Compare Vacation Rentals & Airbnb in Key West, FL

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Key West, FL vacation rentals
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4265 Rentals and Airbnb in Key West, FL

Best family friendly Key West, FL vacation rentals

Among the 4265 accommodations in Key West, FL, here are the 4 best family friendly rentals

Key West Downtown Waterfront, Sleeps 8, Dock & Pool Pet-friendly - Key West, FL
9.9 16 reviews

Key West Downtown Waterfront, Sleeps 8, 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.
40ft Sailboat, 3 Bdrm, 2 Bath, Sleeps Up To 6 - Key West, FL
10 1 review

40ft Sailboat, 3 Bdrm, 2 Bath, Sleeps Up To 6

houseboat, Stock Island
This luxury yacht, docked at Perry Marina on Stock Island, Key West, offers easy access via free shuttle to Key West's attractions such as the Ernest Hemingway Home and Museum and Smathers Beach, with the exact distances not specified.
The 12-metre vessel boasts three staterooms, two bathrooms, sleeping up to six guests, and includes a kitchen with a fridge, air conditioning, and access to Perry Marina's pools, restaurants, fitness centre, and free parking.
Hyatt Windward Pointe 2 Bdrm 2 Ba Full Kitch View - Key West, FL
9.6 4 reviews

Hyatt Windward Pointe 2 Bdrm 2 Ba Full Kitch View

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.
Ocean Views! <Br>i Didnt Do It Too - Key West, FL
9.8 32 reviews

Ocean Views! <Br>i Didnt Do It Too

houseboat, Stock Island
This barge is situated on Stock Island in Key West, close to Robbie's and the Key West Golf Club, offering a peaceful waterfront location. It has consistently received excellent ratings for user experience, location, and cleanliness.
The barge features two bedrooms, comfortably accommodating up to six guests. It is equipped with a full kitchen, a spacious rooftop deck with stunning views, and modern amenities like a washer and dryer, dishwasher, and air conditioning, as well as access to kayaking, paddleboarding, and boating.

Best Key West, FL vacation rentals with a pool

Among the 4265 accommodations in Key West, FL, here are the 4 best rentals with a pool

Kwss202 Sunrise Suites - Big Kahuna Suite 202 - Key West, FL
No reviews

Kwss202 Sunrise Suites - Big Kahuna Suite 202

house, Key West
This Key West apartment is situated approximately 1 kilometre from Key West International Airport and 6.4 kilometres from the Southernmost Point and Ernest Hemingway Home and Museum, with Duval Street a further 6.4 kilometres away.
This 72 square metre residence accommodates up to seven guests and features two bedrooms, two bathrooms (one with a hot tub), air conditioning, a well-equipped kitchen, a balcony, and access to a communal swimming pool, fitness centre, and tennis court.
Henry's Piece Of Paradise On The Ocean In Key West - Key West, FL
9.6 144 reviews

Henry's Piece Of Paradise On The Ocean In Key West

apartment, Key West
This beachfront Key West condo is situated less than 5km from Duval Street and Mallory Square, offering easy access to Key West's nightlife, sunset celebrations, and Florida Keys Beaches, and a 15-minute drive from Clarence S. Higgs Memorial Beach Park and the Key West AIDS Memorial.
The 125 square metre property boasts two bedrooms, two bathrooms, a fully equipped kitchen, private balcony, in-unit laundry, and access to a swimming pool, jacuzzi, sauna, fitness centre, and tennis court; perfect for couples or small families seeking a luxurious Key West getaway.
Key West Villas - Key West, FL
9.8 810 reviews

Key West Villas

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.
Sunrise 307-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
9.6 30 reviews

Sunrise 307-2br/2ba Condo Near Beaches With Pool, Parking, Balcony

apartment, Key West
This Key West seaside apartment, near the southern beaches, is 1.9km from Smathers Beach and 1.9km from the Fort Zachary Taylor Historic State Park.
This 74 square metre self-catering property boasts three bedrooms, two bathrooms, sleeps six, and includes a private balcony, swimming pool, parking, and barbecue facilities.

Frequently Asked Questions about vacation rentals in Key West, FL

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

    You've got to see the sunset at Mallory Square, it's a real Key West institution. And don't forget to visit the Ernest Hemingway Home and Museum, it's a fascinating place to learn about the famous author's life in Key West.
  • What are the best Airbnb and vacation 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 great choice, it's right in the heart of everything, with lots of restaurants, shops, and attractions. If you're looking for something a bit quieter, try the historic Bahama Village, it's got a more laid-back vibe.
  • 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 big hit with kids, they've got all sorts of fascinating sea creatures. The Butterfly Conservatory is another great option, with hundreds of beautiful butterflies fluttering around you.
  • 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?

    You'll want to book well in advance, especially if you're travelling during peak season, which is from December to April. If you're looking for a bit more flexibility, try booking in the shoulder seasons, 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 Key West Food and Wine Festival is a big one, with lots of food and drink tastings. The Hemingway Days Festival is another great option, celebrating the life and work of Ernest Hemingway. If you're here in October, don't miss Fantasy Fest, it's a wild and colourful celebration.
  • 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 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?

    Take a stroll along Duval Street, it's full of shops, bars, and restaurants. You can also visit the Key West Cemetery, it's a fascinating place to wander around and learn about the history of Key West. And don't forget to check out the free sunset celebrations at Mallory Square.
  • What are the best restaurants with local dishes in Key West, FL?

