Holiday Rentals in Key West, FL

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

127 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.5 30 reviews
Key West, FL
02/07 – 07/07
SG$1351/nighttotal: SG$6755 (5 )

127 M² House ∙ 2 Bedrooms ∙ 6 Guests

2 2
house , Key West
This Old Town Key West property is situated just one block from Duval Street's entertainment and four blocks from the Atlantic Ocean.
This two-bedroom, two-bathroom house boasts 137 square metres of living space, featuring an open-plan layout with Key West décor, a private pool (with optional heating, subject to seasonal availability), a lush tropical garden including an orchid house, and parking; it comfortably sleeps six guests.
Ocean Views! <Br>luxury Suites - Key West, FL
9.7 56 reviews
Key West, FL
20/06 – 27/06
SG$922/nighttotal: SG$6454 (7 )

Ocean Views! <Br>luxury Suites

1 1
houseboat , Stock Island
This family-friendly houseboat is situated on the waterfront in Stock Island, just a mile from Robbie's and the Key West Tropical Forest and Botanical Garden. The property has received excellent ratings for location, cleanliness and user experience.
This floating home has one bedroom and can accommodate up to six guests. Amenities include a kitchen with a fridge, microwave oven and dishwasher, air conditioning, a terrace, a garden and parking. Guests can also enjoy internet access, a playground and a smoke-free environment.
Key West Villas - Key West, FL
9.6 1122 reviews
Key West, FL
14/10 – 16/10
SG$868/nighttotal: SG$1736 (2 )

Key West Villas

2 2
house , Key West
This charming house is situated in Old Town Key West, just a minute's walk from Duval Street and within a 10-minute walk of The Southernmost Point, the Ernest Hemingway Home and Museum, and Mallory Square. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The house offers spacious rooms with private bathrooms, small refrigerators, and microwaves, while apartments offer fully-equipped kitchens and seating areas. Guests can enjoy a heated pool, daily continental breakfast, free Wi-Fi, a guest launderette, and even rent bicycles to explore the charming streets of Key West.
Beautiful Sanctuary Private Island Connected By Bridge To Key West - Key West, FL
9.6 117 reviews
Key West, FL
14/10 – 16/10
SG$3744/nighttotal: SG$7488 (2 )

Beautiful Sanctuary Private Island Connected By Bridge To Key West

9 2
apartment , Stock Island
This waterfront property is situated on Stock Island, just a short distance from the Key West Tropical Forest and Botanical Garden and Smathers Beach, offering easy access to the island's attractions. The house has received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The spacious nine-bedroom home provides ample room for large groups or families, spanning over 743 square metres. Guests can enjoy a range of amenities, including a private pool and spa tub, a fully equipped kitchen, a tennis court, and a barbecue grill, offering both relaxation and entertainment options.

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

Cozy Dog-friendly Condo W/ Shared Pool, Hot Tub, Private Deck & Parking - Key West, FL
8.8 124 reviews
Key West, FL
26/10 – 28/10
SG$590/nighttotal: SG$1180 (2 )

Cozy Dog-friendly Condo W/ Shared Pool, Hot Tub, Private Deck & Parking

2 4
apartment , Key West
This Key West condo is located near the sea, approximately 5.6 kilometres from Old Town and Duval Street, and within 6.4 kilometres of Mallory Square and Fort Zachary Taylor.
This 72 square metre apartment offers two bedrooms, two bathrooms, and accommodates up to six guests, featuring resort-style amenities including a heated swimming pool, hot tub, tennis courts, and a fitness centre, with a private deck providing tropical views and dog-friendly accommodation available for a nightly fee.
Poolside Suite - Key West, FL
9.0 330 reviews
Key West, FL
20/06 – 27/06
SG$525/nighttotal: SG$3675 (7 )

Poolside Suite

1 2
apartment , Key West
This Key West apartment enjoys a central location, a short walk (less than 0.5km) from the Ernest Hemingway Home and Museum, South Beach, and Duval Street, with easy access to Fort Zachary Taylor State Park Beach and Simonton Street Beach.
The self-catering property offers two bedrooms, a fully equipped kitchen including a fridge, microwave, and dishwasher, free Wi-Fi, on-site parking, a swimming pool, and a terrace/balcony, ideal for families or groups.
Blue Horizon Hideaway - Key West, FL
Key West, FL
21/12 – 18/01
SG$419/nighttotal: SG$11732 (28 )

Blue Horizon Hideaway

3 1
house , Key West
This Key Cove townhouse provides waterfront accommodation on two sides, situated a mere 5 minutes' drive from Key West's shopping, dining, and Duval Street.
This family-friendly property accommodates up to six guests with two bedrooms and two bathrooms, featuring a private outdoor patio, a shared community swimming pool, and a chef's kitchen with a wet bar.
The James Classic | Ground Floor King - Key West, FL
9.6 4 reviews
Key West, FL
20/06 – 21/06
SG$589/nightfor 1 night

The James Classic | Ground Floor King

1 2
apartment , Key West
This Key West apartment, situated in the Historic District, is a short distance (less than 0.16 km) from Duval Street and adjacent to the Curry Mansion.
The one-bedroom, one-bathroom flat sleeps two guests and offers a terrace, swimming pool access, complimentary parking (subject to availability), shared laundry facilities, and contactless check-in.

