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

Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk To Duval - Key West, FL
10 4 reviews

Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk To Duval

apartment, Key West
This newly constructed coastal-modern residence is located in Old Town Key West, a mere 160 metres from Truman Avenue and an 8-minute walk to Duval Street, offering excellent access to local attractions.
This detached property accommodates up to 8 guests, featuring a private heated and chilled swimming pool, gated off-street parking for one car and one golf cart, and a fully equipped kitchen with a wine cooler and coffee station.
Ibis Bay Resort - Key West, FL
8.0 3799 reviews

Ibis Bay Resort

resort, Key West
Ibis Bay Beach Resort is a Key West hotel situated on the north side, offering a tranquil escape yet within 5km of attractions such as Duval Street, Mallory Square, and Regal Key West.
This family-friendly hotel boasts a private beach, an outdoor pool, and convenient access to a marina for water sports, plus on-site amenities including a restaurant, bar, and room service.
Parrot Key Hotel & Villas - Key West, FL
8.5 4793 reviews

Parrot Key Hotel & Villas

resort, Key West
Parrot Key Hotel & Villas is located in Florida Bay, a short drive from the historic Old Town of Key West, offering a peaceful escape from the bustling city centre. This resort consistently receives very good ratings for its location, cleanliness, and overall experience.
The hotel features a range of accommodation options, including villas and rooms, all with private terraces offering stunning ocean views. Guests can enjoy a variety of amenities, activities and features, from multiple swimming pools and a fitness centre to kayaking excursions and on-site dining.
House ∙ 2 Bedrooms ∙ 4 Guests - Key West, FL
No reviews

House ∙ 2 Bedrooms ∙ 4 Guests

house, Key West
This two-bedroom, two-bathroom holiday flat on Caroline Street offers a historic Key West district location, placing you within easy reach of local attractions.
This well-appointed abode accommodates up to four guests, featuring a shared swimming pool, a generous balcony for observing street life, and a minimum 29-day rental period ideal for extended stays.

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

Colony Sunset- Bright And Airy Cottage In The Heart Of Old Town Key West - Key West, FL
9.8 118 reviews

Colony Sunset- Bright And Airy Cottage In The Heart Of Old Town Key West

cottage, Key West
This charming cottage is situated in The Colony, a peaceful gated community just a short walk from the lively Duval Street in Key West. The cottage boasts excellent user ratings and is a popular choice for travellers seeking a relaxing escape.
The cottage offers 49 square metres of living space and comfortably accommodates four guests. The cottage features a private deck, a shared swimming pool, a well-equipped kitchen, and a spa, ensuring a comfortable and enjoyable stay.
Newly Furnished Suite With Pool, Hot Tub, Tennis, Balcony, Parking - Dog Ok - Key West, FL
8.6 124 reviews

Newly Furnished Suite With Pool, Hot Tub, Tennis, Balcony, Parking - Dog Ok

apartment, Key West
This two-bedroom flat, located in the Sunrise Suites resort community on Key West's eastern side, offers an oceanfront setting with easy access to Smathers Beach and Ernest Hemingway's former home, approximately 1.6 kilometres away.
Boasting 72 square meters of living space, this accommodation accommodates up to six guests and features a private balcony, air conditioning, a swimming pool, jacuzzi, and allows one dog, with convenient private parking available.
Sunrise Suites Resort Key West, Fl U #111 2bdr2bth - Key West, FL
9.3 271 reviews

Sunrise Suites Resort Key West, Fl U #111 2bdr2bth

apartment, Key West
This apartment is conveniently located just across the road from the ocean, a short 3 km drive from Duval Street, Key West’s lively main street, and within easy reach of two beautiful beaches, Smather’s Beach and Higgs Beach. The property has received excellent ratings for location, cleanliness and user experience.
This comfortable two-bedroom, two-bathroom apartment can accommodate up to six guests and features a fully equipped kitchen, a private balcony, and a range of modern amenities, including air conditioning, free parking, and fast Wi-Fi. Guests can enjoy access to a swimming pool, a jacuzzi, a fitness centre, and a garden, as well as step-free access to the entrance and bathroom.
St John - Downtown Waterfront Penthouse Pool Parking Dock - Key West, FL
9.3 3 reviews

St John - Downtown Waterfront Penthouse Pool Parking Dock

house, Key West
This Key West penthouse, situated 1.8km from both the Ernest Hemingway Home and Museum and Duval Street, and 1.9km from Key West International Airport, offers stunning sea views from its direct waterfront location.
The 186 square metre property boasts four bedrooms, four bathrooms, sleeps 24 guests, includes a private pool, free Wi-Fi, and a fully equipped kitchen; nearby activities include cycling.

