Key West, FL vacation rentalscozycozy

Vacation rentals in Key West, FL

4265 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Key West, FL

The Curry Poolside | Ground Floor King - Key West, FL
Key West, FL
2 1
813 ﺩ.ﺇ/nighttotal: 5691 ﺩ.ﺇ (7 )

The Curry Poolside | Ground Floor King

apartment - Key West
This historic flat, located on Caroline Street, is a mere 80 metres from Duval Street, offering convenient access to the Historic Seaport and downtown attractions.
This pet-friendly accommodation for two includes a kitchen with a fridge and microwave, air conditioning, a shared heated swimming pool, and all-day access for luggage storage and parking.
Honeymoon Banyan Suite Near Higgs Beach - Key West, FL
9.8 8 reviews
Key West, FL
2 1
2566 ﺩ.ﺇ/nightfor 1 night

Honeymoon Banyan Suite Near Higgs Beach

apartment - Key West
This Midtown Key West apartment, a short walk from Higgs Beach and White Street Pier and a 1.6km drive from Key West's downtown area, offers convenient access to local attractions.
The 33 square metre flat features a king-size bed, flat-screen TV, kitchenette with microwave and fridge, and accommodates two guests, with access to a shared garden, bikes, and the option to rent the adjoining Palm Suite.
Blue Moonshine On The Atlantic - Key West, FL
9.5 2 reviews
Key West, FL
2 2
3361 ﺩ.ﺇ/nighttotal: 30249 ﺩ.ﺇ (9 )

Blue Moonshine On The Atlantic

house - Key West
Blue Moonshine on the Atlantic, a Key West property, is located 2.6 km from the Southernmost Point and 3.2 km from the Ernest Hemingway Home and Museum.
This 130-square-metre house boasts two bedrooms, two bathrooms, a hot tub, and sleeps up to 11 guests, offering a fully equipped kitchen, swimming pool, jacuzzi, sauna, fitness centre, tennis court, and ocean views from a private balcony, with free Wi-Fi and proximity to Smathers, Rest, and Higgs Beach.
Sunrise Suites Resort, Key West Fl U #408 2bdr2bth - Key West, FL
9.5 242 reviews
Key West, FL
2 2
1630 ﺩ.ﺇ/nighttotal: 6520 ﺩ.ﺇ (4 )

Sunrise Suites Resort, Key West Fl U #408 2bdr2bth

apartment - Key West
This apartment is located close to the salt ponds bird sanctuary, just a short distance from Smathers Beach and a couple of miles from Higgs Beach, offering a peaceful setting with easy access to some of Key West's most popular beaches. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The two-bedroom, two-bathroom apartment can accommodate up to six guests, providing ample space for families or groups of friends. It offers a range of amenities, including a swimming pool, Jacuzzi, garden, fitness centre, and a private balcony with panoramic views, ensuring a relaxing and enjoyable stay.
Resort Escape | Pool+hot Tub | Sleeps 6 - Key West, FL
9.8 72 reviews
Key West, FL
6 2
1917 ﺩ.ﺇ/nighttotal: 3834 ﺩ.ﺇ (2 )

Resort Escape | Pool+hot Tub | Sleeps 6

apartment - Key West
This newly renovated two-bedroom Key West condo is situated in New Town, approximately 3.2km from Smathers Beach and 7.2km from Duval Street, offering easy access to Key West International Airport.
The 2-bathroom apartment sleeps six guests and boasts a private parking space, swimming pool, jacuzzi, and fitness centre, plus themed bedrooms and proximity to turtle ponds.
Superb Location, Affordably Priced - Key West, FL
9.8 318 reviews
Key West, FL
2 1
1138 ﺩ.ﺇ/nighttotal: 4552 ﺩ.ﺇ (4 )

Superb Location, Affordably Priced

apartment - Key West
This Old Town Key West studio flat is centrally located, within easy walking distance of Duval Street, the Ernest Hemingway Home and Museum, and the Butterfly & Nature Conservatory.
The 28-square-metre self-catering property features a king-size bed, full kitchen, small patio, and accommodates two guests; nearby attractions include the Southernmost Point buoy and Southernmost Beach (approximately 0.5 kilometres away).
Hyatt Centric Key West Resort & Spa - Key West, FL
8.8 2724 reviews
Key West, FL
8 4
20588 ﺩ.ﺇ/nighttotal: 164704 ﺩ.ﺇ (8 )

