Vacation Rentals in Key West, FL

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Key West, FL holiday rentals
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4265 Holiday rentals and Airbnb in Key West, FL

The Best Family-Focused Holiday Rentals in Key West, FL, United States

Browse family holiday rentals in Key West, FL, United States with space for everyone to relax.

Luxury Waterfront Home With Private Pool And Dock! - Key West, FL
9.8 92 reviews

Luxury Waterfront Home With Private Pool And Dock!

apartment, Key West
This four-bedroom, three-bathroom residence in the Meadows district of Key West offers a prime location bordering Old Town, providing picturesque views of Garrison Bight and within a 500-meter walk of the Ernest Hemingway Home and Museum and the Southernmost Point. This spacious 263-square-meter flat accommodates up to ten guests, featuring two master suites, a chef-ready kitchen, a private balcony overlooking the charter fishing fleet, a private boat slip, and a heated swimming pool.
La Brisa - Ocean Views Across From Smathers Beach - Key West, FL
10 197 reviews

La Brisa - Ocean Views Across From Smathers Beach

apartment, Key West
This two-bedroom apartment is situated directly across the street from Smathers Beach, one of Key West's most popular beaches, offering easy access to the sand and surf. The apartment has received excellent ratings for user experience, location, and cleanliness.
The 136 square metre property comfortably accommodates up to six guests and features a modern kitchen, two bathrooms, a spacious living area, a private balcony, and air conditioning throughout. Enjoy the on-site amenities, including a swimming pool, hot tub, tennis courts, and a garden, or take advantage of the beach rentals available for chairs, umbrellas, paddle boards, kayaks, and sailboats.
The Marker Key West Harbor Resort - Key West, FL
9.2 1106 reviews

The Marker Key West Harbor Resort

resort, Key West
The Marker Key West Harbor Resort is located in the Historic District, just a short walk from Mallory Square, the Florida Keys National Marine Sanctuary, and a slightly longer walk from Southernmost Point. It has consistently received very good user ratings, with excellent ratings for its location and cleanliness.
The hotel offers three outdoor pools, a restaurant, a bar, and a fitness centre. Guests can enjoy a range of amenities and activities, including a terrace, a garden, and a business centre, all while enjoying free Wi-Fi access in public areas.
Oceanfront Living And Expansive Views - Stunning Coastal Sanctuary - Key West, FL
9.6 82 reviews

Oceanfront Living And Expansive Views - Stunning Coastal Sanctuary

apartment, Key West
This Key West Beach Club residence provides direct oceanfront living with immediate beach access and spectacular sunrise views, located on the water in Key West.
This two-bedroom, two-bathroom flat accommodates up to four guests and features a large oceanfront balcony, resort amenities including two swimming pools and a tennis court, and convenient garage parking.

Holiday Rentals with a Pool in Key West, FL, United States

Walk right out of your kitchen and jump into a crystal-clear swimming pool at island holiday rentals in Key West, FL, United States.

Meadows Manor | Elegant Oasis With Private Pool - Key West, FL
9.6 21 reviews

Meadows Manor | Elegant Oasis With Private Pool

apartment, Key West
This Key West holiday home, centrally located in the Historic District, offers easy access to attractions such as the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park, although precise distances aren't specified.
The four-bedroom, four-bathroom property sleeps eight guests and features a private pool, fully equipped kitchen, on-site parking, and a private washer and dryer.
Nautical Wheeler - Key West, FL
No reviews

Nautical Wheeler

house, Key West
Nautical Wheeler, a Key West holiday home near Key West International Airport, is situated approximately 3.9 kilometres from the Ernest Hemingway Home and Museum and Duval Street.
This three-bathroom property sleeps fifteen guests and boasts a private pool, spa, terrace, free Wi-Fi, and free private parking, plus massage services are available on-site.
New The Cottage At James House - Key West, FL
8.5 8 reviews

New The Cottage At James House

house, Key West
New The Cottage at James House, a centrally located Key West holiday home, is a short walk (approx. 0.8km) from the Key West Aquarium, Mallory Dock, and Simonton Street Beach.
This 56 square metre self-catering property boasts one bedroom, one bathroom, sleeps four guests, and features a private patio, swimming pool access, free Wi-Fi, and a fully equipped kitchen including a fridge and microwave.
Parrot Key Hotel & Villas - Key West, FL
8.5 4773 reviews

Parrot Key Hotel & Villas

resort, Key West
Parrot Key Hotel & Villas is located in Florida Bay, a short drive from the historic Old Town of Key West, offering a peaceful escape from the bustling city centre. This resort consistently receives very good ratings for its location, cleanliness, and overall experience.
The hotel features a range of accommodation options, including villas and rooms, all with private terraces offering stunning ocean views. Guests can enjoy a variety of amenities, activities and features, from multiple swimming pools and a fitness centre to kayaking excursions and on-site dining.

