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

Sunnyside Up - Shared Pool - Key West, FL
9.8 10 reviews
Key West, FL
25/07 – 27/07
NZ$1852/nighttotal: NZ$3704 (2 )

Sunnyside Up - Shared Pool

2 3
apartment , Key West
This Key West Historic District flat is a short walk from the Key West Firehouse Museum and Duval Street, and under 1.6 km from South Beach and the Southernmost Point.
This 108-square-metre self-catering apartment sleeps six, boasting two bedrooms, two bathrooms, a terrace, a garden, a swimming pool, and free internet access.
Downtown Paradise - Key West, FL
9.7 89 reviews
Key West, FL
02/07 – 03/07
NZ$2396/nightfor 1 night

Downtown Paradise

1 5
apartment , Key West
This Key West house, situated just off Duval Street, offers easy access to the island's attractions and nightlife.
Sleeping six guests, this three-bedroom, three-bathroom property boasts a private pool, fully equipped kitchen, in-house laundry, and two off-street parking spaces – a rare find in Key West.
Sea La Vie Suite - Pool View & Close To The Beach - Key West, FL
Key West, FL
20/06 – 27/06
NZ$615/nighttotal: NZ$4305 (7 )

Sea La Vie Suite - Pool View & Close To The Beach

2 2
apartment , Key West
This Key West residence is located 6.4 kilometres from the Southernmost Point and 6.9 kilometres from the Ernest Hemingway Home and Museum, offering a peaceful pool view near the beach and convenient access to attractions such as Duval Street (6.9 kilometres) and Mallory Dock (7.6 kilometres), with Key West International Airport a mere 0.9 kilometres away.
This two-bedroom, two-bathroom flat, spanning 74 square metres and accommodating up to 11 guests, features air conditioning, free Wi-Fi, a fully equipped kitchen, and a private balcony with a pool view, ensuring a comfortable stay for families and groups.
Heron Hideaway - Key West, FL
9.6 12 reviews
Key West, FL
26/10 – 28/10
NZ$1008/nighttotal: NZ$2016 (2 )

Heron Hideaway

1 4
apartment , Key West
This Key West apartment, a 17-minute walk from Higgs Beach and 3km from Key West International Airport, offers easy access to the Ernest Hemingway Home and Museum and Duval Street.
The 56-square-metre flat features one bedroom, one bathroom, sleeps seven guests, and includes a private pool, hot tub, fully equipped kitchen, and access to on-site spa and fitness facilities.

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

2 Bedroom 1 Bath Condo At Bayfront Suites & Marina - Cleaning Fee Included - Key West, FL
9.6 803 reviews
Key West, FL
05/10 – 19/10
NZ$768/nighttotal: NZ$10752 (14 )

2 Bedroom 1 Bath Condo At Bayfront Suites & Marina - Cleaning Fee Included

2 1
apartment , Key West
This apartment is located in the Meadows district of Key West, just a short walk from Duval Street, the Hemingway Home, and the beaches. It has consistently received excellent ratings for its location, cleanliness, and overall user experience. The apartment itself offers a comfortable and well-equipped space for your stay. Guests can enjoy a range of amenities including a swimming pool, tennis court, fitness centre, and a restaurant, as well as a private balcony and a fully equipped kitchen.
Kw Canalfront 3br: Htd Pool, Boat Tie-up, Pet Ok - Key West, FL
8.8 5 reviews
Key West, FL
30/12 – 10/01
NZ$1287/nighttotal: NZ$14157 (11 )

Kw Canalfront 3br: Htd Pool, Boat Tie-up, Pet Ok

1 5
apartment , Key West
This private Key West residence offers 66 feet of canal frontage with dockage, providing direct access to the Atlantic and Gulf, and is a short cycle of less than 1 kilometre to Key West's beaches, waterfront dining, Old Town, and Mallory Square.
This three-bedroom, one-and-a-half-bathroom holiday home accommodates up to six guests, featuring air conditioning, a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, a swimming pool, garden, parking, and high-speed Wi-Fi, with a boat ramp located just 100 metres away.
Sunshine Suite Condo  Enjoy Outdoor Hot Tub & Pool - Key West, FL
9.4 486 reviews
Key West, FL
24/07 – 25/07
NZ$896/nightfor 1 night

Sunshine Suite Condo Enjoy Outdoor Hot Tub & Pool

1 4
apartment , Key West
This two-bedroom apartment is situated in a family-friendly area of Key West, just a short walk from the beach and other popular attractions. The accommodation has received excellent ratings for its location, cleanliness, and overall experience.
The flat comfortably sleeps six guests, with a king-size bed in each bedroom and a queen-size pull-out sofa bed in the living room. The apartment features a fully equipped kitchen, a private balcony, and access to a range of on-site amenities, including a swimming pool, hot tub, tennis court, gym, BBQ area, and laundry facilities.
Salvador's Seclusion | Cozy Studio Retreat W/ Heated Pool - Key West, FL
8.6 51 reviews
Key West, FL
20/06 – 27/06
NZ$296/nighttotal: NZ$2072 (7 )

Salvador's Seclusion | Cozy Studio Retreat W/ Heated Pool

1 2
studio , Key West
This Old Town Key West flat is situated a short walk from Florida Keys beaches and Duval Street, within 1.6km of the Southernmost Point and South Beach.
The one-bedroom, one-bathroom apartment sleeps two, offering a private patio, in-unit laundry, a pool, and essential kitchen appliances; nearby attractions include the Ernest Hemingway Home and Museum.

