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

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.
La Brisa - Ocean Views Across From Smathers Beach - Key West, FL
10 186 reviews
Key West, FL
05/09 – 19/09
1787 ﺩ.ﺇ/nighttotal: 25018 ﺩ.ﺇ (14 )

La Brisa - Ocean Views Across From Smathers Beach

2 4
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.
Sky Loft In Key West - Key West, FL
9.5 234 reviews
Key West, FL
29/12 – 27/01
2653 ﺩ.ﺇ/nighttotal: 76937 ﺩ.ﺇ (29 )

Sky Loft In Key West

1 2
house , Key West
Sky Loft in Key West by Brightwild is centrally located in Key West, a short walk from Simonton Street Beach and South Beach, offering easy access to the island's attractions and nightlife. This property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The one-bedroom apartment is perfect for a family of four, with a spacious 63 square metres of living space. Enjoy a comfortable stay with amenities such as a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, and free Wi-Fi.
Luxury High End, 2 Bikes,  Highspeed Wi-fi, Work Station,  Pool, Hot Tub, Gym - Key West, FL
9.8 318 reviews
Key West, FL
05/09 – 19/09
1570 ﺩ.ﺇ/nighttotal: 21980 ﺩ.ﺇ (14 )

Luxury High End, 2 Bikes, Highspeed Wi-fi, Work Station, Pool, Hot Tub, Gym

1 4
apartment , Key West
This Key West Midtown condo is situated less than 5 km from Duval Street, Mallory Square, and Florida Keys Beaches, offering easy access to Key West's attractions.
The 102-square-metre apartment features one bedroom, one bathroom, sleeps four guests, and includes a private pool, a fully equipped kitchen, a terrace, and access to a fitness centre, spa, and tennis court.

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

The James Classic | Ground Floor King - Key West, FL
9.6 4 reviews
Key West, FL
03/07 – 05/07
2209 ﺩ.ﺇ/nighttotal: 4418 ﺩ.ﺇ (2 )

The James Classic | Ground Floor King

1 2
apartment , Key West
This Key West apartment, situated in the Historic District, is a short distance (less than 0.16 km) from Duval Street and adjacent to the Curry Mansion.
The one-bedroom, one-bathroom flat sleeps two guests and offers a terrace, swimming pool access, complimentary parking (subject to availability), shared laundry facilities, and contactless check-in.
High Tide In Key West - Key West, FL
9.0 206 reviews
Key West, FL
12/11 – 15/11
2581 ﺩ.ﺇ/nighttotal: 7743 ﺩ.ﺇ (3 )

High Tide In Key West

2 5
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.
Enjoy Your Paradise Stay - Key West, FL
Key West, FL
21/12 – 18/01
1065 ﺩ.ﺇ/nighttotal: 29820 ﺩ.ﺇ (28 )

Enjoy Your Paradise Stay

1 1
apartment , Key West
This peaceful family-friendly flat is located in a quiet Key West neighbourhood, a short distance from Duval Street and Mallory Square.
This accommodation offers a tranquil escape with air conditioning, a swimming pool, a jacuzzi, and a fully equipped kitchen, and can host up to 15 guests.
Sunrise Suites Bonaire Suite #210 - Key West, FL
8.8 242 reviews
Key West, FL
02/07 – 05/07
1310 ﺩ.ﺇ/nighttotal: 3930 ﺩ.ﺇ (3 )

Sunrise Suites Bonaire Suite #210

2 4
apartment , Key West
Sunrise Suites Bonaire Suite #210 is a two-bedroom Key West apartment, conveniently located 1 kilometre from Key West International Airport and within a short drive of attractions such as the Southernmost Point (6.4 km), Ernest Hemingway Home and Museum (7.4 km), Duval Street (7.4 km), and Mallory Square (8 km).
This 72 square metre self-catering flat offers two bathrooms, a private balcony, a fully equipped kitchen, in-unit laundry facilities, and access to a swimming pool, hot tub, fitness centre, and tennis court; sleeping up to four 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.

Destinations nearby

Best Key West, FL vacation rentals with a balcony

The Perry Hotel & Marina Key West - Key West, FL
9.2 2522 reviews
Key West, FL
29/12 – 31/12
2285 ﺩ.ﺇ/nighttotal: 4570 ﺩ.ﺇ (2 )

The Perry Hotel & Marina Key West

1 2
resort , Stock Island
The Perry Hotel & Marina Key West is located on Stock Island, just 8km from Key West's Old Town and 5km from Key West International Airport. It has excellent user ratings, with particularly high marks for cleanliness and location.
The hotel has a waterfront setting with two pools and direct marina access. Guests can enjoy a range of amenities, including restaurants, a spa, a fitness centre, tennis courts, and complimentary shuttle service to Old Town.
~Vista Fresco~ Oceanside Condominiums With Resort-style Amenities - Key West, FL
9.6 148 reviews
Key West, FL
05/09 – 19/09
1752 ﺩ.ﺇ/nighttotal: 24528 ﺩ.ﺇ (14 )

