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

161 M² House ∙ 3 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

161 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Key West
This family-friendly holiday home is situated in Midtown Key West, offering convenient access to local beaches, restaurants, and shops, with Old Town attractions such as Duval Street and the Southernmost Point a short drive or bike ride away.
This 161 square meter property accommodates up to six guests across three bedrooms and two bathrooms, featuring a private backyard with a fenced tropical setting, a swimming pool, outdoor dining for six, a grill, and in-home laundry facilities.
Pool View 3br Residence | Beachside Resort - Key West, FL
9.6 13 reviews

Pool View 3br Residence | Beachside Resort

apartment, Key West
This luxurious 3-bedroom condominium is located on a seven-acre resort in north Key West, offering Gulf of Mexico views and situated approximately 1.6 kilometres from Duval Street, with an on-site shuttle service available for convenient access to attractions.
This family-friendly apartment provides accommodation for up to eight guests and features a private balcony with resort pool views, a fully equipped kitchen with stainless-steel appliances, air conditioning, a swimming pool, a Jacuzzi, and a fitness centre.
Key West Oasis:charming Retreat - Key West, FL
9.8 8 reviews

Key West Oasis:charming Retreat

boat, Stock Island
This Key West houseboat is located in a marina a short distance (less than 1.6 km) from Duval Street, offering easy access to Key West's attractions.
The vessel sleeps four, featuring a queen bed, pull-out sofa, fully equipped kitchen with fridge, freezer and microwave, plus air conditioning, Wi-Fi, a swimming pool, jacuzzi, and private garden.
Tropical Oasis With Shared Pool And Outdoor Shower - Charming Escape - Key West, FL
9.8 46 reviews

Tropical Oasis With Shared Pool And Outdoor Shower - Charming Escape

house, Key West
This 1930s Conch holiday cottage, Toon Hall, is situated within a secure, high-end gated complex of six historic Old Key West rental properties, located merely 200 metres from Higgs Beach and within easy walking distance of the Key West Butterfly and Nature Museum, Southernmost Point, and West Martello Tower.
This three-bedroom, two-bathroom holiday home comfortably accommodates up to ten guests and features air conditioning, a modern kitchen, a private deck with alfresco dining, and access to shared amenities including a swimming pool and gas grill.

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

Signature King At Beachside Resort - Key West, FL
9.2 340 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.
The Cayo Coco | Key West Condo With Pool, Hot Tub! - Key West, FL
9.6 15 reviews

The Cayo Coco | Key West Condo With Pool, Hot Tub!

apartment, Key West
This two-bedroom, two-bathroom holiday flat in Key West's Sunrise Suites community offers a convenient base, situated approximately 1.6 kilometres from Smathers Beach and Higgs Beach, and a short distance from Duval Street and Key West International Airport.
This 74 square meter apartment accommodates up to six guests and features resort-style amenities including a heated communal pool and hot tub, a private balcony, on-site tennis courts, and in-unit laundry, with a pet-friendly policy for pets under 18 kilograms for an additional fee.
Signature King At Beachside Resort - Key West, FL
9.4 3 reviews

Signature King At Beachside Resort

apartment, Key West
This one-bedroom flat offers a luxury resort experience in north Key West, set on 2.8 hectares overlooking the Gulf of Mexico and a 10-minute drive from Duval Street, with convenient shuttle service to attractions like the Ernest Hemingway Home and Museum and Southernmost Point.
This 28-square-metre apartment accommodates two guests and includes air conditioning, Wi-Fi, a swimming pool, and a hot tub, with on-site dining options and opportunities for bike and watercraft rentals.
Key West Sunrise Condo - Special Summer Rates! - Key West, FL
10 7 reviews

Key West Sunrise Condo - Special Summer Rates!

apartment, Key West
This two-bedroom Key West condo, part of the Sunrise Condo complex in the Seaside district, offers convenient access to attractions such as Smathers Beach and Fort Zachary Taylor Historic State Park, though precise distances aren't provided.
The 111-square-metre (1194 square feet) property sleeps six, boasting two bathrooms, a fully equipped kitchen including a dishwasher, a private terrace, a shared swimming pool and Jacuzzi, free Wi-Fi, parking, and pet-friendly accommodation (one dog up to 11 kg, fee applies); reduced rates are available until the end of September with a minimum two-night stay.

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

Kate's Krawl Off Duval ~ 1 Br/1 Ba Private Home/outdoor Deck/steps To Duval! - Key West, FL
9.6 94 reviews

Kate's Krawl Off Duval ~ 1 Br/1 Ba Private Home/outdoor Deck/steps To Duval!

apartment, Key West
This Key West Historic District apartment, a short walk from Duval Street and minutes from Key West's beaches, offers easy access to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 59-square-metre (635-square-foot) single-family home features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, private balcony, and on-site washer/dryer, plus concierge services for booking local activities.
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.
Cloud Suite On Duval - Key West, FL
9.7 369 reviews

Cloud Suite On Duval

apartment, Key West
Sky Suites Retreat, a centrally located Key West apartment, is a short walk (less than 1km) from the Ernest Hemingway Home and Museum, South Beach, and Duval Street.
This four-bedroom dwelling offers guests a fully equipped kitchen, private patio, in-unit laundry, free Wi-Fi, and parking, ideal for families or groups.
Paradise Found Cayo Hueso - Key West, FL
9.3 229 reviews

Paradise Found Cayo Hueso

house, Key West
Paradise Found Cayo Hueso, near Smathers Beach in Key West, Florida, offers convenient access to attractions such as the Southernmost Point (2.6 km) and Ernest Hemingway's Home (3.2 km).
This 126-square-metre, two-bedroom, two-bathroom apartment boasts a balcony with sea views, a fully equipped kitchen, private parking, complimentary Wi-Fi, and access to a swimming pool, Jacuzzi, sauna, fitness centre, and tennis court.

Best Key West, FL holiday rentals with parking

Utopia @ Tropical Village - Key West, FL
8.8 13 reviews

Utopia @ Tropical Village

apartment, Key West
This two-bedroom flat offers a gated location in Key West's historic Casa Marina Neighbourhood, placing it within a 1-kilometre stroll of Higgs Beach, the Southernmost Point, and the Key West Butterfly and Nature Museum.
Guests can enjoy a private balcony with treetop views, a shared swimming pool, and a modern kitchen, with accommodation for up to four people and pets permitted for an additional fee.
Turtle Nest Condo + Pool / 2nd Floor - Key West, FL
No reviews

Turtle Nest Condo + Pool / 2nd Floor

apartment, Key West
This one-bedroom flat in Key West's Historic District offers convenient access, being a 10-minute walk from Bayview Park and a 14-minute walk from Duval Street, with the Keys beaches a 4-minute drive away.
Guests can enjoy on-site parking, complimentary Wi-Fi, a swimming pool, and a private veranda, alongside essential amenities such as a laundry room, towels, and an ironing board, with Fort Zachary Taylor Historic State Park also nearby.
Key West Paradise - Key West, FL
9.7 7 reviews

Key West Paradise

apartment, Key West
This Old Town Key West duplex is centrally located, within easy walking distance of Key West's beaches, parks, and restaurants.
This fully renovated apartment sleeps families or groups, offering a microwave, air conditioning, parking, and Wi-Fi; pets are welcome.
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.
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