Key West, FL vacation rentalscozycozy

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Best Vacation rentals and Airbnb offers in Key West, FL

Away From It All @ The Truman Annex - Key West, FL
9.0 29 reviews
Key West, FL
2 2
$458/nighttotal: $40304 (88 )

Away From It All @ The Truman Annex

apartment - Key West
This Key West condo rental is located in the prestigious Truman Annex, a gated community in Old Town, two blocks from Duval Street and a quarter-mile from Fort Zachary Taylor State Park.
This 680-square-foot, two-bedroom, one-bathroom unit sleeps four and features two balconies, a fully equipped kitchen, washer/dryer, community pool access, and free parking.
Summer Special@ 129 Sun Thru Wed.ngts Lodging  Only 129 + Extras - Key West, FL
9.6 255 reviews
Key West, FL
2 1
$196/nighttotal: $784 (4 )

Summer Special@ 129 Sun Thru Wed.ngts Lodging Only 129 + Extras

apartment - Key West
This Key West Historic District home is a 15-minute walk from Duval Street, the Key West Firehouse Museum, and Florida Keys beaches, and under 1.2 miles from the Ernest Hemingway Home and Museum and South Beach.
This 500-square-foot house features one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen, patio, free parking, Wi-Fi, a tennis court, and a spa.
Rose Petal Petite Suite - Near Duval Street - Key West, FL
9.3 69 reviews
Key West, FL
2 1
$293/nighttotal: $586 (2 )

Rose Petal Petite Suite - Near Duval Street

apartment - Key West
This Key West apartment boasts a central downtown location, offering easy walking access to Duval Street and Mallory Square.
The unit, perfect for two guests, features a fully equipped kitchen, in-unit laundry, a private balcony and deck, reserved parking, and access to a shared pool and outdoor shower.
Sailors Cabin  Old Town - Walk To Duval ! - Key West, FL
9.8 155 reviews
Key West, FL
2 1
$202/nighttotal: $404 (2 )

Sailors Cabin Old Town - Walk To Duval !

apartment - Key West
The Cozy Little Cottage, a centrally located Key West apartment, offers easy access to Duval Street and Mallory Square.
This one-bedroom, one-bathroom suite sleeps two guests and features a private entrance, keyless entry, air conditioning, free internet, parking, and a full kitchen with refrigerator, freezer, and microwave.
Amelia Home By Avantstay - Key West, FL
9.6 60 reviews
Key West, FL
4 2
$1660/nighttotal: $4980 (3 )

Amelia Home By Avantstay

house - Key West
The Amelia Home by AvantStay is located in Key West's historic Old Town, just a short walk from the Ernest Hemingway Home and Museum and Duval Street. This vacation rental has received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom home offers a comfortable living space with a fully equipped kitchen and private outdoor patio. Enjoy modern amenities like air conditioning, free Wi-Fi, a TV, and a private parking space, a rare find in Key West.
High Tide In Key West - Key West, FL
9.0 208 reviews
Key West, FL
2 2
$758/nighttotal: $5306 (7 )

High Tide In Key West

house - Key West
This Key West apartment is just a short walk from Smathers Beach, one of the island's most popular beaches, and within a mile of Rest Beach and Higgs Beach. The apartment has received excellent ratings for cleanliness, location, and overall user experience.
This two-bedroom rental comfortably accommodates up to six guests. Enjoy modern amenities like air conditioning, free Wi-Fi, a private balcony with ocean views, and a fully equipped kitchen. You'll also have access to a swimming pool, jacuzzi, fitness center, tennis court, and more.
Sunrise 307-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
9.6 30 reviews
Key West, FL
2 2
$689/nighttotal: $2067 (3 )

Sunrise 307-2br/2ba Condo Near Beaches With Pool, Parking, Balcony

apartment - Key West
This Key West oceanfront condo is situated 1.2 miles from Fort Zachary Taylor Historic State Park and 1.9 miles from Smathers Beach, offering convenient access to local attractions.
This 800-square-foot unit features three bedrooms, two bathrooms, and sleeps six, boasting a fully equipped kitchen, private balcony, swimming pool, and on-site barbecue grills.
Tropical Paradise Key West - Key West, FL
9.4 192 reviews
Key West, FL
4 2
$493/nighttotal: $1479 (3 )