~Vista Fresco~ Oceanside Condominiums With Resort-style Amenities

2 4
apartment , Key West
This two-bedroom apartment is located on 1800 Atlantic in Key West, just east of Smathers Beach, the island's largest beach. The property has excellent user, location, and cleanliness ratings.
The apartment is 122 square metres and can accommodate up to six guests. It offers a range of amenities including a swimming pool, a jacuzzi, a sauna, a spa, a fitness centre, and a garden.
Poolside Suite - Key West, FL
9.0 333 reviews
Key West, FL
03/07 – 05/07
2885 ﺩ.ﺇ/nighttotal: 5770 ﺩ.ﺇ (2 )

Poolside Suite

1 2
apartment , Key West
This Key West apartment enjoys a central location, a short walk (less than 0.5km) from the Ernest Hemingway Home and Museum, South Beach, and Duval Street, with easy access to Fort Zachary Taylor State Park Beach and Simonton Street Beach.
The self-catering property offers two bedrooms, a fully equipped kitchen including a fridge, microwave, and dishwasher, free Wi-Fi, on-site parking, a swimming pool, and a terrace/balcony, ideal for families or groups.
~ Petite Maison ~ 2 King Ensuite Bedrooms On A Quiet Lane Near Duval Street. - Key West, FL
9.9 452 reviews
Key West, FL
20/07 – 22/07
2837 ﺩ.ﺇ/nighttotal: 5674 ﺩ.ﺇ (2 )

~ Petite Maison ~ 2 King Ensuite Bedrooms On A Quiet Lane Near Duval Street.

2 1
apartment , Key West
This Key West house, situated on the southern end of Duval Street, is within walking distance of cafes, nightclubs, the Southernmost Point buoy, and the Key West Butterfly and Nature Conservatory.
The property offers four ensuite bedrooms sleeping up to eight guests, a private saline pool (seasonally heated for a fee), a modern kitchen with stainless steel appliances, and a dog is allowed (up to 25 lbs, with restrictions).

Best Key West, FL vacation rentals with parking

H2o Suites- Adults Only - Key West, FL
9.6 1688 reviews
Key West, FL
20/07 – 27/07
1666 ﺩ.ﺇ/nighttotal: 11662 ﺩ.ﺇ (7 )

H2o Suites- Adults Only

1 1
resort , Key West
H2O Suites is located in Key West, just a short walk from Duval Street, the heart of the city's nightlife, dining, and shopping scene. This adults-only hotel has received excellent ratings for its location, cleanliness, and overall experience.
The hotel offers a range of amenities and activities, including a rooftop pool with a sun terrace, a bar, and tropical courtyard views. Guests can also enjoy private pools in select rooms, a welcome drink upon arrival, and daily happy hour.
Rose Lane Villas - Key West, FL
9.0 925 reviews
Key West, FL
06/07 – 09/07
2833 ﺩ.ﺇ/nighttotal: 8499 ﺩ.ﺇ (3 )

Rose Lane Villas

3 6
house , Key West
These villas are situated on Duval Street in Key West, just a short walk from the Key West Aquarium and a mile from the Southernmost Point, putting you right in the heart of the action. The villas have received excellent ratings for location, cleanliness, and user experience.
The properties offer a range of features including fully equipped kitchens, private balconies, flat-screen TVs, free Wi-Fi, and parking. The heated outdoor pool provides a welcome respite from the Florida sun, while the proximity to local attractions makes exploring the island easy.
Royal Poinciana >>Weekly Rental! Truman Annex In Key West - Key West, FL
9.6 40 reviews
Key West, FL
27/06 – 04/07
1703 ﺩ.ﺇ/nighttotal: 11921 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.
The Margaret Suite - Key West, FL
10 1 review
Key West, FL
13/09 – 27/09
1390 ﺩ.ﺇ/nighttotal: 19460 ﺩ.ﺇ (14 )

The Margaret Suite

1 2
apartment , Key West
The Margaret Suite, a studio flat in Key West, is located 2.57 kilometres from Mallory Dock, Mallory Square, and the Key West Aquarium, and 1.93 kilometres from the Southernmost Point, offering easy access to the Ernest Hemingway Home and Museum, Duval Street, and Rest Beach, with Key West International Airport a mere 1.93 kilometres away.
This 37-square-metre studio apartment accommodates up to five guests and features air conditioning, a kitchen with a fridge and microwave, complimentary on-site parking and WiFi, an outdoor swimming pool, a garden, and a private entrance for a comfortable stay.
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