Vacation Rentals in Key West, FL

4265 available vacation rental offers

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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

Little Paradise, Historic Harbor Old Town Key West 2/1.5 - Key West, FL
8.2 25 reviews

Little Paradise, Historic Harbor Old Town Key West 2/1.5

apartment, Key West
This Key West Historic District property is situated less than 1.6km from Duval Street and under 1.6km from the Ernest Hemingway Home and Museum, offering easy access to Key West's attractions.
This 81 square metre house sleeps four guests and boasts two bedrooms, two bathrooms, a fully equipped kitchen, a jacuzzi, a terrace, a garden, and free Wi-Fi; nearby attractions include the Key West Burlesque Theatre and beaches.
122 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.3 19 reviews

122 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
This Key West property is situated near Smather's Beach, a short walk from a couple of kilometres of Atlantic Oceanfront promenade, and adjacent to nature preserves.
This two-bedroom, two-bathroom house offers 122 square metres of living space, including a modern living room, king-size beds in each bedroom, a queen sleeper sofa, Olympic-sized pool, tennis courts, and a covered garage; accommodating up to six guests and providing access to nearby nature trails.
Apartment ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
No reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Key West
This one-bedroom apartment is located within a resort complex in Key West, just a short distance from Duval Street and the attractions of Old Town. The apartment boasts a private balcony with pool views, a fully equipped kitchen, and a whirlpool tub, perfect for relaxing after a day of exploring the island.
Apartment ∙ 2 Bedrooms ∙ 8 Guests - Key West, FL
No reviews

Apartment ∙ 2 Bedrooms ∙ 8 Guests

apartment, Key West
Sweet Caroline, situated on Caroline Street in Key West's downtown area, offers easy walking access to numerous attractions.
This two-bedroom, two-bathroom house, part of Banana's Foster Guesthouse, sleeps seven guests and boasts a gourmet kitchen, private porch, shared pool, and designated parking; pet-friendly (fees apply).

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

Treehouse Condo 2nd Floor Balcony Sleeps 6 Free Parking - Key West, FL
9.0 9 reviews

Treehouse Condo 2nd Floor Balcony Sleeps 6 Free Parking

apartment, Key West
This Key West flat is located in the Old Town district, a 4-minute walk from Keys Archipelago Beaches, 11 minutes from South Beach and Duval Street, and 13 minutes from the Southernmost Point.
This property offers air conditioning and Wi-Fi, with a dryer, ironing board, towels, soap, toilet paper, and hairdryer provided for your convenience.
Pool View Suite | Beachside Resort - Key West, FL
9.5 301 reviews

Pool View Suite | Beachside Resort

apartment, Key West
This one-bedroom apartment is situated in a resort complex on a 2.8-hectare site overlooking the Gulf of Mexico in Key West, just a short distance from Duval Street and the Southernmost Point. The apartment offers a king-size bed, a queen sleeper sofa, a fully equipped kitchen, a private washer/dryer, and a private balcony, as well as access to a 24-hour heated pool, hot tub, on-site marina, restaurant, and waterview fitness centre.
Sombrero Reef Light Suite - Key West, FL
10 2 reviews

Sombrero Reef Light Suite

house, Key West
Sombrero Reef Light Suite is a centrally located Key West property, a short 0.8km walk from South Beach and the Ernest Hemingway Home and Museum, and less than 1.6km from Duval Street and Mallory Square, placing it within Key West's historic district.
This self-catering apartment offers 48 square metres of space, sleeping up to seven guests in one bedroom and one bathroom, and includes a fully equipped kitchen with dishwasher, air conditioning, a swimming pool, and free Wi-Fi.
Anchor Drop Modern Elegance Upgrades Throughout Vi - Key West, FL
9.7 311 reviews

Anchor Drop Modern Elegance Upgrades Throughout Vi

apartment, Key West
This two-bedroom apartment in Beachside, Key West is just a 15-minute walk from the Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, and within a short drive of Duval Street and Mallory Square. The property has received excellent ratings for location, cleanliness and user experience.
The 126 square metre apartment comfortably sleeps six guests and features a fully equipped kitchen, a terrace, a garden, a swimming pool, a Jacuzzi, a sauna, a fitness centre and a tennis court. Guests will also enjoy access to parking, air conditioning and internet.

