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

Sunnyside Up - Shared Pool - Key West, FL
10 12 reviews

Sunnyside Up - Shared Pool

apartment, Key West
This Key West Historic District flat is a short walk from the Key West Firehouse Museum and Duval Street, and under 1.6 km from South Beach and the Southernmost Point.
This 108-square-metre self-catering apartment sleeps six, boasting two bedrooms, two bathrooms, a terrace, a garden, a swimming pool, and free internet access.
Apartment ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
No reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Key West
This Key West apartment is centrally located in downtown Key West, approximately 1.6km from Key West International Airport (EYW) and within walking distance of many attractions.
The one-bedroom flat sleeps four, featuring a newly renovated kitchen with modern appliances, a private washer/dryer, central air conditioning, free Wi-Fi, a terrace, and a king-size bed plus a queen-size sleeper sofa; nearby paid parking is available.
127 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.5 30 reviews

127 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
This Old Town Key West property is situated just one block from Duval Street's entertainment and four blocks from the Atlantic Ocean.
This two-bedroom, two-bathroom house boasts 137 square metres of living space, featuring an open-plan layout with Key West décor, a private pool (with optional heating, subject to seasonal availability), a lush tropical garden including an orchid house, and parking; it comfortably sleeps six guests.
Coastal Comfort & 3/4 Time Compound - Key West, FL
9.8 6 reviews

Coastal Comfort & 3/4 Time Compound

apartment, Key West
This expansive Key West compound, located in the Northside Resort district, offers immediate access to essential amenities, being within 500 meters of a Publix supermarket and the island's principal shopping centre.
This 372 square meter residence, ideal for up to 16 guests across eight bedrooms and seven bathrooms, features a private heated swimming pool, a fully equipped chef's kitchen, and eight en-suite bedrooms, including master suites with Jacuzzi tubs, providing a comfortable stay with ample space and modern conveniences.

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 Curry Classic | Main Mansion King - Key West, FL
8.2 24 reviews

The Curry Classic | Main Mansion King

apartment, Key West
This Key West apartment, situated in the Historic District half a kilometre from Duval Street, offers easy walking access to Mallory Square and numerous restaurants including First Flight and Bagatelle.
The self-catering flat, sleeping two guests in a king-size bed, features a private bathroom, mini-fridge, and access to a shared heated pool and laundry facilities within a historic 1869 mansion; contactless check-in is available.
The Saint Kitts Suite | Breathtaking View, Heated Pool - Key West, FL
9.6 5 reviews

The Saint Kitts Suite | Breathtaking View, Heated Pool

apartment, Key West
This pet-friendly condominium in the Sunrise Suites community is situated on Key West's southeast side, approximately 3.2 kilometres from Smathers Beach and a short journey from Duval Street's attractions.
This newly renovated two-bedroom, two-bathroom condo offers 74 square metres of living space, accommodating up to six guests with a queen sofa bed, and features a private balcony, a fully equipped kitchen, air conditioning, and access to a communal heated pool, hot tub, and tennis court.
Duval Square Penthouse - Key West, FL
No reviews

Duval Square Penthouse

apartment, Key West
Duval Square Penthouse is centrally located in Key West, Florida, a 0.6km walk from Duval Street and less than 1.6km from South Beach and the Southernmost Point.
This 228 square metre, four-bedroom penthouse sleeps nineteen guests and boasts five bathrooms, a fully equipped kitchen, private parking, a swimming pool, tennis court, balcony, and free Wi-Fi.
Colony Calypso - A Quaint 1 Bedroom Cottage - Key West, FL
9.4 141 reviews

Colony Calypso - A Quaint 1 Bedroom Cottage

apartment, Key West
Colony Calypso is a one-bedroom bungalow in Old Town Key West, just 0.3 km from Duval Street and its lively atmosphere. The cottage has received excellent ratings for location, cleanliness and user experience.
The bungalow is 49 square metres and comfortably sleeps two guests. Guests can enjoy a private deck with a gas grill, a shared swimming pool, and access to a spa.

