Holiday 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

Best family friendly Key West, FL holiday rentals

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

Absolutely Paradise - Key West, FL
No reviews

Absolutely Paradise

house, Key West
This townhome offers a prime Old Town Key West location, just a short walk from Duval Street and providing island paradise tranquility with immediate access to the district.
This family-friendly property sleeps up to eight across three bedrooms, boasting a private heated swimming pool, a rare onsite parking space, and a fully equipped kitchen, perfect for enjoying year-round indoor/outdoor living.
Apartment ∙ 5 Bedrooms ∙ 16 Guests - Key West, FL
No reviews

Apartment ∙ 5 Bedrooms ∙ 16 Guests

apartment, Key West
This spacious Key West property is centrally located in downtown, within easy walking distance of many attractions.
The three-unit compound, sleeping up to 16 guests in five bedrooms and four bathrooms, boasts fully equipped kitchens, private outdoor spaces including a hot tub and BBQ, and two on-site washer/dryers.
Waterfront Condo + Pool Downtown + Boat Slip - Key West, FL
No reviews

Waterfront Condo + Pool Downtown + Boat Slip

apartment, Key West
This waterfront condominium in Key West's Pelican Landing offers direct access to the water, complete with a private boat slip, dockage, and fish cleaning station, situated approximately 1.6 kilometres from Duval Street, the Historic Seaport, and Hemingway House, and a short distance from Higgs and Smathers beaches.
This 111 square metre apartment accommodates up to eight guests with two bedrooms and two bathrooms, featuring a full kitchen, dining area, living room, private balcony, air conditioning, on-site parking, a heated swimming pool, and BBQ grills, and permits one dog up to 11.3 kilograms for a pet fee.
Conch Style Home In Oldtown With Private Pool And Dock! - Key West, FL
9.8 138 reviews

Conch Style Home In Oldtown With Private Pool And Dock!

apartment, Key West
This waterfront holiday rental, a Conch House with modern amenities, is situated in the Meadows district of Key West, offering easy access to Old Town attractions like the Ernest Hemingway Home and Museum and Southernmost Point, and is within 500 metres of Bayview Park.
This spacious 269 square metre holiday home sleeps up to 10 guests, featuring four bedrooms including two master suites with private balconies, a heated swimming pool, a private boat slip, two off-street parking spaces, and is ideal for those interested in water sports such as jet skiing and scuba diving, or cycling to Duval Street.

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

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.
Pool, Laundry, And Grilling Area - Key West, FL
10 1 review

Pool, Laundry, And Grilling Area

apartment, Key West
This Old Town Key West flat, situated two blocks from Duval Street, is close to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
The one-bedroom, one-bathroom apartment sleeps two guests and boasts a king-size bed, full kitchen with dishwasher, private deck with pool and waterfall, and a luxurious jacuzzi tub; nearby amenities include a convenience store and Cuban coffee shop.
Amelia Home By Avantstay - Key West, FL
9.6 60 reviews

Amelia Home By Avantstay

house, Key West
This charming house is located in the historic Old Town district of Key West, just 800 metres from the Ernest Hemingway Home and Museum and 800 metres from Duval Street. The property has received excellent ratings for location, cleanliness, and overall user experience.
The house offers two bedrooms, a living room, and a fully equipped kitchen, providing ample space for relaxation and privacy. Enjoy amenities such as a private swimming pool, a garden, free Wi-Fi, and free parking, making it a perfect base for exploring the vibrant city of Key West.
The Blue Flamingo Resort Key West - Key West, FL
No reviews

The Blue Flamingo Resort Key West

resort, Key West
The Blue Flamingo Resort Key West is located 5 kilometres from Key West's city centre, offering easy access to attractions such as the Key West Tropical Forest and Botanical Garden and the Lower Keys Medical Centre.
This resort provides a variety of amenities, including indoor and outdoor swimming pools, a fitness centre, a bar, a restaurant, and family-friendly facilities, with the Blue Flamingo Resort Key West offer including live entertainment and happy hour access.

Frequently asked questions about holiday rentals in Key West, FL

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

    You absolutely must visit the Southernmost Point of the Continental US, a landmark in Key West. If you're a history buff, the Ernest Hemingway Home and Museum is a must-see. And don't forget to take a sunset cruise to enjoy the stunning views of the Florida Keys.
  • 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, vibrant nightlife, and proximity to attractions. If you prefer a more relaxed vibe, consider the quieter neighbourhoods of New Town or the Sunset Key. But if you're looking for a more affordable option, you can find some great deals in the Stock Island neighbourhood.
  • 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 learn about the marine life of the Florida Keys. The Butterfly Conservatory is also a popular choice, with its beautiful butterflies and exotic plants. For a fun day out, visit the Key West Waterfront and enjoy the various water activities on offer, such as kayaking and paddle boarding.
  • 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?

    The best time to book a vacation rental in Key West is during the shoulder seasons, from April to May and September to October. You'll avoid the crowds and enjoy more affordable prices. But if you're looking for a more lively experience, the peak season from December to April is when the island comes alive with festivals and events.
  • 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 Hemingway Days festival in July is a must-see, with its literary readings, fishing tournaments, and a look-alike contest. The Fantasy Fest in October is a colourful and lively celebration with parades, parties, and costumes. If you're looking for something more relaxed, the Key West Sunset Celebration is a beautiful way to end the day.
  • 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 Downtown Retreat - A++ Location W\/ Private Heated Pool\/hot Tub.

  • 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 soak up the atmosphere. Visit the Key West Historic Seaport and explore the historic ships and boats. And don't forget to enjoy the free concerts and events held at the various parks and squares around the island.
  • What are the best restaurants with local dishes in Key West, FL?