Frequently asked questions about holiday rentals in Key West, FL

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

    You definitely want to visit the Southernmost Point of the Continental US, the Hemingway House, and take a sunset cruise. And don't forget to try a Key Lime Pie, a local favourite!
  • 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 and proximity to Duval Street. If you prefer a quieter vibe, try the New Town area, which is known for its beautiful beaches and relaxed atmosphere.
  • 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 Butterfly and Nature Conservatory is always a hit with kids, and the Key West Aquarium is a great place to learn about local marine life. The Fort Zachary Taylor Historic State Park is a good option for a family picnic and exploring the fort.
  • 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?

    Key West is a popular destination year-round, but prices tend to be highest during the peak season from December to April. If you're looking for a better deal, consider visiting during the shoulder seasons, from April 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 Fantasy Fest in October is a huge celebration with parades and costumes, while the Key West Songwriters Festival in May is a great event for music lovers. The Key West Food & Wine Festival in January is another popular choice.
  • 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 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?

    Strolling along Duval Street, visiting the Key West Cemetery, and enjoying the free sunset at Mallory Square are all great ways to experience Key West without breaking the bank. You can also take a walk or bike ride around the island, enjoying the views and the fresh air.
  • What are the best restaurants with local dishes in Key West, FL?

    For authentic Key West cuisine, try the Blue Heaven, a historic restaurant with a charming atmosphere, or the Lazy Lobster, known for its fresh seafood. The Hogfish Bar & Grill is another favourite for its casual atmosphere and delicious dishes.
  • What are the best walking or cycling routes in Key West, FL?

    The scenic route along the waterfront, from the Southernmost Point to Mallory Square, is a popular choice for walking and cycling. The Key West Historic District is also a great place to explore on foot, with its charming streets and historic buildings.
  • Are there pet-friendly attractions in Key West, FL?

    Many restaurants and bars in Key West are pet-friendly, and you can often find dog-friendly beaches. The Key West Butterfly and Nature Conservatory is also pet-friendly, allowing well-behaved dogs on a leash.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals often offer more space and privacy than hotels, and they can be a more affordable option, especially for families or groups. You can also find rentals in different locations, giving you the opportunity to experience different parts of the island.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a great place for watersports, with opportunities for sailing, fishing, kayaking, and windsurfing. The Key West Yacht Club offers facilities for sailing and other water activities. There are also several golf courses on the island, including the Key West Golf Club.

Popular destinations

Holiday Rentals with a Balcony in Key West, FL, United States

Wake up to the soothing sight of the blue ocean right from your private rental balcony in Key West, FL, United States.

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.
Atlantic Hideaway- Key West - Key West, FL
9.6 86 reviews

Atlantic Hideaway- Key West

apartment, Key West
This Key West apartment, situated in the Beachside neighbourhood, is one kilometre from Key West International Airport and three kilometres from Duval Street.
The 122-square-metre, two-bedroom, two-bathroom property in the 1800 Atlantic condo complex sleeps six, boasting a private lanai, access to two pools, a spa, and a fully equipped kitchen; beach chairs and towels are provided.
113 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.1 21 reviews

113 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
This Duval Square holiday home is situated on Duval Street in Key West's Old Town, a short walk from restaurants and bars, and within a couple of kilometres of Key West's beaches.
This two-storey property offers 113 square metres of living space, sleeping up to six guests in two en-suite bedrooms plus a sofa bed, and boasts a private pool, parking, and a well-equipped kitchen.
Bayview South 801 Eisenhower Dr. #6 - Key West, FL
No reviews

Bayview South 801 Eisenhower Dr. #6

house, Key West
Bayview South 801 Eisenhower Drive #6, Key West, offers convenient access to Rest Beach (a 3km walk), Duval Street (1.4km), the Ernest Hemingway Home and Museum (3km), and Key West International Airport (1.9km).
This three-bathroom property sleeps fifteen guests, boasting a swimming pool, tennis court, fitness centre, concierge service, private parking, and a balcony with sea views; massage services are also available on-site.

