Vacation Rentals in Key West, FL

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Key West, FL vacation rentals
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4265 Vacation rentals and Airbnb in Key West, FL

Best family friendly Key West, FL vacation rentals

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

Casa Havana | Old Town Condo W/ Pool & Balcony - Key West, FL
No reviews

Casa Havana | Old Town Condo W/ Pool & Balcony

house, Key West
This two-bedroom, two-bathroom holiday cottage, Casa Havana, is located in Duval Square on the 1000 block of Duval Street, offering a 10-minute walk to downtown Key West's attractions and situated 800 meters from the Southernmost Point.
The property features an open-concept living area with coastal furnishings, air conditioning, a private deck, a balcony, and access to a communal rooftop swimming pool, with parking provided in a private garage for one vehicle and a guest capacity of six.
Stay At Sunrise Suites 203! - Key West, FL
9.2 122 reviews

Stay At Sunrise Suites 203!

apartment, Key West
This Key West condo is situated 1.9 km from Smathers Beach and 1.9 km from the Fort East Martello Museum and Gallery, with other attractions such as the Key West Art & Historical Society within a 3.2 km radius.
This 74 square metre, two-bedroom, two-bathroom apartment sleeps six, offering a fully equipped kitchen, private balcony, in-unit laundry, swimming pool, jacuzzi, fitness centre and spa access.
Doubletree By Hilton Grand Key Resort - Key West, FL
8.3 1668 reviews

Doubletree By Hilton Grand Key Resort

resort, Key West
The Doubletree By Hilton Grand Key Resort offers a convenient base on the outskirts of historic Old Town Key West, just a 2-minute drive from Key West International Airport, Duval Street, and Old Town, with a complimentary shuttle service to these key areas and Smathers Beach.
This resort features a swimming pool with a poolside tiki bar, on-site dining at Palm Haven Restaurant and Sanctuary Lounge, and guest rooms equipped with flat-screen TVs and mini-refrigerators, with select rooms offering balconies and sofa beds, alongside bicycle rentals and a fitness centre.
Key Wests Atlantic Sunrise Penthouse  Upgraded C - Key West, FL
8.9 31 reviews

Key Wests Atlantic Sunrise Penthouse Upgraded C

apartment, Key West
This apartment is located on Smathers Beach, just 2.4 kilometres from the southernmost point of Duval Street and 4 kilometres from Mallory Square, offering a peaceful retreat from the bustling city centre. The apartment has received very good ratings for user experience, cleanliness and location.
The apartment is spacious, with three bedrooms and three bathrooms, spanning 195 square metres and accommodating up to eight guests. It offers a range of amenities, including a swimming pool, jacuzzi, fitness centre, and a private balcony with stunning ocean views.

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

Sunrise Suites Condo With Balcony - Shared Pool - Key West, FL
9.1 249 reviews

Sunrise Suites Condo With Balcony - Shared Pool

apartment, Key West
This two-bedroom apartment is located on the eastern side of Key West, less than five miles from the island's most popular attractions, offering a peaceful escape while still being close to the action. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The apartment spans 72 square metres and comfortably accommodates up to six guests. It features a fully equipped kitchen, a private balcony, and access to a range of resort amenities, including a swimming pool, hot tub, tennis courts, and a fitness centre.
Key West Oceanfront Escape With Pool, Balcony & Steps From Smathers Beach - Key West, FL
9.4 18 reviews

Key West Oceanfront Escape With Pool, Balcony & Steps From Smathers Beach

apartment, Key West
This beachfront Key West condo, less than 3.2km from Duval Street and the Southernmost Point buoy, offers easy access to Mallory Square and Smathers Beach within 4.8km.
The 135 square metre property boasts three bedrooms, two bathrooms, sleeping six guests, and includes a fully equipped kitchen, private balcony, swimming pool, Jacuzzi, sauna, and tennis court.
Henry's Penthouse On The Ocean - Key West, FL
9.8 12 reviews

Henry's Penthouse On The Ocean

apartment, Key West
This two-bedroom, two-bathroom condo, part of the 1800 Atlantic complex in Key West, Florida, offers spectacular ocean views and is conveniently located near the ocean (distance unspecified) and other attractions.
The 128 square metre apartment features a large 45 ft private balcony, sleeps four guests, and includes amenities such as a swimming pool, jacuzzi, fitness centre, and parking; the Henry's Piece Of Paradise apartment is also available within the same complex for alternative dates.
Atlantic Parrot | Oceanfront Condo W/ Pool - Key West, FL
9.9 14 reviews

Atlantic Parrot | Oceanfront Condo W/ Pool

apartment, Key West
This fourth-floor oceanfront condominium in Key West offers direct Atlantic views from its private balcony and is situated 200 metres from Smathers Beach and a short walk to Higgs Beach and its pier, with convenient access to the Florida Keys Overseas Heritage Trail for cycling and walking.
This two-bedroom, two-bathroom apartment accommodates up to five guests and features resort-style amenities including a swimming pool, hot tub, and fitness centre, along with on-site tennis courts and secure, contactless entry.

