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3908 Lodgings in Key West, FL
Key West, FL
12/21 – 01/18
$407/nighttotal: $11396 (28 )
Old Town Getaway
1 1
house , Key West
Old Town Getaway, a one-bedroom Key West vacation rental, is conveniently located in Old Town, a six-minute walk from Duval Street, seventeen minutes from Mallory Square, and fourteen minutes from South Beach. This 610-square-foot house sleeps seven guests and features a fully equipped kitchen with a dishwasher, free Wi-Fi, a washer, and air conditioning.
9.4 61 reviews
Key West, FL
07/02 – 07/07
$468/nighttotal: $2340 (5 )
Osprey Studio @ The Colony-sleeps Up To 4
1 2
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.
9.5 83 reviews
Key West, FL
07/24 – 07/28
$940/nighttotal: $3760 (4 )
Sunnyside Up
1 7
apartment , Key West
This Key West apartment is located in downtown, just an 8-minute walk from Higgs Beach and half a mile from South Beach, making it easy to explore the island's attractions. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience. The 2-bedroom unit offers 1160 square feet of space and can accommodate up to 9 guests. Amenities include a private patio, a swimming pool, a fully equipped kitchen, free Wi-Fi, and a washer and dryer, ensuring a comfortable and convenient stay.
9.7 257 reviews
Key West, FL
07/02 – 07/03
$911/nightfor 1 night
Waterfront Dock Pool Key West Near Duval
1 5
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.
8.8 162 reviews
Key West, FL
10/14 – 10/16
$345/nighttotal: $690 (2 )
Elegant Condo With Entertainment & Private Parking - Great Central Location
1 2
apartment , Key West
This one-bedroom condo offers ocean air and tropical sunset views in a prime downtown Key West location, just a short walk to Duval Street's bars and restaurants and the Ernest Hemingway Home and Museum. This 510 square foot apartment accommodates up to four guests with air conditioning, free WiFi, and private parking, providing easy access to Florida Keys Beaches and South Beach.
9.8 10 reviews
Key West, FL
07/24 – 07/28
$1024/nighttotal: $4096 (4 )
Sunnyside Up - Shared Pool
2 7
apartment , Key West
This Key West apartment is located in the Historic District, just a short walk from Duval Street, the Key West Firehouse Museum, and the beaches. It has received excellent user ratings. The 1160-square-foot apartment comfortably accommodates up to 9 guests in two bedrooms and two bathrooms. You can enjoy a private balcony, a fully equipped kitchen, a swimming pool, a garden, and parking on-site.
9.0 2 reviews
Key West, FL
07/24 – 07/25
$575/nightfor 1 night
Royal Palm Suite At Travelers Palm Inn Key West
1 4
house , Key West
The ROYAL PALM SUITE, a centrally located Key West rental, is an 8-minute walk from South Beach and less than 1.5 miles from the Key West Aquarium and Mallory Square. This one-bedroom, one-bathroom apartment sleeps four, features a fully equipped kitchen with a dishwasher and microwave, a private terrace, a swimming pool, and free Wi-Fi, plus convenient on-site parking.
9.4 11 reviews
Key West, FL
06/20 – 06/27
$680/nighttotal: $4760 (7 )
Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock
2 7
house , Key West
This Key West waterfront condo is located approximately 1.1 miles from the Ernest Hemingway Home and Museum and Duval Street, and 1.2 miles from Key West International Airport, offering convenient access to major attractions. This 1300-square-foot property features two bedrooms, two bathrooms, a fully equipped kitchen, a private pool, and free Wi-Fi; it comfortably sleeps 11 guests and is near cycling opportunities.
9.0 144 reviews
Key West, FL
07/02 – 07/03
$672/nightfor 1 night
New Grenada Suite - Parking Pool & Pets 209
1 5
house , Key West
The NEW Grenada Suite is located in Key West, just a short drive from popular attractions like Duval Street and Mallory Square. This vacation rental has excellent ratings for location, cleanliness, and user experience. The suite has two bedrooms and can accommodate up to six guests. Enjoy the amenities like a private patio, swimming pool, and fitness center, perfect for relaxing and staying active during your Key West getaway.
