Vacation Rentals in Key West, FL

3183 available vacation rental offers

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Key West, FL vacation rentals
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3183 Vacation rentals and Airbnb in Key West, FL

Best family friendly Key West, FL vacation rentals

Among the 3183 accommodations in Key West, FL, here are the 4 best family friendly rentals

Apartment ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
No reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Key West
This Key West apartment, part of Banana's Foster Guest House, is located on Simonton Street, approximately 24 kilometres from Key West International Airport and within walking distance of downtown attractions.
The one-bedroom flat offers a king-size bed, queen sleeper sofa, fully equipped kitchen, private balcony overlooking Simonton Street, access to a shared pool and grill, free Wi-Fi, parking, and accommodates up to four guests.
122 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.4 20 reviews

122 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
This Key West condo is situated near Smather's Beach, a short walk from the beach and approximately 2.4 kilometres from Key West's downtown area, offering easy access to shops, restaurants and bars.
This 122 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a private balcony, swimming pool, Jacuzzi, fitness centre, and free Wi-Fi; shared amenities such as tennis courts are also available within the complex.
Mar Y Sol Luxurious Oceanfront  Key West Breathta - Key West, FL
9.3 247 reviews

Mar Y Sol Luxurious Oceanfront Key West Breathta

apartment, Key West
This beachfront apartment is located just 1.5 kilometres from Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, offering a peaceful retreat from the bustling Duval Street and Mallory Square, which are both within 5 kilometres. This property has received excellent ratings for user experience, location, and cleanliness.
The apartment has three bedrooms, spanning 186 square metres, and can accommodate up to eight guests. Enjoy a range of amenities, including a swimming pool, Jacuzzi, sauna, fitness centre, tennis court, and a private balcony with stunning ocean views.
Royal Escape - Key West, FL
No reviews

Royal Escape

house, Key West
Royal Escape, a Key West property, is centrally located less than 1.3 km from Duval Street, 1.1 km from South Beach, and 2.2 km from the Ernest Hemingway Home.
This three-bedroom, three-bathroom house sleeps 19 guests and boasts a private pool, garden, tennis court, free parking, and a fully equipped kitchen including a dishwasher; free Wi-Fi and satellite TV are also provided.

Best Key West, FL vacation rentals with a pool

Among the 3183 accommodations in Key West, FL, here are the 4 best rentals with a pool

Coconut Palm Studio At Travelers Palm Inn Key West - Key West, FL
No reviews

Coconut Palm Studio At Travelers Palm Inn Key West

studio, Key West
Coconut Palm Studio is situated in Key West, Florida, 0.6km from South Beach and within 2km of the Key West Aquarium and Mallory Square.
This self-catering apartment sleeps two, boasts a kitchenette with microwave and fridge, a private terrace, and access to an on-site swimming pool and tennis court; free Wi-Fi and parking are also provided.
Kwss212 Sunrise Suites Saint Croix Suite #212 - Key West, FL
8.2 135 reviews

Kwss212 Sunrise Suites Saint Croix Suite #212

apartment, Key West
Sunrise Suites Saint Croix Suite #212 is located in Key West, Florida, just a short distance from the airport and within easy reach of popular landmarks like the Southernmost Point. The property has received very good ratings for its location, cleanliness, and overall experience.
This two-bedroom suite offers 72 square metres of space, comfortably accommodating up to six guests. The property boasts a range of amenities including a swimming pool, Jacuzzi, fitness centre, and tennis court, ensuring a comfortable and enjoyable stay.
Claro At Azul Mansion Key West - Key West, FL
No reviews

Claro At Azul Mansion Key West

house, Key West
CLARO at Azul Mansion, a Key West apartment, is centrally located less than 0.6km from the city centre, a 12-minute walk from South Beach, and near the Ernest Hemingway Home and Museum, Duval Street, and the Southernmost Point.
This one-bedroom, one-bathroom property sleeps two guests and offers a swimming pool, terrace, free Wi-Fi, on-site parking, and air conditioning; nearby attractions include Key West International Airport (3km away).
**The Cozy Starfish @ The Annex** Condo Near Duval & Beach + Last Key Services - Key West, FL
9.2 5 reviews

**The Cozy Starfish @ The Annex** Condo Near Duval & Beach + Last Key Services

apartment, Key West
This first-floor condo is located in the private, gated Truman Annex community in Old Town Key West, a mere 500 metres from Mallory Square and Duval Street, and within 800 metres of Fort Zachary Taylor State Park and its beach.
This well-appointed apartment offers 56 square metres of living space with two bedrooms and one bathroom, accommodating up to four guests, and features a private patio with a covered porch, dining table, and a gas grill, alongside access to a communal swimming pool.

Frequently asked questions about holiday rentals in Key West, FL

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

    You really must visit the Southernmost Point of the Continental US, it's iconic. You can't miss the Hemingway House, it's full of history and six-toed cats. And for a taste of Key West's history, visit the Fort Zachary Taylor Historic State Park.
  • What are the best Airbnb and vacation rentals in Key West, FL?

    Leaward Isle Island Retreat, Mango Hideaway @ The Eyebrow House Off Duval and At Mine | Lovely Suite Steps From Duval Street are the most popular Airbnb and vacation rentals in Key West, FL among travelers.

  • 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 the heart of Key West, with lots of shops, restaurants, and bars. If you want a quieter stay, consider the historic Bahama Village, known for its vibrant culture and colourful houses.
  • 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 favourite for kids, and the Butterfly Conservatory is a beautiful place to learn about exotic insects. For some outdoor fun, the Key West Wildlife Center is a great place to see native animals.
  • 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?

    Key West is popular year-round, but if you want to avoid the crowds and get the best deals, book your vacation rental in the shoulder seasons, like April-May or September-October.
  • What are the best rentals for families and kids in Key West, FL?

