Vacation rentals in Key West, FL

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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

56 M² House ∙ 2 Bedrooms ∙ 4 Guests - Key West, FL
No reviews

56 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, Key West
The Grinnell Cottage is situated in Old Town Key West, a short walk from Duval Street, the Historic Seaport, and Mallory Square.
This 56 square meter cottage accommodates up to four guests with two bedrooms and one bathroom, offering a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a garden, parking, and access to a shared swimming pool, with pets allowed for a fee.
Luxury 3-bedroom Waterfront Home With Pool And Dock! - Key West, FL
9.8 144 reviews

Luxury 3-bedroom Waterfront Home With Pool And Dock!

apartment, Key West
This Key West house is located in Meadows, a short distance from Duval Street, the Ernest Hemingway Home and Museum, and the Unitarian Universalist Fellowship, offering easy access to the island's attractions. The property has consistently received excellent ratings for location, cleanliness, and user experience.
The three-bedroom property provides ample space for families or groups of friends. Guests can enjoy a private pool, a spa tub, a barbecue grill, and a garden, along with concierge services, free Wi-Fi, and a fully equipped kitchen.
Casa Tranquila - Fully-renovated 2-bedroom Townhome In Old Town Key West - Key West, FL
9.6 4 reviews

Casa Tranquila - Fully-renovated 2-bedroom Townhome In Old Town Key West

apartment, Key West
This Old Town Key West holiday home is less than a kilometre from the Key West Firehouse Museum and Duval Street, and within a 2.4km radius of the Ernest Hemingway Home and Museum and Florida Keys beaches.
The 74 square metre property boasts two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, jacuzzi, patio, and on-site laundry facilities.
Apartment ∙ 3 Bedrooms ∙ 8 Guests - Key West, FL
9.0 2 reviews

Apartment ∙ 3 Bedrooms ∙ 8 Guests

apartment, Key West
This three-bedroom apartment is situated in Beachside Key West, just a short distance from Duval Street and its attractions.
The apartment offers private parking with electric charging stations, a fully equipped kitchen, a spacious living area with a queen sleeper sofa, and a private balcony, comfortably accommodating up to eight guests.

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

Dockside Daydreams At Coconut Mallory - Key West, FL
9.7 150 reviews

Dockside Daydreams At Coconut Mallory

house, Key West
This two-bedroom house is situated in Key West, Florida, within 3.2 kilometres of the Key West Tropical Forest and Botanical Garden.
The 65 square metre property features a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and a garden, comfortably accommodating up to six guests.
4 Blocks From Duval And 7 Blocks From The Beach - Key West, FL
10 2 reviews

4 Blocks From Duval And 7 Blocks From The Beach

apartment, Key West
This Old Town Key West flat is situated less than a kilometre from Duval Street and St Mary Star of the Sea Church, offering easy access to beaches and the Southernmost Point within a 2.4km radius.
The one-bedroom, one-bathroom apartment sleeps four, features a private patio, in-unit laundry, and a kitchen with a dishwasher, microwave, and fridge, plus free Wi-Fi and use of the swimming pool and garden.
The Cornish Suite At Inn On Fleming Key West! - Key West, FL
9.7 3 reviews

The Cornish Suite At Inn On Fleming Key West!

house, Key West
THE CORNISH SUITE at the Inn on Fleming Key West is centrally located, less than 1.6km from Mallory Square and Duval Street, and a short walk from Simonton Street Beach.
This 31 square metre self-catering property sleeps four guests in two bedrooms and one bathroom, and offers free Wi-Fi, on-site parking, a swimming pool, and a terrace; nearby attractions include the Ernest Hemingway Home and Museum and Key West International Airport (3km).
Waterfront Dock Pool Key West Near Duval - Key West, FL
9.7 262 reviews

Waterfront Dock Pool Key West Near Duval

apartment, Key West
This waterfront Key West condo, situated in the historic Downtown district, is conveniently located approximately 1.6 kilometres from Duval Street, the Historic Seaport, and the Hemingway House.
The 112 square metre apartment features two bedrooms (king and two queen-size beds), two bathrooms, a full kitchen, and a large balcony with direct pool and dock access; it sleeps six guests and includes a private boat slip (up to 12 metres).