9.4 129 reviews
Key West, FL
06/20 – 06/27
$327/nighttotal: $2289 (7 )
La Casa De Luna Near The Southernmost Point
1 2
apartment , Key West
This Old Town Key West condo is located half a block from Duval Street, offering easy access to Key West's nightlife and attractions. The 450-square-foot ground-level unit features one bedroom with a king bed, one bathroom, a queen sleeper sofa, full kitchen, and access to a shared pool three blocks away; it comfortably sleeps four guests and includes amenities such as air conditioning, Wi-Fi, and parking.
9.6 10 reviews
Key West, FL
07/25 – 07/27
$430/nighttotal: $860 (2 )
Elegant Escape | Outdoor Pool. Island Experience
1 3
B&B , Key West
This studio apartment is located in Historic Old Town on Key West's Atlantic Coast, adjacent to the Southernmost Point Buoy and within 2,640 feet of Mallory Square and the Key West Lighthouse. This elegant studio offers two queen beds for up to four guests, featuring contemporary coastal design, a sun-drenched patio with pool or ocean views, and access to three heated resort pools, two private beaches, a fitness center, on-site bars and restaurants, and 24/7 concierge services.
9.6 1122 reviews
Key West, FL
07/25 – 07/27
$534/nighttotal: $1068 (2 )
Key West Villas
2 3
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.
Top Lodgings with a Pool in Key West, FL
On-site pool access at your lodging in Key West, FL makes a refreshing swim the perfect way to complement a day by the water.
8.8 2731 reviews
Key West, FL
07/02 – 07/03
$633/nightfor 1 night
Hyatt Centric Key West Resort & Spa
1 5
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.
9.4 27 reviews
Key West, FL
06/20 – 06/27
$276/nighttotal: $1932 (7 )
The Curry Poolside | Ground Floor King
1 2
apartment , Key West
This Key West apartment rental, located in the Historic District, is a half-block from Duval Street and within walking distance of Mallory Square, offering easy access to restaurants, attractions like the Mel Fisher Maritime Museum, and Fury Water Adventures. The one-bedroom, one-bathroom unit in a historic 1869 mansion sleeps two guests and includes a shared heated pool, on-site laundry facilities with detergent provided, and access to a terrace; contactless check-in is available, and pets are welcome.
9.6 9 reviews
Key West, FL
07/25 – 07/27
$441/nighttotal: $882 (2 )
The Saint Kitts Suite | Breathtaking View
2 3
apartment , Key West
This newly renovated 2-bedroom, 2-bathroom corner condo in Key West's Sunrise Suites community is located on the southeast side, two miles from Smathers Beach and minutes from Duval Street. This dog-friendly vacation rental accommodates up to six guests and features a private balcony, a communal heated pool, a hot tub, and an in-unit washer/dryer.
9.8 17 reviews
Key West, FL
10/05 – 10/19
$360/nighttotal: $5040 (14 )
Oceanfront Oasis Smathers Beach Condo Sunrise Views Island Charm Book Today
2 1
apartment , Key West
This oceanfront condo in Key West's La Brisa complex sits directly on Smather's Beach, offering easy access to attractions like the Southernmost Point and the Ernest Hemingway Home and Museum. This 1190-square-foot, three-bedroom, two-bathroom rental sleeps six, boasting a fully equipped kitchen, private balcony with ocean views, in-unit laundry, and access to a heated pool, hot tub, sauna, and tennis court.
Best family friendly Key West, FL lodging
Among the 3908 accommodations in Key West, FL, here are the 4 best for families
9.0 2 reviews
Key West, FL
06/27 – 06/28
$1283/nightfor 1 night
Apartment ∙ 3 Bedrooms ∙ 8 Guests
3 7
apartment , Key West
This three-bedroom, three-bathroom Key West condo is conveniently located near Duval Street, offering easy access to Key West attractions via a complimentary shuttle service (9 am-11 pm). The 3-bedroom beachfront rental boasts a fully equipped kitchen, private balcony, in-unit washer/dryer, and access to on-site bike and watercraft rentals through Brightwild Adventures, accommodating up to eight guests.
