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Key West, FL vacation rentals
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Best Vacation rentals and Airbnb offers in Key West, FL

Best Key West, FL vacation rentals with a balcony

Osprey Colony - Key West, FL
Key West, FL
07/02 – 07/07
$437/nighttotal: $2185 (5 )

Osprey Colony

1 2
house , Key West
This Key West house rental, located in Osprey Colony, is a 7-minute walk from Duval Street, an 11-minute walk from South Beach, and 400 yards from the city center, placing you near the Southernmost Point and Ernest Hemingway Home and Museum.
This 480-square-foot Key West vacation home features one bedroom, one bathroom, accommodates seven guests, and includes a private balcony, swimming pool, tennis court, free Wi-Fi, and parking.
Waterfront Dock Pool Downtown Near Duval Pet - Key West, FL
9.8 8 reviews
Key West, FL
06/23 – 06/24
$663/nightfor 1 night

Waterfront Dock Pool Downtown Near Duval Pet

2 2
apartment , Key West
This waterfront condo is located in Key West's Meadows neighborhood, under 1 mile from Duval Street, the Historic Seaport, and Hemingway House, offering direct waterfront access with harbor views and an included boat slip.
This 1190 sq ft, 2-bedroom, 2-bathroom apartment accommodates up to 8 guests and features a private elevator, on-site parking, a shared heated pool, tiki bar, BBQ grills, and in-unit laundry.
Waterfront Dock Pool Key West Near Duval - Key West, FL
9.7 257 reviews
Key West, FL
07/02 – 07/03
$926/nightfor 1 night

Waterfront Dock Pool Key West Near Duval

2 5
apartment , Key West
This waterfront condo rental in historic Downtown Key West is located one mile from Duval Street and attractions like the Historic Seaport and Hemingway House.
The 1350-square-foot unit features two bedrooms (king and two queen beds), two bathrooms, a pull-out couch (sleeps six), a fully equipped kitchen, washer/dryer, private balcony with pool and dock access, reserved boat slip (up to 40ft), and on-site amenities including a heated pool, tiki bar & grill, and bike rentals.
Pilars Secret - Key West, FL
10 1 review
Key West, FL
12/30 – 01/10
$2570/nighttotal: $28270 (11 )

Pilars Secret

3 5
house , Key West
This Key West vacation home offers a prime location, situated steps from Duval Street and the city center, a 4-minute walk to the Ernest Hemingway Home and Museum, and a 10-minute walk to South Beach.
This 1910 square foot residence accommodates up to 15 guests with 3 bedrooms and 2 bathrooms, featuring air conditioning, a full kitchen with a dishwasher, WiFi, a swimming pool, spa, tennis court, and garden.

Our Favorite Family-Friendly Vacation Rentals in Key West, FL

Family beach vacations in Key West, FL are better in spacious rentals that offer plenty of room to spread out near the shore.

Conch Style Home In Oldtown With Private Pool And Dock! - Key West, FL
9.8 133 reviews
Key West, FL
10/14 – 10/16
$1815/nighttotal: $3630 (2 )

Conch Style Home In Oldtown With Private Pool And Dock!

4 2
apartment , Key West
This waterfront vacation home, an architectural reflection of old Key West 'Conch House' with modern luxury amenities, is located in Key West's Meadows neighborhood, near Ernest Hemingway Home and Museum and Southernmost Point, offering easy access to Fort Zachary Taylor Historic State Park and Florida Keys Beaches.
This 2900 square foot rental property, accommodating up to 10 guests, features four bedrooms, three bathrooms, a private heated pool, a private boat slip, and is equipped with air conditioning, internet, a full kitchen, and two off-street parking spaces.
Ocean Key Resort & Spa, A Noble House Resort - Key West, FL
8.9 10070 reviews
Key West, FL
10/14 – 10/16
$398/nighttotal: $796 (2 )

Ocean Key Resort & Spa, A Noble House Resort

1 2
resort , Key West
The Opal Key Resort & Marina is located in the heart of Key West's old town, just a short walk from the lively Duval Street and across from the Mel Fisher Maritime Heritage Society & Museum. The resort consistently receives high ratings for its location, cleanliness, and overall experience.
The property offers a range of accommodations including rooms, suites, and villas, all equipped with modern amenities. Guests can enjoy a variety of activities and amenities, such as a heated pool, a hot tub, a fitness center, a spa, and a restaurant.
Luxury Waterfront Home With Private Pool And Dock! - Key West, FL
9.8 89 reviews
Key West, FL
07/02 – 07/07
$1846/nighttotal: $9230 (5 )

Luxury Waterfront Home With Private Pool And Dock!

