Holiday Rentals in Key West, FL

4265 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
Key West, FL holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

4265 Holiday Rentals and Airbnb 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

Kidney Shaped Pool And Semi-private Deck - Charming Tropical Haven - Key West, FL
No reviews

Kidney Shaped Pool And Semi-private Deck - Charming Tropical Haven

cottage, Key West
This restored Key West shotgun house, offering two bedrooms and one bathroom for up to four guests, is situated in a Key West district just a few steps from Duval Street's dining establishments.
The villa features a semi-private deck with direct access to a kidney-shaped swimming pool with a waterfall, a loft second bedroom accessible via a spiral staircase, and kitchen windows that bi-fold to the pool deck, with an option to expand to a four-bedroom configuration by adding Pete's East Cottage.
Courtyard Access And Shared Pool - Stylish Urban Retreat - Key West, FL
No reviews

Courtyard Access And Shared Pool - Stylish Urban Retreat

apartment, Key West
This three-bedroom, two-bathroom flat in Old Town, Key West, is situated above shops and restaurants in the Duval Square complex, offering direct views of Duval Street from its shared pool and sunning area.
This family-friendly accommodation for up to eight guests features air conditioning, a kitchen with a fridge, microwave, and dishwasher, a swimming pool, spa, tennis court, parking, and a balcony, providing access to a classic Key West walk-up experience.
Poolside Oasis With Custom Pool And Luxurious Amenities - Stunning Retreat - Key West, FL
No reviews

Poolside Oasis With Custom Pool And Luxurious Amenities - Stunning Retreat

house, Key West
This poolside villa is situated in Old Town Key West, offering easy access to Duval Street and the historic seaport, approximately 200 metres from each.
This family-friendly residence accommodates up to eight guests with four ensuite bedrooms, featuring a private swimming pool, jacuzzi, and outdoor dining area, with the option to access additional amenities at the adjacent Watson House Grand Estate.
Breezy Retreat - 2bd/2bath - Windward Park - Pool - 5min Walk To Duval! - Key West, FL
10 26 reviews

Breezy Retreat - 2bd/2bath - Windward Park - Pool - 5min Walk To Duval!

apartment, Key West
This Key West Historic District property is a short walk from the Tennessee Williams Key West Exhibit and Duval Street, and within 1 km of the Ernest Hemingway Home and Museum and Florida Keys beaches.
This 145-square-metre house, sleeping four guests in two bedrooms and two bathrooms, boasts a private fenced yard, swimming pool, tennis court, and concierge service, offering a luxurious Key West getaway.

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

Hemingway Caribbean Townhome/private Pool By Beach,key West Charm,free Parking - Key West, FL
9.2 15 reviews

Hemingway Caribbean Townhome/private Pool By Beach,key West Charm,free Parking

apartment, Key West
This Key West townhome is situated in the Casa Marina residential district, a 3-minute walk to Higgs Beach and within walking distance of Duval Street and the Southernmost Point.
This 2-bedroom, 2-bathroom holiday home accommodates up to 6 guests and offers a private heated lagoon-style pool, a gourmet kitchen, and concierge services, with free off-street parking provided.
Upper Bayview South - Key West, FL
9.7 3 reviews

Upper Bayview South

house, Key West
This detached property in Upper Bayview South, Key West, is located a mere 2.25 kilometres from the Ernest Hemingway Home and Museum and Duval Street, with Rest Beach a 19-minute stroll away.
This residence offers accommodation for up to 15 guests, featuring a well-equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, a terrace with sea views, concierge services, a tennis court, and on-site private parking with complimentary Wi-Fi.
Hyatt Vacation Club At Beach House - Key West, FL
9.3 1775 reviews

Hyatt Vacation Club At Beach House

resort, Key West
The Hyatt Vacation Club At Beach House is located in Key West, just a short drive from Duval Street and the airport, offering a peaceful retreat from the bustling downtown. The resort has consistently received excellent ratings for its cleanliness and overall experience, and the location itself is rated very good.
The resort offers spacious two-bedroom suites with a floor area of 111 square metres, each featuring a fully equipped kitchen and private balcony. Guests can enjoy a range of amenities, including a swimming pool, hot tub, fitness centre, and spa, as well as on-site dining and bike rentals for exploring the island.
Key West On My Mind - Key West, FL
9.4 152 reviews

Key West On My Mind

house, Key West
Key West On My Mind is a two-bedroom apartment situated near Smathers Beach, a 2.6 km walk from the Southernmost Point and 3.2 km from the Ernest Hemingway Home and Museum.
This 126 square metre property boasts a private balcony with sea views, two bathrooms, a fully equipped kitchen, free Wi-Fi, private parking, and access to a swimming pool, jacuzzi, sauna, fitness centre, and tennis court.

