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

Poolside Paradise/3bed, 2.5 Bath/pvt. Pool And Spa - Key West, FL
10 20 reviews
Key West, FL
11/07 – 18/07
SG$1316/nighttotal: SG$9212 (7 )

Poolside Paradise/3bed, 2.5 Bath/pvt. Pool And Spa

1 4
apartment , Key West
This two-bedroom holiday let is situated just 80 metres from Duval Street, offering excellent access to Key West's attractions.
This architect-designed property, built in 1993, accommodates up to six guests and features a private heated swimming pool and spa, a fully equipped kitchen, and a washer/dryer.
Green Goddess - Sunsets Included - 4bd/3bath - 360° Rooftop - Private Pool - Key West, FL
8.4 5 reviews
Key West, FL
21/12 – 18/01
SG$1081/nighttotal: SG$30268 (28 )

Green Goddess - Sunsets Included - 4bd/3bath - 360° Rooftop - Private Pool

4 1
apartment , Key West
This Key West Historic District house is situated a short walk from the Key West Butterfly and Nature Conservatory and the Southernmost Point buoy, with Duval Street and South Beach less than 0.8 km away.
This 204 square metre property offers four bedrooms, three bathrooms, sleeps eight guests, and boasts a private pool, terrace, garden, and concierge service; nearby attractions include tennis courts and barbecue facilities.
Waterfront Condo Free Slip & Pool 2b2b In Key West - Key West, FL
9.8 118 reviews
Key West, FL
26/10 – 28/10
SG$819/nighttotal: SG$1638 (2 )

Waterfront Condo Free Slip & Pool 2b2b In Key West

1 4
apartment , Key West
This Key West condo, situated on Garrison Bight Marina, offers direct marina views and is a short cycle ride (approximately 1-2 km) from Duval Street and a short walk from Bayview Park.
Sleeping up to six guests, this two-bedroom, two-bathroom apartment boasts a fully equipped kitchen, shared swimming pool, garden, parking and excellent guest ratings; enjoy tennis and basketball at the nearby park.
Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
10 2 reviews
Key West, FL
17/07 – 21/07
SG$595/nighttotal: SG$2380 (4 )

Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 4
apartment , Key West
This Key West apartment, situated near Key West International Airport, offers convenient access to the island's attractions.
Sleeping up to six guests, this two-bedroom, two-bathroom second-floor suite features a king and queen bedroom, a queen sofa bed, private balcony, in-unit laundry, and designated parking; amenities include a swimming pool, garden, and free Wi-Fi.

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

~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine! - Key West, FL
8.4 7 reviews
Key West, FL
29/12 – 27/01
SG$649/nighttotal: SG$18821 (29 )

~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine!

1 2
cottage , Key West
This pet-friendly Key West cottage is located in Old Town, a short walk from St Mary Star of the Sea Church and the Key West Firehouse Museum, offering easy access to the ocean.
The self-catering property sleeps two guests and features a fully equipped kitchen, air conditioning, a private porch, shared pool, in-unit laundry, and Wi-Fi; nearby attractions include the Southernmost Point and the Ernest Hemingway Home and Museum.
The Truman Room At Inn On Fleming Key West! - Key West, FL
9.0 1 review
Key West, FL
31/07 – 02/08
SG$399/nighttotal: SG$798 (2 )

The Truman Room At Inn On Fleming Key West!

1 2
house , Key West
The Truman Room at the Inn on Fleming, Key West, offers a centrally located one-bedroom apartment less than 1.6km from Mallory Square, a short walk from Simonton Street Beach and Duval Street.
This 15-square-metre self-catering flat sleeps two, boasting a private terrace/balcony, air conditioning, free Wi-Fi, on-site parking, and access to a swimming pool and tennis court.
Pool, Laundry, And Grilling Area - Key West, FL
Key West, FL
13/09 – 27/09
SG$413/nighttotal: SG$5782 (14 )

Pool, Laundry, And Grilling Area

1 2
apartment , Key West
This Old Town Key West flat, situated two blocks from Duval Street, is close to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
The one-bedroom, one-bathroom apartment sleeps two guests and boasts a king-size bed, full kitchen with dishwasher, private deck with pool and waterfall, and a luxurious jacuzzi tub; nearby amenities include a convenience store and Cuban coffee shop.
Alligator Reef Light Suite - Key West, FL
9.8 75 reviews
Key West, FL
06/01 – 08/01
SG$1632/nighttotal: SG$3264 (2 )

Alligator Reef Light Suite

2 5
house , Key West
This luxury Key West suite, situated in Old Town, is a half-block from Duval Street and within walking distance (0.8km) of the Ernest Hemingway Home and Museum and 1.9km from Fort Zachary Taylor Historic State Park.
The two-bedroom apartment sleeps six, offering a king and queen bed plus a queen sofa bed, a fully equipped kitchen with granite worktops, and access to shared heated plunge pools, a fire pit, outdoor kitchen, and BBQ 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.

