Vacation Rentals in Key West, FL

3183 available vacation rental offers

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Key West, FL vacation rentals
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3183 Vacation rentals and Airbnb 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

Condo ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
10 2 reviews
Key West, FL
01/10 – 01/11
₹22242/nighttotal: â‚¹689502 (31 )

Condo ∙ 2 Bedrooms ∙ 6 Guests

2 2
apartment , Key West
This family-friendly condominium offers direct beach access from a gated community in Key West, boasting oceanfront Atlantic views and refreshing sea breezes.
This spacious 2-bedroom, 2-bathroom condo accommodates up to 6 guests and features a full kitchen, private balcony with dining, an in-unit washer/dryer, and access to an on-site swimming pool, hot tub, and tennis/pickleball court.
Island Sanctuary Key West - 3 Bedroom / 2 Bathroom With Pool And Parking! - Key West, FL
Key West, FL
01/10 – 01/11
₹38211/nighttotal: â‚¹1184541 (31 )

Island Sanctuary Key West - 3 Bedroom / 2 Bathroom With Pool And Parking!

3 2
apartment , Key West
This Key West holiday home, situated in Midtown, is six blocks from White Street Pier and Higgs Beach, and less than 1.6 kilometres from Key West International Airport and Duval Street.
The 142-square-metre property boasts three bedrooms, two bathrooms, a private pool with a splash pad, and a fully equipped kitchen; it comfortably accommodates up to six guests and includes a bonus office space.
Apartment ∙ 2 Bedrooms ∙ 8 Guests - Key West, FL
10 1 review
Key West, FL
28/06 – 02/07
₹74806/nighttotal: â‚¹299224 (4 )

Apartment ∙ 2 Bedrooms ∙ 8 Guests

2 4
apartment , Key West
This Key West apartment, situated in the downtown area with a balcony overlooking Duval Street, offers easy walking access to numerous attractions.
The two-bedroom, one-bathroom dwelling sleeps eight guests, featuring a fully equipped kitchen with a stove, refrigerator, dishwasher, and Keurig coffee machine, plus a washer/dryer, and free Wi-Fi.
Hidden Oasis 3 Blocks From Duval - Key West, FL
9.6 100 reviews
Key West, FL
30/10 – 04/11
₹53835/nighttotal: â‚¹269175 (5 )

Hidden Oasis 3 Blocks From Duval

1 2
cottage , Key West
This charming cottage is situated just a short walk from Duval Street, Key West Cemetery, and the waterfront, offering easy access to the island's vibrant attractions and the beautiful ocean. It has received excellent reviews from previous guests, highlighting its convenient location and comfortable amenities.
The cottage spans 47 square meters and comfortably accommodates up to four guests in one bedroom and one bathroom. It features a private terrace, shared pool access, a barbecue area, a fully equipped kitchen, laundry facilities, and parking, ensuring a relaxing and enjoyable stay.

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

Fontana At Azul Mansion Key West - Key West, FL
Key West, FL
22/08 – 29/08
₹21661/nighttotal: â‚¹151627 (7 )

Fontana At Azul Mansion Key West

1 2
house , Key West
FONTANA at Azul Mansion, a centrally located Key West property, is 0.6km from the city centre, 1.9km from both the Key West Aquarium and Mallory Dock, and a 12-minute walk from South Beach.
This self-catering apartment offers one bedroom, one bathroom, sleeps two, and includes a private pool, tennis court, parking, and Wi-Fi; enjoy nearby attractions such as the Ernest Hemingway Home and Museum and Duval Street.
Pool View 3br Residence | Beachside Resort - Key West, FL
Key West, FL
27/06 – 28/06
₹113262/nightfor 1 night

Pool View 3br Residence | Beachside Resort

3 7
apartment , Key West
This three-bedroom flat is located on seven acres overlooking the Gulf of Mexico in north Key West, approximately 10 minutes by car or shuttle from Duval Street.
This expansive condo offers accommodation for eight guests, featuring a private balcony with resort pool views, a heated swimming pool, hot tub, ocean marina, and on-site dining at Tavern N Town and Chicken Walk, with electric vehicle charging stations available for a nightly fee.
Key Wes't Best- Upgraded Condo 5 Mins To Smathers Beach Fantastic Value - Key West, FL
9.6 249 reviews
Key West, FL
11/07 – 18/07
₹53955/nighttotal: â‚¹377685 (7 )

