Compare Vacation Rentals & Airbnb in Key West, FL

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Key West, FL vacation rentals
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3183 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

Pagitt House - 4/3.5 - Old Town Key West With Pool! - Key West, FL
9.8 39 reviews
Key West, FL
27/06 – 28/06
$4243/nightfor 1 night

Pagitt House - 4/3.5 - Old Town Key West With Pool!

4 7
apartment , Key West
This Key West Historic District property is a short walk from the Donkey Milk House and Duval Street, and within a 2.4km radius of Mallory Square and Florida Keys beaches.
The three-bedroom, two-bathroom house sleeps six, boasting a private pool, terrace, fully equipped kitchen including a dishwasher, free Wi-Fi, and concierge services; barbecue facilities are also available.
Wake Up On The Water With Southernmost Serenity - Key West, FL
Key West, FL
29/12 – 31/12
$1356/nighttotal: $2712 (2 )

Wake Up On The Water With Southernmost Serenity

2 2
houseboat , Stock Island
This unique waterfront yacht stay is situated at Perry Hotel & Marina on Stock Island, offering convenient access to the attractions of Key West, just 4.8 kilometres away.
This two-bedroom houseboat accommodates up to five guests, featuring a kitchen with a fridge and microwave, air conditioning, internet, and resort-style amenities including two swimming pools and a jacuzzi, with complimentary shuttle service to Old Town Key West available every half hour.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
10 2 reviews
Key West, FL
24/07 – 25/07
$1328/nightfor 1 night

Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 4
apartment , Key West
This Key West condo, offering easy access to Duval Street via a complimentary shuttle service, is conveniently located near a marina providing boat slip rentals and watersports access.
The two-bedroom, two-bathroom apartment sleeps six guests, features king-size beds in both bedrooms, a queen sleeper sofa, a full kitchen with stainless-steel appliances, a private balcony, and access to an on-site swimming pool, garden, and ballroom.
102 M² House ∙ 2 Bedrooms ∙ 4 Guests - Key West, FL
Key West, FL
01/10 – 01/11
$334/nighttotal: $10354 (31 )

102 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 2
house , Key West
This oceanfront Key West condominium, situated within the La Brisa community directly opposite Smathers Beach, offers unparalleled access to the beach and stunning sunrise views.
The 102 square metre (1100 square foot) property boasts two bedrooms sleeping four, a fully equipped kitchen with marble counters and stainless steel appliances, a private balcony, and access to La Brisa's amenities including a swimming pool, Jacuzzi, and tennis courts.

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

Sunny Condo With Pool, Lovely Deck, Central Ac & Washer/dryer - Central Location - Key West, FL
9.4 181 reviews
Key West, FL
13/09 – 27/09
$566/nighttotal: $7924 (14 )

Sunny Condo With Pool, Lovely Deck, Central Ac & Washer/dryer - Central Location

1 2
apartment , Key West
This Key West cottage is located in Old Town, a few blocks from Duval Street, and within 500 meters of the Key West Lighthouse and the Ernest Hemingway Home and Museum.
This one-bedroom, one-bathroom flat offers 53 square meters of living space for up to two guests, featuring air conditioning, a kitchen with a fridge, microwave, and dishwasher, complimentary WiFi, a shared swimming pool, and an in-unit washer/dryer.
Brisa Del Mar By Avantstay - Key West, FL
9.2 56 reviews
Key West, FL
23/11 – 29/11
$1022/nighttotal: $6132 (6 )

Brisa Del Mar By Avantstay

2 6
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.
Watch Sunsets From Your Deck, Shared Pool/hot Tub - Perfect For The Whole Family - Key West, FL
8.8 216 reviews
Key West, FL
14/10 – 16/10
$427/nighttotal: $854 (2 )

Watch Sunsets From Your Deck, Shared Pool/hot Tub - Perfect For The Whole Family

2 2
apartment , Key West
This two-bedroom condo, situated on Key West's eastern edge, offers west-facing views ideal for watching the sunset and is located a few kilometres from Key West International Airport and the downtown area's attractions.
This 72-square-meter apartment accommodates up to four guests and features a private balcony with ocean views, a fully equipped kitchen, air conditioning, on-site swimming pool, jacuzzi, exercise room, and is dog-friendly.
Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
9.2 53 reviews
Key West, FL
02/07 – 05/07
$515/nighttotal: $1545 (3 )

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

2 4
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.