    The best rentals for families and kids in Key West, FL are Leaward Isle Island Retreat, Mango Hideaway @ The Eyebrow House Off Duval and Key West Villas.

  • 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 Fantasy Fest in October is a wild and colourful celebration, and the Key West Songwriters Festival in May is great for music lovers. The Hemingway Days Festival in July is a fun event celebrating the famous author.
  • 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, Mango Hideaway @ The Eyebrow House Off Duval and Key West Villas.

  • 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?

    Take a stroll along Duval Street and enjoy the street performers, or visit the Key West Cemetery for a unique and interesting historical experience. You can also enjoy the free sunset celebrations at Mallory Square.
  • What are the best restaurants with local dishes in Key West, FL?

    For authentic Key West cuisine, try the Blue Heaven for their famous chicken and waffles, or the Hogfish Bar for their fresh seafood. The Cuban Coffee Queen is a great spot for a traditional Cuban breakfast.
  • What are the best walking or cycling routes in Key West, FL?

    The Key West Historic Seaport is a great place to start a walk or bike ride. The route along the waterfront offers stunning views, and you can also explore the charming streets of Old Town.
  • Are there pet-friendly attractions in Key West, FL?

    The Key West Butterfly & Nature Conservatory welcomes well-behaved dogs on a leash, and many of the beaches in Key West allow dogs, but make sure to check the specific rules.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than hotels, and often come with amenities like kitchens and laundry facilities. They can also be more affordable, especially for larger groups or families.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular destination for watersports, with great opportunities for sailing, fishing, diving, and kayaking. You can also find tennis courts and golf courses in the area.

Popular destinations

Best Key West, FL holiday rentals with a balcony

Duval Sea Turtle By Avantstay - Key West, FL
9.5 270 reviews

Duval Sea Turtle By Avantstay

house, Key West
This Key West property is conveniently located just a six-minute walk from South Beach and a short distance from Fort Zachary Taylor State Park Beach, putting you right in the heart of the action. It has received excellent ratings for location, cleanliness and overall user experience.
The two-bedroom house, spanning 114 square metres, comfortably sleeps six guests. It offers a range of amenities, including a shared pool, air conditioning, a fully equipped kitchen, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Spectacular Ocean View Amazing Quality- Massage Chair. Newly Renovated - Key West, FL
10 37 reviews

Spectacular Ocean View Amazing Quality- Massage Chair. Newly Renovated

apartment, Key West
This Key West beachfront apartment is situated less than 3.2km from Duval Street and the Southernmost Point, and under 4.8km from the Ernest Hemingway Home and Museum and Mallory Square.
This 139 square metre property sleeps six, boasting three bedrooms, two bathrooms, a fully equipped kitchen, and access to a swimming pool, jacuzzi, sauna, fitness centre, and tennis court.
3-story Spacious Conch Style Home W/ Private Pool & Dock! - Key West, FL
9.8 153 reviews

3-story Spacious Conch Style Home W/ Private Pool & Dock!

apartment, Key West
This Key West house is situated in the Meadows district, just under 2 kilometres from Duval Street, Ernest Hemingway Home and Museum, and Mallory Square. The house has received excellent ratings for cleanliness, location, and user experience.
The house has four bedrooms, making it suitable for families or groups of friends. It comes with a private pool, spa tub, barbecue grill, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
Docked In Paradise - Key West, FL
9.0 7 reviews

Docked In Paradise

houseboat, Stock Island
This Stock Island houseboat, situated at The Perry Hotel & Marina in Key West, offers convenient access to downtown Key West via a free shuttle service and is within a reasonable distance of attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point.
The one-bedroom, one-bathroom floating home sleeps four guests and includes air conditioning, a relaxing deck, and access to hotel amenities such as pools, restaurants, and a fitness centre.

Best Key West, FL holiday rentals with parking

Key Wes't Best- Upgraded Condo 5 Mins To Smathers - Key West, FL
9.6 251 reviews

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.
Orchid Suite - Key West, FL
No reviews

Orchid Suite

apartment, Key West
The Orchid Suite is centrally located in Key West, Florida, less than 0.6 km from the Ernest Hemingway Home and Museum and within 0.5 km of Duval Street and South Beach.
This one-bedroom apartment sleeps seven guests, offering a fully equipped kitchen, private balcony, access to an on-site spa, swimming pool and tennis court, and is perfect for exploring Key West's attractions.
5 Cabin Catamaran Sailboat "Devine Sailing" At The Perry Hotel Marina & Resort - Key West, FL
9.4 3 reviews

5 Cabin Catamaran Sailboat "Devine Sailing" At The Perry Hotel Marina & Resort

houseboat, Stock Island
This five-bedroom floating home in Key West offers proximity to landmarks such as the Ernest Hemingway Home and Museum and Southernmost Point, with Fort Zachary Taylor Historic State Park and Smathers Beach within 1.6 kilometres.
This houseboat accommodation for ten guests features air conditioning, internet, and allows pets, providing a unique waterfront experience with opportunities to explore attractions like the Key West Tropical Forest and Botanical Garden and the Sails To Rails Museum at Flagler Station.
Summer July Special@129 Sun. Thru Wed. Ngts.lodging Only 129. + Extras. - Key West, FL
9.0 196 reviews

Summer July Special@129 Sun. Thru Wed. Ngts.lodging Only 129. + Extras.

apartment, Key West
This one-bedroom house in Key West's Historic District is located within a 15-minute walk of Duval Street, the Key West Firehouse Museum, and the Florida Keys Beaches.
The property offers a comfortable stay for up to four guests with a fully equipped kitchen, a sofa bed, a dining area, a patio, and a garden, as well as free parking nearby.
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