Hyatt Centric Key West Resort & Spa

resort - Key West
The Hyatt Centric Key West Resort & Spa is situated on Key West Island, just a short walk from the lively Duval Street, known for its nightlife and restaurants. The resort has received very good user ratings, with excellent marks for location and very good ratings for cleanliness.
The hotel has a waterfront location with a swimming pool, a jacuzzi and a spa. Guests can enjoy a range of activities, including relaxing by the pool, exploring the surrounding area via jet ski, scuba diving, snorkelling, and island tours, as well as dining at two on-site restaurants.
The Blue Flamingo Resort Key West - Key West, FL
Key West, FL
8 4
9046 ﺩ.ﺇ/nighttotal: 72368 ﺩ.ﺇ (8 )

The Blue Flamingo Resort Key West

resort - Key West
The Blue Flamingo Resort Key West is located 5 kilometres from Key West's city centre, offering easy access to attractions such as the Key West Tropical Forest and Botanical Garden and the Lower Keys Medical Centre.
This resort provides a variety of amenities, including indoor and outdoor swimming pools, a fitness centre, a bar, a restaurant, and family-friendly facilities, with the Blue Flamingo Resort Key West offer including live entertainment and happy hour access.
Kingfish Keep | Lively Escape On Duval! Balcony! - Key West, FL
9.7 12 reviews
Key West, FL
2 1
1524 ﺩ.ﺇ/nighttotal: 6096 ﺩ.ﺇ (4 )

Kingfish Keep | Lively Escape On Duval! Balcony!

apartment - Key West
Kingfish Keep, a self-catering apartment in Key West's historic district, is situated steps from Duval Street and a short walk (less than 0.8 km) from the beach and the Southernmost Point buoy.
This pet-friendly (one dog up to 13.6 kg allowed) apartment offers a king-size bed, a kitchenette with microwave, stove and fridge, complimentary WiFi, two cable TVs, and a private balcony overlooking Duval Street, accommodating up to four guests.
**Summer Solstice @ Old Town** 9br Compound + Last Key White Glove Service... - Key West, FL
9.9 364 reviews
Key West, FL
7 4
7004 ﺩ.ﺇ/nighttotal: 21012 ﺩ.ﺇ (3 )

**Summer Solstice @ Old Town** 9br Compound + Last Key White Glove Service...

apartment - Key West
This Key West property is located in the Historic District, just 500 metres from Duval Street and the Ernest Hemingway Home and Museum, with beaches within a 2.4 kilometre radius. It has received excellent user ratings.
The house offers five bathrooms and is equipped with a fully-fitted kitchen, a washing machine, a refrigerator, a Smart TV, and free Wi-Fi. Guests can enjoy a private pool, a terrace or balcony, a garden, a spa, and parking.
Royal Palm Studio At Travelers Palm Inn Key West - Key West, FL
Key West, FL
2 1
1246 ﺩ.ﺇ/nighttotal: 3738 ﺩ.ﺇ (3 )

Royal Palm Studio At Travelers Palm Inn Key West

studio - Key West
ROYAL PALM STUDIO is centrally located in Key West, Florida, 0.6km from the city centre and an 8-minute walk from South Beach, placing it within easy reach of Mallory Dock and the Key West Aquarium (1.9km).
This self-catering apartment sleeps two guests in one bedroom, boasts a kitchenette with fridge and microwave, a private terrace, and access to an on-site swimming pool and tennis court; free Wi-Fi and parking are also provided.
Oceanview Condo W/pool, Jacuzzi And Tennis Court - Key West, FL
9.8 13 reviews
Key West, FL
2 2
987 ﺩ.ﺇ/nighttotal: 6909 ﺩ.ﺇ (7 )

Oceanview Condo W/pool, Jacuzzi And Tennis Court

apartment - Key West
This Key West oceanfront condo, part of the gated La Brisa resort, offers stunning Atlantic views and direct access to Smathers Beach.
The two-bedroom, two-bathroom apartment sleeps six, boasting a fully equipped kitchen (fridge, freezer, microwave, dishwasher), private balcony, swimming pool, jacuzzi, sauna, parking, and elevator access within the building.