Tropical Paradise Key West

house - Key West
This Key West condo is situated in the peaceful Beachside district, just a short walk from the stunning Florida Keys Beaches and a 2-mile radius of major tourist attractions such as Clarence S. Higgs Memorial Beach Park, Duval Street, and Southernmost Point. With excellent user, location, and cleanliness ratings, this condo offers a comfortable and convenient stay for travelers.
The condo features 2 spacious bedrooms, a fully equipped kitchen, and a sofa bed, accommodating up to 6 guests in its 1360 square feet of floor area. Guests can enjoy access to a fitness center, sauna, spa tub, garden, barbecue grills, and a swimming pool, making this condo an ideal choice for those seeking relaxation and entertainment during their stay in Key West.
Key West At Hyatt Beach House - Key West, FL
10 12 reviews
Key West, FL
4 2
$444/nighttotal: $888 (2 )

Key West At Hyatt Beach House

apartment - Key West
This Key West condo is ideally located in the northeast of the island, minutes from Mallory Square and Duval Street.
The two-bedroom, two-bathroom unit sleeps six guests, features a fully equipped kitchen, screened balcony, and access to resort amenities including a pool, spa, grills, and private beach.
Kw23 Atlantic Ocean View - Key West, FL
8.9 157 reviews
Key West, FL
2 2
$357/nighttotal: $2499 (7 )

Kw23 Atlantic Ocean View

apartment - Key West
This Key West house is located just a short walk from Duval Street and the Southernmost Point, offering easy access to the island's main attractions. Guests have consistently rated it as "very good" for its user experience, "excellent" for its location, and "excellent" for its cleanliness.
The 2-bedroom house, with a floor area of 1360 square feet, features a fully equipped kitchen, air conditioning, a private bathroom, satellite TV, and a terrace or balcony. Enjoy amenities like a swimming pool, Jacuzzi, sauna, spa, tennis court, and parking, all while taking in the beautiful ocean views.
The Samana Cay | Tropical, Airy Retreat W/ Pool - Key West, FL
9.8 22 reviews
Key West, FL
3 2
$409/nighttotal: $818 (2 )

The Samana Cay | Tropical, Airy Retreat W/ Pool

apartment - Key West
The Samana Cay apartment is conveniently located near Key West International Airport (0.6 miles) and offers easy access to Mallory Square (5 miles), the Southernmost Point, and the Ernest Hemingway Home and Museum.
This two-bedroom, two-bathroom Key West rental sleeps six guests and features a fully equipped kitchen, private balcony, in-unit washer/dryer, access to a shared pool and jacuzzi, and ample on-site parking.
The Salt Cay | Updated! Stunning Sunset View, Pool - Key West, FL
9.6 57 reviews
Key West, FL
3 2
$398/nighttotal: $796 (2 )

The Salt Cay | Updated! Stunning Sunset View, Pool

apartment - Key West
This Sunrise Suites condo, located on the east side of Key West, is a mile from Smathers Beach and a ten-minute drive from Duval Street.
The 800-square-foot, three-bedroom, two-bathroom apartment in Key West sleeps six, features a private balcony with sunset views, a fully equipped kitchen, in-unit laundry, and access to a shared pool, hot tub, and tennis court.

Best Key West, FL vacation rentals with a balcony

Upper Sunset South - Key West, FL
Key West, FL
2 3
$1059/nighttotal: $2118 (2 )

Upper Sunset South

house - Key West
This Key West villa in Upper Sunset South is a short walk from Duval Street and the Ernest Hemingway Home and Museum, with Rest Beach located 10080 feet away.
This residence accommodates up to 11 guests and offers a private balcony with city views, an outdoor swimming pool, on-site massage services, and includes complimentary WiFi and private parking.
Good Visibility ~ 4 Bedroom, 3 Bathroom Condo W/ Pool And Ocean Views! - Key West, FL
9.8 57 reviews
Key West, FL
7 4
$578/nighttotal: $4046 (7 )

Good Visibility ~ 4 Bedroom, 3 Bathroom Condo W/ Pool And Ocean Views!

apartment - Key West
This luxurious oceanfront condo, located in Key West's Beachside neighborhood, is 0.2 miles from Higgs Beach and 0.8 miles from Smathers Beach, offering easy access to White Street Pier and Duval Street.
This 2,030-square-foot Key West rental boasts four bedrooms, three bathrooms, sleeps eight, and includes a private balcony, a fully equipped kitchen, and access to Key West Beach Club amenities such as pools and a tennis court.
Duval Sea Turtle By Avantstay - Key West, FL
9.5 272 reviews
Key West, FL
2 2
$958/nighttotal: $3832 (4 )

Duval Sea Turtle By Avantstay

house - Key West
This Key West vacation rental is ideally situated in the heart of the city, just a short walk from South Beach, the Southernmost Point, and Duval Street, putting you right in the middle of the action. The home has received excellent ratings for location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The house offers 1230 square feet of living space and comfortably accommodates up to 6 guests in its 2 bedrooms. Enjoy a range of amenities including a shared pool, a fully equipped kitchen, air conditioning, and a terrace, perfect for relaxing after a day of exploring the island.
Kwss108 Sunrise Suites - Martinique Suite 108 - Key West, FL
Key West, FL
4 2
$303/nighttotal: $606 (2 )

Kwss108 Sunrise Suites - Martinique Suite 108

house - Key West
This Key West rental house is located 0.6 miles from Key West International Airport, 4 miles from Southernmost Point, and 4.3 miles from Ernest Hemingway Home and Museum and Duval Street.
This 780 square foot house accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, a swimming pool, hot tub, balcony, and elevator access.