Frequently asked questions about holiday rentals in Key West, FL

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

    You absolutely must visit the Southernmost Point of the Continental US, a landmark in Key West. If you're a history buff, the Ernest Hemingway Home and Museum is a must-see. And don't forget to take a sunset cruise to enjoy the stunning views of the Florida Keys.
  • What are the best Airbnb and holiday 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 popular choice, with its historic architecture, vibrant nightlife, and proximity to attractions. If you prefer a more relaxed vibe, consider the quieter neighbourhoods of New Town or the Sunset Key. But if you're looking for a more affordable option, you can find some great deals in the Stock Island neighbourhood.
  • 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 learn about the marine life of the Florida Keys. The Butterfly Conservatory is also a popular choice, with its beautiful butterflies and exotic plants. For a fun day out, visit the Key West Waterfront and enjoy the various water activities on offer, such as kayaking and paddle boarding.
  • What are the best holiday 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 seasons, from April to May and September to October. You'll avoid the crowds and enjoy more affordable prices. But if you're looking for a more lively experience, the peak season from December to April is when the island comes alive with festivals and events.
  • 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 Hemingway Days festival in July is a must-see, with its literary readings, fishing tournaments, and a look-alike contest. The Fantasy Fest in October is a colourful and lively celebration with parades, parties, and costumes. If you're looking for something more relaxed, the Key West Sunset Celebration is a beautiful way to end the day.
  • What are the best rentals or Airbnbs with a jacuzzi in Key West, FL?

    The best holiday rentals or Airbnb with a jacuzzi in Key West, FL are Leaward Isle Island Retreat, Key West Villas and Downtown Retreat - A++ Location W\/ Private Heated Pool\/hot Tub.

  • 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 soak up the atmosphere. Visit the Key West Historic Seaport and explore the historic ships and boats. And don't forget to enjoy the free concerts and events held at the various parks and squares around the island.
  • What are the best restaurants with local dishes in Key West, FL?

    For fresh seafood, try The Stoned Crab or The Blue Heaven. For a taste of Key West's history, visit The Cuban Coffee Queen. And if you're looking for something a little more upscale, try The Restaurant at the Ocean Key Resort.
  • What are the best walking or cycling routes in Key West, FL?

    The Key West Greenway is a great option for a scenic walk or bike ride. It stretches for about 10 kilometres and passes by some of the island's most beautiful spots. You can also take a walk or bike ride along the historic Duval Street, stopping to enjoy the shops and restaurants along the way.
  • Are there pet-friendly attractions in Key West, FL?

    Yes, many attractions in Key West are pet-friendly, including the Key West Historic Seaport, the Key West Aquarium, and the Butterfly Conservatory. Many restaurants and shops also welcome well-behaved dogs. Just be sure to check with the individual establishment for their pet policy.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than a hotel room. They often come with amenities such as a kitchen, laundry facilities, and a private balcony or patio. You can also find vacation rentals in a variety of locations, from the heart of Old Town to the quieter neighbourhoods on the outskirts of the island.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a great place for water sports, with opportunities for swimming, kayaking, paddleboarding, and fishing. The Key West Waterfront is a popular spot for these activities. For golfers, there is the Key West Golf Club, which offers a challenging 18-hole course with stunning views of the ocean.

