Compare Vacation Rentals & Airbnb in Key West, FL

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Key West, FL vacation rentals
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3183 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

Two-bedroom, Two-bath Condo Close To The Ocean. Full Kitchen, Living R & Balcony - Key West, FL
9.2 45 reviews
Key West, FL
24/07 – 25/07
$581/nightfor 1 night

Two-bedroom, Two-bath Condo Close To The Ocean. Full Kitchen, Living R & Balcony

3 4
apartment , Key West
This two-bedroom Key West apartment is located within a 3km radius of the Fort East Martello Museum and Gallery, Key West Art and Historical Society, and Key West Tropical Forest and Botanical Garden, with Smathers Beach and Lower Keys Medical Center within 5km.
The 74 square metre apartment features a fully equipped kitchen, a private balcony, and a swimming pool, comfortably accommodating up to six guests.
Sunnyside Up - Key West, FL
9.5 83 reviews
Key West, FL
02/07 – 03/07
$1672/nightfor 1 night

Sunnyside Up

1 5
apartment , Key West
Sunnyside Up, a Key West apartment, enjoys a central location, a short 1.3km walk from Higgs Beach and within 1.6km of the Ernest Hemingway Home and Museum and the Southernmost Point.
This 108 square metre, two-bedroom flat sleeps eight guests and offers a fully equipped kitchen, private patio, in-unit laundry, swimming pool access, and free Wi-Fi; nearby attractions include South Beach, Rest Beach, and Fort Zachary Taylor State Park Beach.
Osprey Studio @ The Colony-sleeps Up To 4 - Key West, FL
9.4 61 reviews
Key West, FL
02/07 – 07/07
$654/nighttotal: $3270 (5 )

Osprey Studio @ The Colony-sleeps Up To 4

1 2
studio , Key West
Osprey studio, a ground-floor apartment in Key West's Old Town Colony neighbourhood on Olivia Street, is situated two blocks from Duval Street, offering easy access to restaurants and bars and proximity to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 45-square-metre self-catering unit sleeps four, featuring a queen bed, a couch, a kitchenette with microwave and refrigerator, a bathroom with shower, a private deck, and access to a shared swimming pool and spa; nearby activities include jet skiing and kayaking.
113 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.7 39 reviews
Key West, FL
13/09 – 27/09
$578/nighttotal: $8092 (14 )

113 M² House ∙ 2 Bedrooms ∙ 6 Guests

2 2
house , Key West
This Key West townhome is situated on upper Duval Street, offering convenient access to shops, restaurants, and attractions such as the Butterfly Conservatory and the Southernmost Point.
The 121 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, community pool access, WiFi, and three TVs.

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

Coconut Mallory Studio-402 - Key West, FL
9.0 14 reviews
Key West, FL
20/06 – 27/06
$260/nighttotal: $1820 (7 )

Coconut Mallory Studio-402

1 2
apartment , Key West
This studio apartment at Coconut Mallory Resort and Marina is situated approximately 3.2 kilometres from Smathers Beach, providing easy access to Key West attractions such as Fort Jefferson, the Shipwreck Museum, and the Ernest Hemingway Home.
This deluxe studio condo, accommodating up to two guests, features a kitchenette with essential appliances, a spacious bathroom with a walk-in shower, and an outdoor patio, with resort amenities including two swimming pools, a hot tub, and hammocks for relaxation.
Tropical Old Town Bungalow - Key West, FL
9.8 287 reviews
Key West, FL
22/08 – 29/08
$397/nighttotal: $2779 (7 )

Tropical Old Town Bungalow

1 2
apartment , Key West
This Key West bungalow, situated in the White Street Art Gallery District, is less than 1.6km from the beach and 1.9km from Duval Street.
The one-bedroom apartment sleeps two, features a fully equipped kitchen, in-unit laundry, private balconies, and access to a shared pool and barbecue area, all within easy reach of Bay View Park.
Poolside Suite - Key West, FL
9.0 330 reviews
Key West, FL
20/06 – 27/06
$519/nighttotal: $3633 (7 )

