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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

**Soul Of Duval @ Duval** Modern/centrally Located + Last Key Services... - Key West, FL
10 54 reviews

**Soul Of Duval @ Duval** Modern/centrally Located + Last Key Services...

apartment, Key West
This Key West condo, located in the Historic District, is a half block from Duval Street, offering easy access to attractions like the Cuban Coffee Queen.
The 650-square-foot apartment features two queen suites, accommodating four guests, a fully equipped kitchen with Keurig and drip coffee makers, a private balcony overlooking the promenade, reserved parking, and access to Last Key Realty's five-star guest services.
Mother Ocean - Key West, FL
No reviews

Mother Ocean

house, Key West
Mother Ocean, a residence in Key West, is located 2.3 miles from the Ernest Hemingway Home and Museum and 2.4 miles from Duval Street, offering easy access to local attractions.
This vacation rental accommodates 15 guests and features a private pool, a balcony with sea views, a full kitchen with a dishwasher, and three bathrooms, along with complimentary Wi-Fi and private parking.
Completely Renovated Condo With Pool, Hot Tub, & Private Patio - Free Parking - Key West, FL
9.0 138 reviews

Completely Renovated Condo With Pool, Hot Tub, & Private Patio - Free Parking

apartment, Key West
This Key West condo is located by the sea, minutes from Key West International Airport and near Smathers Beach, offering ocean breezes and views from its private patio.
This 780 sq ft, 2-bedroom, 2-bathroom condo accommodates up to 6 guests and features a fully renovated interior, an upgraded kitchen, air conditioning, a swimming pool, a jacuzzi, and tennis court access.
Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach! - Key West, FL
9.8 230 reviews

Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach!

apartment, Key West
This newly renovated condo is located in a quiet gated waterfront community in Key West, just minutes from Duval Street and a short walk to two beaches, Higgs and Smathers. The apartment is rated excellent by previous guests and is a perfect choice for families or groups of friends looking to enjoy the beauty of Key West.
The apartment features a spacious open floor plan with a fully equipped kitchen, a dining room table, and a balcony with a patio table. This vacation rental offers a king-size bedroom, a guest room with twin beds that convert to a king, and a queen-size pull-out couch in the living room, accommodating up to 6 guests. Enjoy the large heated, saltwater community pool overlooking the ocean, a community grill, a fitness center, tennis courts, a sauna, and concierge service for planning activities and booking excursions.

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.

Blue Horizon Hideaway - Key West, FL
No reviews

Blue Horizon Hideaway

house, Key West
This Key West residence in the Key Cove community offers waterfront views on two sides and is located just minutes from shopping, dining, and Duval Street.
This three-bedroom, two-bathroom house accommodates up to six guests and features a shared community pool, a private patio with alfresco dining, a chef's kitchen, and a master suite with water views.
Private Paradise With Heated Waterfall Pool - Key West, FL
10 4 reviews

Private Paradise With Heated Waterfall Pool

apartment, Key West
This Key West New Town home, less than a mile from Florida Keys Beaches and within three miles of Duval Street and Mallory Square, offers easy access to Key West's attractions. This two-bedroom, one-bathroom vacation rental sleeps six and boasts a private pool, hot tub, full kitchen, laundry facilities, and barbecue grills, perfect for a relaxing Key West getaway.
Key Wests Atlantic Sunrise Penthouse  Upgraded C - Key West, FL
8.9 31 reviews

Key Wests Atlantic Sunrise Penthouse Upgraded C

apartment, Key West
This Key West vacation rental is situated directly on Smathers Beach, just a short drive from Duval Street and Mallory Square, offering easy access to the island's best attractions. The apartment has received very good user ratings, with an excellent location rating and very good cleanliness rating.
This spacious 3-bedroom, 3-bathroom condo comfortably accommodates 8 guests and features a large private balcony with ocean views. Enjoy access to a heated pool, Jacuzzi, tennis courts, fitness center, and grilling areas, perfect for relaxing and entertaining.
Tortuga Hammock -2 Bedroom/ 2.5 Bathroom Townhouse With Shared Pool & Parking - Key West, FL
10 23 reviews

Tortuga Hammock -2 Bedroom/ 2.5 Bathroom Townhouse With Shared Pool & Parking

apartment, Stock Island
This Stock Island vacation home is located just a mile from Stock Island Yacht Club & Marina and Clark Maxwell Environmental Habitat, offering easy access to the island's natural beauty and activities. It's also close to Key West Tropical Forest and Botanical Garden, making it a great choice for exploring the area. This vacation rental has received excellent user ratings, ensuring a comfortable and enjoyable stay.
The 1,070-square-foot house has two bedrooms and three bathrooms, comfortably accommodating up to four guests. It features a fully equipped kitchen, a refreshing swimming pool, a relaxing terrace, a lush garden, free WiFi, and plenty of parking.