    For a taste of Key West, try the conch fritters at The Waterfront Brewery. If you're looking for something a bit fancier, head to Latitudes for their award-winning seafood. And for a taste of Cuban cuisine, check out El Siboney.
  • What are the best walking or cycling routes in Key West, FL?

    The Truman Waterfront is a great place for a walk or cycle, with beautiful views of the harbour. For a longer ride, try the scenic route along the Overseas Highway, it's a stunning drive with views of the ocean and the Keys.
  • Are there pet-friendly attractions in Key West, FL?

    Yes, there are plenty of pet-friendly attractions in Key West. You can take your dog to the beach at Higgs Beach, or for a walk along the Truman Waterfront. Many restaurants and shops also welcome well-behaved dogs.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than hotels, and they're often a more affordable option. You'll also have access to a kitchen, so you can save money by cooking some of your own meals.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular spot for watersports, with plenty of opportunities for fishing, sailing, and kayaking. You can also find golf courses, tennis courts, and a fitness centre.

Popular destinations

Best Key West, FL vacation rentals with a balcony

Tom's Spectacular Oceanfront 3 Bdrm  Endless Atlantic View, Key West Amazing - Key West, FL
9.8 149 reviews

Tom's Spectacular Oceanfront 3 Bdrm Endless Atlantic View, Key West Amazing

apartment, Key West
This beachfront Key West condo is situated near Duval Street, less than 3km from the Southernmost Point buoy and Florida Keys Beaches, with Mallory Square 4.4km away.
This 186 square metre property boasts three bedrooms, two bathrooms, sleeping up to eight guests, and features a private pool, hot tub, fully equipped kitchen, and access to a shared fitness centre, tennis court, and sauna.
Two-bedroom, Two-bath Condo Close To The Ocean. Full Kitchen, Living R & Balcony - Key West, FL
9.2 47 reviews

Two-bedroom, Two-bath Condo Close To The Ocean. Full Kitchen, Living R & Balcony

apartment, Key West
This two-bedroom Key West apartment is located within a 3km radius of the Fort East Martello Museum and Gallery, Key West Art and Historical Society, and Key West Tropical Forest and Botanical Garden, with Smathers Beach and Lower Keys Medical Center within 5km.
The 74 square metre apartment features a fully equipped kitchen, a private balcony, and a swimming pool, comfortably accommodating up to six guests.
Apartment ∙ 3 Bedrooms ∙ 10 Guests - Key West, FL
No reviews

Apartment ∙ 3 Bedrooms ∙ 10 Guests

apartment, Key West
The Mesa House, a Key West dwelling in Old Town, is conveniently located near Simonton Street, offering easy access to numerous attractions.
This self-catering property comprises two separate condos, sleeping up to ten guests, and boasts two full kitchens, four cable TVs, free WiFi, a private washer/dryer, and a terrace/balcony plus garden.
Treehouse On Margaret ~ New! Private 1 Br/2 Ba Single Family Home! - Key West, FL
No reviews

Treehouse On Margaret ~ New! Private 1 Br/2 Ba Single Family Home!

apartment, Key West
This intimate tropical escape, a private single-family home, is situated in Old Town Key West, a short stroll from Mallory Square and Duval Street, and within cycling distance of Hemingway House, Fort Zachary Taylor Park, and Smathers and Higgs beaches.
This 82 square metre abode offers a dog-friendly, remodelled interior with an open-plan living, dining, and kitchen area, accommodating up to six guests with a king bedroom, two bathrooms, a private courtyard, and concierge services for planning local activities.

Best Key West, FL vacation rentals with parking

Luxury Island Resort Living At 1800 Atlantic, Pool, Beach, Tennis,in Key West - Key West, FL
10 2 reviews

Luxury Island Resort Living At 1800 Atlantic, Pool, Beach, Tennis,in Key West

apartment, Key West
This two-bedroom, two-bathroom condominium in Key West's Beachside district offers direct beach access and is situated within easy reach of the Southernmost Point and the Ernest Hemingway Home and Museum, just 0.5 kilometres away.
This fully furnished flat, spanning 125 square metres and accommodating up to four guests, boasts a private balcony with partial sea views and offers access to resort amenities including a heated swimming pool, Jacuzzi, and fitness centre.
Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking - Key West, FL
8.9 197 reviews

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

house, Key West
The Tortuga by Brightwild-Pool, Parking & Pets! is situated in Key West, just over 6km from the famous Duval Street and Mallory Square.
This two-bedroom property, spanning 74 square metres, features a private swimming pool, a hot tub, and a fully equipped kitchen, as well as free parking and Wi-Fi.
Another Day In Paradise - Key West, FL
9.9 62 reviews

Another Day In Paradise

apartment, Stock Island
This three-bedroom townhome, situated in the Coral Hammock community on Stock Island, offers easy access to Key West's attractions, a short drive away.
Sleeping up to eleven guests, this Stock Island property boasts three bathrooms, a fully equipped kitchen including a dishwasher, and access to a communal swimming pool and fitness centre.
Pier House Resort & Spa - Key West, FL
8.9 10221 reviews

Pier House Resort & Spa

resort, Key West
The Opal Key Resort & Marina is in Old Town, Key West, just a short walk from Duval Street and the Key West Aquarium. The hotel has excellent location and cleanliness ratings and is considered very good overall.
The resort has a waterfront location with a marina offering water sports. Guests can enjoy a heated pool, hot tub, spa, fitness centre, tennis court, restaurant, bar, and room service.
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