Vacation Rentals in Key West, FL

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Key West, FL vacation rentals
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4265 Vacation 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

Apartment ∙ 3 Bedrooms ∙ 8 Guests - Key West, FL
9.0 2 reviews

Apartment ∙ 3 Bedrooms ∙ 8 Guests

apartment, Key West
This three-bedroom apartment is situated in Beachside Key West, just a short distance from Duval Street and its attractions.
The apartment offers private parking with electric charging stations, a fully equipped kitchen, a spacious living area with a queen sleeper sofa, and a private balcony, comfortably accommodating up to eight guests.
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.
Inviting Deck And Shared Pool - Charming Studio Retreat - Key West, FL
No reviews

Inviting Deck And Shared Pool - Charming Studio Retreat

cottage, Key West
This ground-floor studio apartment in Key West's Old Town offers a prime location on Olivia Street, a mere 400 metres from Duval Street, placing you within easy walking distance of bars, restaurants, shops, and galleries in a quiet neighbourhood.
This family-friendly cottage sleeps four and features air conditioning, a kitchenette with a fridge and microwave, Wi-Fi, a shared swimming pool, a garden, and a spa, with French doors opening onto a deck near the pool, perfect for a relaxing stay.
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.

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

The Lark's Landing At Sunrise Suites - Key West, FL
9.9 29 reviews

The Lark's Landing At Sunrise Suites

apartment, Key West
This Sunrise Suites apartment in Key West boasts a top-floor location, 0.8km from Key West International Airport, 3.2km from Smathers Beach, and 4.8km from Duval Street.
The two-bedroom, two-bathroom flat sleeps six, offering a fully equipped kitchen, balcony, and access to a swimming pool, jacuzzi, fitness centre, and parking; all new furniture and TVs complete the modern feel.
Hyatt Centric Key West Resort & Spa - Key West, FL
8.8 2724 reviews

Hyatt Centric Key West Resort & Spa

resort, Key West
The Hyatt Centric Key West Resort & Spa is situated on Key West Island, just a short walk from the lively Duval Street, known for its nightlife and restaurants. The resort has received very good user ratings, with excellent marks for location and very good ratings for cleanliness.
The hotel has a waterfront location with a swimming pool, a jacuzzi and a spa. Guests can enjoy a range of activities, including relaxing by the pool, exploring the surrounding area via jet ski, scuba diving, snorkelling, and island tours, as well as dining at two on-site restaurants.
Contra House - Private Pool & Steps To Duval St. - Key West, FL
9.6 74 reviews

Contra House - Private Pool & Steps To Duval St.

house, Key West
This Key West property, a luxurious two-house complex, is ideally situated just 0.16 kilometres from Duval Street, providing easy access to the island's shops and restaurants.
The 4-bedroom, 4-bathroom dwelling boasts a private heated pool, two gourmet kitchens each with a wine cooler, and a contactless check-in process, comfortably accommodating up to 12 guests.
Colony Poolside: A Charming Bungalow Near Duval - Key West, FL
9.8 180 reviews

Colony Poolside: A Charming Bungalow Near Duval

apartment, Key West
Colony Poolside is a one-bedroom bungalow situated in the historic Old Town district of Key West, just a short walk from Duval Street and a few kilometres from the beach. The property has received excellent ratings for its location, cleanliness, and overall experience.
The bungalow is 51 square metres and can accommodate two guests. It has a fully equipped kitchen, a private deck, a shared pool, and a garden, offering everything you need 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 really must visit the Southernmost Point of the Continental US, it's iconic. You can't miss the Hemingway House, it's full of history and six-toed cats. And for a taste of Key West's history, visit the Fort Zachary Taylor Historic State Park.
  • What are the best Airbnb and vacation rentals in Key West, FL?

    Leaward Isle Island Retreat, Mango Hideaway @ The Eyebrow House Off Duval and At Mine | Lovely Suite Steps From Duval Street 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 lots of shops, restaurants, and bars. If you want a quieter stay, consider the historic Bahama Village, known for its vibrant culture and colourful houses.
  • 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 favourite for kids, and the Butterfly Conservatory is a beautiful place to learn about exotic insects. For some outdoor fun, the Key West Wildlife Center is a great place to see native animals.
  • 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?

    Key West is popular year-round, but if you want to avoid the crowds and get the best deals, book your vacation rental in the shoulder seasons, like April-May or September-October.
  • What are the best rentals for families and kids in Key West, FL?

    The best rentals for families and kids in Key West, FL are Leaward Isle Island Retreat, Mango Hideaway @ The Eyebrow House Off Duval and Key West Villas.

  • 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 wild and colourful celebration, and the Key West Songwriters Festival in May is great for music lovers. The Hemingway Days Festival in July is a fun event celebrating the famous author.
  • 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, Mango Hideaway @ The Eyebrow House Off Duval and Key West Villas.

