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

Tropical Heron Hideaway With Hot Tub, Pool - Key West, FL
9.6 12 reviews
Key West, FL
14/10 – 16/10
2071 ﺩ.ﺇ/nighttotal: 4142 ﺩ.ﺇ (2 )

Tropical Heron Hideaway With Hot Tub, Pool

1 2
apartment , Key West
This Key West apartment, a 17-minute walk from Higgs Beach and 3km from Key West International Airport, offers easy access to the Ernest Hemingway Home and Museum and Duval Street.
The 56-square-metre flat features one bedroom, one bathroom, sleeps seven guests, and includes a private pool, hot tub, fully equipped kitchen, and access to on-site spa and fitness facilities.
110 M² Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.1 30 reviews
Key West, FL
02/07 – 07/07
2459 ﺩ.ﺇ/nighttotal: 12295 ﺩ.ﺇ (5 )

110 M² Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 2
apartment , Key West
This oceanfront condominium, situated in the La Brisa gated community in Key West, offers direct access to Smathers Beach.
The 110 square metre property features two bedrooms, two bathrooms, sleeps up to six guests, and includes a fully equipped kitchen, private balcony with spectacular ocean views, a swimming pool, and covered parking; AvantStay services are also available.
Apartment ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
Key West, FL
20/06 – 27/06
1560 ﺩ.ﺇ/nighttotal: 10920 ﺩ.ﺇ (7 )

Apartment ∙ 1 Bedroom ∙ 4 Guests

1 2
apartment , Key West
This Key West studio flat is located in Old Town, a short walk or cycle from Key West's historic attractions.
The self-catering apartment, sleeping up to four guests, offers a chef's kitchen with stainless steel appliances, a private courtyard, and free Wi-Fi; nearby parking is available at 204 Simonton Street.
Apartment ∙ 2 Bedrooms ∙ 9 Guests - Key West, FL
10 2 reviews
Key West, FL
24/07 – 28/07
3954 ﺩ.ﺇ/nighttotal: 15816 ﺩ.ﺇ (4 )

Apartment ∙ 2 Bedrooms ∙ 9 Guests

2 7
apartment , Key West
This Key West apartment, ideally situated for exploring the island's attractions, offers convenient access to various transport options.
The two-bedroom, two-bathroom flat sleeps eight guests, features a private patio with shared pool access, and includes a fully equipped kitchen, washer/dryer, and smart TVs.

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

Sunrise Suite 203 - Key West, FL
9.0 1 review
Key West, FL
20/06 – 27/06
1099 ﺩ.ﺇ/nighttotal: 7693 ﺩ.ﺇ (7 )

Sunrise Suite 203

2 2
apartment , Key West
Sunrise Suite 203, a two-bedroom Key West apartment, is situated 1km from Key West International Airport and within 6-8km of Mallory Square, the Ernest Hemingway Home and Museum, and Duval Street.
This 74 square metre self-catering property sleeps up to 11 guests and boasts two bathrooms, a fully equipped kitchen, a swimming pool, jacuzzi, tennis court, parking, and a balcony; free Wi-Fi is also provided.
Waterfront Condo With Dock, Pool, Downtown Key West Near Duval - Key West, FL
9.7 220 reviews
Key West, FL
26/10 – 28/10
2813 ﺩ.ﺇ/nighttotal: 5626 ﺩ.ﺇ (2 )

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

2 4
apartment , Key West
This waterfront apartment in historic Downtown Key West offers a private boat slip (maximum 12 metres long, 4 metres wide, 5.5 metres clearance) and is less than 1.6km from Duval Street, the Historic Seaport, and the Hemingway House.
The 118 square metre, two-bedroom, two-bathroom flat sleeps six, boasts a private balcony overlooking the harbour and pool, includes a fully equipped kitchen, in-suite laundry, and access to an on-site heated pool, tiki bar, and secure keyless entry; a golf cart is also provided.
Waterfront Dock Pool Pet Friendly Near Duval St - Key West, FL
9.8 248 reviews
Key West, FL
20/06 – 27/06
4189 ﺩ.ﺇ/nighttotal: 29323 ﺩ.ﺇ (7 )

Waterfront Dock Pool Pet Friendly Near Duval St

4 7
apartment , Key West
This luxurious Key West penthouse, less than 1.6km from Duval Street, the Historic Seaport, and the Hemingway House, offers stunning waterfront views and a private boat slip.
The 172 square metre dwelling boasts four bedrooms sleeping sixteen guests, four bathrooms, a loft with bunks, two living areas, a fully equipped kitchen, a heated pool, and on-site bike rentals.
Leaward Isle Island Retreat - Key West, FL
9.8 2622 reviews
Key West, FL
05/10 – 19/10
1617 ﺩ.ﺇ/nighttotal: 22638 ﺩ.ﺇ (14 )

Leaward Isle Island Retreat

2 1
house , Key West
This Key West property is a short walk from Smathers Beach, a popular stretch of sand known for its beautiful sunsets and water activities, and just a short distance from Rest Beach. The property boasts excellent user, location and cleanliness ratings.
This spacious house offers a fully equipped kitchen, air conditioning, free Wi-Fi and a private balcony with sea views. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, sauna, spa, fitness centre, tennis court, and a bar.

