights. Whether your plans involve beach days, sunset strolls, poolside afternoons, or exploring the island by bike, A Siesta Bay keeps you close to it all while giving you a peaceful place to come home to.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrLocal Attractions: Key West Shipwreck Treasure Museum, Hemingway Home and Museum, Mel Fisher Maritime Museum, Harry S. Truman Little White House, Conch Tour Train, Dry Tortugas National Park, Lazy Dog Adventures, Dolphin encounters, Ghosts & Gravestones Tour, Old Town Trolley, Sloppy Joe’s Bar, Audubon House & Tropical Gardens, Florida Keys Eco-Discovery Center, Bike Tours, Seaplane adventures, Key West Aquarium, Sebago Day Tours, Private boat charters, Sportfishing, Rick’s Entertainment Complex, Duval Street (shop strips, shops, bar, and cafes), Mallory Square (waterfront plaza), Key West Garden Club, Sunset Pier, Grand, Cafe Key West, Island House, El Meson de Pepé, Cafe Sole.brbr*Home Truths:*br- This home has access to a shared pool and is part of a gated community.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that the twins at the property can not be converted into a king.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.br- PLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests.brbrParking Details:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Two twin bedsbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. All bookings over 30 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud.
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Exceptional(9)

$526.5

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2-Bedroom Villa at Hyatt Beach House! Quiet Beachfront Location! Sleeps 6

Key West, Florida, United States

Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only a few miles from Old Town. The property is on a corner of the island featuring its own private beach, a rarity in Key West. Located 2.7 miles from Smathers Beach and 3.8 miles from the Ernest Hemingway Home & Museum, this quiet piece of Key West is the best location for relaxation. The property is on a corner of the island featuring its own private beach and water access.brbrThis light and airy two bedroom, two bath condo is spacious enough to accommodate up to six guests. It features complimentary wi-fi, a flat-screen TVs, a washer and dryer, and a fully furnished balcony. The primary bedroom features a king bed with an ensuite bathroom. The bathroom features a large walk-in shower and a large vanity. The guest bedroom has a king bed and access to a full bathroom as well. The living room features a sleeper sofa, while the separate dining area features a large table for six. Prepare meals in the fully equipped kitchen with full-size refrigerator, microwave, stove, oven, coffee maker, dishes, utensils, and cookware. brbrAmenities include an outdoor pool, a jacuzzi, a private beach, dock, concierge, and a delicious restaurant with Bay views. There's also a bar, concierge, business center, complimentary parking, and onsite grills.brbrUnits are assigned at check-in, pictures are representative of the unit, and decor, layout, and room view may vary.brbrComplimentary parking is available for the first vehicle. Height restriction is 6 feet 8 inches. A $10 charge per day, per vehicle, applies for additional vehicles. Additional parking is subject to availability. There is no RV parking available.brbrThis is a Cashless Resort and credit cards are the only acceptable form of payment.brbrResort fee of $20/day is due at check-in. (Subject to change at any time)brbrThis property welcomes ADA service animals. Pets are not permitted.brbrLate Arrivals - Check-in is from 4:00 pm to 11:00 pm. If arriving after 11:00 pm, advance arrangements must be made by calling the property's Front desk.brbrA split week fee of approximately $125 may apply for reservations shorter than one week. (Subject to Change).brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.
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Exceptional(31)

$311.32

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The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

