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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

The Bartlum-luxurious Studio - Key West, FL
9.6 344 reviews

The Bartlum-luxurious Studio

studio, Key West
This Key West apartment is conveniently located just a 5-minute walk from Simonton Street Beach and a mile from South Beach, placing you in the heart of the action. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment features a separate bedroom, comfortably accommodating up to 4 guests. Enjoy amenities like free Wi-Fi, a fully equipped kitchen with a dishwasher, air conditioning, a terrace or balcony, and a garden.
One Bedroom Suite | Beachside Resort - Key West, FL
10 5 reviews

One Bedroom Suite | Beachside Resort

apartment, Key West
This 1-bedroom condo is located on seven acres overlooking the Gulf of Mexico in north Key West, approximately a 10-minute drive from Duval Street.
This luxury resort condo offers a private balcony, a fully-equipped kitchen with stainless-steel appliances, and access to a resort pool, hot tub, and on-site dining.
**Suite Sanctuary** Oceanfront Condo & Pool + Last Key White Glove Service... - Key West, FL
10 33 reviews

**Suite Sanctuary** Oceanfront Condo & Pool + Last Key White Glove Service...

apartment, Key West
This beachfront Key West condo offers direct beach access and is located within 3 miles of Duval Street, Mallory Square, and Smathers Beach.
The two-bedroom, two-bathroom unit sleeps six, features a fully equipped kitchen, private balcony, free WiFi, and access to a swimming pool, jacuzzi, sauna, spa, fitness center, and tennis court.
Pool View Two Bedroom Residence - Key West, FL
9.6 4 reviews

Pool View Two Bedroom Residence

apartment, Key West
This two-bedroom, two-and-a-half-bathroom condo offers Gulf of Mexico views from its north Key West location, approximately 10 minutes or 5,280 feet from Duval Street.
This luxury resort condo sleeps six and features a fully-equipped kitchen, private balcony with resort and pool views, and access to resort amenities including a heated pool, hot tub, and fitness center.

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

Spacious floor plans and full kitchens make these family-friendly vacation rental properties the ideal home base after an exciting afternoon at the Key West Butterfly & Nature Conservatory or snorkeling at Fort Zachary Taylor Historic State Park.

71 M² House ∙ 2 Bedrooms ∙ 4 Guests - Key West, FL
10 1 review

71 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, Key West
This private Key West house offers seclusion while remaining accessible to the island's nightlife and historic sites, located in a tranquil setting.
This recently renovated 760 sq ft, two-bedroom home accommodates up to 4 guests and features a lagoon-style pool, a steel-roof gazebo, a brand-new kitchen with granite countertops and stainless steel appliances, and ample parking for multiple vehicles.
Apartment ∙ 8 Bedrooms ∙ 24 Guests - Key West, FL
No reviews

Apartment ∙ 8 Bedrooms ∙ 24 Guests

apartment, Key West
This downtown Key West rental is centrally located, within walking distance of Duval Street and Mallory Square.
This eight-bedroom, seven-bathroom home sleeps up to 24 guests and features two living areas, a private balcony with a hot tub, two laundry units, and a full kitchen with stainless steel appliances.
Bahama Gardens - Turtle House - Key West, FL
No reviews

Bahama Gardens - Turtle House

house, Key West
Vacation rental. Your accommodation will be located in Key West.
Facilities and services include a swimming pool, a kitchen and a washing machine. This house in Key West also has a Jacuzzi to relax in!
Two Fully Independent Units In A Duplex, With Independent Entrances. One Rent! - Key West, FL
8.0 1 review

Two Fully Independent Units In A Duplex, With Independent Entrances. One Rent!

apartment, Key West
This Key West duplex, located in the Historic District, offers easy walking access to the Historic Seaport, Duval Street, and beaches.
This four-bedroom, four-bathroom rental sleeps twelve, features two fully renovated homes, a fully equipped kitchen with dishwasher, and includes parking; a minimum 28-night stay is required.

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.

Popular destinations

Best Key West, FL vacation rentals with parking

Ocean Front Two Bedroom Residence - Key West, FL
9.6 28 reviews

Ocean Front Two Bedroom Residence

apartment, Key West
This luxurious two-bedroom condo at the Beachside Resort & Residences in Key West overlooks the Gulf of Mexico, offering easy access to resort amenities and nearby attractions.
The 2-bedroom, 2-bathroom unit sleeps six, features a fully equipped kitchen with stainless steel appliances, a private balcony with Gulf views, a private washer/dryer, and access to a heated pool, hot tub, on-site marina, and award-winning restaurants.
Casablanca Too ~Chicly Updated Home With Hot Tub - Key West, FL
9.6 150 reviews

Casablanca Too ~Chicly Updated Home With Hot Tub

apartment, Key West
Casablanca Too is a charming vacation home situated in a quiet residential neighborhood just a short walk from the lively Duval Street and a quick bike ride to Higgs Beach and the Southernmost Point. This Key West rental receives excellent ratings for location, cleanliness, and overall user experience.
This 1-bedroom, 1-bathroom house offers 610 square feet of comfortable living space for up to 2 guests. Enjoy modern amenities like a private hot tub, a fully equipped kitchen, and a cozy outdoor living area perfect for relaxing after a day of exploring Key West.
Petite Maison ~ 2 King Ensuite Bedrooms - Key West, FL
9.9 470 reviews