Key Wes't Best- Upgraded Condo 5 Mins To Smathers Beach Fantastic Value

2 4
apartment , Key West
This beachfront apartment is located just a 15-minute walk from Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, and within 3 miles of Duval Street and Mallory Square, offering easy access to Key West's attractions. The property has consistently received excellent ratings for cleanliness, location, and overall guest experience.
The apartment features two bedrooms and two bathrooms, comfortably accommodating up to six guests. It provides a range of amenities, including a swimming pool, jacuzzi, sauna, fitness centre, tennis court, and a private terrace or balcony, ensuring a relaxing and enjoyable stay.
Heated Rooftop Pool, Gated Parking - Casa Caribe - Key West, FL
8.8 25 reviews
Key West, FL
06/01 – 08/01
₹115629/nighttotal: â‚¹231258 (2 )

Heated Rooftop Pool, Gated Parking - Casa Caribe

2 5
apartment , Key West
This Key West apartment, a two-storey townhouse in the Historic District, is situated steps from the Southernmost Point buoy and a short 1.6km walk from Key West's downtown attractions on Duval Street.
The 116 square metre property boasts a spacious layout with two bedrooms, three bathrooms, and sleeps six, including a queen sofa bed, plus a private deck, rooftop pool access, in-unit laundry, and off-street parking.

Frequently asked questions about holiday rentals in Key West, FL

  • What should a first-time visitor not miss in Key West, FL?

    You really must visit the Southernmost Point of the Continental US, it's iconic. You can't miss the Hemingway House, it's full of history and six-toed cats. And for a taste of Key West's history, visit the Fort Zachary Taylor Historic State Park.
  • What are the best Airbnb and vacation rentals in Key West, FL?

    Leaward Isle Island Retreat, Mango Hideaway @ The Eyebrow House Off Duval and At Mine | Lovely Suite Steps From Duval Street are the most popular Airbnb and vacation rentals in Key West, FL among travelers.

  • 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 the heart of Key West, with lots of shops, restaurants, and bars. If you want a quieter stay, consider the historic Bahama Village, known for its vibrant culture and colourful houses.
  • 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 favourite for kids, and the Butterfly Conservatory is a beautiful place to learn about exotic insects. For some outdoor fun, the Key West Wildlife Center is a great place to see native animals.
  • 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?

    Key West is popular year-round, but if you want to avoid the crowds and get the best deals, book your vacation rental in the shoulder seasons, like April-May or September-October.
  • What are the best rentals for families and kids in Key West, FL?

    The best rentals for families and kids in Key West, FL are Leaward Isle Island Retreat, Mango Hideaway @ The Eyebrow House Off Duval and Key West Villas.

  • 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 Fantasy Fest in October is a wild and colourful celebration, and the Key West Songwriters Festival in May is great for music lovers. The Hemingway Days Festival in July is a fun event celebrating the famous author.
  • What are the best rentals or Airbnbs with a jacuzzi in Key West, FL?

    The best vacation rentals or Airbnb with a jacuzzi in Key West, FL are Leaward Isle Island Retreat, Mango Hideaway @ The Eyebrow House Off Duval and Key West Villas.

  • 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?

    Take a stroll along Duval Street and enjoy the street performers, or visit the Key West Cemetery for a unique and interesting historical experience. You can also enjoy the free sunset celebrations at Mallory Square.
  • What are the best restaurants with local dishes in Key West, FL?

    For authentic Key West cuisine, try the Blue Heaven for their famous chicken and waffles, or the Hogfish Bar for their fresh seafood. The Cuban Coffee Queen is a great spot for a traditional Cuban breakfast.
  • What are the best walking or cycling routes in Key West, FL?

    The Key West Historic Seaport is a great place to start a walk or bike ride. The route along the waterfront offers stunning views, and you can also explore the charming streets of Old Town.
  • Are there pet-friendly attractions in Key West, FL?

    The Key West Butterfly & Nature Conservatory welcomes well-behaved dogs on a leash, and many of the beaches in Key West allow dogs, but make sure to check the specific rules.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than hotels, and often come with amenities like kitchens and laundry facilities. They can also be more affordable, especially for larger groups or families.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular destination for watersports, with great opportunities for sailing, fishing, diving, and kayaking. You can also find tennis courts and golf courses in the area.