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 ∙ 4 Bedrooms ∙ 12 Guests - Key West, FL
Key West, FL
4 4
$7109/nighttotal: $21327 (3 )

Apartment ∙ 4 Bedrooms ∙ 12 Guests

apartment - Key West
This Key West house rental is centrally located in downtown Key West, within walking distance of Duval Street and Mallory Square.
The property features two houses with four bedrooms and four bathrooms, accommodating up to twelve guests, complete with two fully equipped kitchens, a private heated pool, and two off-street parking spots.
Charming Deck And Inviting Living Space - Serene Coastal Retreat - Key West, FL
Key West, FL
2 1
$305/nighttotal: $1220 (4 )

Charming Deck And Inviting Living Space - Serene Coastal Retreat

cottage - Key West
Colony Poolside, a cottage within The Colony, is located in a secluded compound just steps from Duval Street, offering convenient access to award-winning restaurants, shopping, and beaches.
This family-friendly cottage accommodates up to 4 guests with 1 bedroom and 1 bathroom, featuring a private deck for grilling and al fresco dining, a fully equipped kitchen, air conditioning, and access to a shared swimming pool and a porch with Adirondack chairs.
Hidden Oasis 3 Blocks From Duval - Key West, FL
9.6 102 reviews
Key West, FL
2 1
$536/nighttotal: $2144 (4 )

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.
Osprey Studio @ The Colony-sleeps Up To 4 - Key West, FL
9.4 63 reviews
Key West, FL
2 1
$406/nighttotal: $812 (2 )

Osprey Studio @ The Colony-sleeps Up To 4

studio - Key West
Osprey studio, a Key West Old Town apartment rental in the Colony neighborhood on Olivia Street, is two blocks from Duval Street, near the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 480-square-foot ground-floor unit features a queen bed, a couch, a kitchenette with a fridge and microwave, a private deck near a shared pool, and accommodates up to four guests, offering easy access to nearby water activities and biking trails.

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

Sugar Palm Studio ~ Adult Only Studio W/ Community Pool & Close To Town! - Key West, FL
9.6 360 reviews
Key West, FL
2 1
$619/nighttotal: $2476 (4 )

Sugar Palm Studio ~ Adult Only Studio W/ Community Pool & Close To Town!

studio - Key West
This Key West apartment is located in the Historic District, just a short walk from Duval Street, beaches, and the Saint Mary Star of the Sea church. The apartment has received excellent user ratings.
The apartment can accommodate up to two guests and includes a kitchen with a refrigerator and microwave. Enjoy amenities like a swimming pool, tennis court, and a terrace, as well as concierge services and free Wi-Fi.
Poolside Suite - Key West, FL
9.1 340 reviews
Key West, FL
2 1
$396/nighttotal: $792 (2 )

Poolside Suite

apartment - Key West
This Key West apartment is located in the heart of the city, just a short walk from South Beach and Fort Zachary Taylor State Park Beach. Guests rave about its excellent location, cleanliness, and overall experience.
The apartment offers a private patio for relaxing, a fully equipped kitchen for preparing meals, and access to a refreshing swimming pool. You'll also enjoy amenities like free Wi-Fi, cable TV, and a washing machine.
The Mallory Suite At Inn On Fleming Key West! - Key West, FL
9.5 2 reviews
Key West, FL
2 1
$386/nighttotal: $772 (2 )

The Mallory Suite At Inn On Fleming Key West!

house - Key West
The Mallory Suite is a Key West apartment conveniently located near Mallory Square, the Ernest Hemingway Home and Museum, and Duval Street, a short walk from Simonton Street Beach.
This 220-square-foot, one-bedroom unit sleeps two guests and features a private balcony, free Wi-Fi, on-site parking, and access to a swimming pool and tennis court.
Duval Hideaway | Dog-friendly W/ Shared Hot Tub - Key West, FL
9.7 13 reviews
Key West, FL
4 2
$489/nighttotal: $978 (2 )

Duval Hideaway | Dog-friendly W/ Shared Hot Tub

apartment - Key West
This Key West vacation rental boasts a prime Duval Street location, two blocks from Fort Zachary Taylor State Park and steps from the area's famed attractions.
The two-bedroom, one-bathroom house sleeps six, features a fully equipped kitchen, in-unit laundry, three cable TVs, free WiFi, a shared hot tub, and private parking—a rare find in Key West.