    For fresh seafood, try The Stoned Crab or The Blue Heaven. For a taste of Key West's history, visit The Cuban Coffee Queen. And if you're looking for something a little more upscale, try The Restaurant at the Ocean Key Resort.
  • What are the best walking or cycling routes in Key West, FL?

    The Key West Greenway is a great option for a scenic walk or bike ride. It stretches for about 10 kilometres and passes by some of the island's most beautiful spots. You can also take a walk or bike ride along the historic Duval Street, stopping to enjoy the shops and restaurants along the way.
  • Are there pet-friendly attractions in Key West, FL?

    Yes, many attractions in Key West are pet-friendly, including the Key West Historic Seaport, the Key West Aquarium, and the Butterfly Conservatory. Many restaurants and shops also welcome well-behaved dogs. Just be sure to check with the individual establishment for their pet policy.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than a hotel room. They often come with amenities such as a kitchen, laundry facilities, and a private balcony or patio. You can also find vacation rentals in a variety of locations, from the heart of Old Town to the quieter neighbourhoods on the outskirts of the island.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a great place for water sports, with opportunities for swimming, kayaking, paddleboarding, and fishing. The Key West Waterfront is a popular spot for these activities. For golfers, there is the Key West Golf Club, which offers a challenging 18-hole course with stunning views of the ocean.

Popular destinations

Best Key West, FL holiday rentals with a balcony

Atlantic Paradise Found - Key West, FL
9.6 237 reviews

Atlantic Paradise Found

house, Key West
This apartment in Key West is conveniently located just a short walk from Smathers Beach and Rest Beach, offering easy access to the beautiful beaches and the relaxed atmosphere of this popular destination. It boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment is spacious, with 126 square metres of living space and comfortably accommodates up to 6 guests. It comes with a range of amenities including a fully equipped kitchen, a swimming pool, a jacuzzi, a tennis court and a fitness centre, providing everything you need for a relaxing and enjoyable holiday.
Leaward Isle Island Retreat - Key West, FL
9.8 2197 reviews

Leaward Isle Island Retreat

house, Key West
This Key West property is a short walk from Smathers Beach, a popular stretch of sand known for its beautiful sunsets and water activities, and just a short distance from Rest Beach. The property boasts excellent user, location and cleanliness ratings.
This spacious house offers a fully equipped kitchen, air conditioning, free Wi-Fi and a private balcony with sea views. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, sauna, spa, fitness centre, tennis court, and a bar.
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.
**Havana Especial @ Duval** Cottage & Hot Tub + Last Key White Glove Service... - Key West, FL
No reviews

**Havana Especial @ Duval** Cottage & Hot Tub + Last Key White Glove Service...

apartment, Key West
This two-bedroom cottage is located on Duval Street in Old Town Key West, a short walk from the Southernmost Point and Hemingway House, and includes a rare private parking space.
This property accommodates up to four guests with two en-suite bedrooms, a fully equipped kitchen, a rear courtyard with a barbecue, and a front porch, all complemented by Five-Star Guest Services from Last Key Realty.

Best Key West, FL holiday rentals with parking

Seaport Suite - Key West, FL
9.2 247 reviews

Seaport Suite

apartment, Key West
Commodore Compound, a centrally located Key West apartment, is less than 0.8 km from Simonton Street Beach, Mallory Dock, and the Key West Aquarium, and under 5 km from Key West International Airport.
This eight-bedroom property, perfect for large groups, boasts a fully equipped kitchen, in-unit laundry, private entrance, Jacuzzi, terrace, garden, parking, and free Wi-Fi; nearby attractions include the Key West Butterfly and Nature Conservatory.
Royal Palm Studio At Travelers Palm Inn Key West - Key West, FL
No reviews

Royal Palm Studio At Travelers Palm Inn Key West

studio, Key West
ROYAL PALM STUDIO is centrally located in Key West, Florida, 0.6km from the city centre and an 8-minute walk from South Beach, placing it within easy reach of Mallory Dock and the Key West Aquarium (1.9km).
This self-catering apartment sleeps two guests in one bedroom, boasts a kitchenette with fridge and microwave, a private terrace, and access to an on-site swimming pool and tennis court; free Wi-Fi and parking are also provided.
Waterfront Condo | Pool, Dock, Parking, Sleeps 8 - Key West, FL
9.7 342 reviews

Waterfront Condo | Pool, Dock, Parking, Sleeps 8

apartment, Key West
This waterfront apartment in historic Downtown Key West offers a private boat slip (max 35ft, 13ft beam) and is less than 1.6km from Duval Street, the Historic Seaport, and the Hemingway House.
The 121 square metre, two-bedroom, two-bathroom flat sleeps six, includes a full kitchen, washer/dryer, large balcony overlooking the harbour, and is close to a park with tennis courts; one dog up to 25lbs is permitted for a £160 fee.
El Corazon~ Renovated Home W/ Direct Access To Duval St. W/ Pool & Parking! - Key West, FL
9.8 123 reviews

El Corazon~ Renovated Home W/ Direct Access To Duval St. W/ Pool & Parking!

apartment, Key West
This Key West Historic District flat boasts private gated access to Duval Street and is under 1.6km from Simonton Beach, South Beach, Fort Zachary Taylor Beach, Higgs Beach, and Smathers Beach.
This 214 square metre, five-bedroom, four-bathroom dwelling sleeps ten guests, offering a heated plunge pool, fully equipped kitchen, concierge service, parking, and easy access to Key West's attractions.
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