Poolside Suite

1 1
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.
Road's End | Prime Old Town Location! Updated Home W/ Pool - Key West, FL
9.8 14 reviews
Key West, FL
24/07 – 25/07
$346/nightfor 1 night

Road's End | Prime Old Town Location! Updated Home W/ Pool

1 4
apartment , Key West
This pet-friendly holiday let is situated in Key West's Old Town district, a 5-minute walk from Duval Street and the Ernest Hemingway Home and Museum, offering convenient access to seaside activities.
This 68 square metre flat, suitable for up to four guests, features two bedrooms, two bathrooms, air conditioning, a full kitchen with a dishwasher, and on-site laundry facilities, with a swimming pool available.

Frequently Asked Questions about vacation rentals in Key West, FL

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

    You've got to see the sunset at Mallory Square, it's a real Key West institution. And don't forget to visit the Ernest Hemingway Home and Museum, it's a fascinating place to learn about the famous author's life in Key West.
  • 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 choice, it's right in the heart of everything, with lots of restaurants, shops, and attractions. If you're looking for something a bit quieter, try the historic Bahama Village, it's got a more laid-back vibe.
  • 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 big hit with kids, they've got all sorts of fascinating sea creatures. The Butterfly Conservatory is another great option, with hundreds of beautiful butterflies fluttering around you.
  • 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?

    You'll want to book well in advance, especially if you're travelling during peak season, which is from December to April. If you're looking for a bit more flexibility, try booking in the shoulder seasons, May to June or September to November.
  • 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 big one, with lots of food and drink tastings. The Hemingway Days Festival is another great option, celebrating the life and work of Ernest Hemingway. If you're here in October, don't miss Fantasy Fest, it's a wild and colourful celebration.
  • 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, Key West Villas and Southernmost Sanctuary.

  • 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, it's full of shops, bars, and restaurants. You can also visit the Key West Cemetery, it's a fascinating place to wander around and learn about the history of Key West. And don't forget to check out the free sunset celebrations at Mallory Square.
  • What are the best restaurants with local dishes in Key West, FL?

    For a taste of Key West, try the conch fritters at The Waterfront Brewery. If you're looking for something a bit fancier, head to Latitudes for their award-winning seafood. And for a taste of Cuban cuisine, check out El Siboney.
  • What are the best walking or cycling routes in Key West, FL?

    The Truman Waterfront is a great place for a walk or cycle, with beautiful views of the harbour. For a longer ride, try the scenic route along the Overseas Highway, it's a stunning drive with views of the ocean and the Keys.
  • Are there pet-friendly attractions in Key West, FL?

    Yes, there are plenty of pet-friendly attractions in Key West. You can take your dog to the beach at Higgs Beach, or for a walk along the Truman Waterfront. Many restaurants and shops also welcome well-behaved dogs.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than hotels, and they're often a more affordable option. You'll also have access to a kitchen, so you can save money by cooking some of your own meals.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular spot for watersports, with plenty of opportunities for fishing, sailing, and kayaking. You can also find golf courses, tennis courts, and a fitness centre.

Destinations nearby

Best Key West, FL vacation rentals with a balcony

Waterfront Dock Pool Condo Near Duval St Pet Ok - Key West, FL
9.8 311 reviews
Key West, FL
24/07 – 28/07
$1616/nighttotal: $6464 (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.
Absolutely Paradise - Key West, FL
10 1 review
Key West, FL
24/07 – 28/07
$1633/nighttotal: $6532 (4 )

Absolutely Paradise

3 7
house , Key West
Absolutely Paradise, a Key West house, is centrally located less than 1.6km from Duval Street, South Beach, and Southernmost Point, offering easy access to Key West International Airport and attractions such as Fort Zachary Taylor State Park Beach and the Ernest Hemingway Home and Museum.
This 174 square metre property boasts three bedrooms, two bathrooms, sleeps fifteen guests, and includes a private pool, tennis court, free parking, a fully equipped kitchen, and free Wi-Fi.
Charming, Colorful Two-story Apartment With Two Balconies - Walk Everywhere - Key West, FL
9.0 18 reviews
Key West, FL
14/10 – 16/10
$554/nighttotal: $1108 (2 )