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.

Tropical Retreat ~ 3 Bedroom/3.5 Bath 1/2 Block From Duval W/ Heated Pool! - Key West, FL
9.6 115 reviews
Key West, FL
7 3
$716/nighttotal: $5012 (7 )

Tropical Retreat ~ 3 Bedroom/3.5 Bath 1/2 Block From Duval W/ Heated Pool!

apartment - Key West
This Key West Historic District rental is a half block from Duval Street, near the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 1450-square-foot, three-bedroom, four-bathroom apartment sleeps eight, boasts a private heated pool, poolside cottage, and fully equipped kitchen, plus concierge service for booking local activities.
Carey's Corner | Updated Studio With Heated Pool - Key West, FL
8.6 46 reviews
Key West, FL
2 1
$454/nighttotal: $39952 (88 )

Carey's Corner | Updated Studio With Heated Pool

studio - Key West
This Key West Historic District condo is steps from Duval Street and a five-minute walk from the Florida Keys beaches.
The one-bedroom, one-bathroom apartment sleeps two guests and features a patio, in-unit laundry, free WiFi, and access to a shared swimming pool; explore Hemingway's Home, the Southernmost Point, and South Beach, all within a ten-minute radius.
Oceanfront Condo In Key West - Key West, FL
9.9 40 reviews
Key West, FL
2 2
$391/nighttotal: $2737 (7 )

Oceanfront Condo In Key West

apartment - Key West
This Key West Beach Club condo rental boasts a direct waterfront location in an upscale, gated community, within walking or biking distance of Duval Street and Key West's best beaches.
The two-bedroom, two-bathroom unit sleeps four guests and features a full kitchen with dishwasher, in-unit laundry, air conditioning, a swimming pool, fitness center, and on-site parking.
Rose Lane Villas - Key West, FL
9.2 578 reviews
Key West, FL
2 1
$245/nighttotal: $490 (2 )

Rose Lane Villas

house - Key West
This Key West house is located just off Duval Street, putting you within walking distance of the Key West Aquarium and a short drive from the Southernmost Point. It boasts excellent ratings for location, cleanliness, and user experience.
The house has a fully equipped kitchen, private bathrooms with hairdryers and toiletries, and some units offer balconies or porches. You can enjoy a heated outdoor swimming pool, free Wi-Fi, and parking, making it a comfortable and convenient stay.

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.

Waterfront Luxury Home With Private Pool - Key West, FL
9.8 96 reviews
Key West, FL
7 4
$820/nighttotal: $5740 (7 )

Waterfront Luxury Home With Private Pool

apartment - Key West
The Perry Hotel & Marina Key West - Key West, FL
9.2 2444 reviews
Key West, FL
4 1
$729/nighttotal: $2187 (3 )

The Perry Hotel & Marina Key West

resort - Stock Island
Happys Houseboat - Key West, FL
9.6 291 reviews
Key West, FL
3 1
$595/nighttotal: $2975 (5 )

Happys Houseboat

barge - Key West
The Cat Island Suite | Charmingly Renovated W/ Pool - Key West, FL
Key West, FL
3 2
$402/nighttotal: $804 (2 )

The Cat Island Suite | Charmingly Renovated W/ Pool

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.

Poolside Cottage #412 - Key West, FL
9.7 356 reviews
Key West, FL
4 1
$835/nighttotal: $2505 (3 )

Poolside Cottage #412

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.

Sundial On The Atlantic Ocean View - Key West, FL
8.7 3 reviews
Key West, FL
2 2
$459/nighttotal: $3213 (7 )

Sundial On The Atlantic Ocean View

house - Key West
Ocean Hideaway On The Atlantic - Key West, FL
9.2 154 reviews
Key West, FL
2 2
$422/nighttotal: $1688 (4 )

Ocean Hideaway On The Atlantic

house - Key West
Key West Beachfront Luxury 2/2 Condo A212 - Key West, FL
10 172 reviews
Key West, FL
2 2
$688/nighttotal: $2752 (4 )

Key West Beachfront Luxury 2/2 Condo A212

apartment - Key West
Henry's Piece Of Paradise On The Ocean In Key West - Key West, FL
9.6 144 reviews
Key West, FL
2 2
$533/nighttotal: $3731 (7 )

Henry's Piece Of Paradise On The Ocean In Key West

apartment - Key West
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