Holiday Rentals in Key West, FL

4265 available vacation rental offers

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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

The Mesa House - One Block From Duval St - Key West, FL
No reviews

The Mesa House - One Block From Duval St

house, Key West
This residence, located in Old Town Key West, offers oceanfront proximity with easy beach access and is situated just 50 metres from Duval Street and a short walk to the Key West Seaport.
This family-friendly dwelling sleeps up to 10 guests, featuring three bedrooms, two bathrooms, two full kitchens, air conditioning, free WiFi, and a private washer and dryer.
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.
42 M² House ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
9.4 26 reviews

42 M² House ∙ 1 Bedroom ∙ 4 Guests

house, Key West
This Old Town Key West apartment, situated in the Palm Gardens community within the Art District, is eight blocks from Duval Street and a short cycle from the Historic Seaport and Higgs Beach.
The 42-square-metre (452-square-foot) one-bedroom condo sleeps four, boasting a king-size bed, queen-size sofa bed, compact kitchen with dishwasher, a shared pool and garden, and AvantStay services including 24/7 support.
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.

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

Florida - Spacious Updated Waterfront Condo 2x2 Pool Dock - Key West, FL
9.0 2 reviews

Florida - Spacious Updated Waterfront Condo 2x2 Pool Dock

house, Key West
This Key West waterfront condo, a short walk from Rest Beach and 1.8km from South Beach, offers easy access to Higgs Beach, the Ernest Hemingway Home and Museum, and Duval Street.
The 121 square metre property features two bedrooms, two bathrooms, a fully equipped kitchen, and a private patio with sea views, accommodating up to 10 guests and including a swimming pool, elevator, free Wi-Fi, and parking.
Rose Petal Petite Suite - Near Duval Street - Key West, FL
9.3 69 reviews

Rose Petal Petite Suite - Near Duval Street

apartment, Key West
This Key West apartment boasts a central downtown location, offering easy walking access to Duval Street and Mallory Square.
The self-catering flat comprises a king-size bedroom, one bathroom, a fully equipped kitchen, private balconies, and access to a shared pool; it sleeps two guests and includes reserved parking.
The Caroline Suite - Key West, FL
No reviews

The Caroline Suite

house, Key West
The Caroline Suite, a Key West apartment, is conveniently located 1.8km from Higgs Beach, 1.9km from the Southernmost Point buoy, and 1.9km from Key West International Airport.
This one-bedroom, one-bathroom property offers 33 square metres of living space, sleeping up to seven guests and including a fully equipped kitchen, in-unit laundry, air conditioning, a swimming pool, and free Wi-Fi.
Sugar Palm Suite At Travelers Palm Inn Key West - Key West, FL
No reviews

Sugar Palm Suite At Travelers Palm Inn Key West

house, Key West
The Sugar Palm Suite offers a central Key West location, an 8-minute walk from South Beach and within 1.9km of the Key West Aquarium and Mallory Dock.
This self-catering apartment sleeps four, featuring a bedroom, living room, fully equipped kitchen with dishwasher, air conditioning, a private swimming pool, and free Wi-Fi; tennis is available on-site.

Frequently asked questions about holiday rentals in Key West, FL

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

    You absolutely have to visit the Southernmost Point of the Continental US, marking the very tip of Key West. A stroll down Duval Street is a must, with its vibrant atmosphere and shops. And no trip is complete without a sunset at Mallory Square, watching the street performers and enjoying the lively atmosphere.
  • 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, proximity to Duval Street, and easy access to the waterfront. For a quieter vibe, consider the New Town area, known for its charming cottages and proximity to the beach. If you want to be closer to the action, the Historic Seaport area is a good option with its lively atmosphere and proximity to the harbour.
  • 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 hit with kids of all ages, with its diverse marine life and interactive exhibits. The Butterfly Conservatory is a beautiful and peaceful place to spend a few hours, and the Key West Wildlife Center offers up-close encounters with rescued animals. For a fun day out, head to the Key West Shipwreck Treasure Museum, where you can learn about the history of shipwrecks and see real treasure.
  • 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, so it's best to book your vacation rental well in advance, especially during peak season, which runs from December to April. If you're looking for a more affordable trip, consider visiting during the shoulder seasons, from 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 with parades, parties, and costumes. The Key West Hemingway Days Festival in July celebrates the famous author with a look-alike contest and other events. There's also the Key West Songwriters Festival in May, featuring live music and performances.
  • 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 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 the waterfront and enjoy the views of the ocean and the historic buildings. Visit the Key West Cemetery, a unique and quirky attraction with interesting headstones. Explore the historic streets of Old Town and admire the architecture. Take a dip in the ocean at Smathers Beach, a popular spot for swimming and sunbathing.
  • What are the best restaurants with local dishes in Key West, FL?

    For a taste of Key West's unique cuisine, try the famous Key Lime Pie at the Kermit's Key West Key Lime Shop. For a casual and delicious meal, head to the Blue Heaven, a popular spot for its fresh seafood and laid-back atmosphere. For a more upscale dining experience, try the Latitudes Restaurant, known for its stunning views and innovative dishes.
  • What are the best walking or cycling routes in Key West, FL?