4 2
apartment , Key West
This four-bedroom, three-bathroom residence is situated in Key West's Meadows neighborhood, offering a prime location on the edge of Old Town with views of Garrison Bight and just a short walk to charter fishing fleets, the Ernest Hemingway Home and Museum, and the Southernmost Point.
This spacious 2830 square foot rental accommodates up to 10 guests and features a private boat slip, heated swimming pool, a chef's kitchen, a private balcony overlooking the fishing fleet, and flexible sleeping arrangements including two master suites and a loft area, with amenities like air conditioning, internet, and parking provided.
Seas The Breeze, Poolside Condo Near The Beach - Key West, FL
Key West, FL
06/20 – 06/27
$307/nighttotal: $2149 (7 )

Seas The Breeze, Poolside Condo Near The Beach

2 2
apartment , Key West
This apartment in Key West is located 0.6 miles from Key West International Airport and approximately 4 miles from Southernmost Point and Duval Street.
This family-friendly, 800 square foot apartment features 2 bedrooms, 2 bathrooms, air conditioning, a kitchen, a swimming pool, a jacuzzi, a balcony, and parking for up to 11 guests, with free Wi-Fi available.

Frequently Asked Questions about vacation rentals in Key West, FL

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

    For a first-timer, you have to see the Southernmost Point Buoy, it's a must-see! You should also check out Mallory Square for the sunset celebration and take a walk down Duval Street to experience the vibrant atmosphere.
  • 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 for a vacation rental, it's close to everything. If you want a quieter spot, try the historic Bahama Village, it's charming and has a unique 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.
  • When is the best time to book a vacation rental in Key West, FL?

    It's best to book your vacation rental in Key West as early as possible, especially if you're traveling during peak season, which is from December to April. You'll get the best selection and prices.
  • 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.
  • What events or festivals should visitors check out in and around Key West, FL?

    Key West has a lot going on! The Fantasy Fest in October is a big one, it's a wild celebration. The Hemingway Days Festival in July celebrates the famous author, and the Key West Songwriters Festival in February is a great event for music lovers.
  • 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 are the best budget-friendly activities in Key West, FL?

    You can easily enjoy Key West without breaking the bank. Take a walk or bike ride around the island, explore the historic Fort Zachary Taylor, or visit the Key West Cemetery, it's a unique place.
  • 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 restaurants with local dishes in Key West, FL?

    For a taste of Key West, try the conch fritters at the Blue Heaven, they're a classic. The Hogfish Bar & Grill is another good option, they have fresh seafood and a laid-back atmosphere.
  • What are the best walking or cycling routes in Key West, FL?

    A walk or bike ride along the Overseas Highway is a beautiful way to see the island. You can also check out the scenic route around the Key West Lighthouse.
  • Are there pet-friendly attractions in Key West, FL?

    Key West is pretty pet-friendly! Many restaurants have outdoor seating that welcomes dogs, and you can bring your furry friend to the beach at Higgs Beach.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy compared to hotels. You can also often find rentals with unique features like a private pool or a waterfront view.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is known for its watersports. You can go snorkeling, diving, fishing, or kayaking. The Key West Yacht Club is a great place to watch sailing races.

Destinations nearby

Best Key West, FL vacation rentals with parking

Reynolds Paradise - Key West, FL
9.5 2 reviews
Key West, FL
12/21 – 01/18
$474/nighttotal: $13272 (28 )

Reynolds Paradise

1 1
apartment , Key West
This Key West vacation rental is located in Old Town, just a short walk from Duval Street, the Key West Firehouse Museum, and the beach. The home has received excellent ratings for location, cleanliness, and overall user experience.
The house has two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the private fenced yard, the luxurious spa tub, and the barbecue grill for outdoor dining, all while enjoying the comfortable amenities and modern appliances.
Beachside Resort & Residences - Key West, FL
8.3 4159 reviews
Key West, FL
10/14 – 10/16
$227/nighttotal: $454 (2 )

Beachside Resort & Residences

1 2
resort , Key West
The Key West Marriott Beachside Hotel is located in the New Town district, just under 1.2 miles from Key West Airport, offering easy access to the island's attractions. The resort consistently receives very good ratings for user experience, location, and cleanliness.
The hotel features a private sandy beach with Gulf of Mexico views and a pool with stunning views. Amenities include on-site dining options, a fitness center, a hot tub, and a free shuttle to the Key West city center, ensuring a comfortable and enjoyable stay.
Coconut Palm Studio At Travelers Palm Inn Key West - Key West, FL
Key West, FL
06/23 – 06/24
$360/nightfor 1 night

Coconut Palm Studio At Travelers Palm Inn Key West

1 2
studio , Key West
Coconut Palm Studio offers a convenient Key West location, an 8-minute walk from South Beach and less than 1.2 miles from both the Key West Aquarium and Mallory Square.
This air-conditioned studio apartment sleeps two, features a kitchenette with a fridge and microwave, a private terrace, and access to an on-site pool, tennis court, and free parking.