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

Coastal Comfort & 3/4 Time Compound - Key West, FL
9.8 6 reviews

Coastal Comfort & 3/4 Time Compound

apartment, Key West
This expansive Key West compound, located in the Northside Resort district, offers immediate access to essential amenities, being within 500 meters of a Publix supermarket and the island's principal shopping centre.
This 372 square meter residence, ideal for up to 16 guests across eight bedrooms and seven bathrooms, features a private heated swimming pool, a fully equipped chef's kitchen, and eight en-suite bedrooms, including master suites with Jacuzzi tubs, providing a comfortable stay with ample space and modern conveniences.
Key West Paradise Found - Experience The Best Views At 1800 Atlantic - Key West, FL
9.8 339 reviews

Key West Paradise Found - Experience The Best Views At 1800 Atlantic

apartment, Key West
This oceanfront condominium in Key West's Beachside district offers direct Atlantic views from a private balcony and is situated just 20 metres from Smathers Beach, placing it within two kilometres of Duval Street's attractions.
This three-bedroom, two-bathroom flat, covering 126 square metres and accommodating up to six guests, boasts a private terrace, a communal swimming pool, a jacuzzi, a garden, a sauna, and tennis courts, with parking also available.
Blue Moonshine Upgrades Throughout Modern Finishes - Key West, FL
9.6 167 reviews

Blue Moonshine Upgrades Throughout Modern Finishes

apartment, Key West
This apartment is situated in Beachside, Key West, just a short walk from Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, and a short drive from the vibrant Duval Street and Mallory Square. This property has received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom apartment, with a floor area of 130 square meters, comfortably accommodates up to six guests. Enjoy a range of amenities, including a swimming pool, jacuzzi, terrace, garden, fitness centre, sauna, and tennis court, making this an ideal choice for a relaxing and enjoyable stay in Key West.
Key West Condo With Balcony Ocean View - Key West, FL
10 194 reviews

Key West Condo With Balcony Ocean View

apartment, Key West
This two-bedroom apartment is situated directly across the street from Smathers Beach, one of Key West's most popular beaches, offering easy access to the sand and surf. The apartment has received excellent ratings for user experience, location, and cleanliness.
The 136 square metre property comfortably accommodates up to six guests and features a modern kitchen, two bathrooms, a spacious living area, a private balcony, and air conditioning throughout. Enjoy the on-site amenities, including a swimming pool, hot tub, tennis courts, and a garden, or take advantage of the beach rentals available for chairs, umbrellas, paddle boards, kayaks, and sailboats.

Best Key West, FL vacation rentals with parking

Hemingways Atlantic Retreat - Key West, FL
9.0 128 reviews

Hemingways Atlantic Retreat

house, Key West
This apartment is located in Key West, a short walk from Smathers Beach and close to Rest Beach, offering easy access to the island's beautiful beaches and vibrant atmosphere. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment is spacious, with two bedrooms and two bathrooms, ideal for families or groups of up to six guests. It also boasts a range of amenities, including a swimming pool, a Jacuzzi, a fitness center, and a tennis court, ensuring a comfortable and enjoyable stay.
Big Blu -5 Bed, 4 Bath Old Town - Key West, FL
9.9 645 reviews

Big Blu -5 Bed, 4 Bath Old Town

apartment, Key West
This studio apartment is situated in the Cuban district, just a short walk from the best 'con leche' in Key West and a few minutes from all the island's attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment is 42 square metres and features a modern kitchen with an induction cooktop and convection oven. Guests can enjoy free Wi-Fi, digital HD cable, beach chairs, and a shared courtyard for relaxing and storing beach gear.
Aria At Azul Mansion Key West - Key West, FL
10 3 reviews

Aria At Azul Mansion Key West

house, Key West
This Key West apartment, ARIA at Azul Mansion, enjoys a central location, a short walk from South Beach and less than 2.4 kilometres from the Key West Aquarium and Mallory Square.
The self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a swimming pool, tennis court, parking, and Wi-Fi; all within easy reach of the Ernest Hemingway Home and Museum and Duval Street.
Old Town Bali Hideaway For 2, Just Steps From Duval - Key West, FL
9.8 93 reviews

Old Town Bali Hideaway For 2, Just Steps From Duval

apartment, Key West
This Key West Historic District holiday home is located steps from the Curry Mansion Museum and Duval Street, within 1.6km of Mallory Square and Florida Keys beaches.
The 37 square metre property features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, private garden, and balcony; enjoy easy access to Duval Street's shops and the house's smoke-free environment.
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