Vacation Rentals in Key West, FL

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Key West, FL holiday rentals
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4265 Holiday rentals and Airbnb in Key West, FL

The Best Family-Focused Holiday Rentals in Key West, FL, United States

Browse family holiday rentals in Key West, FL, United States with space for everyone to relax.

Hyatt Centric Key West Resort & Spa - Key West, FL
8.8 2727 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.
Waterfront 3-bedroom Condo At Bayfront Suites & Marina- Cleaning Fee Included - Key West, FL
9.6 96 reviews

Waterfront 3-bedroom Condo At Bayfront Suites & Marina- Cleaning Fee Included

apartment, Key West
This apartment is located in the Meadows district of Key West, just 1.6 kilometres from Duval Street and the Ernest Hemingway Home and Museum. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and covers 107 square metres. It offers a range of amenities, including a swimming pool, tennis court, and free parking, making it a great choice for families or groups of friends.
Private Paradise With Heated Waterfall Pool - Key West, FL
10 4 reviews

Private Paradise With Heated Waterfall Pool

apartment, Key West
This Key West New Town property is conveniently located less than 1.3 km from Florida Keys Beaches and within 4.8 km of Duval Street and Mallory Square.
This two-bedroom, one-bathroom holiday home sleeps six, boasting a private pool, hot tub, barbecue, fully equipped kitchen, laundry facilities, free Wi-Fi, and a private fenced yard.
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.

Holiday Rentals with a Pool in Key West, FL, United States

Walk right out of your kitchen and jump into a crystal-clear swimming pool at island holiday rentals in Key West, FL, United States.

La Concha Key West, Autograph Collection - Key West, FL
8.8 705 reviews

La Concha Key West, Autograph Collection

resort, Key West
The Crowne Plaza Key West-La Concha hotel is situated on Duval Street in Old Town Key West, just a short walk from the Southernmost Point buoy and a few blocks from Mallory Square. This hotel has received very good ratings for its cleanliness and user experience, and its location is considered excellent.
The hotel offers a range of modern amenities including a swimming pool, a spa, a fitness centre, and a restaurant. Guests can enjoy a comfortable stay with access to a terrace or balcony, a garden, and free high-speed internet.
The Reach Key West, Curio Collection By Hilton - Key West, FL
8.4 1355 reviews

The Reach Key West, Curio Collection By Hilton

resort, Key West
The Reach Key West, Curio Collection by Hilton is located in Old Town, Key West, just 1.5 kilometres from Duval Street, a lively area with a wide selection of restaurants, shops, and nightlife. The resort has received very good ratings for both its location and overall experience, with good marks for cleanliness.
This hotel offers a range of rooms, including suites and studios, all with private balconies offering views of the ocean or the town. Guests can enjoy a private beach, a swimming pool, a spa, a fitness centre, and a variety of activities like scuba diving, snorkelling, and deep-sea fishing.
Southard Sunset ~ 2 Bedroom 1st Floor Unit In Truman Annex W/ Shared Pool! - Key West, FL
9.6 36 reviews

Southard Sunset ~ 2 Bedroom 1st Floor Unit In Truman Annex W/ Shared Pool!

apartment, Key West
This Old Town Key West apartment is located less than a kilometre from Duval Street and Fort Zachary Taylor Historic State Park, with Ernest Hemingway's Home and Museum within a 2.4km radius.
This 63 square metre flat offers two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, private patio, swimming pool, and concierge service.
Shipyard 297-condo In Truman Annex-2 Bedroom 2 Bath, Close To Duval W/ Pool - Key West, FL
8.6 17 reviews

Shipyard 297-condo In Truman Annex-2 Bedroom 2 Bath, Close To Duval W/ Pool

apartment, Key West
This two-bedroom condominium is located in Key West's Truman Annex district, offering a 500-metre walk to downtown shops and restaurants, and is close to the Southernmost Point and Ernest Hemingway Home and Museum.
This 60 square metre apartment, accommodating up to six guests, features a shared swimming pool, a private patio, in-unit laundry, and is equipped with a fridge, microwave, and dishwasher, with parking provided and water activities readily accessible nearby.

Frequently asked questions about holiday rentals in Key West, FL

  • What should a first-time visitor not miss in Key West, FL?

