Holiday Rentals in Key West, FL

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Key West, FL holiday rentals
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3183 Holiday rentals and Airbnb in Key West, FL

Best family friendly Key West, FL holiday rentals

Among the 3183 accommodations in Key West, FL, here are the 4 best family friendly rentals

Waterfront 3-bedroom Condo At Bayfront Suites & Marina- Cleaning Fee Included - Key West, FL
9.6 95 reviews
Key West, FL
12/11 – 15/11
1599 €/nighttotal: 4797 € (3 )

Waterfront 3-bedroom Condo At Bayfront Suites & Marina- Cleaning Fee Included

3 5
apartment , Key West
This apartment is located in the Meadows district of Key West, just 1.6 kilometres from Duval Street and the Ernest Hemingway Home and Museum. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and covers 107 square metres. It offers a range of amenities, including a swimming pool, tennis court, and free parking, making it a great choice for families or groups of friends.
The Gardens Hotel - Key West, FL
9.7 1494 reviews
Key West, FL
08/01 – 17/01
942 €/nighttotal: 8478 € (9 )

The Gardens Hotel

1 2
hotel , Key West
The Gardens Hotel is located in Key West, just a minute's walk from lively Duval Street and a short drive from the Key West Butterfly and Nature Conservatory. The hotel is rated 4 stars and has received excellent reviews from previous guests.
This adult-only hotel offers a peaceful escape with two outdoor pools and private balconies or patios. Guests can enjoy live jazz music in the gardens, on-site bicycle rentals, massage services, and a range of other amenities including a restaurant, bar, fitness centre and tennis court.
Osprey Studio @ The Colony-sleeps Up To 4 - Key West, FL
9.4 61 reviews
Key West, FL
27/06 – 04/07
339 €/nighttotal: 2373 € (7 )

Osprey Studio @ The Colony-sleeps Up To 4

1 2
studio , Key West
Osprey studio, a ground-floor apartment in Key West's Old Town Colony neighbourhood on Olivia Street, is situated two blocks from Duval Street, offering easy access to restaurants and bars and proximity to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 45-square-metre self-catering unit sleeps four, featuring a queen bed, a couch, a kitchenette with microwave and refrigerator, a bathroom with shower, a private deck, and access to a shared swimming pool and spa; nearby activities include jet skiing and kayaking.
Hyatt Windward Pointe 2 Bdrm 2 Ba Full Kitch View - Key West, FL
9.6 4 reviews
Key West, FL
12/11 – 15/11
1305 €/nighttotal: 3915 € (3 )

Hyatt Windward Pointe 2 Bdrm 2 Ba Full Kitch View

2 5
apartment , Key West
This Key West apartment is conveniently located near Key West International Airport, a short drive (approximately 5km) from the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
The two-bedroom suite, sleeping up to six guests, boasts a full kitchen, private screened balcony, in-unit laundry, and access to resort amenities including a pool and barbecue grills; a 5, 6, or 7-night stay discount is available.

Best Key West, FL holiday rentals with a pool

Among the 3183 accommodations in Key West, FL, here are the 4 best rentals with a pool

Island Breezes At The Truman Annex In Key West - Key West, FL
9.6 24 reviews
Key West, FL
27/06 – 04/07
459 €/nighttotal: 3213 € (7 )

Island Breezes At The Truman Annex In Key West

2 3
apartment , Key West
This Key West Old Town apartment is situated less than 1 km from Duval Street, the Ernest Hemingway Home and Museum, and We Cycle Key West, with Fort Zachary Taylor Historic State Park and Mallory Square within a 2.4 km radius.
The two-bedroom, one-bathroom flat sleeps four guests and features a fully equipped kitchen, private patio, free Wi-Fi, in-unit laundry, and access to a swimming pool and garden; parking is also provided.
42 M² House ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
9.4 26 reviews
Key West, FL
20/07 – 27/07
313 €/nighttotal: 2191 € (7 )

42 M² House ∙ 1 Bedroom ∙ 4 Guests

1 1
house , Key West
This Old Town Key West apartment, situated in the Palm Gardens community within the Art District, is eight blocks from Duval Street and a short cycle from the Historic Seaport and Higgs Beach.
The 42-square-metre (452-square-foot) one-bedroom condo sleeps four, boasting a king-size bed, queen-size sofa bed, compact kitchen with dishwasher, a shared pool and garden, and AvantStay services including 24/7 support.
The Osprey's Nest At Sunrise Suites - Key West, FL
9.9 16 reviews
Key West, FL
11/07 – 18/07
304 €/nighttotal: 2128 € (7 )

The Osprey's Nest At Sunrise Suites

2 4
apartment , Key West
This Key West apartment, ideally located 4.8km from Duval Street, 3.2km from Smathers Beach, and 0.8km from Key West International Airport, offers superb access to major attractions.
The two-bedroom, two-bathroom flat sleeps six, boasting a fully equipped kitchen, private balcony with stunning views, access to a swimming pool, jacuzzi, fitness centre, and designated parking; BBQ facilities and picnic tables are also available for guest use.
La Brisa - Ocean Views Across From Smathers Beach - Key West, FL
10 186 reviews
Key West, FL
17/07 – 21/07
505 €/nighttotal: 2020 € (4 )

La Brisa - Ocean Views Across From Smathers Beach

2 4
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.