Frequently Asked Questions about vacation rentals in Key West, FL

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

    You've got to see the sunset at Mallory Square, it's a real Key West institution. And don't forget to visit the Ernest Hemingway Home and Museum, it's a fascinating place to learn about the famous author's life in Key West.
  • 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 choice, it's right in the heart of everything, with lots of restaurants, shops, and attractions. If you're looking for something a bit quieter, try the historic Bahama Village, it's got a more laid-back vibe.
  • 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 big hit with kids, they've got all sorts of fascinating sea creatures. The Butterfly Conservatory is another great option, with hundreds of beautiful butterflies fluttering around you.
  • 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?

    You'll want to book well in advance, especially if you're travelling during peak season, which is from December to April. If you're looking for a bit more flexibility, try booking in the shoulder seasons, May to June or September to November.
  • 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 big one, with lots of food and drink tastings. The Hemingway Days Festival is another great option, celebrating the life and work of Ernest Hemingway. If you're here in October, don't miss Fantasy Fest, it's a wild and colourful celebration.
  • 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, Key West Villas and Southernmost Sanctuary.

  • 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, it's full of shops, bars, and restaurants. You can also visit the Key West Cemetery, it's a fascinating place to wander around and learn about the history of Key West. And don't forget to check out the free sunset celebrations at Mallory Square.
  • What are the best restaurants with local dishes in Key West, FL?

    For a taste of Key West, try the conch fritters at The Waterfront Brewery. If you're looking for something a bit fancier, head to Latitudes for their award-winning seafood. And for a taste of Cuban cuisine, check out El Siboney.
  • What are the best walking or cycling routes in Key West, FL?

    The Truman Waterfront is a great place for a walk or cycle, with beautiful views of the harbour. For a longer ride, try the scenic route along the Overseas Highway, it's a stunning drive with views of the ocean and the Keys.
  • Are there pet-friendly attractions in Key West, FL?

    Yes, there are plenty of pet-friendly attractions in Key West. You can take your dog to the beach at Higgs Beach, or for a walk along the Truman Waterfront. Many restaurants and shops also welcome well-behaved dogs.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than hotels, and they're often a more affordable option. You'll also have access to a kitchen, so you can save money by cooking some of your own meals.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular spot for watersports, with plenty of opportunities for fishing, sailing, and kayaking. You can also find golf courses, tennis courts, and a fitness centre.

Destinations nearby

Best Key West, FL vacation rentals with a balcony

Condo ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
Key West, FL
01/10 – 01/11
$314/nighttotal: $9734 (31 )

Condo ∙ 2 Bedrooms ∙ 6 Guests

2 2
apartment , Key West
This renovated monthly rental, offering direct ocean views from a private balcony, is situated at 1800 Atlantic, Key West, with the pool, spa, and sunning beach operational.
This two-bedroom, two-bathroom flat accommodates up to six guests, boasting a luxuriously renovated interior with a king-size master suite, a fully equipped gourmet kitchen, in-unit laundry, high-speed wireless internet, and year-round air conditioning with UV light and a whole-house water filter.
Poolside Breeze Retreat - Key West, FL
9.6 198 reviews
Key West, FL
22/08 – 29/08
$546/nighttotal: $3822 (7 )

Poolside Breeze Retreat

2 2
house , Key West
This apartment is located in Key West, just a short walk from Smathers Beach and Rest Beach, with Higgs Beach also within easy reach. The property has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This two-bedroom, two-bathroom flat spans 126 square metres and comfortably accommodates six guests. The apartment offers a range of amenities, including a fully equipped kitchen, a private balcony with sea views, a swimming pool, a Jacuzzi, a fitness centre, a tennis court, and free parking.
Rooftop Penthouse - Key West, FL
9.8 238 reviews
Key West, FL
24/07 – 25/07
$1898/nightfor 1 night