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

Comfortable Condo With Pool, Private Balcony, & Beach Access - Key West, FL
8.6 139 reviews

Comfortable Condo With Pool, Private Balcony, & Beach Access

apartment, Key West
This Key West condo offers a prime waterfront position in the Beachside district, providing direct access to the Florida Keys Overseas Heritage Trail and situated 800 metres from Smathers Beach and Indigenous Park, 3.2 kilometres from the Ernest Hemingway Home and Museum, and less than 4.8 kilometres from Mallory Square.
This spacious 126 square metre apartment, accommodating up to six guests, features two bedrooms and two bathrooms, along with central air conditioning, a full kitchen, private washer and dryer, three cable televisions, complimentary WiFi, and a private balcony with seating.
The Curry Poolside | Ground  Floor King - Key West, FL
No reviews

The Curry Poolside | Ground Floor King

apartment, Key West
This Key West apartment, situated in the Historic District, is 0.4 km from Duval Street and within easy walking distance of Mallory Square and the Ernest Hemingway Home and Museum.
The one-bedroom, one-bathroom flat sleeps two guests and offers amenities including a shared heated pool, on-site parking (subject to availability), and a private terrace; shared laundry facilities with detergent are also available.
Dancing Palms @ The Truman Annex In Key West - Key West, FL
9.4 51 reviews

Dancing Palms @ The Truman Annex In Key West

apartment, Key West
This Key West Old Town property is conveniently located less than 1 km from Duval Street, the Ernest Hemingway Home and Museum, and We Cycle Key West, and within a 2.4 km walk of Fort Zachary Taylor Historic State Park and Mallory Square.
This two-bedroom, two-bathroom house sleeps four guests and boasts a fully equipped kitchen, private balcony, washer-dryer, and swimming pool, offering easy access to Key West's attractions.
Key West Condo With Balcony Ocean View - Key West, FL
10 194 reviews

Key West Condo With Balcony Ocean View

apartment, Key West
This two-bedroom apartment is situated directly across the street from Smathers Beach, one of Key West's most popular beaches, offering easy access to the sand and surf. The apartment has received excellent ratings for user experience, location, and cleanliness.
The 136 square metre property comfortably accommodates up to six guests and features a modern kitchen, two bathrooms, a spacious living area, a private balcony, and air conditioning throughout. Enjoy the on-site amenities, including a swimming pool, hot tub, tennis courts, and a garden, or take advantage of the beach rentals available for chairs, umbrellas, paddle boards, kayaks, and sailboats.

Best Key West, FL holiday rentals with parking

Caribbean Conch 5 Minutes To Smathers Beach & 10 M - Key West, FL
9.2 155 reviews

Caribbean Conch 5 Minutes To Smathers Beach & 10 M

apartment, Key West
This two-bedroom apartment is situated in Beachside, Key West, just a 15-minute walk from the beautiful Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, and within 2 miles of Duval Street and Southernmost Point. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment is comfortably furnished and features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. Enjoy the on-site amenities, including a swimming pool, jacuzzi, terrace, garden, sauna, fitness centre, tennis court, and parking.
Secret Villa I @ Old Town With Private Pool, Close To Duval! - Key West, FL
10 185 reviews

Secret Villa I @ Old Town With Private Pool, Close To Duval!

house, Key West
Secret Villa I is situated in Key West's Historic District, just a short walk from Duval Street, the town's main entertainment hub, and within easy reach of three popular beaches. This property has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and well-equipped accommodation. This three-bedroom, three-bathroom villa offers 151 square metres of space, comfortably accommodating up to six guests. The villa features a private pool, lush gardens, a fully equipped kitchen, a washer and dryer, high-speed internet, and a selection of games for entertainment.
Nautical Adventures In Paradise - Key West, FL
9.3 459 reviews

Nautical Adventures In Paradise

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.
Waterfront Condo Free Slip & Pool 2b2b In Key West - Key West, FL
9.8 118 reviews

Waterfront Condo Free Slip & Pool 2b2b In Key West

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.
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