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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

Pier House Resort & Spa - Key West, FL
9.0 9196 reviews

Pier House Resort & Spa

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.
Watch Sunsets From Your Deck, Shared Pool/hot Tub - Perfect For The Whole Family - Key West, FL
8.8 218 reviews

Watch Sunsets From Your Deck, Shared Pool/hot Tub - Perfect For The Whole Family

apartment, Key West
This dog-friendly condo is located on the eastern edge of Key West, approximately 2 miles from Key West International Airport, downtown attractions, Southernmost Point, and the Ernest Hemingway Home.
This 780 sq ft residence accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, complimentary WiFi, a shared community pool and exercise room, and a private deck for enjoying west-facing sunset views.
Parrot Key Hotel & Villas - Key West, FL
8.5 4770 reviews

Parrot Key Hotel & Villas

resort, Key West
Parrot Key Hotel & Villas is located in Florida Bay, a short drive from Key West's historic Old Town. The resort consistently receives high ratings for its location, cleanliness, and overall experience.
The hotel offers a variety of accommodations, including rooms and villas, each with a private terrace. Guests can enjoy multiple pools, a fitness center, on-site dining, and a range of activities like kayaking and massage services.
Doubletree By Hilton Grand Key Resort - Key West, FL
8.3 1864 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.

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.

Casa Marina Key West, Curio Collection By Hilton - Key West, FL
8.1 1410 reviews

Casa Marina Key West, Curio Collection By Hilton

resort, Key West
The Casa Marina Key West, Curio Collection by Hilton offers a historic 1920s resort experience directly on a private beach, located a 7-minute drive from Duval Street and approximately 2.7 miles from Fort Zachary Taylor Historic State Park. This hotel features oceanside massages, two oceanfront pools, and the Spa al Mare, with rooms offering flat-screen TVs and private bathrooms, and is a 13-minute drive from Key West Golf Club.
3-story Spacious Conch Style Home W/ Private Pool & Dock! - Key West, FL
9.8 157 reviews

3-story Spacious Conch Style Home W/ Private Pool & Dock!

apartment, Key West
This 4-bedroom vacation home is located in Key West's Historic District. It is within walking distance of major attractions like Studios of Key West, Duval Street, and Florida Keys Beaches. The house has excellent user, location, and cleanliness ratings.
The house features a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, a garden, a concierge, a tennis court, and parking. Pets are allowed, and the house is family-friendly. It also has internet access.
Oceanview At 1800 Atlantic, Short Walk To Smathers Beach Wish Island Paradise - Key West, FL
9.6 33 reviews

Oceanview At 1800 Atlantic, Short Walk To Smathers Beach Wish Island Paradise

apartment, Key West
This Key West apartment is located in the Beachside district, just a short walk from the Keys beaches and an 11-minute walk from Higgs Beach. The surrounding area offers a relaxed and tropical ambiance, perfect for enjoying the laid-back Key West lifestyle.
The 1310 square foot apartment comfortably accommodates up to 6 guests and features 2 bedrooms and 2 bathrooms. You'll enjoy modern amenities like Wi-Fi, a fully equipped kitchen, a washer/dryer, and access to a shared pool, tennis court, and other on-site activities.
Ocean Front Presidential Suite | Beachside Resort - Key West, FL
No reviews

Ocean Front Presidential Suite | Beachside Resort

apartment, Key West
This three-bedroom, three-bathroom luxury condo offers Gulf of Mexico views on seven acres in north Key West, a 10-minute drive from Duval Street.
This family-friendly residence features a fully-equipped kitchen, private balcony, swimming pool, hot tub, and fitness center, with options for sandbar cruises and bike rentals.

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

Pool, Laundry, And Grilling Area - Key West, FL
10 1 review

Pool, Laundry, And Grilling Area

apartment, Key West
This Old Town Key West apartment rental is two blocks from Duval Street, offering easy access to Key West's historic attractions.
The one-bedroom, one-bathroom suite features a king-size bed, full kitchen with dishwasher, a private deck with a pool and waterfall, and a luxurious Jacuzzi tub; it comfortably sleeps two guests.
**Dos Casitas** Old Town Cottage & Pool + Last Key White Glove Service... - Key West, FL
10 2 reviews

**Dos Casitas** Old Town Cottage & Pool + Last Key White Glove Service...

apartment, Key West
This Old Town Key West rental, less than half a block from Duval Street, offers easy access to Key West's nightlife and attractions.
This two-unit cottage features 2570 square feet of space, five bedrooms, five bathrooms, and accommodates up to 14 guests, complete with a private pool, hot tub, and fully equipped kitchens in each unit.
Resort-style Amenities And Expansive Pool - Stunning Oceanfront Retreat - Key West, FL
No reviews

