Key West is known for its crack of dawn-manner and early risers. It also has one of the largest barrier reefs in the world. It points all its arrows to the great varieties of water sports and the sunshine that is around all year long. Well, who doesn’t want to enjoy the tanning sun rays and the beaches on their trips anyway? The historic sites and its Duval Street, the stunning conch-style architecture, and the fun walking tours are the best to have an inclusive look over the island. You will love your rental for not only their modern designs but also their colorful gardens. Have a look over these amazing vacation rentals in Key West, Florida:
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 03, 2024.
1. A remodeled antique (from USD 445)
This renewed 100+ years old cottage combines the features of a modernly furnished home and the history of the building. The rental house could accommodate 4 guests by providing them 2 bedrooms containing 2 queen beds and 1 bathroom. The spacious backyard is the best choice for enjoying your morning coffee and some nature; barbecue using their gas grill, and keep your pets secure. The home offers WiFi, TV, washing machine (plus dryer), linen change, a prepared kitchen with a dishwasher, a microwave, and cookware. It is a monthly rental house that is located in Old Town, which is just a walk away from Higgs beach, bars, restaurants, art galleries, and Duval Street.
Top guest reviews
Amenities & Room:
our family had a relaxing and very comfortable stay at ceres' charming historic conch house in key westwe loved the nice touches like the gas range and the beautiful showerCleanliness:
everything was seamless comfortable and cleanHost:
ceres was super helpful and responsiveceres was very helpful in providing information both before our trip and when we arrivedRead more reviewsLocation:
amazing stay this property is positioned so that everything on the island is closeeverything was as described and the location was convenient with parking opportunities right outsidethe location was excellent and did not run into any issues during my time therehowever there are plenty of free parking spots in the street
2. A heaven on earth experience (from USD 180)
Bird of Paradise consists of 2 bedrooms, a living room, 2 washrooms, and could welcome 6 guests. While the master bed has a king bed and the 2nd room has a queen-sized bed, both include designed glass doors that allow the natural sun light in, a shower each, TV, fan, and a closet. The living room has a hidden queen bed in the dresser that folds open. A big heated pool, privately fenced backyard, and barbecue facilities are provided for a more fun evening. The amenities offered include a washing machine/dryer, AC and heating system, fans, linen change and towels, and WiFi upon request.
3. A house of dreams (from USD 275)
This extravagant house has a lounge on the outside porch to enjoy the fresh air, a fancy restroom with a couples shower, a TV in the bedroom, maybe for a late night movie, free bicycles, and a washer and dryer set. Their french doors allow the warm sun rays to come in and let you enjoy the brilliant green palm trees from comfort.
Top guest reviews
Amenities & Room:
The kitchen is well stocked with everything you might needThe kitchen and bathroom are very modernPlenty of room and quiet off the parking areasThe beds were very comfortablegreat condo kept in great conditionhighly reccomendCleanliness:
The condo is beautifully decorated and had everything we neededBed was very comfortable and patio was great with the fansHost:
Sherri was helpful guiding us through our first trip to Key West providing us with information about the areaSherri was wonderful to work with and very informativeand she was quick to answer all my questionsWe walked everywhere even the beachSherri and Michael were very gracious hostsRead more reviewsLocation:
The complex is in a great location quiet but a short walk or bike ride to the action in Duval or to the Fort Zachary beach parkAll around lovely condo Close to all the action on downtown Key WestThe apartment is beautifully decorated in a safe gated community within a few minutes walking distance to all of the attractions in Key West SherriJust a couple blocks from all the "action" yet quiet and peaceful for a good night's sleepWe enjoyed sitting on the patio with a glass of wine after a day in the sun
4. Renovated home with a yard and pool (from USD 242)
This vacation house has more than a modern style. The light color shades used for the walls, bathroom, and ceiling and the large windows ensure a relaxing time. Their perfect backyard will allow your eyes to roam freely on the natural, colorful beautiful scenery. It is located one block away from the well-known Duval Street where you can shop and find restaurants to suit your taste. The spacious house ensures a relaxing experience. It’s also very close to beaches and is dog-friendly, which seals the deal.
Top guest reviews
Amenities & Room:
The house also has off-street gated parking for two vehiclesCleanliness:
The house is spacious and very nicely furnished with large rooms/bathrooms and a phenomenal kitchenHost:
They were friendly and helpfulEveryone went out of their way to make us feel welcomeI was so happy with this rental property that ten minutes after I entered the houseFrom the moment we arrived my family and I felt very comfortable dealing with the staffThe rental agents at Vacasa are wonderful to work withRead more reviewsLocation:
Located one block from DuvalAlso there is a white picket fence surrounding the entire property which gives you a feeling of privacyThe property was centrally located placing us within walking distance from almost every amenity in Key WestThis house was absolutely beautiful and the location was perfect
5. Gorgeous home with a pool (from USD 171)
The unique feature of this house is the vibrant color combination of the clear blue pool, the bright green trees, the light shades of the house, and the red umbrella which makes the picture complete. Its well-furnished kitchen, large soft sofas, shiny wooden floors, and the seasonally heated pool are all features to leave you with an extraordinary experience.