9.4 2561 reviews
Key West, FL
06/27 – 06/28
$1292/nightfor 1 night
Santa Maria Suites Resort
4 7
resort , Key West
The Santa Maria Suites Resort is located just one block from both the Atlantic Ocean and Duval Street, making it easy to explore Key West's beaches, nightlife, and shops. The resort consistently receives excellent ratings for its location, cleanliness, and overall experience. Each suite offers a full kitchen, a 48-inch flat-screen cable TV, and a terrace or balcony. The resort also features two outdoor heated pools, a restaurant serving Japanese cuisine, a bar, a fitness center, and a spa.
9.8 39 reviews
Key West, FL
06/20 – 06/27
$1932/nighttotal: $13524 (7 )
Pagitt House - 4/3.5 - Old Town Key West With Pool!
4 1
apartment , Key West
This Key West Historic District home is a short walk from Donkey Milk House and Duval Street, and within a 15-minute drive of Mallory Square and area beaches. The three-bedroom, two-bathroom house sleeps six guests and boasts a private pool, patio, fully equipped kitchen (including fridge, microwave, and dishwasher), free Wi-Fi, and concierge service.
Key West, FL
06/20 – 06/27
$307/nighttotal: $2149 (7 )
Seas The Breeze, Poolside Condo Near The Beach
2 2
apartment , Key West
This apartment in Key West is located 0.6 miles from Key West International Airport and approximately 4 miles from Southernmost Point and Duval Street. This family-friendly, 800 square foot apartment features 2 bedrooms, 2 bathrooms, air conditioning, a kitchen, a swimming pool, a jacuzzi, a balcony, and parking for up to 11 guests, with free Wi-Fi available.
Frequently Asked Questions about accommodations in Key West, FL
What are the top attractions and must-see sites in Key West, FL?
You've got to see the Southernmost Point Buoy, it's a classic Key West photo op. Don't miss the Hemingway House, the author's former home, and the Key West Butterfly and Nature Conservatory, a beautiful place to escape the sun. Of course, you'll want to stroll down Duval Street, the heart of Key West, and check out the shops and restaurants.
Which cultural festivals and seasonal events should visitors attend in Key West, FL?
The Fantasy Fest in October is a wild, colorful, and fun event with parades and parties. The Key West Songwriters Festival in May brings in some great musicians. And if you're there in January, the Key West Food & Wine Festival is a must-do for foodies.
What are the best accommodations with a pool in Key West, FL?
What are the most convenient modes of transportation within Key West, FL?
Key West is a very walkable city, so you can get around easily on foot. If you want to explore further, the Conch Tour Train is a fun way to see the sights, and the Old Town Trolley is another option. Of course, you can always rent a bike or scooter to get around.
What are the best accommodations with a jacuzzi in Key West, FL?
What outdoor activities and adventures are popular in and around Key West, FL?
Key West is a paradise for watersports. You can go snorkeling, diving, kayaking, or even parasailing. If you're feeling adventurous, try a sunset sail or a dolphin watching tour. And don't forget to relax on the beach, there are plenty of beautiful spots to choose from.
What are the best accommodations for families and kids in Key West, FL?
What types of accommodations are available in Key West, FL?
You have tons of options in Key West, from luxury resorts and boutique hotels to cozy guesthouses and vacation rentals. There are even some unique places to stay like the historic Old Town Manor or the funky Mermaid and the Alligator.
What are the best pet friendly accommodations in Key West, FL?
The best time to visit Key West is during the shoulder seasons, from April to May and September to October. The weather is still great, but the crowds are smaller and the prices are lower. You can also visit during the winter, but it can get a bit crowded and expensive.
What are the best accommodations with parking in Key West, FL?
What local dishes and culinary experiences are a must-try in Key West, FL?
You have to try the Key Lime Pie, it's a Key West classic. Fresh seafood is also a must, especially the conch fritters. And don't forget to sample some of the local craft beers at one of the many breweries in town.
In which part of Key West, FL should you consider renting accommodation?
Old Town is the heart of Key West, with lots of shops, restaurants, and attractions. If you want to be close to the action, this is the place to stay. If you prefer a quieter setting, you might consider staying in the New Town area, which is still within walking distance of the main attractions.
