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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

Gated Oceanfront Condo At Smather's Beach - Key West, FL
9.2 151 reviews

Gated Oceanfront Condo At Smather's Beach

apartment, Key West
LaBrisa Beachfront Condo offers a prime beachfront location on Smather's Beach, voted among Florida's top 10 beaches, with direct access to the white sands and crystal-clear waters. This beachfront condo has earned excellent user ratings, ensuring a high-quality stay.
The condo features a spacious layout with 1100 square feet of living space, two bedrooms, two bathrooms, and a guest capacity of six. It offers a fully equipped kitchen, entertainment options, and a private terrace or balcony. Guests can enjoy resort-style amenities such as a heated pool, whirlpool spa, sauna, tennis court, and lounges.
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 Dock Pool Penthouse Near Duval St - Key West, FL
9.8 514 reviews

Waterfront Dock Pool Penthouse Near Duval St

apartment, Key West
This Key West penthouse condo, located in historic downtown, is less than a mile from Duval Street, the Historic Seaport, and the Hemingway House.
The 2000-square-foot unit sleeps up to 16 guests in four bedrooms and four bathrooms, boasting a private boat slip (up to 35 feet, 13-foot beam), a heated pool, and two balconies with sunrise and sunset views; on-site amenities include a tiki bar, bike rentals, and free parking.
Cuban Paradise Cuban Club - Key West, FL
10 1 review

Cuban Paradise Cuban Club

apartment, Key West
This Key West condo is located 4 minutes on foot from the Ernest Hemingway Home and Museum and 500 yards from Southernmost Point, placing it 400 yards from the city center.
This 1,270 sq ft, 2-bedroom, 2-bathroom apartment accommodates up to 11 guests and features a private balcony, a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, and access to a spa and wellness 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.

Apartment ∙ 2 Bedrooms ∙ 9 Guests - Key West, FL
10 2 reviews

Apartment ∙ 2 Bedrooms ∙ 9 Guests

apartment, Key West
This Key West apartment rental, perfect for families, is centrally located, offering easy access to Key West's attractions via various transportation options.
The two-bedroom, two-bathroom unit sleeps eight, features a fully equipped galley kitchen, in-unit laundry, and a private balcony, plus access to a shared pool and patio area with grill.
Atlantic Hideaway- Key West - Key West, FL
9.6 82 reviews

Atlantic Hideaway- Key West

apartment, Key West
This Key West condo is located just one mile from the airport and two miles from Duval Street, making it easy to explore the island's attractions. It has earned an excellent user rating, indicating a high level of satisfaction from previous guests.
The 2-bedroom, 2-bathroom apartment offers 1310 square feet of space and can comfortably accommodate up to 6 guests. It features a private beach, two swimming pools, a spa, tennis courts, fitness facilities, a BBQ area, and a recreation room, providing a wide range of amenities and activities for relaxation and entertainment.
Coastal Comfort & 3/4 Time Compound - Key West, FL
9.8 6 reviews

Coastal Comfort & 3/4 Time Compound

apartment, Key West
This expansive 4000 sq ft estate in Key West's Key Cove Landings offers a quiet neighborhood setting within walking distance of Publix and the island's largest shopping center, and is a short drive to landmarks like the Ernest Hemingway Home and Museum, Southernmost Point, and Fort Zachary Taylor Historic State Park.
This luxury compound accommodates up to 16 guests with 8 bedrooms, featuring 7 bathrooms, a chef's kitchen with gourmet appliances, a private heated pool with a BBQ grill, high-speed internet, and central air conditioning.
186 M² Condo ∙ 3 Bedrooms ∙ 8 Guests - Key West, FL
10 1 review

186 M² Condo ∙ 3 Bedrooms ∙ 8 Guests

apartment, Key West
This oceanfront penthouse in Key West offers direct beach access and is conveniently located near the elevator within the complex.
This expansive 2,000 sq. ft. condo features 3 bedrooms, 2 bathrooms, accommodates up to 8 guests, and boasts a 60-foot wraparound balcony with ocean views, plus access to an Olympic-size swimming pool, spa, sauna, and fitness center.

