Vacation rentals in Key West, FL

4265 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 4265 accommodations in Key West, FL, here are the 4 best family friendly rentals

New The Windrose House - Pool & Pets - Key West, FL
No reviews

New The Windrose House - Pool & Pets

house, Key West
Accommodation. You will be in Key West.
Services and facilities: a washing machine, a kitchen and a barbecue.
Sunnyside Up - Shared Pool - Key West, FL
No reviews

Sunnyside Up - Shared Pool

apartment, Key West
This two-bedroom, two-bathroom apartment is situated in Old Town, Key West, offering a 10-minute walk to the beach and a 15-minute walk to Duval Street.
This pet-friendly accommodation features a shared swimming pool, a fully equipped galley kitchen, air conditioning, and parking, accommodating up to nine guests with a 10:00 AM check-out.
Luxury Waterfront Home With Private Pool And Dock! - Key West, FL
9.8 92 reviews

Luxury Waterfront Home With Private Pool And Dock!

apartment, Key West
This four-bedroom, three-bathroom residence in the Meadows district of Key West offers a prime location bordering Old Town, providing picturesque views of Garrison Bight and within a 500-meter walk of the Ernest Hemingway Home and Museum and the Southernmost Point. This spacious 263-square-meter flat accommodates up to ten guests, featuring two master suites, a chef-ready kitchen, a private balcony overlooking the charter fishing fleet, a private boat slip, and a heated swimming pool.
Spectacular Pool And Scenic Balcony - Luxury Coastal Sanctuary - Key West, FL
No reviews

Spectacular Pool And Scenic Balcony - Luxury Coastal Sanctuary

house, Key West
This two-bedroom, two-bathroom villa is situated in Key West, adjacent to a nature preserve and approximately 3.2 kilometres from Smather's Beach and the Atlantic Ocean.
This family-friendly property offers accommodation for six guests with amenities including an Olympic-sized swimming pool with ocean views, a jacuzzi, spa, tennis courts, a gym, and a secure gated complex with parking, with personalised concierge services available.

Best Key West, FL vacation rentals with a pool

Among the 4265 accommodations in Key West, FL, here are the 4 best rentals with a pool

Blue Moonshine On The Atlantic - Key West, FL
9.5 2 reviews

Blue Moonshine On The Atlantic

house, Key West
Blue Moonshine on the Atlantic, a Key West property, is located 2.6 km from the Southernmost Point and 3.2 km from the Ernest Hemingway Home and Museum.
This 130-square-metre house boasts two bedrooms, two bathrooms, a hot tub, and sleeps up to 11 guests, offering a fully equipped kitchen, swimming pool, jacuzzi, sauna, fitness centre, tennis court, and ocean views from a private balcony, with free Wi-Fi and proximity to Smathers, Rest, and Higgs Beach.
Colony Poolside: A Charming Bungalow Near Duval - Key West, FL
9.8 179 reviews

Colony Poolside: A Charming Bungalow Near Duval

apartment, Key West
Colony Poolside is a one-bedroom bungalow situated in the historic Old Town district of Key West, just a short walk from Duval Street and a few kilometres from the beach. The property has received excellent ratings for its location, cleanliness, and overall experience.
The bungalow is 51 square metres and can accommodate two guests. It has a fully equipped kitchen, a private deck, a shared pool, and a garden, offering everything you need for a relaxing and enjoyable stay.
Frost Free In Cayo Hueso - Key West, FL
9.3 238 reviews

Frost Free In Cayo Hueso

house, Key West
This apartment is located just a short walk from Smathers Beach, Key West's most popular beach, and a few blocks from Rest Beach, making it ideal for enjoying the beautiful beaches and vibrant atmosphere of Key West. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom, two-bathroom apartment can comfortably accommodate up to six guests. It features a fully equipped kitchen, a private balcony with sea views, a swimming pool, a Jacuzzi, a fitness centre, and a tennis court.
Key West Happy Hideaway! Beautifully Renovated! 2 - Key West, FL
10 2 reviews

Key West Happy Hideaway! Beautifully Renovated! 2

house, Key West
This two-bedroom, 1.5-bathroom townhome is located within the Key West Golf Club neighbourhood, a short drive or bike ride from Old Town Key West, the Tennessee Williams Fine Art Centre and the Key West Tropical Forest and Botanical Garden.
This pet-friendly property offers island living with a fully equipped kitchen, air conditioning, internet, a private screened patio overlooking landscaping and a pond, and access to two community swimming pools and a fitness centre for up to six guests.

