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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

Luxury Waterfront Home With Private Pool And Dock! - Key West, FL
9.8 91 reviews

Luxury Waterfront Home With Private Pool And Dock!

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.
Fully Renovated 2/2 Bath Condo W/ Shared Pool! - Key West, FL
9.9 277 reviews

Fully Renovated 2/2 Bath Condo W/ Shared Pool!

apartment, Key West
This two-bedroom, two-bathroom Key West apartment is conveniently located within a 2-mile radius of Fort East Martello Museum and Gallery, Key West Art and Historical Society, and Key West Tropical Forest and Botanical Garden. The apartment features a fully equipped kitchen, a private balcony, and a swimming pool, perfect for families or groups of up to six people.
Waterfront Condo Dock Pool Downtown Near Duval - Key West, FL
9.6 29 reviews

Waterfront Condo Dock Pool Downtown Near Duval

apartment, Key West
This Key West Meadows condo, less than a mile from Duval Street, the Ernest Hemingway Home and Museum, and Florida Keys beaches, offers a peaceful retreat near Key West's major attractions.
This 1300-square-foot, two-bedroom, two-bathroom unit sleeps six and includes a fully equipped kitchen, private balcony, in-unit laundry, and access to a community pool, garden, and barbecue grills.

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.

Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
This two-bedroom, one-bathroom Key West condo is centrally located downtown, offering easy walking access to many attractions.
The 6-guest unit features a fully equipped kitchen, private parking, a washer/dryer, central A/C, free WiFi, and a private porch and patio.
Waterfront Condo Free Slip & Pool 2b2b In Key West - Key West, FL
9.9 121 reviews

Waterfront Condo Free Slip & Pool 2b2b In Key West

apartment, Key West
This Key West condo, located on Garrison Bight Marina, offers direct access to the marina with stunning water views and is a short bike ride from Duval Street and a stroll from Bayview Park.
This two-bedroom, two-bathroom unit sleeps six, features a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, a private patio, and access to a shared pool; enjoy nearby tennis and basketball courts at Bayview Park.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
This Key West apartment rental near Key West International Airport offers easy access to the island's attractions while enjoying tranquil salt marsh views.
The two-bedroom, two-bathroom unit sleeps six guests comfortably, featuring a fully equipped kitchen, in-unit laundry, a private balcony, and free parking; nearby activities include biking, golf cart rentals, and ride-sharing services for exploring the island.
The Reach Key West, Curio Collection By Hilton - Key West, FL
8.4 1352 reviews

The Reach Key West, Curio Collection By Hilton

resort, Key West
The Reach Key West, Curio Collection by Hilton is located in Old Town, a short walk from Duval Street's bustling nightlife and the Ernest Hemingway Museum. The resort receives consistently good ratings for its location, cleanliness, and overall experience.
The hotel has a private beach and offers a range of amenities and activities including a spa, fitness center, multiple restaurants, and various water sports like snorkeling and kayaking. The resort also provides comfortable rooms, a pool, and a jacuzzi for relaxation.

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

Poolside Cottage #411 - Key West, FL
9.8 224 reviews

Poolside Cottage #411

house, Key West
This Key West cottage, located in the Coconut Mallory Resort & Marina on the island's eastern end, is 2.5 miles from Smathers Beach and 3.5 miles from Duval Street.
The one-bedroom, one-bathroom unit sleeps six with a queen bed, queen sofa bed, and full-size Murphy bed, and features a full kitchen, in-unit laundry, and access to resort amenities including a pool, hot tub, and Gumbo's bar & grill.
Moonlight Paradise Upgraded Family Oasis Tropical Views Expansive Balcony - Key West, FL
9.4 97 reviews

Moonlight Paradise Upgraded Family Oasis Tropical Views Expansive Balcony

apartment, Key West
This Key West beachside condo is a short walk from Florida Keys beaches and within three miles of Duval Street and Mallory Square.
The 1,360-square-foot unit features two bedrooms, two bathrooms, and sleeps six, offering a fully equipped kitchen, swimming pool, jacuzzi, fitness center, tennis court, and a private terrace.
The Perch On Duval- Hip & Modern Duval Suite - Key West, FL
9.9 110 reviews

