Vacation rentals in Key West, FL

3183 available vacation rental offers

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Key West, FL vacation rentals
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Best Vacation rentals and Airbnb offers in Key West, FL

Best family friendly Key West, FL vacation rentals

Among the 3183 accommodations in Key West, FL, here are the 4 best family friendly rentals

La Casa De Luna - 1 Bd/1b Condo Just Off Upper Duval - Key West, FL
9.6 109 reviews
Key West, FL
11/07 – 18/07
1656 ﺩ.ﺇ/nighttotal: 11592 ﺩ.ﺇ (7 )

La Casa De Luna - 1 Bd/1b Condo Just Off Upper Duval

2 4
apartment , Key West
This Key West Old Town flat is ideally located just steps from the City Zoo Gallery and Duval Street, within 1.6km of Ernest Hemingway's Home and Museum and Florida Keys beaches.
The 42-square-metre self-catering apartment sleeps four, boasting a private pool, balcony, fully equipped kitchen including a dishwasher, and in-unit laundry facilities.
Casa De Cuba A Beach House - Cuban Flair Steps From Duval - Key West, FL
10 111 reviews
Key West, FL
30/10 – 04/11
5520 ﺩ.ﺇ/nighttotal: 27600 ﺩ.ﺇ (5 )

Casa De Cuba A Beach House - Cuban Flair Steps From Duval

3 2
apartment , Key West
This Key West holiday home is ideally situated in Old Town, a short walk from Duval Street and the City Zoo Gallery, with the Ernest Hemingway Home and Museum and South Beach within 1.6km.
The three-bedroom property sleeps six, boasting a private pool, fenced garden, fully equipped kitchen including a dishwasher, and free Wi-Fi; gas grills are available for al fresco dining.
House ∙ 3 Bedrooms ∙ 8 Guests - Key West, FL
10 6 reviews
Key West, FL
01/10 – 01/11
918 ﺩ.ﺇ/nighttotal: 28458 ﺩ.ﺇ (31 )

House ∙ 3 Bedrooms ∙ 8 Guests

3 2
house , Key West
This detached house in Key West is located in a quiet neighbourhood, 5 minutes by bicycle from Higgs and Smathers beaches and 10 minutes by bicycle or Uber from Duval Street.
This family-friendly property accommodates up to eight guests and features a private heated and chilled swimming pool with a waterfall, a fully equipped kitchen with quartz countertops and new stainless steel appliances, and off-street parking for up to three vehicles or a boat trailer.
122 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.4 20 reviews
Key West, FL
13/09 – 27/09
1224 ﺩ.ﺇ/nighttotal: 17136 ﺩ.ﺇ (14 )

122 M² House ∙ 2 Bedrooms ∙ 6 Guests

2 2
house , Key West
This Key West condo is situated near Smather's Beach, a short walk from the beach and approximately 2.4 kilometres from Key West's downtown area, offering easy access to shops, restaurants and bars.
This 122 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a private balcony, swimming pool, Jacuzzi, fitness centre, and free Wi-Fi; shared amenities such as tennis courts are also available within the complex.

Best Key West, FL vacation rentals with a pool

Among the 3183 accommodations in Key West, FL, here are the 4 best rentals with a pool

Fontana At Azul Mansion Key West - Key West, FL
Key West, FL
31/07 – 02/08
1520 ﺩ.ﺇ/nighttotal: 3040 ﺩ.ﺇ (2 )

Fontana At Azul Mansion Key West

1 2
house , Key West
FONTANA at Azul Mansion, a centrally located Key West property, is 0.6km from the city centre, 1.9km from both the Key West Aquarium and Mallory Dock, and a 12-minute walk from South Beach.
This self-catering apartment offers one bedroom, one bathroom, sleeps two, and includes a private pool, tennis court, parking, and Wi-Fi; enjoy nearby attractions such as the Ernest Hemingway Home and Museum and Duval Street.
Pool View Suite | Beachside Resort - Key West, FL
9.5 279 reviews
Key West, FL
02/07 – 05/07
1805 ﺩ.ﺇ/nighttotal: 5415 ﺩ.ﺇ (3 )