Top guest reviews
Amenities & Room:
It is short on closet spaceAlthough still comfortable for fourWe did NOT move the car as everything is nearbyThe home is immaculate and freshly remodeled with upscale everythingWas a wonderful house and a wonderful stayCleanliness:
It was incredibly clean andthe house is extremely clean & comfortable walking distance to everything & the kitchen is awesomeI was very satisfied with the condition of the vacation rentalI was very satisfied with the condition of the vacation rentalI was very satisfied with the condition of the vacation rentalHost:
We would rent this home again in a heartbeat House keeping was great and the property manager was attentive and friendlyI was very happy with the locationI was very happy with the locationI was very happy with the locationI was very happy with the locationRead more reviewsLocation:
Faustos is a very easy walkwe found the Key West area in this conditionAnd the upper Duval restaurants and barsThe next door neighbors are long lineage Key West natives and know most every person that walks by and live in the neighborhoodWe were also able to stay a few hours longer due to a late flight
6. Get ready for a tan (from USD 442)
What is a better start to your day than having breakfast in a seaside cafe? This dog-friendly getaway can accept 6 guests as it has 2 bedrooms with 1 queen bed, 1 sofa bed, and 2 twin beds. It also offers a shared pool, WiFi, AC, washing/drying machine, and a canine companion for a little fee. This getaway is located a few minute’s walk from Higgs Beach Pier and dinning restaurants at Duval Street.
Top guest reviews
Amenities & Room:
beds were comfortable and the outdoor space was perfect for my familyvery pretty cottage and poolperfect size cute cottage with nice pool area and bbq grillCleanliness:
clean cottage and serviced wellthe house was very clean and well furnishedclean house witk wverything you would needthe apartment itself was very clean and appeared to have been renovated recentlyloved our stay at this cottage everything inside was nice and clean pool was cleanHost:
the host is very helpfulwonderful kitchen and friendly staffgreat communications from host good location clean stylish and comfortableRead more reviewsLocation:
fabulous location well equipped and cute comfortable placeexcellent cozy house great location easy walk to duval streetgreat location for walking to the beaches and downtown areasgreat location very close to duval street and a 5 minute walk from the southernmost pointthis place was very nice and the location was within walking to everything
7. Shady and cozy house (from USD 365)
This house is cleverly designed. It has an American style kitchen, large windows with curtains to help you sleep better, lavish-styled bathroom, and a shady patio with decks and barbecue space. You should explore this area, not leaving any corner unvisited, including its sandy beaches and the famous Duval Street, which are just less than a minutes worth of walking.
Top guest reviews
Read more reviewsHost:
the owner is very accessible and helpfulhe paid for our fishing charter and was very helpful with passing on his local knowledge
8. A fabulous house that is close to the beach
Hosting 5 guests, it has 2 bedrooms with queen beds, a sofa bed, and 1 bathroom. This house is a lustrous unit with a private balcony and green unique garden. It is located in a great place where you can walk a few minutes to reach Duval Street, Mallory Square and the beach. Shops and supermarkets are also located a few blocks away. The guests are permitted to use the pool, WiFi, free parking and the fully equipped kitchen.
Key West, Florida, United States
425 meters (0.3 ft) from The Hemingway Home and MuseumTop guest reviews
Amenities & Room:
great back patio and comfortable living areapool area was a treat in the midday sunCleanliness:
the property was clean and comfortablethe space was cleanthe condo was a clean comfortable end unit in a quiet neighborhoodhis condo is great very clean and has everything you needaccommodations were comfy and clean would highly recommend this condoHost:
craig is very responsive to any and all questionsthe host craig was immediately available for any help and questionsRead more reviewsLocation:
great location close to duvall loop bus routegreat location and cute spacegreat location walking distance to duval and the downtown waterfronteasy walk to duval street where many of the restaurants are locatedperfect location our second year staying here
9. Annex in Old Town
The house contains 2 bedrooms that could be used by 4 guests. Each room has a queen bed, a private bathroom, a balcony to allow cool fresh air in, a fan, and a TV. A fully equipped kitchen, dining, and living rooms are great to prepare food, dine, and spend some quality chatting time with family or friends. Other provided facilities include air conditioning, washer and dryer, internet, parking, heater, outside swimming pool, and fireplace. An outside deck in the garden will allow you to enjoy a quiet relaxing afternoon. A short walk and you will reach Fort Zachary Taylor Beach, Mallony Square (for the best sunset view), or the well known Duval Street.
555 meters (0.4 ft) from The Hemingway Home and MuseumAccommodates: 4
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
The other bedroom has a full size bed and that room is fairly smallKitchen has everything for cookingThe place was immaculate and very cozyThere are 2 bedrooms; one has a poster bed and is very comfortableParking is tight but we parked a full size SUV so it can be doneCleanliness:
The place was very cleanThis 2 bedroom 2 bath condo was very nicely furnished and very comfortable for 4 adultsHost:
He was equally as responsiveSome difficulty finding the unit; a map before arriving would have been helpful as well as a map to find our way in and out since there are a lot of walkways and several entrancesWe even heard the lovely roosters every morning though 4am was a bit earlyUpon check in we needed some new keys and she was quick to respond via phone and email and put us in touch with Alistairproperty Owner persona lily reached out to introduce herself and was very thorough and timely with responses to any question I had Highly recommendRead more reviewsLocation:
The location is good for the beach Little White HouseWe love staying in Truman Annex because it is close to everything but tucked away in a quiet gated communityThere is really no shelf space (except tucked away in the closet) and no dresserThe proximity to downtown makes Truman Annex an ideal locationEverything was within walking distance for us restaurants bars
A colorful trip
Renting a full-facility house that satisfies all your needs on a trip and exceeds your expectations will make you mentally and physically relaxed. Being close to attractions is a must, and who wouldn’t want to visit Key West for its green palm trees surrounded by the blue sea?
History
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