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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

H2o Suites- Adults Only - Key West, FL
9.5 1602 reviews

H2o Suites- Adults Only

resort, Key West
The H2o Suites- Adults Only is located in Key West, just a short walk from Duval Street, Southernmost Point, and the Ernest Hemingway Home and Museum. This adults-only resort has received excellent ratings for location, cleanliness, and overall user experience.
The resort offers a variety of amenities and features to make your stay enjoyable. You can relax by the rooftop pool, enjoy a drink at the on-site bar, or take advantage of the fitness center, bike rentals, and complimentary amenities.
Sandpiper On The Ocean - Key West, FL
8.8 191 reviews

Sandpiper On The Ocean

house, Key West
This Key West apartment is located just a short walk from Smathers Beach and Rest Beach, offering easy access to the island's top attractions like Higgs Beach and Southernmost Point. It has received very good user ratings, excellent location ratings, and excellent cleanliness ratings. This two-bedroom, two-bathroom rental accommodates up to six guests and features a fully equipped kitchen, air conditioning, free Wi-Fi, a private balcony with ocean views, and access to a swimming pool, Jacuzzi, and fitness center.
Enjoy the convenience of free private parking and explore the island's beautiful beaches, vibrant nightlife, and charming shops and restaurants.
Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
9.2 57 reviews

Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony

apartment, Key West
This two-bedroom condo is located near Smather's Beach, just a short drive from Key West International Airport, offering a peaceful retreat away from the hustle and bustle of downtown. The apartment boasts excellent ratings for user experience, location, and cleanliness.
The apartment comfortably sleeps up to six guests and features a fully equipped kitchen, a private balcony with pool views, and a shared lagoon-style pool. Enjoy the convenience of having a washer and dryer in the unit, plus access to a shared garden, parking, and a Jacuzzi.
Hyatt Centric Key West Resort & Spa - Key West, FL
8.7 2738 reviews

Hyatt Centric Key West Resort & Spa

resort, Key West
The Hyatt Centric Key West Resort & Spa is located on Key West Island, just a short walk from Duval Street and its lively atmosphere. It's rated very good for overall experience, excellent for location, and very good for cleanliness.
The hotel has 1-bedroom suites with private balconies, each with free Wi-Fi. Guests can enjoy a range of amenities, including a pool, hot tub, spa, fitness center, two restaurants, and a bar, plus activities like scuba diving, jet boating, and snorkeling.

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.

Charming Loft With Balcony Overlooking Duval Street - Unique Experience - Key West, FL
No reviews

Charming Loft With Balcony Overlooking Duval Street - Unique Experience

apartment, Key West
This apartment is located on the 500 block of Duval Street in Key West, placing you within walking distance of attractions such as The Ernest Hemingway House, Mallory Square, and the Key West Lighthouse, with Fausto's Food Market and Cuban Coffee Queen just steps away.
This historic loft-style rental accommodates up to 8 guests across 2 bedrooms and 1 bathroom, featuring a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and internet for your convenience.
Apartment ∙ 5 Bedrooms ∙ 16 Guests - Key West, FL
No reviews

Apartment ∙ 5 Bedrooms ∙ 16 Guests

apartment, Key West
This downtown Key West house rental, ideally located for walking to Duval Street and Mallory Square, offers three separate units—Coconut Palm, Traveler's Palm, and Royal Palm—for flexible booking.
Sleeping up to 16 guests, the property boasts a fully equipped kitchen (Coconut Palm), kitchenettes (Traveler's Palm & Royal Palm), two washer/dryers, a backyard with a BBQ, a balcony with a hammock, a private patio with a hot tub, and parking for two compact cars (when all units are booked).
129 M² Villa ∙ 3 Bedrooms ∙ 8 Guests - Key West, FL
9.4 33 reviews

129 M² Villa ∙ 3 Bedrooms ∙ 8 Guests

house, Stock Island
This Stock Island townhome, located in the gated Coral Hammock community near US-1, is minutes from Smathers Beach, Key West International Airport, and local restaurants.
The three-bedroom, three-bathroom property sleeps eight, boasts a private pool, and offers access to community amenities including a clubhouse, along with AvantStay services such as 24/7 support.
Oceanview At 1800 Atlantic, Short Walk To Smathers Beach Wish Island Paradise - Key West, FL
9.6 31 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.

