Holiday Rentals in Key West, FL

4265 available vacation rental offers

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Key West, FL holiday rentals
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Best Holiday rentals and Airbnb offers in Key West, FL

Best family friendly Key West, FL holiday rentals

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

Keys Breeze - Walk To Duval, Private Pool - Key West, FL
No reviews

Keys Breeze - Walk To Duval, Private Pool

house, Key West
This renovated island dwelling is located in the southern district of Key West, a mere 300 meters from the Southernmost Point and within walking distance of Duval Street, the Key West Lighthouse, and the Hemingway Home and Museum.
This family-friendly property accommodates up to six guests across three bedrooms and two bathrooms, featuring a private swimming pool, a fully equipped kitchen with stainless-steel appliances, air conditioning, and high-speed internet, perfect for year-round enjoyment and entertaining.
45 M² House ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
9.2 18 reviews

45 M² House ∙ 1 Bedroom ∙ 4 Guests

house, Key West
This Old Town Key West cottage, in The Colony Suites gated community, is situated two blocks from Duval Street.
The 45-square-metre property offers a loft-style bedroom, a bathroom, a sleeper sofa accommodating four guests, a private backyard with a propane BBQ, and access to a shared pool and coin-operated laundry facilities; AvantStay services are also available.
Sunnyside Up - Shared Pool - Key West, FL
9.6 14 reviews

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.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
10 2 reviews

Apartment ∙ 2 Bedrooms ∙ 6 Guests

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.

Best Key West, FL holiday rentals with a pool

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

St Kitts - Downtown Waterfront Penthouse Pool Dock Parking - Key West, FL
8.3 14 reviews

St Kitts - Downtown Waterfront Penthouse Pool Dock Parking

house, Key West
This Key West penthouse, a short walk from Rest Beach and South Beach, offers direct waterfront views and is conveniently located near Higgs Beach, the Ernest Hemingway Home and Museum, and Duval Street.
This 186 square metre (1997 square foot) property boasts four bedrooms, four bathrooms, and sleeps up to 24 guests, featuring a private pool, elevator, free Wi-Fi, parking, and a fully equipped kitchen; all within easy reach of Key West's attractions.
Waterfront Condo Dock Pool Downtown Near Duval - Key West, FL
9.8 278 reviews

Waterfront Condo Dock Pool Downtown Near Duval

apartment, Key West
This waterfront apartment is located in historic Downtown Key West, just a short walk from Duval Street, the Seaport, and the Hemingway House. The property has received excellent ratings for location, cleanliness, and overall user experience.
The two-bedroom apartment comfortably accommodates six guests and features a fully equipped kitchen, a large living area, and a private balcony with stunning water views. Guests can enjoy on-site amenities such as a heated pool, a tiki bar, bike rentals, and a private boat slip with power and fresh water.
Andy's Attic | Budget-friendly! - Key West, FL
8.0 42 reviews

Andy's Attic | Budget-friendly!

apartment, Key West
This Old Town Key West apartment is situated less than 0.8 km from Duval Street and within 0.8 km of Florida Keys Beaches, offering easy access to the Ernest Hemingway Home and Museum, Southernmost Point, and South Beach (all within 1.6 km).
The one-bedroom, one-bathroom flat sleeps two guests and includes a private patio, swimming pool access, tennis courts, and amenities such as a refrigerator, microwave, and Wi-Fi.
Contra House - Private Pool & Steps To Duval St. - Key West, FL
No reviews

Contra House - Private Pool & Steps To Duval St.

house, Key West
This property is situated in a prime downtown Key West location, just 160 metres from Duval Street and less than 1.6 kilometres from the beach, offering convenient walking access to popular restaurants such as Banana Cafe and Blue Heaven.
This accommodation comprises two separate dwellings, each with two bedrooms and two bathrooms, accommodating up to 12 guests with the convenience of a private heated swimming pool, off-street parking for two vehicles, and individual washer/dryer facilities.

Frequently asked questions about holiday rentals in Key West, FL

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

    Key West is bursting with things to see and do, but you shouldn't miss the iconic Southernmost Point buoy, the Ernest Hemingway Home and Museum, and a sunset at Mallory Square.
  • What are the best Airbnb and vacation rentals in Key West, FL?

    Leaward Isle Island Retreat, At Mine | Lovely Suite Steps From Duval Street and Ambrosia ~ Adults Only - Poolside King Room In Azul Mansion 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 plenty of historic architecture, shops, and restaurants. For a quieter stay, consider the more residential areas of New Town or the Truman Annex.
  • 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 place to see local marine life, while the Butterfly Conservatory is a colourful and educational experience. The Key West Historic Seaport is also a popular choice, with boat tours and interactive exhibits.
  • 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?