Destinations nearby
Best Key West, FL accommodation with a balcony
Key West, FL
07/24 – 07/28
$985/nighttotal: $3940 (4 )
Pool View 3br Residence | Beachside Resort
3 7
apartment , Key West
This expansive 3-bedroom condo offers luxurious resort living on seven acres overlooking the Gulf of Mexico in north Key West, located just 10 minutes from Duval Street and attractions like the Ernest Hemingway Home and Museum. Enjoy a private balcony with resort pool views, access to a heated resort pool and hot tub, on-site dining, and a shuttle service, with accommodations for up to 8 guests.
9.4 192 reviews
Key West, FL
09/13 – 09/27
$343/nighttotal: $4802 (14 )
In Good Spirits ~ Waterfront Condo, Wrap-around Balcony & Community Pool!
2 2
apartment , Key West
This beachfront condo in Key West's Beachside neighborhood offers direct access to Smathers Beach, a short walk from Duval Street and minutes from Key West International Airport. This 1970-square-foot unit features two king bedrooms, a queen sleeper sofa, two bathrooms, and accommodates six guests, boasting a private patio with ocean views, a well-equipped kitchen, and access to a community pool, tennis court, and grilling area.
9.8 108 reviews
Key West, FL
07/24 – 07/28
$1266/nighttotal: $5064 (4 )
A Key Escape ~ 3 Bedroom, 2.5 Bathroom Home In Old Town /Private Heated Pool!
3 7
apartment , Key West
This Key West townhome, located in the Historic District, is blocks from Duval Street and near the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park. The 1,570-square-foot property features three bedrooms, three bathrooms, and accommodates eight guests, offering a private pool, gas grill, and concierge service for arranging activities and pre-arrival grocery stocking.
9.6 109 reviews
Key West, FL
06/20 – 06/27
$354/nighttotal: $2478 (7 )
La Casa De Luna - 1 Bd/1b Condo Just Off Upper Duval
2 1
apartment , Key West
This Old Town Key West condo is located steps from the City Zoo Gallery and Duval Street, within a 10-minute drive of the Ernest Hemingway Home and Museum and Florida Keys beaches. This 450-square-foot apartment features one bedroom, one bathroom, accommodates four guests, and includes a private pool, balcony, fully equipped kitchen, in-unit laundry, and free internet access.
Neighborhoods and points of interest in Key West, FL
Best Key West, FL accommodation with a kitchen
9.2 151 reviews
Key West, FL
10/17 – 10/24
$506/nighttotal: $3542 (7 )
Caribbean Conch 5 Minutes To Smathers Beach & 10 Minute Bike Downtown - Value
2 2
apartment , Key West
This Key West apartment is located in the Beachside neighborhood, just a short walk from beautiful beaches and a popular beach park, and within a 2-mile radius of Duval Street and the Southernmost Point. This rental has received excellent ratings for location, cleanliness, and overall experience. The apartment has two bedrooms and two bathrooms, making it perfect for families or groups of friends. Guests can enjoy a fully equipped kitchen, free Wi-Fi, a swimming pool, a Jacuzzi, a sauna, a fitness center, a tennis court, and a garden.
Key West, FL
06/20 – 06/27
$341/nighttotal: $2387 (7 )
Seas The Breeze Poolside Condo Near The Beach
2 2
apartment , Key West
This Key West condo offers an island retreat on the quieter side of the island, located a short 10-minute drive from Duval Street and Mallory Square. This 800-square-foot suite accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, a private balcony, and access to resort amenities including a heated swimming pool and hot tub.
9.0 925 reviews
Key West, FL
06/27 – 06/28
$1314/nightfor 1 night
Rose Lane Villas
4 7
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.
9.7 338 reviews
Key West, FL
10/14 – 10/16
$261/nighttotal: $522 (2 )
Poolside Cottage #411
1 2
apartment , Key West
This Key West vacation home boasts an oceanfront location, within two miles of the Key West Tropical Forest, Fort Zachary Taylor Historic State Park, and the Key West Art & Historical Society. This 700-square-foot property features one bedroom, one bathroom, sleeps six, and includes a private pool, Jacuzzi, and fully equipped kitchen; BBQ grills are available for outdoor dining.