Destinations nearby

Best Key West, FL holiday rentals with a balcony

Newly Furnished Suite With Pool, Hot Tub, Tennis, Balcony, Parking - Dog Ok - Key West, FL
8.6 124 reviews
Key West, FL
14/10 – 16/10
₹28040/nighttotal: â‚¹56080 (2 )

Newly Furnished Suite With Pool, Hot Tub, Tennis, Balcony, Parking - Dog Ok

2 2
apartment , Key West
This two-bedroom flat, located in the Sunrise Suites resort community on Key West's eastern side, offers an oceanfront setting with easy access to Smathers Beach and Ernest Hemingway's former home, approximately 1.6 kilometres away.
Boasting 72 square meters of living space, this accommodation accommodates up to six guests and features a private balcony, air conditioning, a swimming pool, jacuzzi, and allows one dog, with convenient private parking available.
Oceanfront Oasis Smathers Beach Condo Sunrise Views Island Charm Book Today - Key West, FL
9.8 17 reviews
Key West, FL
06/07 – 09/07
₹48131/nighttotal: â‚¹144393 (3 )

Oceanfront Oasis Smathers Beach Condo Sunrise Views Island Charm Book Today

2 6
apartment , Key West
This oceanfront Key West apartment, situated in the La Brisa complex on Smather's Beach, offers direct access to the beach and is within easy reach of attractions such as the Southernmost Point and the Ernest Hemingway Home and Museum.
The 111 square metre (1194 square feet) property boasts three bedrooms, two bathrooms, sleeping six guests comfortably, and features a fully equipped kitchen, a private terrace, a shared heated swimming pool, hot tub, sauna and a stackable washer/dryer.
Apartment ∙ 4 Bedrooms ∙ 12 Guests - Key West, FL
Key West, FL
01/08 – 08/08
₹94694/nighttotal: â‚¹662858 (7 )

Apartment ∙ 4 Bedrooms ∙ 12 Guests

4 11
apartment , Key West
This Key West apartment, situated on the second floor in the downtown area, offers easy walking access to numerous attractions.
Sleeping up to twelve guests, this four-bedroom, three-bathroom dwelling boasts a private hot tub, a balcony, and a convenient kitchenette; two pets under 40 lbs are welcome for a nightly fee.
Charming 2nd-story Apartment With Balcony & Lighthouse View - Walk Everywhere - Key West, FL
8.8 16 reviews
Key West, FL
14/10 – 16/10
₹37872/nighttotal: â‚¹75744 (2 )

Charming 2nd-story Apartment With Balcony & Lighthouse View - Walk Everywhere

1 2
apartment , Key West
This one-bedroom flat is located in Old Town Key West, a short walk from Duval Street and the Key West Lighthouse, with the Ernest Hemingway Home and Museum and Southernmost Point nearby.
This 46 square metre apartment offers accommodation for two guests and features a private balcony, a modern kitchen, air conditioning, free WiFi, and concierge services, with jet skiing and cycling opportunities in the vicinity.

Best Key West, FL holiday rentals with parking

Off The Hook - 3 Bedroom / 3 Bathroom W/ Pool & Parking - Key West, FL
9.2 5 reviews
Key West, FL
29/12 – 27/01
₹62431/nighttotal: â‚¹1810499 (29 )

Off The Hook - 3 Bedroom / 3 Bathroom W/ Pool & Parking

3 2
apartment , Key West
This three-bedroom, three-bathroom apartment is situated in Key West's New Town, less than 1.6 kilometres from Duval Street, local beaches, and Garrison Bight Marina, offering private gated parking suitable for boat trailers.
This 139 square metre holiday home accommodates up to seven guests, featuring a private swimming pool, impact-resistant windows, air conditioning, and a fully equipped kitchen, with beach chairs and towels provided for convenience.
Get Your Island Stlye On! - Key West, FL
9.6 84 reviews
Key West, FL
11/07 – 18/07
₹46515/nighttotal: â‚¹325605 (7 )

Get Your Island Stlye On!

1 4
cottage , Key West
This charming cottage is located on Duval Street, just a short walk from the Ernest Hemingway House and Museum and Fort Zachary Taylor Historic State Park, placing you in the heart of Key West's lively atmosphere. This property has received excellent reviews from previous guests.
The cottage offers 48 square metres of space, comfortably accommodating up to four guests, and features a well-equipped kitchen, a private patio, and a laundry facility. Guests can also enjoy the use of a barbecue area, a spa, and parking on site.
Hemingways Atlantic Retreat - Key West, FL
9.0 124 reviews
Key West, FL
06/07 – 09/07
₹56491/nighttotal: â‚¹169473 (3 )

Hemingways Atlantic Retreat

2 6
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.
The Larks Landing By Last Key Realty - Key West, FL
8.0 1 review
Key West, FL
30/12 – 10/01
₹69424/nighttotal: â‚¹763664 (11 )

The Larks Landing By Last Key Realty

1 5
apartment , Key West
This Key West apartment, located at Larks Landing, is less than a kilometre from Key West International Airport and within a 6-8 km radius of attractions such as the Southernmost Point, Ernest Hemingway Home, Mallory Square, and Duval Street.
The 74 square metre dwelling boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, swimming pool, jacuzzi, spa, fitness centre, tennis court, parking, and free Wi-Fi.
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