Popular destinations

Best Key West, FL holiday rentals with a balcony

**Star Of The Seaport @ Old Town** Pool + Last Key White Glove Service...... - Key West, FL
10 95 reviews

**Star Of The Seaport @ Old Town** Pool + Last Key White Glove Service......

apartment, Key West
This charming Key West house is located in the Historic District, just a 1.5 kilometre walk from Duval Street and a 3 kilometre walk from Mallory Square, making it ideal for exploring the island's vibrant atmosphere. The house has excellent user ratings and is perfect for families or groups.
The property has five bedrooms and five bathrooms, spanning 398 square metres, offering ample space for relaxation. Guests can enjoy a private pool, a fully equipped kitchen, a washing machine, a refrigerator, and a Smart TV.
Kw31c Jasmine Suite - Key West, FL
No reviews

Kw31c Jasmine Suite

house, Key West
KW31C Jasmine Suite is a holiday flat located in Key West, a short walk from the Key West Aquarium and Mallory Dock, and approximately 0.96 kilometres from Mallory Square, with close proximity to Duval Street and the Ernest Hemingway Home and Museum.
This 47 square metre apartment accommodates up to 7 guests, featuring 1 bedroom, 1 bathroom, air conditioning, a private balcony, a kitchen with a fridge and microwave, and a children's playground.
New Casa Caribe By Brightwild- Two-story Condo Rooftop Pool - Key West, FL
8.2 19 reviews

New Casa Caribe By Brightwild- Two-story Condo Rooftop Pool

house, Key West
This two-bedroom Key West condo, a short walk from South Beach and Duval Street, is centrally located less than 1.6km from the Southernmost Point buoy.
The 116 square metre property boasts a rooftop pool, fully equipped kitchen, three bathrooms, and accommodates up to six guests, offering free Wi-Fi and air conditioning.
Frost Free In Cayo Hueso - Key West, FL
9.3 239 reviews

Frost Free In Cayo Hueso

house, Key West
This apartment is located just a short walk from Smathers Beach, Key West's most popular beach, and a few blocks from Rest Beach, making it ideal for enjoying the beautiful beaches and vibrant atmosphere of Key West. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom, two-bathroom apartment can comfortably accommodate up to six guests. It features a fully equipped kitchen, a private balcony with sea views, a swimming pool, a Jacuzzi, a fitness centre, and a tennis court.

Best Key West, FL holiday rentals with parking

Tiki Suites~the Grand Tiki~private Water Stay - Key West, FL
9.8 362 reviews

Tiki Suites~the Grand Tiki~private Water Stay

barge, Key West
This unique floating accommodation is anchored in Key West harbour, just a short boat ride (around 1.6 kilometres) from the historic Old Town district and Mallory Square. The boat has received excellent ratings for its location, cleanliness, and overall experience.
The tiki boat offers a comfortable and spacious layout, accommodating up to two guests. It comes equipped with modern amenities like air conditioning, a hot water shower, a Keurig coffee maker, and a 50" LED TV, as well as two inflatable paddleboards and two sets of snorkel gear for exploring the surrounding waters.
Conch In The Treetops By Last Key Realty - Key West, FL
9.3 3 reviews

Conch In The Treetops By Last Key Realty

house, Key West
Conch in the Treetops is a Key West property situated 1.9 km from Key West International Airport and within a short drive of landmarks such as the Southernmost Point, Ernest Hemingway Home and Museum, Duval Street, and Mallory Square.
This 126 square metre house boasts two bedrooms, two bathrooms, sleeps eleven guests, and features a private pool, jacuzzi, spa, fitness centre, tennis court, and free parking, plus a fully equipped kitchen and free Wi-Fi.
74 M² Condo ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

74 M² Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Key West
This newly renovated two-bedroom, two-bathroom corner condominium is situated in the Sunrise Suites community on Key West's southeast side, 3.2 kilometres from Smathers Beach and a short distance from Duval Street.
This 74 square metre apartment, accommodating up to six guests, features a fully equipped kitchen, a private washer/dryer, a balcony with tropical views, and access to a communal heated pool, hot tub, and tennis court, with pets allowed subject to a weight limit and fee.
Casa Key West-pool & Free Parking - Key West, FL
9.1 221 reviews

Casa Key West-pool & Free Parking

house, Key West
Villa Coastal by Brightwild-Pool & Free Parking is located just a short walk from Duval Street and the Southernmost Point in Key West, placing you right in the heart of the action. This property has received excellent ratings for location, cleanliness and overall user experience.
This three-bedroom villa offers plenty of space for families or groups of friends. The property includes a private pool, free parking, air conditioning, a dishwasher, and a full kitchen, making it a comfortable and convenient base for exploring Key West.
©2026 cozycozy.com