    The scenic route along the waterfront is a must-do, offering stunning views of the ocean and the historic buildings. For a more adventurous ride, try the Key West Bike Path, which winds its way through the city and out to the coast. For a leisurely stroll, explore the historic streets of Old Town, with its charming shops and restaurants.
  • Are there pet-friendly attractions in Key West, FL?

    Many restaurants and shops in Key West are pet-friendly, and you'll often see dogs enjoying the sunshine on patios and sidewalks. The Key West Aquarium welcomes well-behaved dogs on leashes, and the Key West Butterfly Conservatory also allows dogs in designated areas. Smathers Beach is a popular spot for dog walking and playing.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than a hotel room, and often come with amenities like kitchens and laundry facilities. Many rentals are located in desirable neighbourhoods, offering easy access to attractions and activities. You can often find vacation rentals at more affordable rates than hotels, especially for larger groups or longer stays.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular destination for watersports, with opportunities for swimming, sunbathing, kayaking, paddleboarding, and fishing. The Key West Tennis Club offers courts and lessons for all levels. For a more active experience, try the Key West Marathon, held every year in November.

Popular destinations

Best Key West, FL holiday rentals with a balcony

Duval Breeze By Avantstay - Key West, FL
9.5 2 reviews

Duval Breeze By Avantstay

house, Key West
This Duval Street area dwelling is centrally situated, a mere 6-minute stroll from South Beach and 18 minutes on foot from the Key West Aquarium.
This 113 square meter holiday home accommodates up to 10 guests, featuring 2 bedrooms, 1 bathroom, a fully equipped kitchen with a dishwasher, air conditioning, a shared swimming pool, and complimentary WiFi.
Free Boat Slip - Waterfront Condo - Key West Pool - Key West, FL
No reviews

Free Boat Slip - Waterfront Condo - Key West Pool

house, Key West
This waterfront condominium in Key West offers direct access to the water and a complimentary boat slip, situated 1.6 kilometres from Ernest Hemingway Home and Museum and 2 kilometres from Key West International Airport, with Rest Beach and Duval Street a 17-minute and 19-minute walk away respectively.
This two-bedroom, two-bathroom property spans 112 square metres, accommodates up to ten guests, and features a fully equipped kitchen, air conditioning, a private swimming pool, a balcony, a garden, and on-site parking.
Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking - Key West, FL
10 1 review

Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking

house, Key West
Holiday rental listing with an excellent rating of 100% based on 1 reviews. You will be located in Key West.
Facilities and services: a terrace, a fitness center and air conditioning.
The Grande Vista - Key West, FL
9.1 203 reviews

The Grande Vista

house, Key West
The Grande Vista apartment is located in Key West, just a short walk from Smathers Beach and Rest Beach, with Higgs Beach also within easy reach. The apartment has received very good user ratings, and excellent location and cleanliness ratings.
The apartment has two bedrooms and two bathrooms, and can accommodate up to six guests. It is well-equipped with amenities such as a kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, a garden, a sauna, a fitness centre, a tennis court, parking, and internet access.

Best Key West, FL holiday rentals with parking

Oceanview At 1800 Atlantic, Short Walk To Smathers Beach Wish Island Paradise - Key West, FL
9.6 33 reviews

Oceanview At 1800 Atlantic, Short Walk To Smathers Beach Wish Island Paradise

apartment, Key West
This Beachside, Key West condo is conveniently located near Florida Keys Beaches, offering easy access to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
The 122 square metre apartment features two bedrooms (king and twin beds), two bathrooms, a full kitchen, and a 12-metre private balcony with ocean views; it sleeps six and boasts access to an Olympic-sized pool, jacuzzi, tennis courts, and other amenities within the 1800 Atlantic complex.
Waterfront Escape With Boat Dock And Heated Pool - Charming Retreat - Key West, FL
No reviews

Waterfront Escape With Boat Dock And Heated Pool - Charming Retreat

apartment, Key West
This waterfront corner condominium in Key West's Pelican Landing community offers marina views and is situated approximately 1.6 kilometres from Duval Street, the Historic Seaport, and downtown attractions, with Higgs Beach and Smathers Beach within 2 kilometres.
This 125 square metre apartment sleeps up to eight guests and features a full kitchen, open living space, a private balcony with direct access to the heated community pool and docks, and is pet-friendly with a weight restriction for one dog.
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.
Seafarer's Refuge - Key West, FL
No reviews

Seafarer's Refuge

house, Key West
Seafarer's Refuge, a large villa in Key West, is located 1.5 kilometres from Rest Beach and within walking distance of Duval Street and the Ernest Hemingway Home and Museum.
This villa offers accommodation for 19 guests, featuring a private swimming pool, hot tub, sea-view balcony, and a well-equipped kitchen, alongside concierge services and free Wi-Fi.