Best Key West, FL holiday rentals with parking

Duval Breeze By Avantstay | Week-long Stays - Key West, FL
9.1 16 reviews

Duval Breeze By Avantstay | Week-long Stays

apartment, Key West
This two-bedroom flat, located in the gated Duval Square community on Duval Street, offers prime access within 200 metres of Key West's dining, shopping, and nightlife, with the beach approximately 1.2 kilometres away.
This apartment sleeps six guests and features two en-suite bathrooms, a well-equipped kitchen with fridge, freezer, and dishwasher, air conditioning, a shared swimming pool, and private balconies, with AvantStay concierge services available.
Utopia @ Tropical Village - Key West, FL
8.8 13 reviews

Utopia @ Tropical Village

apartment, Key West
This two-bedroom flat offers a gated location in Key West's historic Casa Marina Neighbourhood, placing it within a 1-kilometre stroll of Higgs Beach, the Southernmost Point, and the Key West Butterfly and Nature Museum.
Guests can enjoy a private balcony with treetop views, a shared swimming pool, and a modern kitchen, with accommodation for up to four people and pets permitted for an additional fee.
High Tide In Key West - Key West, FL
9.0 202 reviews

High Tide In Key West

house, Key West
This Key West apartment, ideally located 2 km from the Ernest Hemingway Home and Museum and 2.6 km from the Southernmost Point buoy, offers easy access to Key West International Airport (1.9 km).
The two-bedroom, two-bathroom flat provides self-catering facilities including a fully equipped kitchen, free Wi-Fi, private parking, and access to a swimming pool, Jacuzzi, fitness centre, tennis court, and sauna; it comfortably sleeps four guests and is close to Smathers Beach, Rest Beach, and Higgs Beach.
The Reach Key West, Curio Collection By Hilton - Key West, FL
8.4 1379 reviews

The Reach Key West, Curio Collection By Hilton

resort, Key West
The Reach Key West, Curio Collection by Hilton is located in Old Town, Key West, just 1.5 kilometres from Duval Street, a lively area with a wide selection of restaurants, shops, and nightlife. The resort has received very good ratings for both its location and overall experience, with good marks for cleanliness.
This hotel offers a range of rooms, including suites and studios, all with private balconies offering views of the ocean or the town. Guests can enjoy a private beach, a swimming pool, a spa, a fitness centre, and a variety of activities like scuba diving, snorkelling, and deep-sea fishing.

Discover Luxury Holiday Rentals in Key West, FL, United States

Bask in absolute tropical privacy with upscale coastal design at luxury holiday rentals in Key West, FL, United States.

Coral Palms Spacious 1br Condo, King, Queen, Sofa Bed, Pool, Block To Duval - Key West, FL
9.4 3 reviews

Coral Palms Spacious 1br Condo, King, Queen, Sofa Bed, Pool, Block To Duval

apartment, Key West

Downtown Holiday Rentals in Key West, FL, United States

Find holiday rentals in the heart of Key West, FL, United States close to shops and beaches.

Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-friendly - Key West, FL
9.6 17 reviews

Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-friendly

house, Key West
Beach Club Ocean Front 2br Condo - Key West, FL
9.9 184 reviews

Beach Club Ocean Front 2br Condo

apartment, Key West
122 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.3 19 reviews

122 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
Key West Beachside Spacious Two Bedroom Condo In The Top Location On The Key - Key West, FL
9.8 381 reviews

Key West Beachside Spacious Two Bedroom Condo In The Top Location On The Key

apartment, Key West

Seashore Holiday Rentals in Key West, FL, United States

Open your glass doors and step directly from your living room onto the warm sand at seashore holiday rentals in Key West, FL, United States.

Oceanview Home With Private Pool & Lush Landscaping! - Key West, FL
9.8 144 reviews

Oceanview Home With Private Pool & Lush Landscaping!

apartment, Key West
The Barbados | Private Balcony, Pool View! - Key West, FL
9.8 11 reviews

The Barbados | Private Balcony, Pool View!

apartment, Key West
Latitude Penthouse Key West - Key West, FL
9.3 243 reviews

Latitude Penthouse Key West

house, Key West
Key West's Best - Key West, FL
No reviews

Key West's Best

house, Key West

Holiday Rentals with a Hot Tub in Key West, FL, United States

Soak under a canopy of stars just steps from the ocean waves at holiday rentals with a hot tub in Key West, FL, United States.

Casa Victoria By Last Key Realty - Key West, FL
No reviews

Casa Victoria By Last Key Realty

house, Key West
Tropical Paradise Key West - Key West, FL
9.4 193 reviews

Tropical Paradise Key West

house, Key West
Casita De Catherine By Avantstay - Key West, FL
9.2 7 reviews

Casita De Catherine By Avantstay

house, Key West
Ocean Key Resort & Spa, A Noble House Resort - Key West, FL
9.0 9174 reviews

Ocean Key Resort & Spa, A Noble House Resort

resort, Key West
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