  • 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 and enjoy the street performers, or visit the Key West Cemetery for a unique and interesting historical experience. You can also enjoy the free sunset celebrations at Mallory Square.
  • What are the best restaurants with local dishes in Key West, FL?

    For authentic Key West cuisine, try the Blue Heaven for their famous chicken and waffles, or the Hogfish Bar for their fresh seafood. The Cuban Coffee Queen is a great spot for a traditional Cuban breakfast.
  • What are the best walking or cycling routes in Key West, FL?

    The Key West Historic Seaport is a great place to start a walk or bike ride. The route along the waterfront offers stunning views, and you can also explore the charming streets of Old Town.
  • Are there pet-friendly attractions in Key West, FL?

    The Key West Butterfly & Nature Conservatory welcomes well-behaved dogs on a leash, and many of the beaches in Key West allow dogs, but make sure to check the specific rules.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than hotels, and often come with amenities like kitchens and laundry facilities. They can also be more affordable, especially for larger groups or families.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular destination for watersports, with great opportunities for sailing, fishing, diving, and kayaking. You can also find tennis courts and golf courses in the area.

Popular destinations

Best Key West, FL holiday rentals with a balcony

Sunrise 307-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
9.6 31 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.
Apartment ∙ 7 Bedrooms ∙ 19 Guests - Key West, FL
No reviews

Apartment ∙ 7 Bedrooms ∙ 19 Guests

apartment, Key West
Banana's Foster Guest House, situated on the corner of Caroline and Simonton Streets in Key West's central district, offers easy access to numerous attractions.
This seven-bedroom, seven-bathroom property comprises six self-contained units with private entrances, accommodating up to 19 guests and featuring a private pool, parking for four vehicles, and a garden; pets are welcome (charges apply).
Spacious Waterfront 4 Bedroom Home - Key West, FL
9.6 106 reviews

Spacious Waterfront 4 Bedroom Home

apartment, Key West
This four-bedroom house is located in Northside Resort, just three miles from Duval Street, Mallory Square, and The Unitarian Universalist Fellowship of Key West. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The 368 square metre house can accommodate up to eight guests, offering plenty of space for families or groups of friends. Amenities include a private pool, Jacuzzi, terrace, garden, and concierge services, along with a fully equipped kitchen, free Wi-Fi, and parking.
One Bedroom Suite | Beachside Resort - Key West, FL
10 7 reviews

One Bedroom Suite | Beachside Resort

apartment, Key West
This luxury resort in North Key West, situated on seven acres of waterfront, offers direct Gulf of Mexico views and is located 1.6 kilometres from Duval Street, placing it close to Florida Keys Beaches and Smathers Beach.
This one-bedroom, two-bathroom apartment accommodates up to four guests and features a fully equipped kitchen with stainless-steel appliances, a private balcony, access to a heated swimming pool and hot tub, and is conveniently located near attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point.

Best Key West, FL holiday rentals with parking

The Marker Key West Harbor Resort - Key West, FL
9.2 1114 reviews

The Marker Key West Harbor Resort

resort, Key West
The Marker Key West Harbor Resort is located in the Historic District, just a short walk from Mallory Square, the Florida Keys National Marine Sanctuary, and a slightly longer walk from Southernmost Point. It has consistently received very good user ratings, with excellent ratings for its location and cleanliness.
The hotel offers three outdoor pools, a restaurant, a bar, and a fitness centre. Guests can enjoy a range of amenities and activities, including a terrace, a garden, and a business centre, all while enjoying free Wi-Fi access in public areas.
Key West On My Mind - Key West, FL
9.4 152 reviews

Key West On My Mind

house, Key West
Key West On My Mind is a two-bedroom apartment situated near Smathers Beach, a 2.6 km walk from the Southernmost Point and 3.2 km from the Ernest Hemingway Home and Museum.
This 126 square metre property boasts a private balcony with sea views, two bathrooms, a fully equipped kitchen, free Wi-Fi, private parking, and access to a swimming pool, jacuzzi, sauna, fitness centre, and tennis court.
Rose Key Cottage - Private Pool & Near Duval - Key West, FL
No reviews

Rose Key Cottage - Private Pool & Near Duval

house, Key West
This Key West holiday home is situated 50 metres from Duval Street, providing convenient access to downtown attractions, dining, and the historic seaport.
This two-bedroom, two-bathroom villa accommodates up to six guests and features a private swimming pool, two fully-equipped kitchens, a spacious garden, and two off-street parking spaces, with pets welcome up to 18 kilograms.
Welcome To Poseidon Too - A Newly, Completely Renovated Condo @ Sunrise Suites! - Key West, FL
10 25 reviews

Welcome To Poseidon Too - A Newly, Completely Renovated Condo @ Sunrise Suites!

apartment, Key West
This two-bedroom apartment is situated on the south side of Key West, just 1.6 kilometres from South Beach and 8 kilometres from Duval Street.
The 74 square metre apartment features a modern design, a fully equipped kitchen, and comfortable sleeping arrangements for up to six guests, making it ideal for families or groups of friends.
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