Destinations nearby

Best Key West, FL holiday rentals with a balcony

Prime Downtown Location - Truman Little Cozy Cottage - Key West, FL
Key West, FL
31/07 – 02/08
SG$502/nighttotal: SG$1004 (2 )

Prime Downtown Location - Truman Little Cozy Cottage

1 2
house , Key West
This property is a detached house located in Key West, 0.96 kilometres from San Carlos Institute Casa Cuba and 0.96 kilometres from South Beach, offering convenient walking access to attractions such as the Key West Aquarium and Mallory Square.
This air-conditioned accommodation, measuring 27 square metres, features a kitchen, private terrace, and WiFi, with a guest capacity of three and a check-out time between 08:00 AM and 11:00 AM.
Dune Wind South By Avantstay | Gated Community | Close To Beach - Key West, FL
Key West, FL
01/10 – 01/11
SG$369/nighttotal: SG$11439 (31 )

Dune Wind South By Avantstay | Gated Community | Close To Beach

2 2
apartment , Key West
This Key West holiday home is ideally located just steps from Smathers Beach, less than 5km from Duval Street and Mallory Square.
The 102 square metre property boasts two bedrooms, two bathrooms, a fully equipped kitchen including a fridge and dishwasher, a private pool and jacuzzi, and can comfortably accommodate four guests; tennis facilities are also available on-site.
The Curry Poolside | Ground Floor Two Queens - Key West, FL
9.2 16 reviews
Key West, FL
29/12 – 31/12
SG$1380/nighttotal: SG$2760 (2 )

The Curry Poolside | Ground Floor Two Queens

1 2
apartment , Key West
This Key West apartment, situated in the Historic District, is half a block from Duval Street and within easy walking distance of attractions such as the Mel Fisher Maritime Museum and Mallory Square.
The one-bedroom, one-bathroom flat in the Curry Mansion (built 1869), sleeps four guests and offers access to a shared heated pool, on-site parking, and a shared laundry with detergent provided; contactless check-in is available.
Waterfront Condo With Dock, Pool, Downtown Key West Near Duval - Key West, FL
9.7 220 reviews
Key West, FL
13/09 – 27/09
SG$766/nighttotal: SG$10724 (14 )

Waterfront Condo With Dock, Pool, Downtown Key West Near Duval

2 2
apartment , Key West
This waterfront apartment in historic Downtown Key West offers a private boat slip (maximum 12 metres long, 4 metres wide, 5.5 metres clearance) and is less than 1.6km from Duval Street, the Historic Seaport, and the Hemingway House.
The 118 square metre, two-bedroom, two-bathroom flat sleeps six, boasts a private balcony overlooking the harbour and pool, includes a fully equipped kitchen, in-suite laundry, and access to an on-site heated pool, tiki bar, and secure keyless entry; a golf cart is also provided.

Best Key West, FL holiday rentals with parking

446 M² Villa ∙ 6 Bedrooms ∙ 16 Guests - Key West, FL
10 3 reviews
Key West, FL
01/08 – 08/08
SG$1703/nighttotal: SG$11921 (7 )

446 M² Villa ∙ 6 Bedrooms ∙ 16 Guests

6 11
house , Key West
This substantial six-bedroom, seven-bathroom residence, a luxurious penthouse and separate three-bedroom guest house, is situated in the heart of Old Town Key West, mere steps from Duval Street's dining and entertainment venues.
Spanning 446 square meters, this property offers two private heated swimming pools, a hot tub with a waterfall, expansive porches, and a large deck, accommodating up to 16 guests for an exceptional Key West escape.
The Ospreys Nest By Last Key Realty - Key West, FL
Key West, FL
11/07 – 18/07
SG$500/nighttotal: SG$3500 (7 )

The Ospreys Nest By Last Key Realty

1 4
house , Key West
The Osprey's Nest is situated in Key West, Florida, less than 1.6km from Key West International Airport and within 8km of attractions including Mallory Square, Duval Street, and the Ernest Hemingway Home and Museum.
This 74 square metre property offers two bedrooms, two bathrooms, and sleeps up to 11 guests, boasting a private pool, Jacuzzi, spa, fitness centre, tennis court, free parking, and free Wi-Fi; self-catering is possible thanks to a fully equipped kitchen.
Flor De Cana At Azul Mansion Key West - Key West, FL
10 1 review
Key West, FL
20/07 – 27/07
SG$295/nighttotal: SG$2065 (7 )

Flor De Cana At Azul Mansion Key West

1 1
house , Key West
FLOR DE CANA at Azul Mansion, a Key West apartment, is conveniently located 0.6km from the city centre and a 12-minute walk from South Beach, close to the Key West Aquarium and Mallory Dock (1.9km).
This one-bedroom, one-bathroom property sleeps two guests and offers free Wi-Fi, on-site parking, a swimming pool, and a terrace; nearby attractions include the Ernest Hemingway Home and Museum, Duval Street, and the Southernmost Point.
Sugar Palm Suite At Travelers Palm Inn Key West - Key West, FL
Key West, FL
24/07 – 25/07
SG$742/nightfor 1 night

Sugar Palm Suite At Travelers Palm Inn Key West

1 4
house , Key West
The Sugar Palm Suite offers a central Key West location, an 8-minute walk from South Beach and within 1.9km of the Key West Aquarium and Mallory Dock.
This self-catering apartment sleeps four, featuring a bedroom, living room, fully equipped kitchen with dishwasher, air conditioning, a private swimming pool, and free Wi-Fi; tennis is available on-site.
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