Holiday Rentals in Key West, FL

4265 available vacation rental offers

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Key West, FL holiday rentals
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Best Holiday rentals and Airbnb offers in Key West, FL

Best family friendly Key West, FL holiday rentals

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

Elegant Waterfront Corner Residence - Key West, FL
No reviews

Elegant Waterfront Corner Residence

apartment, Key West
This elegant corner flat in Key West offers direct beachfront access and is located 8 kilometres from the Ernest Hemingway Home and Museum and Duval Street.
This spacious 145 square metre residence accommodates up to nine guests with two bedrooms and two bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a Jacuzzi, and a terrace, with pets also welcome.
Charming Outdoor Patio And Cozy Fireplace - Inviting Key West Retreat - Key West, FL
10 179 reviews

Charming Outdoor Patio And Cozy Fireplace - Inviting Key West Retreat

house, Key West
This Key West townhome is situated in the Windsor Lane area, providing easy access to Mallory Square's Sunset Celebration, and is within 1 kilometre of the Key West Historic District, Historic Seaport, and the Southernmost Point Buoy.
Sleeping up to eight guests, this property offers three bedrooms, three bathrooms, a private heated swimming pool, a patio, a garden, a tennis court, and on-site parking, with complimentary high-speed WiFi and accommodation for one pet.
Charming Hideaway With Shared Pool - Inviting Location And Unique Amenities - Key West, FL
9.6 28 reviews

Charming Hideaway With Shared Pool - Inviting Location And Unique Amenities

house, Key West
This two-bedroom villa is situated within the Duval Square gated community on Duval Street, offering direct walking access to numerous restaurants, bars, and shops, and is approximately 1.2 kilometres from the nearest beach.
This family-friendly holiday home accommodates up to six guests across two levels, featuring an open-plan living area, a well-equipped kitchen, two bathrooms, a private balcony, and access to a communal swimming pool, with one allocated garage parking space and concierge services available.
Tropical Dreaming By Avantstay | 4 Blks To Beach! Private Pool! - Key West, FL
9.8 51 reviews

Tropical Dreaming By Avantstay | 4 Blks To Beach! Private Pool!

house, Key West
This Key West holiday villa is situated in Old Town, a short walk from Duval Street and 400 metres from the Atlantic Ocean.
This family-friendly property accommodates up to six guests with two en-suite bedrooms, a private swimming pool, and concierge services, and is a brief walk to the beach and Duval Street's amenities.

Best Key West, FL holiday rentals with a pool

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

Key West Paradise Condo W/ Pool, Hot Tub, Tennis - Key West, FL
No reviews

Key West Paradise Condo W/ Pool, Hot Tub, Tennis

apartment, Key West
This Key West condo is situated on the east side, approximately 1.6 kilometres from the beach and a short drive from the airport, offering convenient access to Old Town attractions without the immediate noise of the centre.
This newly remodelled two-bedroom, two-bathroom apartment accommodates up to six guests and features resort-style amenities including a heated lagoon-style pool, hot tub, tennis courts, a private balcony, a fully equipped kitchen, in-unit laundry, central air conditioning, complimentary WiFi, and covered parking.
Vangogh Studio | Updated, Old Town, Heated Pool - Key West, FL
8.8 56 reviews

Vangogh Studio | Updated, Old Town, Heated Pool

studio, Key West
Van Gogh Studio, a pet-friendly apartment in Key West's Old Town, Bahama Village neighbourhood, is located blocks from Duval Street and within walking distance of the Ernest Hemingway Home and Museum.
This self-catering studio sleeps two, features a kitchenette with microwave, mini-fridge and Keurig, cable TV, complimentary Wi-Fi, and access to an on-site heated pool, sundeck, and shared laundry facilities.
The Tahiti Suite | Updated Key West Condo W/ Pool! - Key West, FL
No reviews

The Tahiti Suite | Updated Key West Condo W/ Pool!

apartment, Key West
This Key West flat, located within the Sunrise Suites development, is situated a mere 500 metres from Smathers Beach and offers convenient access to Duval Street and Key West International Airport.
This two-bedroom, two-bathroom condominium accommodates up to six guests and features air conditioning, Wi-Fi, a fully equipped kitchen, a private balcony, a heated communal swimming pool, and a hot tub, with pets welcome.
Sunrise Suites Resort, Key West Fl U #408 2bdr2bth - Key West, FL
9.5 242 reviews

Sunrise Suites Resort, Key West Fl U #408 2bdr2bth

apartment, Key West
This apartment is located close to the salt ponds bird sanctuary, just a short distance from Smathers Beach and a couple of miles from Higgs Beach, offering a peaceful setting with easy access to some of Key West's most popular beaches. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The two-bedroom, two-bathroom apartment can accommodate up to six guests, providing ample space for families or groups of friends. It offers a range of amenities, including a swimming pool, Jacuzzi, garden, fitness centre, and a private balcony with panoramic views, ensuring 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?

    Key West is bursting with things to see and do, but you shouldn't miss the iconic Southernmost Point buoy, the Ernest Hemingway Home and Museum, and a sunset at Mallory Square.
  • What are the best Airbnb and vacation rentals in Key West, FL?

    Leaward Isle Island Retreat, At Mine | Lovely Suite Steps From Duval Street and Ambrosia ~ Adults Only - Poolside King Room In Azul Mansion 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 plenty of historic architecture, shops, and restaurants. For a quieter stay, consider the more residential areas of New Town or the Truman Annex.
  • 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 great place to see local marine life, while the Butterfly Conservatory is a colourful and educational experience. The Key West Historic Seaport is also a popular choice, with boat tours and interactive exhibits.
  • 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?