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.

Popular destinations

Best Key West, FL vacation rentals with a balcony

Harbor House Penthouse- A - Key West, FL
10 31 reviews

Harbor House Penthouse- A

apartment, Key West
This Key West City Centre condo, situated in the Historic District, offers easy access to Mallory Square and its renowned sunset celebrations.
This five-bedroom, four-bathroom apartment boasts a spacious 209 square metre floor area, sleeping up to twelve guests and featuring a fully equipped kitchen, high-speed internet, and a large terrace.
Apartment ∙ 4 Bedrooms ∙ 12 Guests - Key West, FL
No reviews

Apartment ∙ 4 Bedrooms ∙ 12 Guests

apartment, Key West
This Key West duplex is centrally located in downtown, within easy walking distance of Duval Street and other attractions.
The spacious four-bedroom, four-and-a-half-bathroom property sleeps up to twelve guests, offering two kitchens, two private balconies, private laundry facilities, and off-street parking for one small vehicle.
Casa Key West-pool & Free Parking - Key West, FL
9.1 217 reviews

Casa Key West-pool & Free Parking

house, Key West
Villa Coastal by Brightwild-Pool & Free Parking is located just a short walk from Duval Street and the Southernmost Point in Key West, placing you right in the heart of the action. This property has received excellent ratings for location, cleanliness and overall user experience.
This three-bedroom villa offers plenty of space for families or groups of friends. The property includes a private pool, free parking, air conditioning, a dishwasher, and a full kitchen, making it a comfortable and convenient base for exploring Key West.
The Elizabeth Suite | 1 Bedroom Condo, Shared Pool - Key West, FL
9.6 11 reviews

The Elizabeth Suite | 1 Bedroom Condo, Shared Pool

apartment, Key West
This Key West Historic District flat is less than 1.6km from Duval Street, the Ernest Hemingway Home and Museum, and South Beach.
The 56 square metre self-catering apartment sleeps four, boasting a private pool, terrace, and in-unit kitchen with washing machine.

Best Key West, FL vacation rentals with parking

Steps From Duval, Pool On Site & Bikes Included! - Key West, FL
9.6 451 reviews

Steps From Duval, Pool On Site & Bikes Included!

apartment, Key West
This Key West apartment is situated in the Historic District, less than 0.8 km from Duval Street, the Ernest Hemingway Home and Museum, and Florida Keys Beaches, and within 1.6 km of Southernmost Point and South Beach.
The self-catering flat offers a fully equipped kitchen, in-unit laundry, a terrace, swimming pool access, and sleeps two guests, ideal for exploring Key West’s attractions.
St Kitts - Downtown Waterfront Penthouse Pool Dock Parking - Key West, FL
8.3 14 reviews

St Kitts - Downtown Waterfront Penthouse Pool Dock Parking

house, Key West
This Key West penthouse, a short walk from Rest Beach and South Beach, offers direct waterfront views and is conveniently located near Higgs Beach, the Ernest Hemingway Home and Museum, and Duval Street.
This 186 square metre (1997 square foot) property boasts four bedrooms, four bathrooms, and sleeps up to 24 guests, featuring a private pool, elevator, free Wi-Fi, parking, and a fully equipped kitchen; all within easy reach of Key West's attractions.
Sunset Suite Colony - Key West, FL
No reviews

Sunset Suite Colony

house, Key West
Sunset Suite Colony, a Key West property, is centrally located less than 1.6km from Southernmost Point and within walking distance of Simonton Street Beach and Higgs Beach, offering easy access to Duval Street and the city centre.
This one-bedroom, one-bathroom house, boasting 49 square metres of floor space, sleeps seven guests and includes a private patio, swimming pool, tennis court, free Wi-Fi, and a fully equipped kitchen with fridge and microwave; nearby cycling routes enhance its appeal.
Corona At Azul Mansion Key West - Key West, FL
No reviews

Corona At Azul Mansion Key West

B&B, Key West
CORONA at Azul Mansion, a Key West holiday home, is conveniently located 1.9 miles from Key West International Airport and a 12-minute walk from South Beach, close to the Ernest Hemingway Home and Museum and Duval Street.
This one-bedroom, one-bathroom property sleeps three guests and boasts a private swimming pool, terrace, tennis court, free Wi-Fi, and on-site parking; enjoy nearby attractions including the Key West Aquarium and Mallory Dock.
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