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

Seas The Breeze  Poolside Condo Near The Beach - Key West, FL
9.8 8 reviews

Seas The Breeze Poolside Condo Near The Beach

apartment, Key West
This Key West condo is located on the quieter side of the island, a 10-minute drive from Old Town and Duval Street, and within walking distance to the beach and Mallory Square.
This 2-bathroom island retreat accommodates up to 6 guests and features resort-style amenities including a heated swimming pool and hot tub, plus a private balcony and a fully equipped kitchen with a buffet bar.
Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach! - Key West, FL
9.8 233 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.
The Whitehead Room At Inn On Fleming Key West! - Key West, FL
9.0 1 review

The Whitehead Room At Inn On Fleming Key West!

B&B, Key West
THE WHITEHEAD 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 a mile from Mallory Square, offering easy access to the Ernest Hemingway Home and Museum and Key West International Airport.
This 160-square-foot, one-bedroom, one-bathroom Key West vacation rental sleeps two and includes free Wi-Fi, air conditioning, a swimming pool, and on-site parking.
Blue Moonshine On The Atlantic - Key West, FL
9.5 2 reviews

Blue Moonshine On The Atlantic

house, Key West
Blue Moonshine on the Atlantic, a Key West vacation home, is located 1.6 miles from the Southernmost Point and 2 miles from the Ernest Hemingway Home and Museum.
This 1400-square-foot property boasts two bedrooms, two bathrooms, a hot tub, and can comfortably accommodate up to 11 guests, featuring a fully equipped kitchen, private balcony with ocean views, a swimming pool, Jacuzzi, sauna, fitness center, and tennis court.

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.

Little Lobster-newly Renovated! - Key West, FL
No reviews

Little Lobster-newly Renovated!

apartment, Key West
This Key West waterfront rental, a mini-lobster house, offers convenient access to local attractions, though precise distances aren't specified in the listing.
The two-bedroom, one-bathroom house sleeps four with a pull-out sofa, features a full kitchen, washer/dryer, garage parking, kayaks, paddleboards, bikes, two boat lifts (reservations required), and a screened balcony with outdoor dining.
Key West Villas - Key West, FL
9.8 809 reviews

Key West Villas

house, Key West
This Key West house is a minute's walk from Duval Street, placing you in the heart of the action, close to the Southernmost Point, the Ernest Hemingway Home and Museum, and Mallory Square. This property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The house offers a comfortable and convenient stay with fully equipped kitchens, a heated pool, a terrace, a garden, and a guest launderette. Enjoy amenities like free WiFi, daily continental breakfast, concierge service, a restaurant, a bar, a tennis court, and on-site parking.
The Cornish Suite At Inn On Fleming Key West! - Key West, FL
9.7 3 reviews

The Cornish Suite At Inn On Fleming Key West!

B&B, Key West
THE CORNISH SUITE at the Inn on Fleming Key West is centrally located, within one mile of Mallory Square and a short walk from the Ernest Hemingway Home and Museum and Simonton Street Beach.
This 330-square-foot Key West vacation rental boasts two bedrooms, one bathroom, sleeps four guests, and includes a pool, free WiFi, and on-site parking.
Sunrise 308-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
8.6 16 reviews

Sunrise 308-2br/2ba Condo Near Beaches With Pool, Parking, Balcony

apartment, Key West
This beachfront Key West condo, located 1.2 miles from the Fort East Martello Museum and Gallery and 1.9 miles from Smathers Beach, offers stunning ocean views.
The 800-square-foot unit features three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, swimming pool, jacuzzi, fitness center, and free Wi-Fi.

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.

Coastline Comfort - Key West, FL
10 7 reviews

Coastline Comfort

apartment, Key West
37 M² Apartment ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
No reviews

37 M² Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Key West
Beachside Resort & Residences - Key West, FL
8.2 4442 reviews

Beachside Resort & Residences

resort, Key West
Key West Downtown Waterfront, Sleeps 8, Dock & Pool Pet-friendly - Key West, FL
9.9 16 reviews

Key West Downtown Waterfront, Sleeps 8, Dock & Pool Pet-friendly

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.

King Bed | Key West *Best Downtown Locations (4) - Key West, FL
9.7 93 reviews

King Bed | Key West *Best Downtown Locations (4)

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.

Spectacular Ocean View Amazing Quality- Massage Chair. Newly Renovated - Key West, FL
10 37 reviews

Spectacular Ocean View Amazing Quality- Massage Chair. Newly Renovated

apartment, Key West
Tranquility By The Beach - Key West, FL
9.3 468 reviews

Tranquility By The Beach

house, Key West
By The Beautiful Sea - Key West Beach Front Condo - W Pool Access - Key West, FL
9.2 78 reviews

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

apartment, Key West
Key West's Best - Key West, FL
9.4 6 reviews

Key West's Best

house, Key West
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