Pool View Suite | Beachside Resort

1 4
apartment , Key West
This one-bedroom apartment is situated in a resort complex on a 2.8-hectare site overlooking the Gulf of Mexico in Key West, just a short distance from Duval Street and the Southernmost Point. The apartment offers a king-size bed, a queen sleeper sofa, a fully equipped kitchen, a private washer/dryer, and a private balcony, as well as access to a 24-hour heated pool, hot tub, on-site marina, restaurant, and waterview fitness centre.
Meadows Manor - Key West, FL
Key West, FL
27/06 – 28/06
11510 ﺩ.ﺇ/nightfor 1 night

Meadows Manor

4 7
house , Key West
Meadows Manor is located in Key West, Florida, a short distance (approximately 2km) from Higgs Beach, the Ernest Hemingway Home and Museum, and Mallory Square.
This four-bedroom, four-bathroom house sleeps up to 15 guests and boasts a fully equipped kitchen with dishwasher, air conditioning, a swimming pool, in-unit laundry facilities, and is close to Duval Street and Key West International Airport (3km).
Atlantic Parrot - Key West, FL
Key West, FL
02/07 – 03/07
3592 ﺩ.ﺇ/nightfor 1 night

Atlantic Parrot

1 5
house , Key West
Atlantic Parrot, a holiday home in Key West, is located a 2-minute walk from Smathers Beach and 3.4 kilometres from the Southernmost Point, Ernest Hemingway Home and Museum, and Duval Street.
This holiday home offers 122 square metres of living space, accommodates up to 9 guests with 2 bedrooms and 2 bathrooms, and features an outdoor swimming pool, a lift, and a kitchen equipped with a fridge, microwave, and dishwasher.

Frequently Asked Questions about vacation rentals in Key West, FL

  • What should a first-time visitor not miss in Key West, FL?

    You definitely want to see the Southernmost Point Buoy, it's a must-see for any first-timer. The Hemingway House is also a popular choice, and you can see the famous six-toed cats there. And of course, no trip to Key West is complete without a visit to Mallory Square for the sunset celebration.
  • What are the best Airbnb and vacation rentals in Key West, FL?

  • Are there any unusual vacation rentals I can find in Key West?

    Key West has some great places to stay, but if you want something unusual, you'll get plenty to choose from. You can stay in a tiny house, a sailboat, a yacht, a houseboat, or even a camper van!
  • Which neighborhood in Key West, FL should you consider for a vacation rental?

    Old Town is a great option for a vacation rental. It's close to all the action, with plenty of restaurants, bars, and shops within walking distance. If you're looking for something a little quieter, you could consider staying in the New Town area, which is still close to everything, but a bit more residential.
  • What are the most popular Airbnbs in Key West, FL?

  • When is the best time to come to Key West?

    The months between March and May are the best time to visit Key West. Booking accommodation this time of year is going to be less pricy than in the peak winter season, but you won't miss out on the good weather.
  • What are the top family-friendly attractions in Key West, FL?

    The Key West Aquarium is a great option for families, with plenty of interactive exhibits. The Butterfly Conservatory is also a popular choice, and you can see hundreds of butterflies fluttering around you. The Key West Historic Seaport is another good option, with lots of things to see and do for all ages.
  • What are the best vacation rentals with a pool in Key West, FL?

  • What local special dishes should I try in Key West?

    Key Lime Pie is perhaps Key West's most famous dessert, but if you want something savory, there's plenty still to chew through. Key West Pinks is a special local shrimp with a sweet taste that you can find eaten alone or accompanied with some bacon. Conch fritters are also something tasty and different to try and definitely a special in Key West.
  • When is the best time to book a vacation rental in Key West, FL?

    The best time to book a vacation rental in Key West is during the shoulder season, from April to May or September to October. You'll find the best deals and fewer crowds during these months.
  • What are the best rentals for families and kids in Key West, FL?

  • What's the best way to come to Key West?