The Perch On Duval- Hip & Modern Duval Suite

apartment, Key West
This Key West apartment boasts a prime Duval Street location, offering easy access to shops, restaurants, and the island's attractions.
The two-bedroom, one-bathroom rental features a spacious living room, a fully equipped kitchen with dishwasher, assigned parking, and accommodates up to five guests with a king-size bed in the master and queen and twin beds in the guest room.
Botanical Island Delight - Key West, FL
8.0 4 reviews

Botanical Island Delight

house, Key West
Botanical Island Delight, a Key West vacation home, offers convenient access to Smathers Beach (a 4-minute walk), Southernmost Point (1.6 miles), the Ernest Hemingway Home and Museum (2 miles), and Key West International Airport (1.2 miles).
This two-bedroom, two-bathroom rental sleeps seven guests and boasts a private pool, Jacuzzi, tennis court, fitness center, and complimentary Wi-Fi, along with on-site parking and tour organization services.

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.

Hemingways Atlantic Retreat - Key West, FL
9.0 128 reviews

Hemingways Atlantic Retreat

house, Key West
This Key West apartment is just a short walk from Smathers Beach and Rest Beach, putting you right in the heart of the action. It consistently receives excellent ratings for location, cleanliness, and overall experience.
The 1360-square-foot apartment comfortably accommodates up to 6 guests in its two bedrooms. Enjoy a fully equipped kitchen, a private balcony with sea views, a pool, a hot tub, a tennis court, and a fitness center, all within the complex.
Key West Paradise Found - Experience The Best Views At 1800 Atlantic - Key West, FL
9.8 339 reviews

Key West Paradise Found - Experience The Best Views At 1800 Atlantic

apartment, Key West
This oceanfront condo in Key West's Beachside neighborhood is located 20 yards from Smathers Beach and within two miles of Duval Street.
This 1360 square foot apartment offers three bedrooms, two bathrooms, and accommodates up to six guests with amenities including a private balcony, swimming pool, and direct beach access.
Waterfront Dock Pool Key West Near Duval - Key West, FL
9.7 264 reviews

Waterfront Dock Pool Key West Near Duval

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.
Stunning Townhouse * Full Kitchen! * Sleeps 6 - Key West, FL
9.9 372 reviews

Stunning Townhouse * Full Kitchen! * Sleeps 6

apartment, Key West
This Key West townhouse, part of the Santa Maria Suites in Old Town, is ideally located two blocks from Duval Street and two blocks from the beach.
The 1,000-square-foot, two-story property boasts two bedrooms, two and a half bathrooms, a fully equipped kitchen, and a private balcony offering stunning pool views; it sleeps six and includes access to a resort pool and fitness center.

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.

Cozy & Modern Guest House In Key West With Ac, Wifi - Key West, FL
10 4 reviews

Cozy & Modern Guest House In Key West With Ac, Wifi

apartment, Key West
Ocean Hideaway On The Atlantic - Key West, FL
No reviews

Ocean Hideaway On The Atlantic

house, Key West
Tropical Dreaming By Avantstay - Key West, FL
9.5 160 reviews

Tropical Dreaming By Avantstay

house, Key West
La Brisa #303w - Key West, FL
No reviews

La Brisa #303w

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.

Ibis By Avantstay - Key West, FL
10 2 reviews

Ibis By Avantstay

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.

Key West Oceanfront Escape With Pool, Balcony & Steps From Smathers Beach - Key West, FL
9.4 18 reviews

Key West Oceanfront Escape With Pool, Balcony & Steps From Smathers Beach

apartment, Key West
Blue Moonshine Upgrades Throughout Modern Finishes - Key West, FL
9.6 168 reviews

Blue Moonshine Upgrades Throughout Modern Finishes

apartment, Key West
Ocean Hideaway On The Atlantic - Key West, FL
9.2 154 reviews

Ocean Hideaway On The Atlantic

house, Key West
Beachside Resort & Residences - Key West, FL
8.3 4272 reviews

Beachside Resort & Residences

resort, Key West