Rooftop Penthouse

2 4
apartment , Key West
This house is located in Old Town Key West, just a short walk from Duval Street and the San Carlos Institute, and within 15 minutes of the Ernest Hemingway Home and Museum and the Florida Keys Beaches. The property has received excellent ratings for location, cleanliness, and overall experience.
This two-bedroom house offers 167 square metres of space and can comfortably accommodate up to six guests. You'll find a fully equipped kitchen, a terrace, a garden, and laundry facilities, along with air conditioning and free Wi-Fi.
Pool View 3br Residence | Beachside Resort - Key West, FL
Key West, FL
27/06 – 28/06
$1658/nightfor 1 night

Pool View 3br Residence | Beachside Resort

3 7
apartment , Key West
This three-bedroom flat is located on seven acres overlooking the Gulf of Mexico in north Key West, approximately 10 minutes by car or shuttle from Duval Street.
This expansive condo offers accommodation for eight guests, featuring a private balcony with resort pool views, a heated swimming pool, hot tub, ocean marina, and on-site dining at Tavern N Town and Chicken Walk, with electric vehicle charging stations available for a nightly fee.

Best Key West, FL vacation rentals with parking

La Casa Cubana @ Cuban Club Suites - Key West, FL
9.6 74 reviews
Key West, FL
02/07 – 05/07
$931/nighttotal: $2793 (3 )

La Casa Cubana @ Cuban Club Suites

2 4
apartment , Key West
This Duval Street Key West condo, a short 0.48km stroll from South Beach and the Southernmost Point, boasts a unique Cuban art deco design reflecting its 1917 origins as a cigar maker's club.
The 82 square metre apartment offers one bedroom with a loft sleeping up to six guests, featuring two queen beds and a queen-size sofa bed, a fully equipped kitchen, two bathrooms, a private balcony overlooking Duval Street, plus access to a shared pool 0.48km away.
Wonderful Condo In Key West W/free Wifi, Lanai, A/c, Shared Hot Tub & Pool - Key West, FL
9.0 8 reviews
Key West, FL
01/10 – 01/11
$407/nighttotal: $12617 (31 )

Wonderful Condo In Key West W/free Wifi, Lanai, A/c, Shared Hot Tub & Pool

3 2
apartment , Key West
This Key West condo is located by the sea, a short 200-metre walk from Smathers Beach and close to Southernmost Point and the Ernest Hemingway Home and Museum.
This 130 square metre apartment sleeps up to 8 guests and features 3 bedrooms, 2 bathrooms, a fully equipped kitchen, private balcony, and access to a shared swimming pool and tennis court.
446 M² Villa ∙ 6 Bedrooms ∙ 16 Guests - Key West, FL
10 3 reviews
Key West, FL
01/08 – 08/08
$1852/nighttotal: $12964 (7 )

446 M² Villa ∙ 6 Bedrooms ∙ 16 Guests

6 11
house , Key West
This substantial six-bedroom, seven-bathroom residence, a luxurious penthouse and separate three-bedroom guest house, is situated in the heart of Old Town Key West, mere steps from Duval Street's dining and entertainment venues.
Spanning 446 square meters, this property offers two private heated swimming pools, a hot tub with a waterfall, expansive porches, and a large deck, accommodating up to 16 guests for an exceptional Key West escape.
Breezy Condo With Pool & Hot Tub, Private Parking & Great Location - Dog Ok - Key West, FL
8.8 121 reviews
Key West, FL
02/07 – 05/07
$563/nighttotal: $1689 (3 )

Breezy Condo With Pool & Hot Tub, Private Parking & Great Location - Dog Ok

2 4
apartment , Key West
This dog-friendly condominium is located by the sea in Key West, a short distance from the Southernmost Point and the Ernest Hemingway Home and Museum.
This 72 square meter apartment offers accommodation for up to six guests with two bedrooms and two bathrooms, featuring a private balcony, a shared swimming pool and hot tub, and a fully equipped kitchen.
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