    Peak season in Key West runs from December to April, so booking your vacation rental well in advance is essential. If you're looking for better deals, consider travelling during the shoulder seasons of 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 annual Fantasy Fest in October is a wild and colourful celebration. If you're a music lover, the Key West Songwriters Festival in May is a must-see. The Key West Food and Wine Festival in January is another popular event.
  • 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 Location In Down Town Key West W/ 2 Pools - Huge Private Roof Deck & Parking.

  • 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?

    Strolling along Duval Street is free and a great way to soak up the atmosphere. You can also enjoy the free sunset celebrations at Mallory Square or explore the historic Fort Zachary Taylor State Park.
  • What are the best restaurants with local dishes in Key West, FL?

    For authentic Key West cuisine, try the Blue Heaven restaurant, known for its fresh seafood and laid-back atmosphere. The Hogfish Bar & Grill is another popular choice, serving up classic Key West fare.
  • Are there pet-friendly attractions in Key West, FL?

    Many restaurants and shops in Key West are pet-friendly. The Key West Butterfly and Nature Conservatory welcomes well-behaved dogs on a leash. You can also enjoy a walk with your furry friend along the beach at Higgs Beach.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals often offer more space and privacy than a hotel room, and can be a more cost-effective option for families or groups. Many rentals also have unique features like private patios or balconies.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular destination for watersports like fishing, sailing, and kayaking. The Key West Yacht Club offers a variety of sailing and boating activities. For those who prefer land-based activities, the Key West Golf Club offers a challenging 18-hole course.

Popular destinations

Best Key West, FL holiday rentals with a balcony

The Bartlum-luxurious Studio - Key West, FL
9.6 344 reviews

The Bartlum-luxurious Studio

studio, Key West
This Key West apartment is perfectly situated in the heart of the island, just a short walk from the lively Duval Street and the beautiful Simonton Street Beach. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers a comfortable living space for up to four guests, with a separate bedroom for privacy. Amenities include a fully equipped kitchen, air conditioning, a terrace or balcony, and a garden, making it ideal for a relaxing and enjoyable stay.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
This Key West condominium is centrally located downtown, offering easy walking access to numerous attractions.
Sleeping up to six guests, this two-bedroom apartment boasts a fully equipped kitchen, private patio, free Wi-Fi, on-site parking, and a washer/dryer.
Watch Sunsets From Your Deck, Shared Pool/hot Tub - Perfect For The Whole Family - Key West, FL
8.8 218 reviews

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

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.
Crawl To Duval W/ Hot Tub - Key West, FL
8.6 6 reviews

Crawl To Duval W/ Hot Tub

house, Key West
This Key West holiday home is centrally located, a 0.4km walk from South Beach and Fort Zachary Taylor State Park Beach, and less than 0.3km from the city centre.
This two-bedroom property offers 84 square metres of space, sleeping up to 11 guests and boasting a private hot tub, fully equipped kitchen, and free parking; nearby attractions include Higgs Beach, the Ernest Hemingway Home and Museum, and Duval Street.

Best Key West, FL holiday rentals with parking

Darling Of Duval By Last Key Realty - Key West, FL
8.0 2 reviews

Darling Of Duval By Last Key Realty

house, Key West
This Key West house, the Darling of Duval, is centrally located, an 8-minute walk from Mallory Dock and 0.8 km from Duval Street, offering easy access to attractions such as Simonton Street Beach and Fort Zachary Taylor State Park Beach.
This 74 square metre property boasts two bedrooms, two bathrooms, and sleeps seven, featuring a fully equipped kitchen, private parking, a swimming pool, Jacuzzi, spa, and tennis court; in-house laundry facilities and free Wi-Fi are also provided.
Bermuda Retreat-waterfront 2br 2ba Condo W/ Pool & - Key West, FL
9.1 195 reviews

Bermuda Retreat-waterfront 2br 2ba Condo W/ Pool &

apartment, Key West
This Key West apartment is situated just a mile from Duval Street and across the road from Bayview Park, offering a peaceful retreat close to the heart of the action. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment is spacious, with a floor area of 113 square metres, and can comfortably accommodate up to eight guests. Amenities include a private balcony with water views, a fully equipped kitchen, a swimming pool, a garden, and parking, making it ideal for families or groups looking for a relaxing and enjoyable stay.
St Croix - Downtown 4x4 Waterfront Penthouse Pool Dock Pet - Key West, FL
9.2 10 reviews

St Croix - Downtown 4x4 Waterfront Penthouse Pool Dock Pet

house, Key West
This Key West penthouse, located 1.8km from the Ernest Hemingway Home and Museum and Duval Street, and 1.9km from Key West International Airport, offers stunning sea views and easy access to popular beaches like Rest Beach, South Beach, and Higgs Beach.
This 186 square metre property boasts four bedrooms, four bathrooms, a private dock, swimming pool, and parking, comfortably accommodating up to 19 guests and featuring a fully equipped kitchen.
H2o Suites- Adults Only - Key West, FL
9.5 1610 reviews

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.
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