Best family friendly Key West, FL vacation rentals

Among the 4265 accommodations in Key West, FL, here are the 4 best family friendly rentals

Sunnyside Up - Shared Pool - Key West, FL
9.6 14 reviews
Key West, FL
2 2
3785 ﺩ.ﺇ/nighttotal: 11355 ﺩ.ﺇ (3 )

Sunnyside Up - Shared Pool

apartment - Key West
This Key West Historic District flat is a short walk from the Key West Firehouse Museum and Duval Street, and under 1.6 km from South Beach and the Southernmost Point.
This 108-square-metre self-catering apartment sleeps six, boasting two bedrooms, two bathrooms, a terrace, a garden, a swimming pool, and free internet access.
Patio Lounge W/ Hot Tub • 1 Block To Duval St | Casita De Catherine By Avantstay - Key West, FL
Key West, FL
3 1
3520 ﺩ.ﺇ/nighttotal: 49280 ﺩ.ﺇ (14 )

Patio Lounge W/ Hot Tub • 1 Block To Duval St | Casita De Catherine By Avantstay

house - Key West
This detached cottage is located in the Key West district, less than 100 metres from Duval Street, near La Te Da and a few hundred metres from The Southernmost Point.
This family-friendly accommodation offers a private hot tub, capacity for three guests, and concierge services, with an option for one dog under 22.7 kg for an extra charge.
Apartment ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
Key West, FL
2 1
2517 ﺩ.ﺇ/nighttotal: 10068 ﺩ.ﺇ (4 )

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment - Key West
This Key West studio flat is located in Old Town, a short walk or cycle from Key West's historic attractions.
The self-catering apartment, sleeping up to four guests, offers a chef's kitchen with stainless steel appliances, a private courtyard, and free Wi-Fi; nearby parking is available at 204 Simonton Street.
Colorful Retreat With Private Deck And Pool Access - Charming Escape - Key West, FL
Key West, FL
3 1
2479 ﺩ.ﺇ/nighttotal: 34706 ﺩ.ﺇ (14 )

Colorful Retreat With Private Deck And Pool Access - Charming Escape

cottage - Key West
Colony Sunset is a secluded, gated cottage located in The Colony, a mere 200 metres from the attractions of Duval Street in Key West.
This one-bedroom, one-bathroom holiday home accommodates up to four guests and features air conditioning, Wi-Fi, a kitchen with a fridge and microwave, a private deck, and access to a large communal swimming pool, with a 16-kilometre weight limit for pets.

Best Key West, FL vacation rentals with a pool

Among the 4265 accommodations in Key West, FL, here are the 4 best rentals with a pool

The Grand Turk | Spectacular Sunset View, Private - Key West, FL
9.8 16 reviews
Key West, FL
4 2
2382 ﺩ.ﺇ/nighttotal: 9528 ﺩ.ﺇ (4 )

The Grand Turk | Spectacular Sunset View, Private

apartment - Key West
This two-bedroom condo at Sunrise Suites Resort is located on Key West's southeast side, 1.6 kilometres from the beach and a 10-minute drive from Duval Street.
This pet-friendly apartment sleeps six and offers a communal heated swimming pool, hot tub, and a fully equipped kitchen, with Wi-Fi and air conditioning provided for your comfort.
Tropical  Heron Hideaway W/hot Tub + Pool - Key West, FL
10 3 reviews
Key West, FL
2 1
2821 ﺩ.ﺇ/nightfor 1 night

Tropical Heron Hideaway W/hot Tub + Pool

apartment - Key West
This Key West VRBO apartment is situated in the Historic District, a short distance (distances unspecified) from attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point.
This one-bedroom, one-bathroom flat sleeps four guests and boasts a private porch, swimming pool, jacuzzi, and on-site grill, offering convenient access to Key West's attractions.
Key Wes't Best- Upgraded Condo 5 Mins To Smathers - Key West, FL
9.6 255 reviews
Key West, FL
6 2
3457 ﺩ.ﺇ/nighttotal: 17285 ﺩ.ﺇ (5 )

Key Wes't Best- Upgraded Condo 5 Mins To Smathers

apartment - Key West
This beachfront apartment is located just a 15-minute walk from Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, and within 3 miles of Duval Street and Mallory Square, offering easy access to Key West's attractions. The property has consistently received excellent ratings for cleanliness, location, and overall guest experience.
The apartment features two bedrooms and two bathrooms, comfortably accommodating up to six guests. It provides a range of amenities, including a swimming pool, jacuzzi, sauna, fitness centre, tennis court, and a private terrace or balcony, ensuring a relaxing and enjoyable stay.
Southernmost Beach Resort And Guesthouses - Key West, FL
8.6 5075 reviews
Key West, FL
12 4
8936 ﺩ.ﺇ/nighttotal: 26808 ﺩ.ﺇ (3 )