    You definitely want to visit the Southernmost Point of the Continental US, the Hemingway House, and take a sunset cruise. And don't forget to try a Key Lime Pie, a local favourite!
  • What are the best Airbnb and holiday 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 popular choice, with its historic architecture and proximity to Duval Street. If you prefer a quieter vibe, try the New Town area, which is known for its beautiful beaches and relaxed atmosphere.
  • 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 Butterfly and Nature Conservatory is always a hit with kids, and the Key West Aquarium is a great place to learn about local marine life. The Fort Zachary Taylor Historic State Park is a good option for a family picnic and exploring the fort.
  • What are the best holiday 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 a popular destination year-round, but prices tend to be highest during the peak season from December to April. If you're looking for a better deal, consider visiting during the shoulder seasons, from April 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 Fantasy Fest in October is a huge celebration with parades and costumes, while the Key West Songwriters Festival in May is a great event for music lovers. The Key West Food & Wine Festival in January is another popular choice.
  • What are the best rentals or Airbnbs with a jacuzzi in Key West, FL?

    The best holiday 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?

    Strolling along Duval Street, visiting the Key West Cemetery, and enjoying the free sunset at Mallory Square are all great ways to experience Key West without breaking the bank. You can also take a walk or bike ride around the island, enjoying the views and the fresh air.
  • What are the best restaurants with local dishes in Key West, FL?

    For authentic Key West cuisine, try the Blue Heaven, a historic restaurant with a charming atmosphere, or the Lazy Lobster, known for its fresh seafood. The Hogfish Bar & Grill is another favourite for its casual atmosphere and delicious dishes.
  • What are the best walking or cycling routes in Key West, FL?

    The scenic route along the waterfront, from the Southernmost Point to Mallory Square, is a popular choice for walking and cycling. The Key West Historic District is also a great place to explore on foot, with its charming streets and historic buildings.
  • Are there pet-friendly attractions in Key West, FL?

    Many restaurants and bars in Key West are pet-friendly, and you can often find dog-friendly beaches. The Key West Butterfly and Nature Conservatory is also pet-friendly, allowing well-behaved dogs on a leash.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals often offer more space and privacy than hotels, and they can be a more affordable option, especially for families or groups. You can also find rentals in different locations, giving you the opportunity to experience different parts of the island.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a great place for watersports, with opportunities for sailing, fishing, kayaking, and windsurfing. The Key West Yacht Club offers facilities for sailing and other water activities. There are also several golf courses on the island, including the Key West Golf Club.

Popular destinations

Holiday Rentals with a Balcony in Key West, FL, United States

Wake up to the soothing sight of the blue ocean right from your private rental balcony in Key West, FL, United States.

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.
Docked In Paradise - Key West, FL
9.0 7 reviews

Docked In Paradise

houseboat, Stock Island
This Stock Island houseboat, situated at The Perry Hotel & Marina in Key West, offers convenient access to downtown Key West via a free shuttle service and is within a reasonable distance of attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point.
The one-bedroom, one-bathroom floating home sleeps four guests and includes air conditioning, a relaxing deck, and access to hotel amenities such as pools, restaurants, and a fitness centre.
Top Floor Amazing View Toms Chicken Coop Awaits Your Next Stay. Best Value - Key West, FL
9.8 164 reviews

Top Floor Amazing View Toms Chicken Coop Awaits Your Next Stay. Best Value

apartment, Key West
This Key West Midtown condo is situated within 1.6km of Florida Keys Beaches, Duval Street, and South Beach, with Mallory Square, famed for its sunset celebrations, a 3.4km drive away.
This 139 square metre apartment sleeps six guests, boasting three bedrooms, two bathrooms, a fully equipped kitchen, and a private terrace plus access to a swimming pool, Jacuzzi, sauna, fitness centre and tennis court.
Ocean Vista 403e La Brisa - Key West, FL
10 1 review

Ocean Vista 403e La Brisa

apartment, Key West
Ocean Vista 403E La Brisa is a beachfront apartment in Key West, Florida, situated 0.7km from Smathers Beach and 3km from the Southernmost Point.
This 108 square metre, two-bedroom, two-bathroom flat sleeps seven guests and boasts a fully equipped kitchen, air conditioning, a terrace, swimming pool, spa, tennis court, parking, and free Wi-Fi.