Frequently asked questions about holiday rentals in Key West, FL

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

    You absolutely have to visit the Southernmost Point of the Continental US, marking the very tip of Key West. A stroll down Duval Street is a must, with its vibrant atmosphere and shops. And no trip is complete without a sunset at Mallory Square, watching the street performers and enjoying the lively atmosphere.
  • 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, proximity to Duval Street, and easy access to the waterfront. For a quieter vibe, consider the New Town area, known for its charming cottages and proximity to the beach. If you want to be closer to the action, the Historic Seaport area is a good option with its lively atmosphere and proximity to the harbour.
  • 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 hit with kids of all ages, with its diverse marine life and interactive exhibits. The Butterfly Conservatory is a beautiful and peaceful place to spend a few hours, and the Key West Wildlife Center offers up-close encounters with rescued animals. For a fun day out, head to the Key West Shipwreck Treasure Museum, where you can learn about the history of shipwrecks and see real treasure.
  • 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, so it's best to book your vacation rental well in advance, especially during peak season, which runs from December to April. If you're looking for a more affordable trip, consider visiting during the shoulder seasons, from 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 with parades, parties, and costumes. The Key West Hemingway Days Festival in July celebrates the famous author with a look-alike contest and other events. There's also the Key West Songwriters Festival in May, featuring live music and performances.
  • 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 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 the waterfront and enjoy the views of the ocean and the historic buildings. Visit the Key West Cemetery, a unique and quirky attraction with interesting headstones. Explore the historic streets of Old Town and admire the architecture. Take a dip in the ocean at Smathers Beach, a popular spot for swimming and sunbathing.
  • What are the best restaurants with local dishes in Key West, FL?

    For a taste of Key West's unique cuisine, try the famous Key Lime Pie at the Kermit's Key West Key Lime Shop. For a casual and delicious meal, head to the Blue Heaven, a popular spot for its fresh seafood and laid-back atmosphere. For a more upscale dining experience, try the Latitudes Restaurant, known for its stunning views and innovative dishes.
  • What are the best walking or cycling routes in Key West, FL?

    The scenic route along the waterfront is a must-do, offering stunning views of the ocean and the historic buildings. For a more adventurous ride, try the Key West Bike Path, which winds its way through the city and out to the coast. For a leisurely stroll, explore the historic streets of Old Town, with its charming shops and restaurants.
  • Are there pet-friendly attractions in Key West, FL?

    Many restaurants and shops in Key West are pet-friendly, and you'll often see dogs enjoying the sunshine on patios and sidewalks. The Key West Aquarium welcomes well-behaved dogs on leashes, and the Key West Butterfly Conservatory also allows dogs in designated areas. Smathers Beach is a popular spot for dog walking and playing.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than a hotel room, and often come with amenities like kitchens and laundry facilities. Many rentals are located in desirable neighbourhoods, offering easy access to attractions and activities. You can often find vacation rentals at more affordable rates than hotels, especially for larger groups or longer stays.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular destination for watersports, with opportunities for swimming, sunbathing, kayaking, paddleboarding, and fishing. The Key West Tennis Club offers courts and lessons for all levels. For a more active experience, try the Key West Marathon, held every year in November.

Destinations nearby

Best Key West, FL holiday rentals with a balcony

~ Petite Maison ~ 2 King Ensuite Bedrooms On A Quiet Lane Near Duval Street. - Key West, FL
9.9 452 reviews
Key West, FL
20/07 – 22/07
668 €/nighttotal: 1336 € (2 )

~ Petite Maison ~ 2 King Ensuite Bedrooms On A Quiet Lane Near Duval Street.