Key West, Florida, United States

The Salt Cay | Updated! Stunning Sunset View, Pool!brbrEscape to The Salt Cay, a serene, beautifully updated, and well-appointed 2-bedroom condo nestled in the tranquil Sunrise Suites community on east side of Key West. Just a mile from the beach, this charming getaway offers the ideal combination of relaxation and adventure. Whether you're lounging by the pool, exploring nearby attractions, or enjoying the comfort of your condo, The Salt Cay is the perfect place to unwind and make lasting memories.brbrThe Ambiance:brStep into The Salt Cay and experience a tasteful blend of modern coastal charm, where sleek quartz countertops, modern white cabinetry, and an open-concept layout create the perfect space for gathering with family or friends. This gorgeous two-bedroom suite accommodates up to six guests, featuring a king-sized bed in the master bedroom, a queen-sized bed in the second bedroom, and a queen pullout sofa in the living area for additional guests. The fully equipped kitchen, complete with a Keurig and electric stove, makes meal preparation a breeze, while the private balcony offers spectacular sunset views. For added comfort, enjoy cable TV, WiFi, and central air conditioning throughout your stay.brbrGuest Access:brEnjoy a smooth arrival with our contactless check-in process, where you'll receive a personalized access code to enter your unit. During your stay, take advantage of the shared amenities, including:brbr- Shared heated pool and hot tubbr- Tennis courtbr- Walking paths and biking trailsbrbrLocation Highlights:brThe Salt Cay is ideally located within the peaceful Sunrise Suites Resort, just a short distance from Key West's best attractions. A quick 10-minute drive will take you to the lively Duval Street, where you'll find a vibrant mix of restaurants, bars, and entertainment. For added convenience, the Key West airport is just a short drive away, making travel easy and stress-free.brbrGetting Around:brWith parking available, you'll have easy access to explore the island by car. If you prefer to travel by bike, scooter, or golf cart, rentals are nearby for your convenience. Key West's walkability means many attractions are just a short stroll away, and for longer distances, taxis and rideshare services are readily available.brbrOther Things to Note:br- Pet-Friendly! 1 dog (40lbs maximum) with a $20 per pet per night feebr- Private washer/dryer in unitbr- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo 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, walkways, pool, parking areas, 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.
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Exceptional(7)

$205.32

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OUR HAPPY PLACE ~ Adorable 2 Bedroom, 2 Bath Condo Steps from the Beach!

Key West, Florida, United States

PLEASE BE AWARE:brThis community is currently undergoing balcony repair property-wide potentially through May 2026. A 12 person crew will be working section-by-section from 8am-6pm, 5 days a week, and Saturdays will be weather make-up days as-needed. Please understand there will most likely be some amount of noise heard throughout the community. Our rentals have been priced to offset noise issues or any other inconvenience due to the construction project.brbrUNFORGETTABLE KEY WEST…brAllow your Key West creation to unfold within this charming and tranquil retreat embracing the quintessential island spirit of the Keys. Possessing every luxury one could desire within a fun loving space, this setting is sure to wash all your real world worries away. Take a journey through this slice of Paradise located in the community of 1800 Atlantic offering the right amount of R & R from within your private abode with just steps to putting your toes in the sandy beaches. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brStep into this spacious condo with nautical charm immediately pulling you into island time. An open concept brings the whole family together allowing for unforgettable memories to be created. A large kitchen with plenty of counter space, stainless-steel appliances and a cafe table for 2 makes meal prep a breeze. The indoor dining area allows for 6 as you come together after a fun filled day being followed by movie night on cozy living room furnishings. The unit is accessible by an elevator or the stairs. brbrSLEEPING ARRANGEMENTS…brEnjoy a comfortable king guestroom with a TV with access to a hallway bathroom with a shower/tub combination. The primary suite is outfitted with a king bed, TV and an en suite full bathroom with a large shower/tub combination. Both rooms open to a balcony showcasing lush courtyard views beyond. Enjoy a sofa sleeper in the Great Room.brbrOUTDOOR LIVING…brTake your happy hour out on the balcony and soak up the island breeze with courtyard views and a sliver of the blue ocean beyond. A heated, saltwater community pool is equipped with plenty of loungers and views of the sparkling ocean. Tennis courts reside on property as well as a community grill and fitness center. Enjoy being located in these peaceful surroundings with just a short ride into town!brbrPARKING...brEnjoy one covered parking space in the garage (larger SUV's may not fit). Plenty of additional parking available in the open lots in front of the units at no additional cost.brbrPETS...brThis is not a pet-friendly 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)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). brbrISLAND TIME…
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