Southernmost Beach Resort And Guesthouses

resort - Key West
Southernmost Beach Resort is in Old Town Key West, directly on the beach and a short walk from South Beach and the Southernmost Point, and a 1.3 mile drive from Fort Zachary Taylor Historic State Park. The resort has received very good ratings for its location, cleanliness, and overall experience.
This hotel offers a range of amenities and activities for guests to enjoy. The resort has three swimming pools, a full-service spa, a restaurant, a bar, a fitness centre, and room service.

Frequently Asked Questions about vacation rentals in Key West, FL

  • What should a first-time visitor not miss in Key West, FL?

    You definitely want to see the Southernmost Point Buoy, it's a must-see for any first-timer. The Hemingway House is also a popular choice, and you can see the famous six-toed cats there. And of course, no trip to Key West is complete without a visit to Mallory Square for the sunset celebration.
  • 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 option for a vacation rental. It's close to all the action, with plenty of restaurants, bars, and shops within walking distance. If you're looking for something a little quieter, you could consider staying in the New Town area, which is still close to everything, but a bit more residential.
  • 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.
  • What are the top family-friendly attractions in Key West, FL?

    The Key West Aquarium is a great option for families, with plenty of interactive exhibits. The Butterfly Conservatory is also a popular choice, and you can see hundreds of butterflies fluttering around you. The Key West Historic Seaport is another good option, with lots of things to see and do for all ages.
  • 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.
  • When is the best time to book a vacation rental in Key West, FL?

    The best time to book a vacation rental in Key West is during the shoulder season, from April to May or September to October. You'll find the best deals and fewer crowds during these months.
  • 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 events or festivals should visitors check out in and around Key West, FL?

    The Key West Food and Wine Festival is a great event for foodies, held every year in January. The Fantasy Fest is a wild and colourful celebration held in October, and the Hemingway Days celebration in July is a fun time to explore the writer's legacy.
  • What are the best rentals or Airbnbs with a jacuzzi in Key West, FL?

  • 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 budget-friendly activities in Key West, FL?

    You can explore the island on foot or by bike, and there are plenty of free beaches to enjoy. The Key West Cemetery is a fascinating and free attraction, and you can also take a walk along the historic Duval Street.
  • What are the best restaurants with local dishes in Key West, FL?

    For a taste of Key West, you should try the conch fritters at the Blue Heaven restaurant. The Cuban sandwiches at El Siboney are also a local favourite. If you want something a bit more upscale, the Latitudes restaurant at the Sunset Key Guest Cottages offers stunning views and delicious seafood.
  • What are the best walking or cycling routes in Key West, FL?

    For a scenic walk, try the route along the waterfront from Mallory Square to the Southernmost Point Buoy. For a longer bike ride, you can cycle around the island on the Overseas Highway, which offers stunning views of the ocean.
  • Are there pet-friendly attractions in Key West, FL?

    Yes, many of the beaches in Key West are pet-friendly, especially the dog beach at Higgs Beach. You can also bring your furry friend to many restaurants and shops, just be sure to check ahead.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than a hotel room, and you can often find rentals with unique features like a private pool or hot tub. You can also often find rentals in more convenient locations, closer to the beach or other attractions.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular destination for watersports, with plenty of opportunities for fishing, diving, snorkeling, and boating. The Key West Yacht Club is a great place to find information on local sailing events and activities.

Popular destinations

Best Key West, FL vacation rentals with a balcony

Poolside Paradise Tropical Village - Key West, FL
Key West, FL
2 1
1896 ﺩ.ﺇ/nighttotal: 17064 ﺩ.ﺇ (9 )

Poolside Paradise Tropical Village

apartment - Key West
Poolside Paradise Tropical Village offers a Key West apartment, conveniently located 2.2km from the Ernest Hemingway Home and Museum and under 1.5km from Duval Street, close to South Beach and other attractions.
This 31-square-metre flat features one bedroom, one bathroom, sleeps three, and includes a private balcony, swimming pool access, tennis court, parking, Wi-Fi, and a fully equipped kitchen with a microwave and fridge.
Apartment ∙ 2 Bedrooms ∙ 8 Guests - Key West, FL
Key West, FL
7 2
4591 ﺩ.ﺇ/nighttotal: 13773 ﺩ.ﺇ (3 )