Resort-style Amenities And Expansive Pool - Stunning Oceanfront Retreat

apartment, Key West
This oceanfront condo is situated on 400 feet of beach, directly next to Smathers Beach and 1.5 miles from Old Town Key West's shopping and dining.
This family-friendly apartment offers 2 bedrooms, 2 bathrooms, and can accommodate up to 4 guests, featuring amenities like a swimming pool, jacuzzi, fitness center, tennis courts, and a balcony with ocean views.
Two Bedroom Residence - Key West, FL
9.4 152 reviews

Two Bedroom Residence

apartment, Key West
This luxurious two-bedroom Key West condo is located on a seven-acre beachfront property overlooking the Gulf of Mexico, offering easy access to Tavern N Town and Brightwild Adventures.
The 2-bedroom, 2-bathroom unit features a full kitchen, washer/dryer, private balcony, king beds in each bedroom (one with a whirlpool tub), a queen sleeper sofa, accommodating up to six guests, and access to a resort pool, hot tub, fitness center, and boat slip rentals.

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.

Key West 2br | Pool, Hot Tub, Balcony & Parking - Key West, FL
9.2 5 reviews

Key West 2br | Pool, Hot Tub, Balcony & Parking

apartment, Key West
This newly renovated Key West condo, located in New Town, is 1.1 miles from Smathers Beach and 4.5 miles from Duval Street, offering easy access to Key West International Airport.
The 800-square-foot unit features two bedrooms, two bathrooms, sleeps six guests, and includes a private terrace, swimming pool, jacuzzi, and parking; on-site amenities include tennis and pickleball courts, a grilling area, and a small gym.
Sky Loft In Key West - Key West, FL
9.5 237 reviews

Sky Loft In Key West

house, Key West
This Key West home is conveniently located in the heart of the city, just a short walk from Simonton Street Beach and close to other popular attractions like Duval Street and the Ernest Hemingway Home and Museum. Guests consistently rate this rental excellent for its location, cleanliness, and overall experience.
The one-bedroom house offers 680 square feet of space, comfortably accommodating up to four guests. Enjoy amenities like a private pool, a patio, a fully equipped kitchen, and free Wi-Fi.
**The Osprey's Nest** Condo & Pool + Last Key White Glove Service... - Key West, FL
9.4 39 reviews

**The Osprey's Nest** Condo & Pool + Last Key White Glove Service...

apartment, Key West
This oceanfront Key West condo, located 1.2 miles from Fort Zachary Taylor Historic State Park and 1.9 miles from Smathers Beach, offers stunning sea views and proximity to Key West's attractions.
This 800-square-foot unit features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, swimming pool, jacuzzi, fitness center, tennis court, and concierge services.
The Simonton Room At Inn On Fleming Key West - Key West, FL
9.3 3 reviews

The Simonton Room At Inn On Fleming Key West

B&B, Key West
The Simonton Room at the Inn on Fleming Key West is centrally located, 0.6 miles from Key West's city center, a short walk from Simonton Street Beach, and near Duval Street, the Key West Aquarium, and Mallory Dock.
This 220-square-foot, air-conditioned one-bedroom vacation rental sleeps two, offering a private bathroom, free Wi-Fi, on-site parking, a swimming pool, and a terrace—all within easy reach of the Ernest Hemingway Home and Museum and Mallory Square.

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.

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
*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
Southernmost Sanctuary All - Key West, FL
No reviews

Southernmost Sanctuary All

house, Key West
Botanical Island Delight  Key West Fantastic Discounts For Summer & Fall - Key West, FL
9.0 156 reviews

Botanical Island Delight Key West Fantastic Discounts For Summer & Fall

apartment, 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.

The Lark's Landing At Sunrise Suites - Key West, FL
9.9 29 reviews

The Lark's Landing At Sunrise Suites

apartment, 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.

The Grande Vista - Key West, FL
9.1 203 reviews

The Grande Vista

house, Key West
Bright 2br Oceanview Condo - Key West, FL
No reviews

Bright 2br Oceanview Condo

apartment, Key West
Blue Moonshine On The Atlantic - Key West, FL
No reviews

Blue Moonshine On The Atlantic

house, Key West
Blue Haven Unit B416 - Key West, FL
No reviews

Blue Haven Unit B416

house, Key West