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

Sparkling Pool And Ample Lounging Space - Stunning Tropical Retreat - Key West, FL
No reviews

Sparkling Pool And Ample Lounging Space - Stunning Tropical Retreat

house, Key West
This six-bedroom residence is located in the central district of Key West, offering a short walk to Mallory Square and Duval Street.
This property provides accommodation for twelve guests, featuring a private swimming pool, air conditioning, Wi-Fi, and off-street parking for two vehicles, with an electric vehicle charger available.
Seagull Suite | Inviting Studio, Steps From Duval - Key West, FL
No reviews

Seagull Suite | Inviting Studio, Steps From Duval

apartment, Key West
This one-bedroom flat in Key West is situated a mere 160 metres from the Southernmost Point and 480 metres from South Beach, with Duval Street's shops and restaurants easily accessible on foot.
This pet-friendly studio apartment accommodates four guests with a queen bed and a queen sofa bed, offering a kitchenette, air conditioning, complimentary WiFi, and access to shared hot tubs.
121 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.5 26 reviews

121 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
This Old Town Key West property is a short walk from Duval Street and 0.64km from the Atlantic Ocean.
This two-bedroom, two-bathroom house offers 130 square metres of living space, including a private pool, fully equipped kitchen, and accommodates up to six guests; AvantStay services are available.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
This Key West condominium is centrally located downtown, offering easy walking access to numerous attractions.
Sleeping up to six guests, this two-bedroom apartment boasts a fully equipped kitchen, private patio, free Wi-Fi, on-site parking, and a washer/dryer.

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

The Caroline Suite - Key West, FL
No reviews

The Caroline Suite

house, Key West
The Caroline Suite, a Key West apartment, is conveniently located 1.8km from Higgs Beach, 1.9km from the Southernmost Point buoy, and 1.9km from Key West International Airport.
This one-bedroom, one-bathroom property offers 33 square metres of living space, sleeping up to seven guests and including a fully equipped kitchen, in-unit laundry, air conditioning, a swimming pool, and free Wi-Fi.
The Reach Key West, Curio Collection By Hilton - Key West, FL
8.4 1340 reviews

The Reach Key West, Curio Collection By Hilton

resort, Key West
The Reach Key West, Curio Collection by Hilton is located in Old Town, Key West, just 1.5 kilometres from Duval Street, a lively area with a wide selection of restaurants, shops, and nightlife. The resort has received very good ratings for both its location and overall experience, with good marks for cleanliness.
This hotel offers a range of rooms, including suites and studios, all with private balconies offering views of the ocean or the town. Guests can enjoy a private beach, a swimming pool, a spa, a fitness centre, and a variety of activities like scuba diving, snorkelling, and deep-sea fishing.
Casa Serendipity At Old Town - Key West, FL
10 50 reviews

Casa Serendipity At Old Town

house, Key West
This charming Key West cottage is situated in Old Town, just a short walk from Duval Street, the Historic Seaport, and a selection of restaurants and bars. The cottage has received excellent ratings for location, cleanliness, and overall user experience.
The three-bedroom cottage comfortably sleeps six guests and features a fully-equipped kitchen, a private pool, and a spacious outdoor living area with a propane grill. Guests can enjoy the Key West sunshine by relaxing on the porch or by the pool, or explore the surrounding area on foot.
Pool, Laundry, And Grilling Area - Key West, FL
10 11 reviews

Pool, Laundry, And Grilling Area

apartment, Key West
This Old Town Key West apartment, situated in the historic Cuban district, is minutes from Duval Street and within walking distance of many attractions, including the second oldest saltwater tide pool in Key West.
This one-bedroom, one-bathroom self-catering unit sleeps two guests and features a private master suite with garden access, a Florida room with kitchenette and outdoor grill, a heated Jacuzzi tub, and shared access to a pool and garden; nearby amenities include a convenience store and Cuban coffee shop.

