Holiday Rentals in Key West, FL

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Key West, FL holiday rentals
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3183 Holiday Rentals and Airbnb in Key West, FL

Best family friendly Key West, FL holiday rentals

Among the 3183 accommodations in Key West, FL, here are the 4 best family friendly rentals

Luxury Key West Compound With Pool, Guest Cottage, And Walkable Access To Duval - Key West, FL
10 6 reviews
Key West, FL
29/12 – 27/01
NZ$1945/nighttotal: NZ$56405 (29 )

Luxury Key West Compound With Pool, Guest Cottage, And Walkable Access To Duval

4 2
apartment , Key West
This charming cottage is situated in the Historic District of Old Town Key West, just a short walk from the Atlantic Ocean, beachside restaurants, and the Southernmost Point of the United States. It has consistently received excellent guest reviews, indicating a high level of satisfaction.
The 279 square metre property comfortably accommodates up to 10 guests and features a separate guest cottage, a private backyard with a heated saltwater pool and spa, and a chef's kitchen with top-of-the-line appliances. Guests can enjoy modern amenities, such as air conditioning, a large-screen TV, and a washer and dryer, as well as a propane grill, outdoor dining, and an outdoor shower.
Knowles Main House With Pool - Key West, FL
9.8 28 reviews
Key West, FL
06/07 – 09/07
NZ$2777/nighttotal: NZ$8331 (3 )

Knowles Main House With Pool

5 6
apartment , Key West
This Key West property enjoys a central location, offering easy access to the island's attractions, although precise distances to specific landmarks aren't specified.
The five-bedroom, four-bathroom house sleeps ten guests, boasting a private pool, rooftop deck, and convenient driveway parking for two cars; each bedroom includes a private bathroom, ensuring maximum privacy for large groups.
Poolside Paradise/3bed, 2.5 Bath/pvt. Pool And Spa - Key West, FL
10 20 reviews
Key West, FL
11/07 – 18/07
NZ$1761/nighttotal: NZ$12327 (7 )

Poolside Paradise/3bed, 2.5 Bath/pvt. Pool And Spa

1 4
apartment , Key West
This two-bedroom holiday let is situated just 80 metres from Duval Street, offering excellent access to Key West's attractions.
This architect-designed property, built in 1993, accommodates up to six guests and features a private heated swimming pool and spa, a fully equipped kitchen, and a washer/dryer.
Vacation Rental In Coral Hammock - Key West, FL
9.7 188 reviews
Key West, FL
06/01 – 08/01
NZ$1625/nighttotal: NZ$3250 (2 )

Vacation Rental In Coral Hammock

1 5
apartment , Stock Island
This three-bedroom, three-bathroom house is located in the Coral Hammock gated community on Stock Island, a short drive (approximately 8km) from Key West and its attractions.
The 130 square metre property offers a spacious layout, sleeping up to six guests, and boasts a private swimming pool, fitness centre access, and all necessary kitchen appliances; beach gear and baby equipment are also available.

Best Key West, FL holiday rentals with a pool

Among the 3183 accommodations in Key West, FL, here are the 4 best rentals with a pool

Captiva At Azul Mansion Key West - Key West, FL
Key West, FL
08/07 – 09/07
NZ$599/nightfor 1 night

Captiva At Azul Mansion Key West

1 2
house , Key West
CAPTIVA at Azul Mansion, a Key West holiday home, is conveniently located 1.9km from Key West International Airport and a 12-minute walk from South Beach, close to attractions such as the Key West Aquarium and Mallory Square.
This one-bedroom, one-bathroom property sleeps two guests and offers free Wi-Fi, on-site parking, a swimming pool, and a terrace, all within easy reach of Duval Street, the Ernest Hemingway Home and Museum, and the Southernmost Point buoy.
**The Contented Crane @ Old Town** Home & Pool Near Duval + Last Key Services... - Key West, FL
9.9 350 reviews
Key West, FL
01/08 – 08/08
NZ$5036/nighttotal: NZ$35252 (7 )

**The Contented Crane @ Old Town** Home & Pool Near Duval + Last Key Services...

8 11
apartment , Key West
This charming house is located in the Key West Historic District, just a short walk from Duval Street, the Ernest Hemingway Home and Museum, and the Key West Cemetery. The property has received excellent ratings for its location, cleanliness, and overall experience.
The spacious home has six bedrooms, comfortably accommodating up to eight guests. Enjoy the private pool, garden, and terrace, as well as modern amenities like a fully equipped kitchen, air conditioning, and free Wi-Fi.
Doubletree By Hilton Grand Key Resort - Key West, FL
8.3 1662 reviews
Key West, FL
27/06 – 04/07
NZ$456/nighttotal: NZ$3192 (7 )