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

Blue Bungalow ~ 2 Bedroom Townhome In Truman Annex Community With Pool! - Key West, FL
9.8 74 reviews

Blue Bungalow ~ 2 Bedroom Townhome In Truman Annex Community With Pool!

apartment, Key West
This charming Key West bungalow is located in Old Town, just steps from a community pool and a short distance from Fort Zachary State Park and the Truman Little White House. The bungalow has received excellent user ratings and is perfect for those seeking a relaxing and authentic Key West experience.
The 960 square foot bungalow comfortably accommodates up to six guests in its two bedrooms and three bathrooms. This well-equipped vacation home offers a fully equipped kitchen, a private terrace, a swimming pool, and concierge services, ensuring a comfortable and enjoyable stay.
Star Of The Seaport By Last Key Realty - Key West, FL
No reviews

Star Of The Seaport By Last Key Realty

house, Key West
Star of the Seaport, a Key West vacation rental, is centrally located less than half a mile from Key West's city center, a short walk from the Key West Aquarium, Mallory Dock, and Simonton Street Beach.
This 4,280-square-foot house boasts five bedrooms, five bathrooms, and accommodates up to 23 guests, featuring a private pool, spa, tennis court, free Wi-Fi, and free parking; a fully equipped kitchen completes this Key West getaway.
Rum Cay Sunrise Suites - Key West, FL
9.5 4 reviews

Rum Cay Sunrise Suites

apartment, Key West
This Rum Cay Sunrise Suites two-bedroom apartment in Key West is conveniently located just 0.6 miles from Key West International Airport and within a 4-5 mile radius of Duval Street, Mallory Square, the Ernest Hemingway Home and Museum, and the Southernmost Point.
The 800-square-foot unit features two bathrooms, accommodates up to 11 guests, includes a fully equipped kitchen with a dishwasher, and offers amenities such as a swimming pool, spa, tennis court, and free Wi-Fi.
Charming One Bedroom With See Front - Key West, FL
9.2 384 reviews

Charming One Bedroom With See Front

hotel, Key West
This beachfront resort is situated in the historic district of Old Town Key West, within a short walk of Duval Street, Florida Keys Beaches, and other notable landmarks. It offers guests direct access to the pristine beaches of Key West and is surrounded by the charming ambiance of the Old Town district.
The Coconut Beach Resort has excellent user, location, and cleanliness ratings. It features a beachfront location, a historical district ambiance, and proximity to landmarks. The resort offers an array of amenities, including a spa tub, barbecue grills, a fitness center, a bar, and a concierge.

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.

The Cayo Coco | Key West Condo With Pool, Hot Tub! - Key West, FL
9.6 10 reviews

The Cayo Coco | Key West Condo With Pool, Hot Tub!

apartment, Key West
This 2-bedroom, 2-bathroom condo in Key West's Sunrise Suites community is located within 0.5 miles of Smathers Beach and Higgs Beach, and a short distance from Duval Street.
This 800 sq ft accommodation accommodates up to 6 guests and features a full kitchen, private balcony, on-site swimming pool, hot tub, and tennis court, with a stackable washer/dryer in-unit and pet-friendly options up to 40 lbs per pet.
Magical Ocean Penthouse  Top-floor Ocean View Condo In Key West - Key West, FL
9.8 236 reviews

Magical Ocean Penthouse Top-floor Ocean View Condo In Key West

apartment, Key West
This non-smoking condo is situated waterfront in Key West's Beachfront district, a short walk from the Keys archipelago beaches and 0.2 miles from Clarence S. Higgs Memorial Beach Park.
This 1360 square feet apartment accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, Wi-Fi, a communal pool, hot tub, and on-site rentals for boats and bicycles.
Ocean Vista 403e La Brisa - Key West, FL
10 1 review

Ocean Vista 403e La Brisa

apartment, Key West
This beachfront apartment in Key West is located a 7-minute walk from Smathers Beach and is within a few miles of the Southernmost Point, Ernest Hemingway Home and Museum, Duval Street, and Key West Aquarium.
This 1160-square-foot condo accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen, Wi-Fi, air conditioning, a swimming pool, spa, tennis court, and parking.
Hidden Oasis 3 Blocks From Duval - Key West, FL
9.6 101 reviews

Hidden Oasis 3 Blocks From Duval

cottage, Key West
This Key West cottage is just a short walk from Duval Street and the Key West Cemetery, offering easy access to the island's main attractions. It's rated excellent by previous guests and is perfect for a relaxing getaway.
The cottage has one bedroom and one bathroom with a floor area of 510 square feet, comfortably accommodating up to four guests. It offers a full kitchen, laundry facilities, cable TV, a private patio with a barbecue area, and access to a shared pool.

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.

Somewhere On The Beach - Key West, FL
9.7 256 reviews

Somewhere On The Beach

apartment, Key West
Yellow Fin Fantasy One Bedroom Condo - Key West, FL
9.1 33 reviews

Yellow Fin Fantasy One Bedroom Condo

apartment, Key West
By The Beautiful Sea - Key West Beach Front Condo - W Pool Access - Key West, FL
9.2 77 reviews

By The Beautiful Sea - Key West Beach Front Condo - W Pool Access

apartment, Key West
Botanical Island Delight - Key West, FL
8.0 4 reviews

Botanical Island Delight

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.

Colors Of The Keys At The Foundry - Key West, FL
10 196 reviews

Colors Of The Keys At The Foundry

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 Beachfront Luxury 2/2 Condo A212 - Key West, FL
10 171 reviews

Key West Beachfront Luxury 2/2 Condo A212

apartment, Key West
Casa Papa Del Mar - Key West, FL
9.8 6 reviews

Casa Papa Del Mar

house, Key West
Anchor Drop Key West - Key West, FL
10 1 review

Anchor Drop Key West

house, Key West
Moonlight Paradise - Key West, FL
9.7 143 reviews

Moonlight Paradise

house, Key West
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