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

Southern Comfort - Key West, FL
No reviews

Southern Comfort

house, Key West
This residence is situated 1.9 kilometres from Key West International Airport, offering convenient access to the Ernest Hemingway Home and Museum (3.7 kilometres), Duval Street (3.9 kilometres), and the Southernmost Point (4 kilometres).
This detached property accommodates up to 15 guests and features a private swimming pool, hot tub, a balcony with sea views, a well-equipped kitchen with a dishwasher and microwave, air conditioning, Wi-Fi, and parking, with concierge services and an ATM also available on-site.
Bayview South 801 Eisenhower Dr. #6 - Key West, FL
No reviews

Bayview South 801 Eisenhower Dr. #6

house, Key West
Bayview South 801 Eisenhower Drive #6, Key West, offers convenient access to Rest Beach (a 3km walk), Duval Street (1.4km), the Ernest Hemingway Home and Museum (3km), and Key West International Airport (1.9km).
This three-bathroom property sleeps fifteen guests, boasting a swimming pool, tennis court, fitness centre, concierge service, private parking, and a balcony with sea views; massage services are also available on-site.
Apartment ∙ 2 Guests - Key West, FL
No reviews

Apartment ∙ 2 Guests

apartment, Key West
This Key West studio apartment is centrally located in downtown Key West, offering easy walking access to many attractions.
The pet-friendly apartment, sleeping two, features a king-size bed, fully equipped kitchen with dishwasher, in-unit laundry, private balconies, and access to a shared pool; nearby attractions include Duval Street.
Atlantic Hideaway- Key West - Key West, FL
9.6 86 reviews

Atlantic Hideaway- Key West

apartment, Key West
This Key West apartment, situated in the Beachside neighbourhood, is one kilometre from Key West International Airport and three kilometres from Duval Street.
The 122-square-metre, two-bedroom, two-bathroom property in the 1800 Atlantic condo complex sleeps six, boasting a private lanai, access to two pools, a spa, and a fully equipped kitchen; beach chairs and towels are provided.

Best Key West, FL vacation rentals with parking

Flamingo Retreat-waterfront 2br 2ba Condo W/ Pool & Boat Slip - Key West, FL
9.2 109 reviews

Flamingo Retreat-waterfront 2br 2ba Condo W/ Pool & Boat Slip

apartment, Key West
This waterfront apartment is located in the Meadows neighbourhood of Key West, just 1.6 kilometres from Duval Street and across the road from Bayview Park, offering a peaceful escape from the bustling city centre. It has consistently received excellent user ratings, indicating a high level of satisfaction among previous guests.
The apartment offers two bedrooms, two bathrooms, and a total floor area of 113 square metres, providing ample space for a comfortable stay. Guests can enjoy a range of amenities including a private balcony, a swimming pool, and a boat slip, perfect for exploring the beautiful waters of Key West.
High Tide In Key West - Key West, FL
9.0 207 reviews

High Tide In Key West

house, Key West
This Key West apartment, ideally located 2 km from the Ernest Hemingway Home and Museum and 2.6 km from the Southernmost Point buoy, offers easy access to Key West International Airport (1.9 km).
The two-bedroom, two-bathroom flat provides self-catering facilities including a fully equipped kitchen, free Wi-Fi, private parking, and access to a swimming pool, Jacuzzi, fitness centre, tennis court, and sauna; it comfortably sleeps four guests and is close to Smathers Beach, Rest Beach, and Higgs Beach.
Leaward Isle Island Retreat - Key West, FL
9.8 2672 reviews

Leaward Isle Island Retreat

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.
Just Chillin' Out On The Ocean: 1/2 Off Charters! - Key West, FL
9.6 49 reviews

Just Chillin' Out On The Ocean: 1/2 Off Charters!

boat, Key West
This luxury yacht is anchored off the coast of Key West, Florida, offering unparalleled access to the island's attractions.
The vessel boasts two queen-sized bedrooms, two bathrooms, and accommodates four guests, featuring a full kitchen, high-speed internet, and a covered patio; daily breakfast and a complimentary shuttle to Key West are included.
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