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

Absolutely Paradise - Key West, FL
10 1 review
Key West, FL
24/07 – 28/07
4292 ﺩ.ﺇ/nighttotal: 17168 ﺩ.ﺇ (4 )

Absolutely Paradise

3 7
house , Key West
Absolutely Paradise, a Key West house, is centrally located less than 1.6km from Duval Street, South Beach, and Southernmost Point, offering easy access to Key West International Airport and attractions such as Fort Zachary Taylor State Park Beach and the Ernest Hemingway Home and Museum.
This 174 square metre property boasts three bedrooms, two bathrooms, sleeps fifteen guests, and includes a private pool, tennis court, free parking, a fully equipped kitchen, and free Wi-Fi.
Waterfront Condo Dock Pool Downtown Near Duval - Key West, FL
9.6 29 reviews
Key West, FL
24/07 – 25/07
4103 ﺩ.ﺇ/nightfor 1 night

Waterfront Condo Dock Pool Downtown Near Duval

2 4
apartment , Key West
This Meadows condo, situated less than 1.6km from Duval Street, the Ernest Hemingway Home and Museum, and Florida Keys beaches, offers easy access to Key West's attractions.
This 121 square metre apartment sleeps six, boasting two bedrooms, two bathrooms, a fully equipped kitchen, private balcony, and access to a swimming pool, garden, and on-site parking.
Poolside Hide-away Palm Gardens - Key West, FL
Key West, FL
22/08 – 29/08
1231 ﺩ.ﺇ/nighttotal: 8617 ﺩ.ﺇ (7 )

Poolside Hide-away Palm Gardens

1 2
apartment , Key West
Poolside Hide-Away Palm Gardens, a Key West apartment, is situated a 15-minute walk from Rest Beach and a 16-minute walk from Duval Street, 1.8km from the Southernmost Point buoy.
This 42 square metre, one-bedroom flat sleeps seven, offering a fully equipped kitchen, private balcony, swimming pool, jacuzzi, tennis court, parking, and free Wi-Fi; a washing machine adds further convenience.
Bahama Gardens - Conch House - Key West, FL
9.7 396 reviews
Key West, FL
30/12 – 10/01
10050 ﺩ.ﺇ/nighttotal: 110550 ﺩ.ﺇ (11 )

Bahama Gardens - Conch House

4 5
house , Key West
This charming house is located in the heart of Key West, just a short walk from the beautiful beaches of Fort Zachary Taylor State Park and South Beach. It has received excellent ratings for location, cleanliness, and overall user experience, ensuring a comfortable and enjoyable stay.
The property features two bedrooms, a living room, and a well-equipped kitchen, making it ideal for families or groups of friends. Guests can enjoy a range of amenities including a private hot tub, a sun terrace, an indoor play area, and a tennis court, offering plenty of opportunities for relaxation and entertainment.

Best Key West, FL vacation rentals with parking

Royal Poinciana >>Weekly Rental! Truman Annex In Key West - Key West, FL
9.6 40 reviews
Key West, FL
20/06 – 27/06
1702 ﺩ.ﺇ/nighttotal: 11914 ﺩ.ﺇ (7 )

Royal Poinciana >>Weekly Rental! Truman Annex In Key West

1 2
apartment , Key West
This Key West Historic District flat is situated two blocks from Duval Street and 0.4 kilometres from a top-rated beach, close to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
The 63-square-metre self-catering apartment, sleeping two guests, boasts a private courtyard/balcony, a fully equipped kitchen including dishwasher, a swimming pool, parking, and a washer/dryer.
Duval's Duet On Duval - Key West, FL
9.3 502 reviews
Key West, FL
02/07 – 03/07
4743 ﺩ.ﺇ/nightfor 1 night

Duval's Duet On Duval

2 5
apartment , Key West
The Collins on Duval by Brightwild is located in the heart of Key West, just 1.6km from Simonton Street Beach and 1.1km from South Beach, offering easy access to Duval Street and its shops and restaurants. This apartment has excellent user, location and cleanliness ratings.
This two-bedroom flat provides ample space for families or groups of friends. The apartment offers modern amenities such as air conditioning, free Wi-Fi, a kitchen with a fridge, microwave, and dishwasher, as well as a patio for outdoor relaxation.
Bright Condo With Homey Feel, Entertainment & Private Parking - Beach Nearby - Key West, FL
9.2 173 reviews
Key West, FL
14/10 – 16/10
1333 ﺩ.ﺇ/nighttotal: 2666 ﺩ.ﺇ (2 )

Bright Condo With Homey Feel, Entertainment & Private Parking - Beach Nearby

1 2
apartment , Key West
This Key West condo offers a prime downtown Simonton Street position, just 100 metres from Duval Street and a short walk to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 47 square metre flat, accommodating up to four guests, features air conditioning, a kitchen with a fridge and microwave, and a private off-street parking space, with a covered porch providing a relaxing outdoor area.
Waterfront 2br | Pool | Key West | Pet Ok - Key West, FL
9.7 319 reviews
Key West, FL
20/06 – 21/06
3497 ﺩ.ﺇ/nightfor 1 night

Waterfront 2br | Pool | Key West | Pet Ok

2 2
apartment , Key West
This waterfront apartment in historic Downtown Key West offers a private boat slip (max 35ft, 13ft beam) and is less than 1.6km from Duval Street, the Historic Seaport, and the Hemingway House.
The 121 square metre, two-bedroom, two-bathroom flat sleeps six, includes a full kitchen, washer/dryer, large balcony overlooking the harbour, and is close to a park with tennis courts; one dog up to 25lbs is permitted for a £160 fee.
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