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

Affordable Beachfront Luxury Condo Sleeps 6 - Key West, FL
9.6 440 reviews

Affordable Beachfront Luxury Condo Sleeps 6

apartment, Key West
This Key West apartment is located right on Smathers Beach, just a short distance from the vibrant downtown area and the airport. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment has 2 bedrooms and 2 bathrooms, offering 1350 square feet of space for up to 6 guests. Enjoy amenities like a private beach access, Olympic-sized pool, hot tub, gym, sauna, grilling area, picnic areas, tennis courts, and smart TVs in each room.
~Vista Fresco~ Oceanside Condominiums With - Key West, FL
9.6 150 reviews

~Vista Fresco~ Oceanside Condominiums With

apartment, Key West
This Key West apartment is located on 1800 Atlantic, a beachfront property on the southern end of Duval Street, just east of Smathers Beach. The apartment enjoys excellent user ratings for location, cleanliness, and overall experience.
This 2-bedroom, 2-bathroom unit offers 1310 square feet of space and can comfortably accommodate up to 6 guests. It features a spacious living area, a fully equipped kitchen, a private balcony, and access to resort-style amenities like a pool, spa, tennis courts, and a fitness center.
Coconut Beach Resort - Key West, FL
9.2 472 reviews

Coconut Beach Resort

studio, 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.
Aria At Azul Mansion Key West - Key West, FL
10 3 reviews

Aria At Azul Mansion Key West

B&B, Key West
This Key West condo is situated 0.4 miles from the city center, offering a 11-minute walk to the Ernest Hemingway Home and Museum and a 0.6-mile walk to Duval Street.
This non-smoking, 1-bedroom, 1-bathroom unit accommodates up to 3 guests and includes air conditioning, a living room, complimentary Wi-Fi, and on-site parking, with access to an outdoor swimming pool and massage 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.

Spectacular Ocean View Amazing Quality- Massage Ch - Key West, FL
10 57 reviews

Spectacular Ocean View Amazing Quality- Massage Ch

apartment, Key West
This luxurious Key West penthouse, part of the 1800 Atlantic Complex, offers direct ocean views and is conveniently located near Duval Street.
The 2-bedroom, 2-bathroom condo sleeps up to eight guests and boasts an open-concept layout, a gourmet kitchen with a Vitamix blender, an 80-inch smart TV with Sonos sound, and access to resort amenities including an Olympic-size pool, tennis courts, and a fitness center.
Hyatt Sunset Harbor 1 Br Luxury Suite - Key West, FL
8.6 553 reviews

Hyatt Sunset Harbor 1 Br Luxury Suite

hotel, Key West
The Hyatt Residence Club Key West, Sunset Harbor is located in Key West, a short walk from Mallory Square and the Key West Aquarium, making it easy to explore the island's attractions. This 4-star resort boasts a very good user rating, reflecting its comfortable accommodations and convenient location.
The resort offers a variety of amenities and activities, including a swimming pool, jacuzzi, fitness center, and spa. Guests can also enjoy a relaxing terrace or balcony, a garden, and a sauna.
Artist Condo Duval Square #7 - Key West, FL
8.0 2 reviews

Artist Condo Duval Square #7

apartment, Key West
This Key West Artist Condo Duval Square 7 apartment boasts a prime location in Duval Square, just 0.3 miles from South Beach and within walking distance of Ernest Hemingway's Home, Duval Street, and the Southernmost Point.
This 1240-square-foot condo features two bedrooms, three bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, a private balcony, free Wi-Fi, and access to a swimming pool, spa, and tennis court.
**The Larks Landing @ Sunrise Suites** Condo & Pool + Last Key Services - Key West, FL
10 26 reviews

**The Larks Landing @ Sunrise Suites** Condo & Pool + Last Key Services

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, two-bedroom, two-bathroom unit sleeps six and boasts a private balcony, swimming pool, Jacuzzi, fitness center, tennis court, and fully equipped kitchen; BBQ grills are available for guest use.

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.

The Blue Flamingo Resort Key West - Key West, FL
No reviews

The Blue Flamingo Resort Key West

resort, Key West
Underwater Cabana At Custom House Inn | On Duval! - Key West, FL
9.8 24 reviews

Underwater Cabana At Custom House Inn | On Duval!

apartment, Key West
Parrot Key Hotel & Villas - Key West, FL
8.5 4813 reviews

Parrot Key Hotel & Villas

resort, Key West
Commodore's Cove - Key West, FL
9.2 244 reviews

Commodore's Cove

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.

Abbey's Attic - Truman @ Duval | Cozy Getaway In The Heart Of Key West - Key West, FL
9.8 27 reviews

Abbey's Attic - Truman @ Duval | Cozy Getaway In The Heart Of Key West

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.

Oceanview At 1800 Atlantic, Short Walk To Smathers Beach Wish Island Paradise - Key West, FL
9.4 30 reviews

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

apartment, Key West
Hyatt Centric Key West Resort & Spa - Key West, FL
8.7 2732 reviews

Hyatt Centric Key West Resort & Spa

resort, Key West
Henry's Penthouse On The Ocean In Key West  - Weekly / Nightly Rentals - Key West, FL
9.6 100 reviews

Henry's Penthouse On The Ocean In Key West - Weekly / Nightly Rentals

apartment, Key West
Leaward Isle Island Retreat - Key West, FL
9.8 2666 reviews

Leaward Isle Island Retreat

house, Key West
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