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

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.
Gated Parking, Heated Pool  - Villa Positano - Key West, FL
8.8 28 reviews

Gated Parking, Heated Pool - Villa Positano

apartment, Key West
This Duval Square condo offers a prime location on Duval Street, Key West, a 10-minute walk from downtown attractions and a short distance from the Southernmost Point.
The 116 square metre apartment features two en-suite bedrooms, a queen sofa bed sleeping six, a private deck, rooftop pool access, and in-unit laundry facilities; off-street parking is also provided.
Vitamin Sea At Labrisa - Oceanfront View! - Key West, FL
No reviews

Vitamin Sea At Labrisa - Oceanfront View!

apartment, Key West
This Key West flat offers a prime location, just a short walk from Smathers Beach and a brief cycle to Duval Street, placing you within easy reach of the Southernmost Point and the Ernest Hemingway Home and Museum.
This 102-square-meter flat accommodates up to four guests across two bedrooms and two bathrooms, featuring a private fourth-floor balcony with ocean views, a fully equipped kitchen with new appliances, air conditioning, Wi-Fi, and access to a communal swimming pool, with parking also available.
Top Floor Amazing View Toms Chicken Coop Awaits Your Next Stay. Best Value - Key West, FL
9.8 166 reviews

Top Floor Amazing View Toms Chicken Coop Awaits Your Next Stay. Best Value

apartment, Key West
This Key West Midtown condo is situated within 1.6km of Florida Keys Beaches, Duval Street, and South Beach, with Mallory Square, famed for its sunset celebrations, a 3.4km drive away.
This 139 square metre apartment sleeps six guests, boasting three bedrooms, two bathrooms, a fully equipped kitchen, and a private terrace plus access to a swimming pool, Jacuzzi, sauna, fitness centre and tennis court.

Best Key West, FL holiday rentals with parking

Colony Calypso - Key West, FL
No reviews

Colony Calypso

house, Key West
Colony Calypso, a holiday home, is located in Key West, 400 metres from the city centre and an 11-minute walk from South Beach, offering proximity to the Ernest Hemingway Home and Museum and Duval Street.
This property boasts a 49 square metre floor area, accommodating up to 7 guests with 1 bedroom and 1 bathroom, and features a fully equipped kitchen, air conditioning, a swimming pool, spa, fitness centre, tennis court, and private patio with an outdoor dining area.
La Casa Cubana The Cuban Club - Key West, FL
9.0 4 reviews

La Casa Cubana The Cuban Club

apartment, Key West
La Casa Cubana, a centrally located Key West apartment, is 0.4km from South Beach and close to Ernest Hemingway's Home, the Southernmost Point buoy, and Duval Street.
This 82-square-metre flat boasts one bedroom, one bathroom, sleeps eleven guests, and includes a fully equipped kitchen, a balcony, free Wi-Fi, and access to an on-site spa, swimming pool, and tennis court; bike rentals are available nearby.
Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
9.2 56 reviews

Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony

apartment, Key West
This two-bedroom Sunrise Suites condo offers a convenient location in Key West, a short drive from the downtown area and close to Smathers Beach.
The apartment, sleeping up to four comfortably (with a sofa bed for children), boasts two bathrooms, a private balcony, in-unit laundry, and access to a shared pool and jacuzzi within the complex; guaranteed parking is also provided.
Waterfront Dock Pool Penthouse Near Duval St - Key West, FL
9.8 514 reviews

Waterfront Dock Pool Penthouse Near Duval St

apartment, Key West
This Key West penthouse condo, located in the historic downtown area less than 1.6km from Duval Street and close to attractions such as the Historic Seaport and Hemingway House, offers breathtaking waterfront views.
The 172 square metre property boasts four bedrooms, four bathrooms, sleeping up to sixteen guests, and includes a private boat slip (up to 35ft), a heated pool, and a full kitchen; on-site amenities also include a tiki bar & grill and bike rentals.
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