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.

Destinations nearby

Best Key West, FL holiday rentals with a balcony

Stay At Sunrise Suites 203! - Key West, FL
9.2 122 reviews
Key West, FL
20/06 – 27/06
SG$519/nighttotal: SG$3633 (7 )

Stay At Sunrise Suites 203!

2 1
apartment , Key West
This Key West condo is situated 1.9 km from Smathers Beach and 1.9 km from the Fort East Martello Museum and Gallery, with other attractions such as the Key West Art & Historical Society within a 3.2 km radius.
This 74 square metre, two-bedroom, two-bathroom apartment sleeps six, offering a fully equipped kitchen, private balcony, in-unit laundry, swimming pool, jacuzzi, fitness centre and spa access.
Ocean Vista 403e La Brisa - Key West, FL
10 1 review
Key West, FL
13/09 – 27/09
SG$478/nighttotal: SG$6692 (14 )

Ocean Vista 403e La Brisa

2 2
apartment , Key West
Ocean Vista 403E La Brisa is a beachfront apartment in Key West, Florida, situated 0.7km from Smathers Beach and 3km from the Southernmost Point.
This 108 square metre, two-bedroom, two-bathroom flat sleeps seven guests and boasts a fully equipped kitchen, air conditioning, a terrace, swimming pool, spa, tennis court, parking, and free Wi-Fi.
Sky Suites Retreat - Key West, FL
9.7 355 reviews
Key West, FL
02/07 – 03/07
SG$1626/nightfor 1 night

Sky Suites Retreat

2 5
apartment , Key West
Sky Suites Retreat, a centrally located Key West apartment, is a short walk (less than 1km) from the Ernest Hemingway Home and Museum, South Beach, and Duval Street.
This four-bedroom dwelling offers guests a fully equipped kitchen, private patio, in-unit laundry, free Wi-Fi, and parking, ideal for families or groups.
Gypsyginny's Hideaway - Key West, FL
Key West, FL
21/12 – 18/01
SG$604/nighttotal: SG$16912 (28 )

Gypsyginny's Hideaway

3 1
apartment , Key West
This three-bedroom flat is located in Key West's Meadows district on White Street, offering proximity to beaches and dining, and is a short walk to Old Town landmarks such as the Ernest Hemingway Home and Museum and Southernmost Point.
Spanning 111 square metres, this residence accommodates up to six guests with three bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, and a private outdoor space.

Best Key West, FL holiday rentals with parking

Anchor Drop Key West - Key West, FL
10 1 review
Key West, FL
17/10 – 24/10
SG$823/nighttotal: SG$5761 (7 )

Anchor Drop Key West

2 2
house , Key West
Anchor Drop Key West, a luxury villa near Key West International Airport (1.9 km from Southernmost Point and 3.2 km from the Ernest Hemingway Home and Museum), offers convenient access to Key West's major attractions.
This 126 square metre property boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private balcony with sea views, a swimming pool, Jacuzzi, sauna, fitness centre, tennis court, and fully equipped kitchen.
Soul Of Duval At Duval Street - Key West, FL
9.9 34 reviews
Key West, FL
20/06 – 27/06
SG$491/nighttotal: SG$3437 (7 )

Soul Of Duval At Duval Street

2 1
apartment , Key West
This Key West apartment, situated on the 600 block of Duval Street, is a half block from Duval Street's main attractions, offering easy walking access to landmarks such as the Southernmost Point and Hemingway House.
The two-bedroom, one-bathroom flat sleeps four guests and boasts a fully equipped kitchen with luxury appliances, a private balcony overlooking the promenade, in-unit laundry facilities, and dedicated gated parking—a rare find in Key West's Old Town.
Atlantic Paradise Found - Key West, FL
9.6 230 reviews
Key West, FL
02/07 – 07/07
SG$912/nighttotal: SG$4560 (5 )

Atlantic Paradise Found

2 2
house , Key West
This apartment in Key West is conveniently located just a short walk from Smathers Beach and Rest Beach, offering easy access to the beautiful beaches and the relaxed atmosphere of this popular destination. It boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment is spacious, with 126 square metres of living space and comfortably accommodates up to 6 guests. It comes with a range of amenities including a fully equipped kitchen, a swimming pool, a jacuzzi, a tennis court and a fitness centre, providing everything you need for a relaxing and enjoyable holiday.
Upper Bayview North - Key West, FL
Key West, FL
20/06 – 27/06
SG$1464/nighttotal: SG$10248 (7 )

Upper Bayview North

4 7
house , Key West
This detached house, Upper Bayview North, is situated in Key West, a 19-minute stroll from Rest Beach and 1.93 kilometres from Key West International Airport.
This abode accommodates up to 15 guests and offers a swimming pool, a private balcony with sea views, a well-equipped kitchen with a dishwasher, microwave, and oven, complimentary WiFi, on-site parking, and massage services.
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