    You have different options to get to Key West. You can fly, drive, or even take a boat. If you're traveling long distances, then you can fly into Key West with most major US carriers like Delta, American, USAir, United, Southwest, and Cape Air. However, if you want a scenic route, then driving to Key West over the Overseas Highway is a unique experience and worth the long drive (the route runs 113 miles long, or 170 miles long if you start from Miami). There are also buses and shuttle services available too.
  • What events or festivals should visitors check out in and around Key West, FL?

    The Key West Food and Wine Festival is a great event for foodies, held every year in January. The Fantasy Fest is a wild and colourful celebration held in October, and the Hemingway Days celebration in July is a fun time to explore the writer's legacy.
  • What are the best rentals or Airbnbs with a jacuzzi in Key West, FL?

  • What's the must see sites in Key West?

    Visit the southernmost point of the United States before heading back to the northern side of Key West to take in the sights and performances around Mallory Square. Of course, no trip to Key West is complete without a trip to the Ernest Hemingway House!
  • What are the best budget-friendly activities in Key West, FL?

    You can explore the island on foot or by bike, and there are plenty of free beaches to enjoy. The Key West Cemetery is a fascinating and free attraction, and you can also take a walk along the historic Duval Street.
  • What are the best restaurants with local dishes in Key West, FL?

    For a taste of Key West, you should try the conch fritters at the Blue Heaven restaurant. The Cuban sandwiches at El Siboney are also a local favourite. If you want something a bit more upscale, the Latitudes restaurant at the Sunset Key Guest Cottages offers stunning views and delicious seafood.
  • What are the best walking or cycling routes in Key West, FL?

    For a scenic walk, try the route along the waterfront from Mallory Square to the Southernmost Point Buoy. For a longer bike ride, you can cycle around the island on the Overseas Highway, which offers stunning views of the ocean.
  • Are there pet-friendly attractions in Key West, FL?

    Yes, many of the beaches in Key West are pet-friendly, especially the dog beach at Higgs Beach. You can also bring your furry friend to many restaurants and shops, just be sure to check ahead.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than a hotel room, and you can often find rentals with unique features like a private pool or hot tub. You can also often find rentals in more convenient locations, closer to the beach or other attractions.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular destination for watersports, with plenty of opportunities for fishing, diving, snorkeling, and boating. The Key West Yacht Club is a great place to find information on local sailing events and activities.

Destinations nearby

Best Key West, FL vacation rentals with a balcony

Moonlight Paradise Upgraded Family Oasis Tropical Views Expansive Balcony - Key West, FL
9.4 91 reviews
Key West, FL
22/08 – 29/08
1425 ﺩ.ﺇ/nighttotal: 9975 ﺩ.ﺇ (7 )

Moonlight Paradise Upgraded Family Oasis Tropical Views Expansive Balcony

2 2
apartment , Key West
This Key West beachfront apartment is situated a short walk from Florida Keys beaches and within 5km of Duval Street and Mallory Square.
The 126 square metre property boasts two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, swimming pool, jacuzzi, and tennis court; enjoy nearby barbeque grills and a picnic area.
Poolside Suite With Direct Pool Access - Key West, FL
Key West, FL
24/07 – 25/07
1939 ﺩ.ﺇ/nightfor 1 night

Poolside Suite With Direct Pool Access

1 4
apartment , Key West
This Key West condo, located in the north of the island, offers direct access to the Gulf of Mexico and is situated just 1.6 kilometres from Duval Street.
This one-bedroom apartment accommodates up to four guests and features a private balcony with pool views, a fully-equipped kitchen, air conditioning, internet, and access to an on-site heated swimming pool and hot tub, with complimentary shuttle service to local attractions.
Henry's Penthouse On The Ocean In Key West  - Weekly / Nightly Rentals - Key West, FL
9.6 100 reviews
Key West, FL
20/07 – 27/07
2421 ﺩ.ﺇ/nighttotal: 16947 ﺩ.ﺇ (7 )