    Peak season in Key West runs from December to April, so booking your vacation rental well in advance is essential. If you're looking for better deals, consider travelling during the shoulder seasons of 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 annual Fantasy Fest in October is a wild and colourful celebration. If you're a music lover, the Key West Songwriters Festival in May is a must-see. The Key West Food and Wine Festival in January is another popular event.
  • 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 Location In Down Town Key West W/ 2 Pools - Huge Private Roof Deck & Parking.

  • 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?

    Strolling along Duval Street is free and a great way to soak up the atmosphere. You can also enjoy the free sunset celebrations at Mallory Square or explore the historic Fort Zachary Taylor State Park.
  • What are the best restaurants with local dishes in Key West, FL?

    For authentic Key West cuisine, try the Blue Heaven restaurant, known for its fresh seafood and laid-back atmosphere. The Hogfish Bar & Grill is another popular choice, serving up classic Key West fare.
  • Are there pet-friendly attractions in Key West, FL?

    Many restaurants and shops in Key West are pet-friendly. The Key West Butterfly and Nature Conservatory welcomes well-behaved dogs on a leash. You can also enjoy a walk with your furry friend along the beach at Higgs Beach.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals often offer more space and privacy than a hotel room, and can be a more cost-effective option for families or groups. Many rentals also have unique features like private patios or balconies.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular destination for watersports like fishing, sailing, and kayaking. The Key West Yacht Club offers a variety of sailing and boating activities. For those who prefer land-based activities, the Key West Golf Club offers a challenging 18-hole course.

Popular destinations

Best Key West, FL holiday rentals with a balcony

Prime Old Town Location W/ Pool, Walk To Duval Steet | Blue Heron By Avantstay - Key West, FL
10 1 review

Prime Old Town Location W/ Pool, Walk To Duval Steet | Blue Heron By Avantstay

apartment, Key West
This Key West condo is situated in the Historic District, within easy walking distance of the Ernest Hemingway Home and Museum and a local grocery store.
The 60 square metre (646 square feet) apartment sleeps four guests in two en-suite bedrooms and boasts a fully equipped kitchen, private BBQ, shared pool, hammock, and laundry facilities; AvantStay provides 24/7 support and optional extras.
Casa Atlantica One Bedroom - Key West, FL
No reviews

Casa Atlantica One Bedroom

apartment, Key West
Casa Atlantica, a Key West apartment, is situated 2km from Key West International Airport and within a few kilometres of beaches such as Rest Beach, Higgs Beach, and Smathers Beach, and attractions including the Ernest Hemingway Home and Museum and Duval Street.
This 86 square metre, one-bedroom flat sleeps three guests and features a fully equipped kitchen with dishwasher, a balcony, free Wi-Fi, and on-site parking, plus a tennis court for guest use.
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.
H2o Suites- Adults Only - Key West, FL
9.5 1610 reviews

H2o Suites- Adults Only

resort, Key West
H2O Suites is located in Key West, just a short walk from Duval Street, the heart of the city's nightlife, dining, and shopping scene. This adults-only hotel has received excellent ratings for its location, cleanliness, and overall experience.
The hotel offers a range of amenities and activities, including a rooftop pool with a sun terrace, a bar, and tropical courtyard views. Guests can also enjoy private pools in select rooms, a welcome drink upon arrival, and daily happy hour.

Best Key West, FL holiday rentals with parking

Happys Houseboat - Key West, FL
9.6 300 reviews

Happys Houseboat

barge, Key West
This houseboat is located in New Town, Key West, just a short drive from Florida Keys Beaches and within easy reach of Duval Street and Mallory Square. The property has received excellent ratings for location, cleanliness and user experience.
This floating accommodation has one bedroom and one bathroom, comfortably sleeping up to three guests. Enjoy al fresco dining on the terrace, relax in the garden, and make use of the kitchen facilities, which include a fridge and microwave.
Three Palms Condo #3 - Key West, FL
10 4 reviews

Three Palms Condo #3

apartment, Key West
This Key West condo, situated on Truman Avenue opposite Bayview Park, is a 23-minute walk (approximately 1.8km) from Duval Street.
The 623 sq ft (58 sq m) first-floor apartment offers one bedroom, one bathroom, sleeps two, and includes a modern kitchen, in-unit laundry, private patio, and air conditioning; nearby attractions include Bayview Park and its waterfront views.
Latitude Penthouse Key West - Key West, FL
9.3 243 reviews

Latitude Penthouse Key West

house, Key West
This apartment is located in Key West, just a short walk from Smathers Beach, Rest Beach, and Higgs Beach, offering easy access to the area's beautiful beaches. It has received excellent ratings for location, cleanliness, and user experience.
The two-bedroom, two-bathroom apartment spans 143 square meters and comfortably accommodates up to six guests. Guests can enjoy a range of amenities including a fully equipped kitchen, a private balcony with sea views, a swimming pool, a jacuzzi, a fitness centre, and a tennis court.
Chagalls Corner | Newly Remodeled! - Key West, FL
9.7 51 reviews

Chagalls Corner | Newly Remodeled!

apartment, Key West
Chagall's Corner, a newly remodelled self-catering apartment in Key West's Bahama Village, is located within a short walking distance of Duval Street, the Key West Lighthouse, and the Ernest Hemingway Home and Museum.
This pet-friendly Key West studio, sleeping two guests, features a queen-size bed, en-suite bathroom, kitchenette with mini-fridge and microwave, and access to a shared laundry and a heated swimming pool, grill, and sundeck.
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