
Smathers Beach
10/15 – 10/21
$470/nighttotal: $2820 (6 )
Caribbean Conch 5 Minutes To Smathers Beach & 10 Minute Bike Downtown - Value
2 1apartment , 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.
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.

Smathers Beach
06/19 – 06/30
$477/nighttotal: $5247 (11 )
Romantic Captain's Quarters
1 4boat , Stock Island
This unique Hans Christian sailboat is docked at Perry Marina and Resort on Stock Island, offering easy access to Key West via shuttle.
The 2-bedroom, 1-bathroom vessel sleeps four guests and includes a kitchen, air conditioning, internet, and access to resort amenities like swimming pools, restaurants, and happy hour, plus onboard art supplies and musical instruments.
The 2-bedroom, 1-bathroom vessel sleeps four guests and includes a kitchen, air conditioning, internet, and access to resort amenities like swimming pools, restaurants, and happy hour, plus onboard art supplies and musical instruments.

Smathers Beach
08/18 – 08/27
$344/nighttotal: $3096 (9 )
42 M² House ∙ 1 Bedroom ∙ 4 Guests
1 2house , Key West
This Old Town Key West condo, located in the Art District, is eight blocks from Duval Street and a short bike ride from Higgs Beach and the Historic Seaport.
The 450-square-foot, one-bedroom Palm Gardens unit sleeps four, features a king-size bed and queen-size sleeper sofa, a full kitchen with dishwasher, a shared pool, and BBQ grill, plus AvantStay services.
The 450-square-foot, one-bedroom Palm Gardens unit sleeps four, features a king-size bed and queen-size sleeper sofa, a full kitchen with dishwasher, a shared pool, and BBQ grill, plus AvantStay services.

Smathers Beach
06/19 – 06/30
$510/nighttotal: $5610 (11 )
Kwss303 Sunrise Suites - Saint Barts Suite 303
2 4house , Key West
This Key West house is located 0.6 miles from Key West International Airport and within 4 to 4.7 miles of Southernmost Point, the Ernest Hemingway Home and Museum, and Duval Street.
This 780 sq ft vacation home offers 2 bedrooms, 2 bathrooms, a capacity for 11 guests, a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, a Jacuzzi, a terrace, a fitness center, and a tennis court.
This 780 sq ft vacation home offers 2 bedrooms, 2 bathrooms, a capacity for 11 guests, a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, a Jacuzzi, a terrace, a fitness center, and a tennis court.

Smathers Beach
08/18 – 08/27
$252/nighttotal: $2268 (9 )
Claro At Azul Mansion Key West
1 2house , Key West
CLARO at Azul Mansion, a one-bedroom Key West vacation home, is centrally located less than half a mile from the city center and a 12-minute walk from South Beach, placing you within 1.2 miles of the Ernest Hemingway Home and Museum, Duval Street, and Mallory Square.
This air-conditioned rental offers a swimming pool, free Wi-Fi, on-site parking, and accommodates two guests, providing easy access to Key West International Airport (1.9 miles away) and nearby attractions.
This air-conditioned rental offers a swimming pool, free Wi-Fi, on-site parking, and accommodates two guests, providing easy access to Key West International Airport (1.9 miles away) and nearby attractions.

Smathers Beach
06/19 – 06/30
$609/nighttotal: $6699 (11 )
Ocean Views From 90 Ft Balcony
1 4apartment , Key West
This oceanfront Key West condo boasts direct beach access and unparalleled ocean views from its three spacious bedrooms and two bathrooms, sleeping up to six guests.
The unit features a gourmet kitchen, 90-foot balcony, heated pool, hot tub, fitness center, and parking; proximity to Key West attractions requires further specification based on the condo's exact location.
The unit features a gourmet kitchen, 90-foot balcony, heated pool, hot tub, fitness center, and parking; proximity to Key West attractions requires further specification based on the condo's exact location.

Smathers Beach
10/15 – 10/21
$620/nighttotal: $3720 (6 )
Charming Studio In Historic Key West, 5-min Bike Ride To Beach & Bikes Included!
1 1studio , Key West
This Key West studio is located in the heart of the Cuban district, just steps from a famous coffee shop and a short walk to all the island's attractions. The studio has received excellent ratings for location, cleanliness, and overall experience.
The apartment is 450 square feet, offering a modern kitchen with an induction cooktop and convection oven, a vintage claw-foot soaking tub, and a private courtyard. Enjoy free bikes and beach chairs, free Wi-Fi, and on-street parking.
The apartment is 450 square feet, offering a modern kitchen with an induction cooktop and convection oven, a vintage claw-foot soaking tub, and a private courtyard. Enjoy free bikes and beach chairs, free Wi-Fi, and on-street parking.

