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.

The Curry Poolside | Ground Floor King - Key West, FL
No reviews

The Curry Poolside | Ground Floor King

apartment, Key West
This historic flat, located on Caroline Street, is a mere 80 metres from Duval Street, offering convenient access to the Historic Seaport and downtown attractions.
This pet-friendly accommodation for two includes a kitchen with a fridge and microwave, air conditioning, a shared heated swimming pool, and all-day access for luggage storage and parking.
Cozy Studio With Shared Porch And Bbq Grill - Charming Hideaway - Key West, FL
No reviews

Cozy Studio With Shared Porch And Bbq Grill - Charming Hideaway

apartment, Key West
This private studio apartment, part of the Conch Republic Cottages group rental property, is situated a short distance from Duval Street's entertainment district.
The studio accommodates two guests and features a kitchenette, air conditioning, Wi-Fi, and access to shared outdoor amenities including a garden and barbecue grill.
Pool View 3br Residence | Beachside Resort - Key West, FL
No reviews

Pool View 3br Residence | Beachside Resort

apartment, Key West
This luxurious 3-bedroom condominium is located on a seven-acre resort in north Key West, offering Gulf of Mexico views and situated approximately 1.6 kilometres from Duval Street, with an on-site shuttle service available for convenient access to attractions.
This family-friendly apartment provides accommodation for up to eight guests and features a private balcony with resort pool views, a fully equipped kitchen with stainless-steel appliances, air conditioning, a swimming pool, a Jacuzzi, and a fitness centre.
Waterfront Pool And Tiki Bar - Stunning Family Escape - Key West, FL
No reviews

Waterfront Pool And Tiki Bar - Stunning Family Escape

apartment, Key West
This waterfront penthouse in downtown Key West offers expansive marina and sunset views, located approximately 1.6 kilometres from Duval Street and the Historic Seaport.
This spacious 204 square metre residence accommodates up to 16 guests across four bedrooms, a loft, and multiple living areas, featuring dual balconies, a private boat slip, and access to community amenities including a heated pool and tiki area.

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.

Andy's Attic | Budget-friendly! - Key West, FL
8.0 42 reviews

Andy's Attic | Budget-friendly!

apartment, Key West
This Old Town Key West apartment is situated less than 0.8 km from Duval Street and within 0.8 km of Florida Keys Beaches, offering easy access to the Ernest Hemingway Home and Museum, Southernmost Point, and South Beach (all within 1.6 km).
The one-bedroom, one-bathroom flat sleeps two guests and includes a private patio, swimming pool access, tennis courts, and amenities such as a refrigerator, microwave, and Wi-Fi.
Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock - Key West, FL
9.4 11 reviews

Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock

house, Key West
This Key West waterfront condo is situated approximately 1.8km from both the Ernest Hemingway Home and Museum and Duval Street, and 1.9km from Key West International Airport.
The 121 square metre property boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private dock, swimming pool, garden, and free Wi-Fi; self-catering is facilitated by a fully equipped kitchen.
Vangogh Studio | Updated, Old Town, Heated Pool - Key West, FL
8.8 57 reviews

Vangogh Studio | Updated, Old Town, Heated Pool

studio, Key West
Van Gogh Studio, a pet-friendly apartment in Key West's Old Town, Bahama Village neighbourhood, is located blocks from Duval Street and within walking distance of the Ernest Hemingway Home and Museum.
This self-catering studio sleeps two, features a kitchenette with microwave, mini-fridge and Keurig, cable TV, complimentary Wi-Fi, and access to an on-site heated pool, sundeck, and shared laundry facilities.
Bermuda Retreat-waterfront 2br 2ba Condo W/ Pool & Boat Slip - Key West, FL
9.1 195 reviews

Bermuda Retreat-waterfront 2br 2ba Condo W/ Pool & Boat Slip

apartment, Key West
This Key West apartment is situated just a mile from Duval Street and across the road from Bayview Park, offering a peaceful retreat close to the heart of the action. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment is spacious, with a floor area of 113 square metres, and can comfortably accommodate up to eight guests. Amenities include a private balcony with water views, a fully equipped kitchen, a swimming pool, a garden, and parking, making it ideal for families or groups looking for a relaxing and enjoyable stay.

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.

Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking - Key West, FL
10 1 review

Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking

house, Key West
Holiday house rental with an excellent rating of 100% based on 1 reviews. You will be located in Key West.
Services and facilities include free parking, a kitchen and a terrace. Take advantage of the air conditioning in this house!
**Windward Waves @ Old Town** Cottage By Duval + Last Key White Glove Service... - Key West, FL
10 2 reviews

**Windward Waves @ Old Town** Cottage By Duval + Last Key White Glove Service...

apartment, Key West
This Bahamian-style holiday cottage is situated in Old Town Key West, a mere 160 metres from Duval Street and a short walk from the Southernmost Point.
This 117 square metre residence offers accommodation for up to six guests, featuring four bedrooms, two bathrooms, a fully equipped kitchen, a private patio, and access to a shared resort-style swimming pool within a secure, gated community, with off-street parking for one vehicle.
Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
9.3 152 reviews

Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony

apartment, Key West
This two-bedroom Sunrise Suites condo offers a convenient location in Key West, a short drive from the downtown area and close to Smathers Beach.
The apartment, sleeping up to four comfortably (with a sofa bed for children), boasts two bathrooms, a private balcony, in-unit laundry, and access to a shared pool and jacuzzi within the complex; guaranteed parking is also provided.
Ocean Front Suite With Direct Beach Access - Key West, FL
No reviews

Ocean Front Suite With Direct Beach Access

apartment, Key West
This condominium is located on the northern edge of Key West, directly on the beach, offering a 10-minute drive to Duval Street and proximity to the Ernest Hemingway Home and Museum and the Southernmost Point.
This one-bedroom, two-bathroom apartment accommodates up to four guests, featuring direct sandy beach access via a private spiral staircase, a fully equipped kitchen with stainless-steel appliances, a king bed, a queen sleeper sofa, a private balcony, and resort amenities including a heated swimming pool, hot tub, and a fitness centre with sea views.

Best Key West, FL holiday rentals with parking

Gorgeous Romantic Private Villa, Steps From Duval! - Key West, FL
9.9 107 reviews

Gorgeous Romantic Private Villa, Steps From Duval!

house, Key West
This Old Town Key West villa is situated just 18 metres from Duval Street, offering easy walking access to the Key West Lighthouse, Ernest Hemingway Home and Museum, and the Southernmost Point buoy.
The luxurious, recently remodelled two-storey property boasts a king-size bed, queen-size sleeper sofa, two 65-inch smart TVs, a fully equipped kitchen with stainless steel appliances, a private garden courtyard with shared plunge pool, and accommodates up to four guests.
Magical Ocean Penthouse  Top-floor Ocean View Condo In Key West - Key West, FL
9.8 236 reviews

Magical Ocean Penthouse Top-floor Ocean View Condo In Key West

apartment, Key West
This waterfront apartment is located in Key West's Beachfront district, a short walk from the Florida Keys Beaches and 1.8 kilometres from Clarence S. Higgs Memorial Beach Park, offering boat and bicycle rentals on-site.
This spacious 126 square metre condominium sleeps six guests and features a private terrace, air conditioning, free Wi-Fi, a full kitchen with a dishwasher, and access to a communal swimming pool and hot tub.
Flor De Cana At Azul Mansion Key West - Key West, FL
9.3 3 reviews

Flor De Cana At Azul Mansion Key West

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.
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
This Key West holiday home is situated 1.8 kilometres from Duval Street and the Ernest Hemingway Home and Museum.
The 121-square-metre property boasts a spacious layout with two bedrooms, two bathrooms, and a private patio offering sea views, accommodating up to 11 guests and including free bicycle use, a swimming pool, and free Wi-Fi.

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.

Harbor House Suite A - Key West, FL
10 3 reviews

Harbor House Suite A

house, 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.

Waterfront Condo Free Slip & Pool 2b2b In Key West - Key West, FL
9.9 121 reviews

Waterfront Condo Free Slip & Pool 2b2b In Key West

apartment, Key West
Charming Studio In Historic Key West, 5-min Bike Ride To Beach & Bikes Included! - Key West, FL
9.9 653 reviews

Charming Studio In Historic Key West, 5-min Bike Ride To Beach & Bikes Included!

studio, Key West
La Brisa Unit 105 North Building - Key West, FL
10 9 reviews

La Brisa Unit 105 North Building

house, Key West
Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach! - Key West, FL
9.8 234 reviews

Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach!

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.

Blue Moonshine On The Atlantic - Key West, FL
9.5 2 reviews

Blue Moonshine On The Atlantic

house, Key West
Harbor Luxe Celebration Suites - Key West, FL
No reviews

Harbor Luxe Celebration Suites

apartment, Key West
Bright 2br Oceanview Condo - Key West, FL
No reviews

Bright 2br Oceanview Condo

apartment, Key West
Waterfront Dock Pool Condo Near Duval St Pet Ok - Key West, FL
9.8 330 reviews

Waterfront Dock Pool Condo Near Duval St Pet Ok

apartment, 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.

Watch Sunsets From Your Deck, Shared Pool/hot Tub - Perfect For The Whole Family - Key West, FL
8.8 218 reviews

Watch Sunsets From Your Deck, Shared Pool/hot Tub - Perfect For The Whole Family

apartment, Key West
2br Suite | Pool | Hot Tub | Tennis | W/d - Key West, FL
No reviews

2br Suite | Pool | Hot Tub | Tennis | W/d

apartment, Key West
The Osprey's Nest At Sunrise Suites - Key West, FL
9.9 17 reviews

The Osprey's Nest At Sunrise Suites

apartment, Key West
**Casa Victoria @ Old Town** Home & Pool + Last Key White Glove Service... - Key West, FL
10 144 reviews

**Casa Victoria @ Old Town** Home & Pool + Last Key White Glove Service...

apartment, Key West
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