Apartment ∙ 2 Bedrooms ∙ 8 Guests

apartment - Key West
This two-bedroom Key West condo, sleeping up to ten guests, is ideally located on Duval Street, offering easy walking access to numerous attractions in the heart of the city.
The property features a king-size bed, two further king-size beds in a loft, two sofa beds, a fully equipped kitchen including a fridge, microwave, and stove, a private balcony overlooking Duval Street, and a private washer/dryer; parking is available nearby.
Resort-style Amenities And Expansive Pool - Stunning Oceanfront Retreat - Key West, FL
Key West, FL
2 2
1569 ﺩ.ﺇ/nighttotal: 4707 ﺩ.ﺇ (3 )

Resort-style Amenities And Expansive Pool - Stunning Oceanfront Retreat

apartment - Key West
This oceanfront condominium complex is situated directly on 400 feet of coastline, adjacent to Smathers Beach, and is just 2.4 kilometres from Old Town Key West's shops and restaurants.
This family-friendly apartment offers accommodation for four guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, fitness centre, and tennis courts, with a balcony providing ocean views.
Brisa Del Mar By Avantstay - Key West, FL
9.4 56 reviews
Key West, FL
2 2
2111 ﺩ.ﺇ/nighttotal: 14777 ﺩ.ﺇ (7 )

Brisa Del Mar By Avantstay

apartment - Key West
This Key West house is located just a short walk from Rest Beach and Higgs Beach, and within a 9-minute walk of Smathers Beach, offering easy access to the area's top attractions. The property has received excellent ratings for user experience, location, and cleanliness.
The 110 square metre house has two bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, free Wi-Fi, a private balcony with ocean views, a communal swimming pool, a Jacuzzi, and a tennis court.

Best Key West, FL vacation rentals with parking

Oceanview Home With Private Pool & Lush Landscapin - Key West, FL
9.8 145 reviews
Key West, FL
6 4
5882 ﺩ.ﺇ/nighttotal: 29410 ﺩ.ﺇ (5 )

Oceanview Home With Private Pool & Lush Landscapin

apartment - Key West
This Northside Resort property is conveniently located within 5km of Duval Street, Mallory Square, and the Unitarian Universalist Fellowship of Key West.
This 368 square metre Key West house boasts four bedrooms, three bathrooms, sleeps eight, and includes a private pool, Jacuzzi, and fully equipped kitchen; barbecue grills and housekeeping are available.
H2o Suites- Adults Only - Key West, FL
9.5 1608 reviews
Key West, FL
2 1
2971 ﺩ.ﺇ/nighttotal: 11884 ﺩ.ﺇ (4 )

H2o Suites- Adults Only

resort - Key West
H2O Suites is located in Key West, just a short walk from Duval Street, the heart of the city's nightlife, dining, and shopping scene. This adults-only hotel has received excellent ratings for its location, cleanliness, and overall experience.
The hotel offers a range of amenities and activities, including a rooftop pool with a sun terrace, a bar, and tropical courtyard views. Guests can also enjoy private pools in select rooms, a welcome drink upon arrival, and daily happy hour.
Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach! - Key West, FL
9.8 234 reviews
Key West, FL
4 2
3809 ﺩ.ﺇ/nighttotal: 15236 ﺩ.ﺇ (4 )

Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach!

apartment - Key West
This apartment is located in a quiet, gated waterfront community in Key West, just a short distance from the airport, beaches, restaurants, and Duval Street. It has received excellent user ratings, making it a popular choice for travellers.
The property is a two-bedroom, two-bathroom apartment that can accommodate up to six guests. You can enjoy a range of amenities, including a swimming pool, jacuzzi, terrace, garden, sauna, and concierge service, as well as a fully equipped kitchen.
The Mallory Suite At Inn On Fleming Key West! - Key West, FL
9.5 2 reviews
Key West, FL
2 1
2273 ﺩ.ﺇ/nighttotal: 20457 ﺩ.ﺇ (9 )

The Mallory Suite At Inn On Fleming Key West!

house - Key West
The Mallory Suite is a centrally located Key West apartment, 1.6km from Mallory Square, 0.9km from the city centre, and a 16-minute walk from Simonton Street Beach.
This 20 square metre self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a swimming pool, tennis court, parking, and Wi-Fi.
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