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

Bottoms Up Bungalow - Perfect  2 Bed/2 Bath Private Pool - Key West, FL
10 126 reviews

Bottoms Up Bungalow - Perfect 2 Bed/2 Bath Private Pool

apartment, Key West
Bottom's Up Bungalow is situated in the Key West Historic District, just under 1.6 kilometres from Duval Street, the beaches, and the marina. This charming property has received excellent user ratings, making it a popular choice for travellers.
The bungalow has 2 bedrooms and 2 bathrooms, spanning 114 square metres and accommodating up to 6 guests. It offers a range of amenities, including a private pool, a spa, a terrace, and a garden, providing a relaxing and enjoyable stay.
Oceanfront Oasis Smathers Beach Condo Sunrise Views Island Charm Book Today - Key West, FL
9.8 18 reviews

Oceanfront Oasis Smathers Beach Condo Sunrise Views Island Charm Book Today

apartment, Key West
This oceanfront Key West apartment, situated in the La Brisa complex on Smather's Beach, offers direct access to the beach and is within easy reach of attractions such as the Southernmost Point and the Ernest Hemingway Home and Museum.
The 111 square metre (1194 square feet) property boasts three bedrooms, two bathrooms, sleeping six guests comfortably, and features a fully equipped kitchen, a private terrace, a shared heated swimming pool, hot tub, sauna and a stackable washer/dryer.
**Windward Waves @ Old Town** Cozy Cottage Near Duval + Last Key Services... - Key West, FL
10 2 reviews

**Windward Waves @ Old Town** Cozy Cottage Near Duval + Last Key Services...

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.
Summer Is Here - Book Your Dream Stay Now! - Key West, FL
9.4 271 reviews

Summer Is Here - Book Your Dream Stay Now!

apartment, Key West
This Truman Annex condo, situated in Key West's Shipyard neighbourhood, offers easy walking access to Duval Street and Mallory Square.
The 65-square-metre (700 sq ft) two-bedroom, one-bathroom apartment sleeps six, boasting a 65-inch plasma TV, SMEG appliances, a rear patio overlooking the pool, and Hemingway and Jimmy Buffett themed décor; on-site amenities include a swimming pool, jacuzzi, and parking.

Best Key West, FL vacation rentals with parking

Signature King At Beachside Resort - Key West, FL
9.3 332 reviews

Signature King At Beachside Resort

apartment, Key West
Beachside Resort & Residences, a guesthouse in Key West, Florida, boasts a seven-acre beachfront location on the Gulf of Mexico, offering easy access to Key West's attractions.
This self-catering unit features a king-size bed, private bathroom, and access to a resort pool, hot tub, fitness centre, and on-site restaurants including Tavern N Town and Chicken Walk, accommodating up to two guests.
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.
Resort Condo With Pool & Hot Tub, Private Parking - Key West, FL
9.0 2 reviews

Resort Condo With Pool & Hot Tub, Private Parking

apartment, Key West
This Key West condo offers a prime seaside location, providing easy access to the Southernmost Point and the Ernest Hemingway Home and Museum, approximately 1.1 kilometres from Smathers Beach.
This 72-square-metre apartment sleeps six guests across two bedrooms and two bathrooms, featuring a private balcony, a shared swimming pool, a hot tub, and is suitable for dogs up to 11.3 kg.
Seaside Escape- 2 Bed/2 Bath Condo With Shared Pool & Parking - Key West, FL
9.6 4 reviews

Seaside Escape- 2 Bed/2 Bath Condo With Shared Pool & Parking

apartment, Key West
This two-bedroom, two-bathroom condominium in the Sunrise Suites complex is located approximately 3.2 kilometres from Old Town Key West, offering a peaceful base near Smathers Beach and Key West International Airport.
This third-floor end unit provides private lanai views of the tennis courts and access to a communal swimming pool, fitness facility, and on-site convenience store, accommodating up to six guests with a fully equipped kitchen and en-suite bathrooms.
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