Charming, Colorful Two-story Apartment With Two Balconies - Walk Everywhere

1 2
apartment , Key West
This historic 1890s apartment, formerly a Cuban bodega and potter's studio, is located in Old Town Key West, a short walk from Duval Street and near the Ernest Hemingway Home and Museum and the Southernmost Point.
This 46 square metre flat offers 1 bedroom, 2 bathrooms, sleeps 2 guests, and features a fully equipped kitchen, air conditioning, private balconies, and concierge service, with water sports and cycling opportunities nearby.
**Suite Sanctuary @ The Beach** Oceanfront Condo & Pool + Last Key Services... - Key West, FL
9.8 30 reviews
Key West, FL
13/09 – 27/09
$590/nighttotal: $8260 (14 )

**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.

Best Key West, FL vacation rentals with parking

Key West Condo Close To The Ocean. 1 Mile To Smathers & 3 Miles To Duval St. \N - Key West, FL
9.4 113 reviews
Key West, FL
24/07 – 25/07
$581/nightfor 1 night

Key West Condo Close To The Ocean. 1 Mile To Smathers & 3 Miles To Duval St. \N

2 4
apartment , Key West
This two-bedroom apartment, ideal for families or groups of up to six, is located in Key West, just 2 kilometres from the Fort East Martello Museum and Gallery and 3 kilometres from Smathers Beach.
The 74 square metre apartment offers a fully equipped kitchen, a private balcony, a swimming pool, a fitness centre and a jacuzzi, perfect for a relaxing getaway.
Sea Breeze -Great Location! - Key West, FL
9.3 337 reviews
Key West, FL
25/07 – 27/07
$1209/nighttotal: $2418 (2 )

Sea Breeze -Great Location!

2 3
house , Key West
This Key West house, named Sea Breeze, enjoys a prime location less than 1km from South Beach, Duval Street, and the Southernmost Point, offering easy access to Fort Zachary Taylor State Park Beach and the Ernest Hemingway Home and Museum.
The 74 square metre property comprises two bedrooms, one bathroom, a fully equipped kitchen including a dishwasher, and a terrace; free Wi-Fi and on-site parking are also provided for guests.
53' Yacht Sleeps 8 & Selfdrive 20' Pontoon Fishing Lobstering Snorkeling Sandbar - Key West, FL
Key West, FL
02/07 – 07/07
$513/nighttotal: $2565 (5 )

53' Yacht Sleeps 8 & Selfdrive 20' Pontoon Fishing Lobstering Snorkeling Sandbar

3 2
apartment , Key West
This unique offshore anchoring offers a secluded yacht experience near Key West Island, accessible by boat from downtown Key West, providing open water views and convenient access to landmarks such as the Ernest Hemingway Home and Museum, approximately 1.6 kilometres away.
This 3-bedroom, 2-bathroom yacht accommodates up to 8 guests and includes a smaller boat for exploration, fishing and snorkelling gear, a full indoor kitchen, and spacious outdoor decks, making it an ideal base for water activities and special occasions.
The Flagler Room At Inn On Fleming Key West! - Key West, FL
Key West, FL
21/12 – 18/01
$757/nighttotal: $21196 (28 )

The Flagler Room At Inn On Fleming Key West!

1 1
house , Key West
THE FLAGLER ROOM at the Inn on Fleming Key West offers a centrally located self-catering apartment, a short walk from Simonton Street Beach and Duval Street, and within 1.6km of Mallory Square and the Ernest Hemingway Home and Museum.
This 24 square metre studio apartment sleeps two, boasting a private bathroom, air conditioning, free Wi-Fi, a swimming pool, tennis court, and free on-site parking; all within easy reach of Key West's attractions.
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