Neighborhoods and points of interest in Key West, FL

Search Vacation Rentals with Swimming Pool in Key West, FL

A vacation rental with a pool in Key West, FL is the ideal way to complement your daily coastal adventures.

Old Town Bali Hideaway For 2, Just Steps From Duval - Key West, FL
9.8 93 reviews
Key West, FL
06/20 – 06/27
$427/nighttotal: $2989 (7 )

Old Town Bali Hideaway For 2, Just Steps From Duval

1 2
apartment , Key West
This Key West studio is located in the Historic District, a half block from Duval Street and near the Historic Seaport.
The 400-square-foot unit features a queen-size bed, a sitting area, a European-style kitchen with a fridge and microwave, and a private patio; it sleeps two and offers access to a shared pool and garden.
Stay At Sunrise Suites 203! - Key West, FL
9.2 122 reviews
Key West, FL
06/20 – 06/27
$390/nighttotal: $2730 (7 )

Stay At Sunrise Suites 203!

2 2
apartment , Key West
This Key West condo rental is conveniently located near Fort Zachary Taylor Historic State Park (1.2 miles) and Smathers Beach (1.9 miles), also close to the Key West Butterfly and Nature Conservatory and the Key West Art & Historical Society.
This 800-square-foot, two-bedroom, two-bathroom unit sleeps six and boasts a fully equipped kitchen, private balcony, in-unit laundry, a fitness center, hot tub, and swimming pool.
Sundial  Luxurious 2 Bedroom Ocean View Condominium- Quality At Its Best. - Key West, FL
9.6 29 reviews
Key West, FL
10/17 – 10/24
$641/nighttotal: $4487 (7 )

Sundial Luxurious 2 Bedroom Ocean View Condominium- Quality At Its Best.

2 2
apartment , Key West
This Key West beachside condo is less than two miles from Duval Street and within three miles of Mallory Square and the Southernmost Point.
This 1350-square-foot, three-bedroom, two-bathroom unit sleeps six and boasts a private terrace, pool, Jacuzzi, fitness center, sauna, and tennis court.

Browse Waterfront Vacation Rentals in Key West, FL

Discover beautiful beach towns with these seaside vacation rentals in Key West, FL, perfect for relaxing near the coast and exploring the shore.

Duval Sea Turtle By Avantstay - Key West, FL
9.5 270 reviews
Key West, FL
06/20 – 06/27
$536/nighttotal: $3752 (7 )

Duval Sea Turtle By Avantstay

2 2
house , Key West
Frost Free In Cayo Hueso - Key West, FL
9.3 232 reviews
Key West, FL
08/22 – 08/29
$418/nighttotal: $2926 (7 )

Frost Free In Cayo Hueso

2 2
house , Key West
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
Key West, FL
06/20 – 06/27
$474/nighttotal: $3318 (7 )

Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 2
apartment , Key West
Coastal Luxe | Outdoor Pool. Island Experience - Key West, FL
9.4 24 reviews
Key West, FL
09/02 – 09/05
$285/nighttotal: $855 (3 )

Coastal Luxe | Outdoor Pool. Island Experience

1 2
B&B , Key West

Browse Luxury Vacation Rentals in Key West, FL

Refined interiors and prime locations make these luxury waterfront vacation rentals in Key West, FL the ideal choice for your stay.

Absolutely Paradise Awaits You By Rent Key West - Key West, FL
9.8 103 reviews
Key West, FL
07/24 – 07/28
$1151/nighttotal: $4604 (4 )

Absolutely Paradise Awaits You By Rent Key West

3 7
apartment , Key West

Choose the Right Vacation Rentals with a Steam Room in Key West, FL

Relax with an on-site sauna at these vacation rentals in Key West, FL, perfect for a steam session after a day by the water.

Hyatt Centric Key West Resort & Spa - Key West, FL
8.8 2731 reviews
Key West, FL
06/20 – 06/27
$327/nighttotal: $2289 (7 )

Hyatt Centric Key West Resort & Spa

1 2
resort , Key West
Blue Moonshine Upgrades Throughout Modern Finishes, Close To Smathers Beach - Key West, FL
9.6 159 reviews
Key West, FL
09/02 – 09/05
$485/nighttotal: $1455 (3 )

Blue Moonshine Upgrades Throughout Modern Finishes, Close To Smathers Beach

2 2
apartment , Key West
Magical Ocean Penthouse - Key West, FL
Key West, FL
10/26 – 10/28
$811/nighttotal: $1622 (2 )

Magical Ocean Penthouse

2 4
house , Key West
Beach Club Ocean Front 2br Condo - Key West, FL
9.9 176 reviews
Key West, FL
08/22 – 08/29
$565/nighttotal: $3955 (7 )

Beach Club Ocean Front 2br Condo

1 2
apartment , Key West
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