Best Key West, FL holiday rentals with parking

Casa Havana | Old Town Condo W/ Pool & Balcony - Key West, FL
9.5 8 reviews

Casa Havana | Old Town Condo W/ Pool & Balcony

house, Key West
This Old Town Key West condo is situated on the 1000 block of Duval Street, offering a 10-minute walk to downtown attractions and immediate access to dining within Duval Square, placing you within 1 kilometre of the Hemingway Home and beaches.
This 2-bedroom, 2-bathroom property accommodates up to 4 guests and features a fully equipped kitchen, in-unit washer and dryer, central air conditioning, free WiFi, a private deck, balcony, garage parking, and access to a rooftop swimming pool.
45 M² House ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
9.2 18 reviews

45 M² House ∙ 1 Bedroom ∙ 4 Guests

house, Key West
This Old Town Key West cottage, in The Colony Suites gated community, is situated two blocks from Duval Street.
The 45-square-metre property offers a loft-style bedroom, a bathroom, a sleeper sofa accommodating four guests, a private backyard with a propane BBQ, and access to a shared pool and coin-operated laundry facilities; AvantStay services are also available.
Ambrosia At Azul Mansion Key West - Key West, FL
8.0 1 review

Ambrosia At Azul Mansion Key West

house, Key West
Ambrosia at Azul Mansion, a Key West apartment, is centrally located less than 0.6km from the city centre, a 12-minute walk from South Beach, and within 1.9km of Duval Street, the Ernest Hemingway Home and Museum, and Mallory Dock.
This self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes free Wi-Fi, on-site parking, a swimming pool, and a terrace; nearby attractions include the beaches and various Key West sights.
The Margaret Suite - Key West, FL
10 3 reviews

The Margaret Suite

apartment, Key West
This studio apartment, located in Key West's Historic District, offers proximity to Mallory Square, the Key West Historic Seaport, the Ernest Hemingway Home and Museum, and Fort Zachary Taylor State Park, all within a short walk.
This 46 square meter self-contained accommodation, ideal for up to three guests, features a queen bed and a sofa bed, a compact kitchenette with a fridge and microwave, air conditioning, and access to shared amenities including a swimming pool and on-site laundry, with first-come, first-serve off-street parking available.

Discover Luxury Holiday Rentals in Key West, FL, United States

Bask in absolute tropical privacy with upscale coastal design at luxury holiday rentals in Key West, FL, United States.

Pavilion Villa  A Key West Private Paradise 1 Block Off Duval W Pool - Key West, FL
8.8 48 reviews

Pavilion Villa A Key West Private Paradise 1 Block Off Duval W Pool

apartment, Key West

Downtown Holiday Rentals in Key West, FL, United States

Find holiday rentals in the heart of Key West, FL, United States close to shops and beaches.

Honeymoon Palm Suite Near Higgs Beach - Key West, FL
10 51 reviews

Honeymoon Palm Suite Near Higgs Beach

apartment, Key West
Hemingways Atlantic Retreat - Key West, FL
9.0 128 reviews

Hemingways Atlantic Retreat

house, Key West
Waterfront Dock Pool Condo Near Duval St Pet Ok - Key West, FL
9.8 320 reviews

Waterfront Dock Pool Condo Near Duval St Pet Ok

apartment, Key West
Sundial  Luxurious 2 Bedroom Ocean View Condominium- Quality At Its Best. - Key West, FL
9.6 32 reviews

Sundial Luxurious 2 Bedroom Ocean View Condominium- Quality At Its Best.

apartment, Key West

Seashore Holiday Rentals in Key West, FL, United States

Open your glass doors and step directly from your living room onto the warm sand at seashore holiday rentals in Key West, FL, United States.

Nautical Wheeler - Key West, FL
No reviews

Nautical Wheeler

house, Key West
Gated Oceanfront Condo At Smather's Beach - Key West, FL
9.2 150 reviews

Gated Oceanfront Condo At Smather's Beach

apartment, Key West
La Brisa - Ocean Views Across From Smathers Beach - Key West, FL
10 194 reviews

La Brisa - Ocean Views Across From Smathers Beach

apartment, Key West
Noah's Retreat - Private Home In Truman Annex - Key West, FL
10 6 reviews

Noah's Retreat - Private Home In Truman Annex

apartment, Key West

Holiday Rentals with a Hot Tub in Key West, FL, United States

Soak under a canopy of stars just steps from the ocean waves at holiday rentals with a hot tub in Key West, FL, United States.

Almost Heaven ~ Stunning 2 Bedroom, 2 Bathroom Condo With Community Pool! - Key West, FL
10 2 reviews

Almost Heaven ~ Stunning 2 Bedroom, 2 Bathroom Condo With Community Pool!

apartment, Key West
Nautical Adventures In Paradise - Key West, FL
9.3 459 reviews

Nautical Adventures In Paradise

house, Key West
Sailor's Son - Key West, FL
No reviews

Sailor's Son

house, Key West
Affordable Key West Beach Front Condo - Key West, FL
9.6 439 reviews

Affordable Key West Beach Front Condo

apartment, Key West
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