Petite Maison ~ 2 King Ensuite Bedrooms

house, Key West
This Key West home is located on the southern end of Duval Street, within walking distance of Duval Street's nightlife, the Southernmost Point buoy, and the Key West Butterfly and Nature Conservatory.
This four-bedroom, four-bathroom house features a private saline pool (seasonally heated for a fee), an open-concept living area with a contemporary kitchen, and a dog-friendly policy (with restrictions and fees); a second property, Petite Maison, is available for rent for larger groups.
Doubletree By Hilton Grand Key Resort - Key West, FL
8.3 1848 reviews

Doubletree By Hilton Grand Key Resort

resort, Key West
The DoubleTree by Hilton Grand Key Resort, located just a 2-minute drive from Key West International Airport, offers a 1-bedroom, 1-bathroom resort with complimentary shuttle service to Old Town Key West and Duval Street, placing it conveniently near Smathers Beach and the Key West Tropical Forest & Botanical Garden.
This family-friendly and pet-friendly accommodation features newly renovated rooms with modern comforts, a swimming pool with a poolside tiki bar, an on-site restaurant and bar, a fitness center, and concierge services to assist with planning visits to attractions like the Ernest Hemingway Home & Museum and Mallory Square.

Neighborhoods and points of interest in Key West, FL

Search Vacation Rentals with Swimming Pool in Key West, FL

Reserving a Key West vacation rental with a private or resort pool lets you transition seamlessly from morning photos at the iconic Southernmost Point Buoy to a refreshing afternoon swim in your backyard paradise.

Old Town Key West Suite W/ Pool & Pet-friendly - Key West, FL
9.4 71 reviews

Old Town Key West Suite W/ Pool & Pet-friendly

apartment, Key West
This Key West Historic District condo is located a half-block from Duval Street and within several blocks of South Beach.
This bi-level suite, featuring two queen beds, a queen-size sofa bed, two bathrooms (one with a custom tumbled marble shower), a private courtyard, and shared pool access, comfortably sleeps four guests and offers proximity to Key West's nightlife and ocean swimming.
The Elizabeth Suite | 1 Bedroom Condo, Shared Pool - Key West, FL
9.4 50 reviews

The Elizabeth Suite | 1 Bedroom Condo, Shared Pool

apartment, Key West
The Fleming Suite at The Bayview House in Key West, Florida offers convenient access to local attractions and landmarks, although specific distances aren't provided.
This one-bedroom, one-bathroom suite features a queen-size bed, fully equipped kitchenette, and accommodates up to four guests, boasting a swimming pool and parking on-site.
Paradise Found Cayo Hueso - Key West, FL
9.3 229 reviews

Paradise Found Cayo Hueso

house, Key West
Paradise Found Cayo Hueso is located in Key West, just a short drive from the airport and popular beaches like Smathers Beach. This apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The 1,360 square foot apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a private balcony with ocean views, a swimming pool, a fitness center, and a tennis court, offering a range of activities and comforts for a relaxing stay.
Julie At Scarlet Mango Inn Key West - Key West, FL
No reviews

Julie At Scarlet Mango Inn Key West

B&B, Key West
JULIE at Scarlet Mango Inn, a Key West vacation rental, is centrally located less than 0.25 miles from Key West's city center, a 10-minute walk from Simonton Street Beach, and under a mile from Mallory Square and Mallory Dock.
This one-bedroom, one-bathroom cottage sleeps two guests and offers free WiFi, on-site parking, a shared pool, and proximity to Duval Street, the Ernest Hemingway Home and Museum, and the Key West Aquarium.

Browse Waterfront Vacation Rentals in Key West, FL

Turquoise Atlantic waters and tropical ocean breezes define each waterfront vacation rental in Key West, placing you just moments from soft sands at Smathers Beach and the energetic spirit of Duval Street.

Waterfront 4-bed 3-bath Condo @ Bayfront Suites - - Key West, FL
9.6 889 reviews

Waterfront 4-bed 3-bath Condo @ Bayfront Suites -

apartment, Key West
Conch In The Treetops By Last Key Realty - Key West, FL
9.3 3 reviews

Conch In The Treetops By Last Key Realty

house, Key West
*August/september Specials* Off Grid Boat Key West - Key West, FL
9.9 89 reviews

*August/september Specials* Off Grid Boat Key West

boat, Key West
Tropical Paradise Key West - Key West, FL
9.4 193 reviews

Tropical Paradise Key West

house, Key West

Browse Luxury Vacation Rentals in Key West, FL

Conch-style architectural design and private outdoor spaces elevate every luxury vacation rental in Key West, positioning you near upscale coastal dining at the Key West Historic Seaport and nightly Sunset Celebrations at Mallory Square.

Heron Suite | Vibrant Retreat, Hot Tubs, Steps From Duval - Key West, FL
10 1 review

Heron Suite | Vibrant Retreat, Hot Tubs, Steps From Duval

house, Key West

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

Turn your island getaway into a private spa retreat by booking a high-end vacation rental equipped with an on-site sauna or steam room for total relaxation after a day of sailing and scuba diving.

Beachside Resort & Residences - Key West, FL
8.2 4555 reviews

Beachside Resort & Residences

resort, Key West
Poolside Breeze Retreat - Key West, FL
9.5 205 reviews

Poolside Breeze Retreat

house, Key West
Blue Moonshine Upgrades Throughout Modern Finishes - Key West, FL
9.6 173 reviews

Blue Moonshine Upgrades Throughout Modern Finishes

apartment, Key West
High Tide In Key West - Key West, FL
9.0 202 reviews

High Tide In Key West

house, Key West
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