Doubletree By Hilton Grand Key Resort

1 2
resort , Key West
The Doubletree By Hilton Grand Key Resort offers a convenient base on the outskirts of historic Old Town Key West, just a 2-minute drive from Key West International Airport, Duval Street, and Old Town, with a complimentary shuttle service to these key areas and Smathers Beach.
This resort features a swimming pool with a poolside tiki bar, on-site dining at Palm Haven Restaurant and Sanctuary Lounge, and guest rooms equipped with flat-screen TVs and mini-refrigerators, with select rooms offering balconies and sofa beds, alongside bicycle rentals and a fitness centre.
Sombreroreef Light Suite - Key West, FL
10 41 reviews
Key West, FL
03/07 – 05/07
NZ$1169/nighttotal: NZ$2338 (2 )

Sombreroreef Light Suite

1 2
house , Key West
This Key West apartment, part of a five-unit compound, enjoys a prime Old Town location just half a block from Duval Street, steps from the Hemingway House and Key West Lighthouse Museum, and within walking distance of Fort Zachary Taylor State Park.
The one-bedroom, one-bathroom flat sleeps four, featuring a fully equipped kitchen, private porch with island views, a king-size bed, queen-size sofa bed, and access to a shared pool; the entire compound is available to rent for larger groups.

Frequently asked questions about holiday rentals in Key West, FL

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

    You absolutely must visit the Southernmost Point of the Continental US, a landmark in Key West. If you're a history buff, the Ernest Hemingway Home and Museum is a must-see. And don't forget to take a sunset cruise to enjoy the stunning views of the Florida Keys.
  • What are the best Airbnb and holiday 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 popular choice, with its historic architecture, vibrant nightlife, and proximity to attractions. If you prefer a more relaxed vibe, consider the quieter neighbourhoods of New Town or the Sunset Key. But if you're looking for a more affordable option, you can find some great deals in the Stock Island neighbourhood.
  • 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 place to learn about the marine life of the Florida Keys. The Butterfly Conservatory is also a popular choice, with its beautiful butterflies and exotic plants. For a fun day out, visit the Key West Waterfront and enjoy the various water activities on offer, such as kayaking and paddle boarding.
  • What are the best holiday 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 seasons, from April to May and September to October. You'll avoid the crowds and enjoy more affordable prices. But if you're looking for a more lively experience, the peak season from December to April is when the island comes alive with festivals and events.
  • 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 Hemingway Days festival in July is a must-see, with its literary readings, fishing tournaments, and a look-alike contest. The Fantasy Fest in October is a colourful and lively celebration with parades, parties, and costumes. If you're looking for something more relaxed, the Key West Sunset Celebration is a beautiful way to end the day.
  • What are the best rentals or Airbnbs with a jacuzzi in Key West, FL?

    The best holiday rentals or Airbnb with a jacuzzi in Key West, FL are Leaward Isle Island Retreat, Key West Villas and Downtown Retreat - A++ Location W\/ Private Heated Pool\/hot Tub.

  • 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 soak up the atmosphere. Visit the Key West Historic Seaport and explore the historic ships and boats. And don't forget to enjoy the free concerts and events held at the various parks and squares around the island.
  • What are the best restaurants with local dishes in Key West, FL?

    For fresh seafood, try The Stoned Crab or The Blue Heaven. For a taste of Key West's history, visit The Cuban Coffee Queen. And if you're looking for something a little more upscale, try The Restaurant at the Ocean Key Resort.
  • What are the best walking or cycling routes in Key West, FL?

    The Key West Greenway is a great option for a scenic walk or bike ride. It stretches for about 10 kilometres and passes by some of the island's most beautiful spots. You can also take a walk or bike ride along the historic Duval Street, stopping to enjoy the shops and restaurants along the way.
  • Are there pet-friendly attractions in Key West, FL?

    Yes, many attractions in Key West are pet-friendly, including the Key West Historic Seaport, the Key West Aquarium, and the Butterfly Conservatory. Many restaurants and shops also welcome well-behaved dogs. Just be sure to check with the individual establishment for their pet policy.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than a hotel room. They often come with amenities such as a kitchen, laundry facilities, and a private balcony or patio. You can also find vacation rentals in a variety of locations, from the heart of Old Town to the quieter neighbourhoods on the outskirts of the island.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a great place for water sports, with opportunities for swimming, kayaking, paddleboarding, and fishing. The Key West Waterfront is a popular spot for these activities. For golfers, there is the Key West Golf Club, which offers a challenging 18-hole course with stunning views of the ocean.