2 1
apartment , Key West
This Key West house, situated on the southern end of Duval Street, is within walking distance of cafes, nightclubs, the Southernmost Point buoy, and the Key West Butterfly and Nature Conservatory.
The property offers four ensuite bedrooms sleeping up to eight guests, a private saline pool (seasonally heated for a fee), a modern kitchen with stainless steel appliances, and a dog is allowed (up to 25 lbs, with restrictions).
Mesa House, Dos -Unreal Location - Key West, FL
9.3 496 reviews
Key West, FL
06/07 – 09/07
519 €/nighttotal: 1557 € (3 )

Mesa House, Dos -Unreal Location

2 6
apartment , Key West
This apartment is located in the heart of Key West, just 0.6 km from Simonton Street Beach and 1.8 km from Fort Zachary Taylor State Park Beach, offering easy access to the island's best beaches and attractions. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has two bedrooms, providing ample space for families or groups of friends. It offers a fully equipped kitchen, air conditioning, a private patio, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
One Bedroom Suite | Beachside Resort - Key West, FL
10 2 reviews
Key West, FL
27/06 – 04/07
264 €/nighttotal: 1848 € (7 )

One Bedroom Suite | Beachside Resort

1 2
apartment , Key West
This luxury resort in North Key West, situated on seven acres of waterfront, offers direct Gulf of Mexico views and is located 1.6 kilometres from Duval Street, placing it close to Florida Keys Beaches and Smathers Beach.
This one-bedroom, two-bathroom apartment accommodates up to four guests and features a fully equipped kitchen with stainless-steel appliances, a private balcony, access to a heated swimming pool and hot tub, and is conveniently located near attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point.
Sunrise Suites Barbados Suite #204 - Key West, FL
8.4 187 reviews
Key West, FL
29/12 – 27/01
775 €/nighttotal: 22475 € (29 )

Sunrise Suites Barbados Suite #204

2 2
apartment , Key West
Sunrise Suites Barbados Suite #204 is situated in Key West, just a short drive from popular attractions like Mallory Square, Key West Aquarium, and the Southernmost Point. This accommodation has received very good ratings for its cleanliness and overall user experience, with a good location rating.
The suite offers 72 square metres of space, accommodating up to 6 guests in two bedrooms. This pet-friendly hotel provides a range of amenities, including a swimming pool, jacuzzi, fitness centre, tennis court, and free Wi-Fi.

Best Key West, FL holiday rentals with parking

Casa Papa Del Mar Ocean Front 1800 Atlantic Spectacular View And Island Charm - Key West, FL
9.5 254 reviews
Key West, FL
05/09 – 19/09
428 €/nighttotal: 5992 € (14 )

Casa Papa Del Mar Ocean Front 1800 Atlantic Spectacular View And Island Charm

2 4
apartment , Key West
This beachfront apartment is conveniently located a short walk from Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, with Duval Street and Mallory Square just a short drive away. The apartment has received excellent ratings for its cleanliness, location and overall experience.
This two-bedroom apartment offers 139 square metres of space, comfortably accommodating up to six guests. The apartment features a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a sauna, a fitness centre, a tennis court, and parking.
Completely Renovated Condo With Pool, Hot Tub, & Private Patio - Free Parking - Key West, FL
9.0 138 reviews
Key West, FL
12/11 – 15/11
544 €/nighttotal: 1632 € (3 )

Completely Renovated Condo With Pool, Hot Tub, & Private Patio - Free Parking

2 5
apartment , Key West
This Key West condominium is located by the sea, a short drive from Key West International Airport and near Southernmost Point and the Ernest Hemingway Home and Museum.
This 72 square metre flat offers 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests, featuring a renovated interior, a fully-equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, and parking, with nearby access to Smathers Beach and water activities.
Casa Atlantica One Bedroom - Key West, FL
Key West, FL
13/09 – 27/09
268 €/nighttotal: 3752 € (14 )

Casa Atlantica One Bedroom

1 2
apartment , Key West
Casa Atlantica, a Key West apartment, is situated 2km from Key West International Airport and within a few kilometres of beaches such as Rest Beach, Higgs Beach, and Smathers Beach, and attractions including the Ernest Hemingway Home and Museum and Duval Street.
This 86 square metre, one-bedroom flat sleeps three guests and features a fully equipped kitchen with dishwasher, a balcony, free Wi-Fi, and on-site parking, plus a tennis court for guest use.
Sun Day, Fun Day ~ Renovated 2/2 Home 2 Blocks From Beach In Casa Marina! - Key West, FL
9.0 2 reviews
Key West, FL
29/12 – 27/01
593 €/nighttotal: 17197 € (29 )

Sun Day, Fun Day ~ Renovated 2/2 Home 2 Blocks From Beach In Casa Marina!

2 2
apartment , Key West
This Old Town Key West holiday home is situated a short walk from the Key West AIDS Memorial and Florida Keys beaches, and within 1.6km of Duval Street and South Beach.
This 105 square metre property boasts two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, private fenced yard, free Wi-Fi, on-site laundry, concierge service, barbecue facilities, and parking.
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