Smathers Beach
08/18 – 08/27
$371/nighttotal: $3339 (9 )
Tranquility By The Beach
2 2house , Key West
This Key West apartment is located just a short walk from Smathers Beach and within a mile of Rest Beach and Higgs Beach, making it a prime spot for beach lovers. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers two bedrooms, a living room, and two bathrooms, providing ample space for a comfortable stay. Guests can enjoy a fully equipped kitchen, a private balcony with ocean views, free parking, Wi-Fi, and access to a swimming pool, jacuzzi, sauna, fitness center, tennis court, and concierge services.
The apartment offers two bedrooms, a living room, and two bathrooms, providing ample space for a comfortable stay. Guests can enjoy a fully equipped kitchen, a private balcony with ocean views, free parking, Wi-Fi, and access to a swimming pool, jacuzzi, sauna, fitness center, tennis court, and concierge services.

Smathers Beach
06/19 – 06/30
$318/nighttotal: $3498 (11 )
Poolside Suite With Direct Pool Access
1 4apartment , Key West
This luxurious one-bedroom condo at the Beachside Resort in Key West offers direct Gulf of Mexico views and easy access to Key West's attractions.
The 1-bedroom, 1-bathroom unit sleeps 4, features a king bed, full kitchen with stainless steel appliances, private balcony with resort pool access, in-unit washer/dryer, and access to resort amenities including a heated pool, hot tub, and the Tavern N Town restaurant.
The 1-bedroom, 1-bathroom unit sleeps 4, features a king bed, full kitchen with stainless steel appliances, private balcony with resort pool access, in-unit washer/dryer, and access to resort amenities including a heated pool, hot tub, and the Tavern N Town restaurant.

Smathers Beach
08/29 – 09/09
$243/nighttotal: $2673 (11 )
The James Suite | Second Floor King
1 3apartment , Key West
This Key West apartment rental is located in the Historic District, one block from Duval Street and steps from the Curry Mansion, offering easy access to Mallory Square and the Mel Fisher Maritime Museum.
The one-bedroom, one-bathroom unit sleeps four guests and features a king bed, daybed, twin trundle, private balcony, en-suite bathroom, mini-fridge, complimentary parking (first-come, first-served), shared laundry facilities, and access to the Curry Mansion's pool.
The one-bedroom, one-bathroom unit sleeps four guests and features a king bed, daybed, twin trundle, private balcony, en-suite bathroom, mini-fridge, complimentary parking (first-come, first-served), shared laundry facilities, and access to the Curry Mansion's pool.

Smathers Beach
06/19 – 06/30
$233/nighttotal: $2563 (11 )
Coconut Mallory 1 Br Condo-409
1 4apartment , Key West
This Key West condo is conveniently located near Smathers Beach (2 miles away) and Coconut Mallory Marina, providing easy access to Key West's attractions.
The one-bedroom unit sleeps four, featuring a queen bed, queen sofa bed, kitchenette with microwave and coffee maker, and access to resort amenities including two pools, a hot tub, and grills; boat slip rentals are available.
The one-bedroom unit sleeps four, featuring a queen bed, queen sofa bed, kitchenette with microwave and coffee maker, and access to resort amenities including two pools, a hot tub, and grills; boat slip rentals are available.

Smathers Beach
06/19 – 06/30
$562/nighttotal: $6182 (11 )
Bahama Gardens - Conch House
1 4house , Key West
This Key West home is conveniently located in the heart of the island, just a short walk from both the beautiful beaches of South Beach and Fort Zachary Taylor State Park, as well as the lively Duval Street. The home has received excellent ratings for location, cleanliness, and user experience.
The vacation home features two bedrooms, a fully equipped kitchen, a spacious living room, and a dining area, making it perfect for families or groups of friends. Guests can enjoy a private hot tub, a sun terrace, an indoor play area, a pool, and a garden, as well as access to a tennis court, parking, and a concierge service.
The vacation home features two bedrooms, a fully equipped kitchen, a spacious living room, and a dining area, making it perfect for families or groups of friends. Guests can enjoy a private hot tub, a sun terrace, an indoor play area, a pool, and a garden, as well as access to a tennis court, parking, and a concierge service.