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

Penthouse Waterfront Dock Pool Condo Near Duval St - Key West, FL
9.8 301 reviews

Penthouse Waterfront Dock Pool Condo Near Duval St

apartment, Key West
This Key West penthouse condo, situated in the historic downtown area less than 1.6km from Duval Street, the Historic Seaport, and the Hemingway House, offers breathtaking waterfront views.
This 171 square metre luxury apartment sleeps up to 16 guests in four bedrooms plus a loft, boasting four en-suite bathrooms, a fully equipped kitchen, two living areas, a private boat slip (up to 40ft), and access to a heated pool, tiki bar, and bike rentals.
Resort-style Amenities And Expansive Pool - Stunning Oceanfront Retreat - Key West, FL
No reviews

Resort-style Amenities And Expansive Pool - Stunning Oceanfront Retreat

apartment, Key West
This oceanfront condominium complex is situated directly on 400 feet of coastline, adjacent to Smathers Beach, and is just 2.4 kilometres from Old Town Key West's shops and restaurants.
This family-friendly apartment offers accommodation for four guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, fitness centre, and tennis courts, with a balcony providing ocean views.
Oceanview Home With Private Pool & Lush Landscaping! - Key West, FL
9.8 137 reviews

Oceanview Home With Private Pool & Lush Landscaping!

apartment, Key West
This Northside Resort property is conveniently located within 5km of Duval Street, Mallory Square, and the Unitarian Universalist Fellowship of Key West.
This 368 square metre Key West house boasts four bedrooms, three bathrooms, sleeps eight, and includes a private pool, Jacuzzi, and fully equipped kitchen; barbecue grills and housekeeping are available.
Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
9.2 57 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.

Best Key West, FL vacation rentals with parking

Tranquility By The Beach - Key West, FL
9.3 469 reviews

Tranquility By The Beach

house, Key West
This two-bedroom apartment in Key West is just a short walk from Smathers Beach and within a mile of Rest Beach and Higgs Beach. The apartment has excellent user, location and cleanliness ratings.
The apartment is fully equipped with a modern kitchen, air conditioning, and a private balcony. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, sauna, fitness centre, tennis court, and free parking.
Frost Free In Cayo Hueso - Key West, FL
9.3 238 reviews

Frost Free In Cayo Hueso

house, Key West
This apartment is located just a short walk from Smathers Beach, Key West's most popular beach, and a few blocks from Rest Beach, making it ideal for enjoying the beautiful beaches and vibrant atmosphere of Key West. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom, two-bathroom apartment can comfortably accommodate up to six guests. It features a fully equipped kitchen, a private balcony with sea views, a swimming pool, a Jacuzzi, a fitness centre, and a tennis court.
Sparkling Pool And Hot Tub - Stunning Ocean View Getaway - Key West, FL
No reviews

Sparkling Pool And Hot Tub - Stunning Ocean View Getaway

apartment, Key West
This two-bedroom, two-bathroom condominium in Key West's Midtown district is situated across from the Atlantic Ocean, mere steps from Smathers Beach, and within 1.6 kilometres of the White Street Pier, offering convenient access to downtown attractions.
This family-friendly apartment accommodates up to six guests and features a newly renovated open-concept living space, a chef's kitchen with a fridge, microwave, and dishwasher, air conditioning, a private balcony with water views, a shared swimming pool, hot tub, BBQ grills, sauna, and tennis courts.
Seagull Suite | Inviting Studio, Steps From Duval - Key West, FL
9.8 32 reviews

Seagull Suite | Inviting Studio, Steps From Duval

apartment, Key West
Seagull Suite, a Key West studio apartment, is situated a short walk from Duval Street, one block from the Southernmost Point buoy, and three blocks from South Beach.
This pet-friendly (small dogs only, maximum 13.6kg) self-catering unit sleeps four, offering a kitchenette, complimentary Wi-Fi, a Jacuzzi, and access to shared laundry facilities and hot tubs; nearby attractions include Duval Street's shops and restaurants.
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