Destinations nearby

Best Key West, FL holiday rentals with a balcony

**Star Of The Seaport @ Old Town** Huge Home & Pool + Last Key Services... - Key West, FL
10 93 reviews
Key West, FL
01/08 – 08/08
NZ$5373/nighttotal: NZ$37611 (7 )

**Star Of The Seaport @ Old Town** Huge Home & Pool + Last Key Services...

6 11
apartment , Key West
This charming Key West house is located in the Historic District, just a 1.5 kilometre walk from Duval Street and a 3 kilometre walk from Mallory Square, making it ideal for exploring the island's vibrant atmosphere. The house has excellent user ratings and is perfect for families or groups.
The property has five bedrooms and five bathrooms, spanning 398 square metres, offering ample space for relaxation. Guests can enjoy a private pool, a fully equipped kitchen, a washing machine, a refrigerator, and a Smart TV.
Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking - Key West, FL
8.9 191 reviews
Key West, FL
29/12 – 31/12
NZ$2610/nighttotal: NZ$5220 (2 )

Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking

2 2
house , Key West
The Tortuga by Brightwild-Pool, Parking & Pets! is situated in Key West, just over 6km from the famous Duval Street and Mallory Square.
This two-bedroom property, spanning 74 square metres, features a private swimming pool, a hot tub, and a fully equipped kitchen, as well as free parking and Wi-Fi.
The Curry Poolside | Ground Floor Two Queens - Key West, FL
9.4 6 reviews
Key West, FL
26/10 – 28/10
NZ$724/nighttotal: NZ$1448 (2 )

The Curry Poolside | Ground Floor Two Queens

1 4
apartment , Key West
This Key West apartment, situated in the historic Curry Mansion (built 1869) on the Historic District, is half a block from Duval Street, offering easy access to Mallory Square and numerous attractions.
The one-bedroom, one-bathroom flat sleeps four guests and includes access to a shared heated pool, on-site parking, a terrace, and laundry facilities with provided detergent and dryer sheets; pets are welcome.
68 M² Studio Flat ∙ 3 Guests - Key West, FL
10 8 reviews
Key West, FL
20/07 – 27/07
NZ$686/nighttotal: NZ$4802 (7 )

68 M² Studio Flat ∙ 3 Guests

1 1
studio , Key West
This studio apartment is situated mere blocks from downtown Key West, offering direct ocean views and convenient access to Duval Street's attractions.
This 68 square metre loft-style apartment accommodates up to three guests and features a custom kitchen, air conditioning, a private patio, and exclusive access to the Hilton Curio Resort's beach and pool, with beach gear provided.

Best Key West, FL holiday rentals with parking

Hemingways Atlantic Retreat - Key West, FL
9.0 124 reviews
Key West, FL
06/07 – 09/07
NZ$1018/nighttotal: NZ$3054 (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.
Oyster's Pearl - Key West, FL
Key West, FL
29/12 – 27/01
NZ$896/nighttotal: NZ$25984 (29 )

Oyster's Pearl

1 2
house , Key West
OYSTER'S PEARL is a centrally located apartment in Key West, situated 700 metres from Duval Street and a 12-minute walk from Fort Zachary Taylor State Park Beach, with Mallory Square and the Southernmost Point in close proximity.
This 63 square metre dwelling offers one bedroom and one bathroom, accommodating up to three guests with a fully equipped kitchen, air conditioning, Wi-Fi, private parking, and access to an on-site swimming pool and a water park.
The Geiger Suite At Inn On Fleming Key West! - Key West, FL
9.0 3 reviews
Key West, FL
24/07 – 25/07
NZ$1030/nightfor 1 night

The Geiger Suite At Inn On Fleming Key West!

2 4
house , Key West
THE GEIGER SUITE at the Inn on Fleming Key West offers a central location, a short walk from Simonton Street Beach and the Ernest Hemingway Home and Museum, and under 3.2km from Key West International Airport.
This self-catering property boasts a 32 square metre floor area, comprising two bedrooms, one bathroom, and accommodating up to four guests, with amenities including a swimming pool, tennis court, free parking, and Wi-Fi.
Completely Renovated Condo With Pool, Hot Tub, & Private Patio - Free Parking - Key West, FL
9.0 138 reviews
Key West, FL
11/07 – 18/07
NZ$1024/nighttotal: NZ$7168 (7 )

Completely Renovated Condo With Pool, Hot Tub, & Private Patio - Free Parking

2 4
apartment , Key West
This Key West condominium is located by the sea, a short drive from Key West International Airport and near Southernmost Point and the Ernest Hemingway Home and Museum.
This 72 square metre flat offers 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests, featuring a renovated interior, a fully-equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, and parking, with nearby access to Smathers Beach and water activities.
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