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

Seas The Breeze  Poolside Condo Near The Beach - Key West, FL
Key West, FL
20/06 – 27/06
NZ$441/nighttotal: NZ$3087 (7 )

Seas The Breeze Poolside Condo Near The Beach

2 2
apartment , Key West
This condo is located in the Sunrise Suites Resort Community, on the quieter side of Key West, 10 kilometres from Old Town's Duval Street and Mallory Square, and a short drive to Smathers Beach.
This 74 square metre apartment offers two bedrooms and three bathrooms, accommodating up to six guests, with a fully equipped kitchen, a private balcony overlooking the pool, and access to resort amenities including a heated swimming pool and hot tub.
**Suite Sanctuary @ The Beach** Oceanfront Condo & Pool + Last Key Services... - Key West, FL
9.8 30 reviews
Key West, FL
02/07 – 07/07
NZ$1258/nighttotal: NZ$6290 (5 )

**Suite Sanctuary @ The Beach** Oceanfront Condo & Pool + Last Key Services...

3 2
apartment , Key West
This beachfront Key West condo is situated near Duval Street, Mallory Square, and Smathers Beach, all within a 4.8km radius.
The two-bedroom, two-bathroom apartment sleeps six, offering a fully equipped kitchen, private balcony, and access to a swimming pool, Jacuzzi, sauna, spa, fitness centre, and tennis court; free Wi-Fi is also included.
The Curry Poolside | Ground  Floor King - Key West, FL
9.2 5 reviews
Key West, FL
20/06 – 27/06
NZ$474/nighttotal: NZ$3318 (7 )

The Curry Poolside | Ground Floor King

1 1
apartment , Key West
This Key West apartment, situated in the Historic District, is half a block from Duval Street and within easy walking distance of attractions such as the Ernest Hemingway Home and Museum and Mallory Square.
The pet-friendly one-bedroom flat, sleeping two guests, in the Curry Mansion (built 1869), offers a shared heated pool, terrace, and laundry facilities, plus contactless check-in and a local guest experience manager.
Ocean Front Two Bedroom Residence - Key West, FL
Key West, FL
02/07 – 03/07
NZ$2097/nightfor 1 night

Ocean Front Two Bedroom Residence

2 5
apartment , Key West
This luxury beachfront resort condominium is located on seven acres in north Key West, 10 minutes by car from Duval Street and within easy reach of the Ernest Hemingway Home and Museum and Smathers Beach.
This two-bedroom, two-bathroom apartment sleeps six and features a fully-equipped kitchen, a private balcony with Gulf of Mexico views, and access to resort amenities including a heated swimming pool and hot tub.

Best Key West, FL holiday rentals with parking

Poolside Suite - Key West, FL
9.0 330 reviews
Key West, FL
20/06 – 27/06
NZ$693/nighttotal: NZ$4851 (7 )

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.
Scarlet At Scarlet Mango Inn Key West - Key West, FL
Key West, FL
20/06 – 21/06
NZ$903/nightfor 1 night

Scarlet At Scarlet Mango Inn Key West

1 2
house , Key West
SCARLET at Scarlet Mango Inn, a Key West apartment, enjoys a central location less than 0.4km from the city centre, a 10-minute walk from Simonton Street Beach, and under 1.6km from Mallory Square and Mallory Dock.
This air-conditioned one-bedroom, one-bathroom property sleeps two, offering free Wi-Fi, on-site parking, a swimming pool, and a terrace; nearby attractions include Duval Street, the Ernest Hemingway Home and Museum, and the Key West Aquarium.
Lady Admiral ~Sweet Cottage & Guest House With Private Heated Pool Off Duval! - Key West, FL
9.8 244 reviews
Key West, FL
24/07 – 28/07
NZ$2396/nighttotal: NZ$9584 (4 )

Lady Admiral ~Sweet Cottage & Guest House With Private Heated Pool Off Duval!

3 7
apartment , Key West
This charming cottage is situated in Old Town Key West, just 0.3 kilometres from South Beach and within walking distance of other popular beaches and attractions, making it an ideal base for exploring the island. The cottage has received excellent reviews from previous guests, highlighting its comfortable and convenient location.
The cottage offers 71 square metres of space, comfortably accommodating up to eight guests across three bedrooms and three bathrooms. It includes a range of amenities, including a private pool, a well-equipped kitchen, and concierge services, ensuring a relaxing and enjoyable stay.
Waterfront Dock Pool Condo Near Duval St Pet Ok - Key West, FL
9.8 311 reviews
Key West, FL
24/07 – 28/07
NZ$1989/nighttotal: NZ$7956 (4 )

Waterfront Dock Pool Condo Near Duval St Pet Ok

2 7
apartment , Key West
This waterfront Key West apartment, situated in the historic downtown area, is approximately 1.6km from Duval Street, the Historic Seaport, and the Hemingway House.
The 118 square metre property boasts two bedrooms (king and two queen-size beds), two bathrooms, accommodates six guests, and includes a private boat slip, heated pool access, and a balcony overlooking the harbour.
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