Henry's Penthouse On The Ocean In Key West - Weekly / Nightly Rentals

2 1
apartment , Key West
This beachfront Key West condo is located less than 5 kilometres from Duval Street, Mallory Square, and Florida Keys Beaches, and within a 15-minute drive of Clarence S. Higgs Memorial Beach Park and the Key West AIDS Memorial.
This 125 square metre apartment offers two bedrooms, two bathrooms, sleeps five guests, and boasts a private balcony, swimming pool, Jacuzzi, and free Wi-Fi, plus access to a fitness centre, tennis court, and sauna.
Waterfront Dock Pool Downtown Near Duval Pet - Key West, FL
9.8 8 reviews
Key West, FL
11/07 – 18/07
2502 ﺩ.ﺇ/nighttotal: 17514 ﺩ.ﺇ (7 )

Waterfront Dock Pool Downtown Near Duval Pet

2 4
apartment , Key West
This waterfront condominium in Key West's Meadows district offers direct harbour views and is situated less than 1 kilometre from Duval Street, the Historic Seaport, and Hemingway House.
This 111 square metre, two-bedroom, two-bathroom flat accommodates up to eight guests and features a private boat slip, a shared heated swimming pool, and on-site parking, with one dog up to 11 kg permitted.

Best Key West, FL vacation rentals with parking

Casa Atlantica One Bedroom - Key West, FL
Key West, FL
13/09 – 27/09
1137 ﺩ.ﺇ/nighttotal: 15918 ﺩ.ﺇ (14 )

Casa Atlantica One Bedroom

1 2
apartment , Key West
Casa Atlantica, a Key West apartment, is situated 2km from Key West International Airport and within a few kilometres of beaches such as Rest Beach, Higgs Beach, and Smathers Beach, and attractions including the Ernest Hemingway Home and Museum and Duval Street.
This 86 square metre, one-bedroom flat sleeps three guests and features a fully equipped kitchen with dishwasher, a balcony, free Wi-Fi, and on-site parking, plus a tennis court for guest use.
Anchor Drop Modern Elegance Upgrades Throughout Views Of Atlantic Ocean - Key West, FL
9.7 309 reviews
Key West, FL
13/09 – 27/09
1452 ﺩ.ﺇ/nighttotal: 20328 ﺩ.ﺇ (14 )

Anchor Drop Modern Elegance Upgrades Throughout Views Of Atlantic Ocean

2 2
apartment , Key West
This two-bedroom apartment in Beachside, Key West is just a 15-minute walk from the Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, and within a short drive of Duval Street and Mallory Square. The property has received excellent ratings for location, cleanliness and user experience.
The 126 square metre apartment comfortably sleeps six guests and features a fully equipped kitchen, a terrace, a garden, a swimming pool, a Jacuzzi, a sauna, a fitness centre and a tennis court. Guests will also enjoy access to parking, air conditioning and internet.
Tropical Dreaming By Avantstay - Key West, FL
9.5 156 reviews
Key West, FL
23/11 – 29/11
4535 ﺩ.ﺇ/nighttotal: 27210 ﺩ.ﺇ (6 )

Tropical Dreaming By Avantstay

2 6
house , Key West
This Key West property is ideally situated just four blocks from the beach and a short walk from popular attractions like South Beach, Fort Zachary Taylor State Park Beach, and Higgs Beach. The house enjoys excellent user, location and cleanliness ratings, making it a highly recommended choice for your Key West stay.
The property offers 2 bedrooms and a spacious 122 square metres of living space. It is fully equipped with amenities including a private pool, a fully equipped kitchen with a dishwasher, a washing machine, air conditioning, free Wi-Fi, and free private parking, ensuring a comfortable and convenient stay.
The Curry Poolside | Second Floor King - Key West, FL
8.0 3 reviews
Key West, FL
29/12 – 31/12
3742 ﺩ.ﺇ/nighttotal: 7484 ﺩ.ﺇ (2 )

The Curry Poolside | Second Floor King

1 2
apartment , Key West
This Key West apartment, situated in the Historic District, is less than 0.8 km from Duval Street and within walking distance of Mallory Square and the seaport.
The one-bedroom, one-bathroom flat, sleeping two guests, offers a shared heated pool, terrace, garden, and on-site parking, plus contactless check-in and laundry facilities within a historic 1869 mansion.
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