Holiday Rentals in Key West, FL

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Key West, FL holiday rentals
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3183 Holiday rentals and Airbnb in Key West, FL

Best family friendly Key West, FL holiday rentals

Among the 3183 accommodations in Key West, FL, here are the 4 best family friendly rentals

Mar Y Sol Luxurious Oceanfront  Key West Breathtaking Atlantic Sunrise Views - Key West, FL
9.3 247 reviews

Mar Y Sol Luxurious Oceanfront Key West Breathtaking Atlantic Sunrise Views

apartment, Key West
This beachfront apartment is located just 1.5 kilometres from Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, offering a peaceful retreat from the bustling Duval Street and Mallory Square, which are both within 5 kilometres. This property has received excellent ratings for user experience, location, and cleanliness.
The apartment has three bedrooms, spanning 186 square metres, and can accommodate up to eight guests. Enjoy a range of amenities, including a swimming pool, Jacuzzi, sauna, fitness centre, tennis court, and a private balcony with stunning ocean views.
The Perry Hotel & Marina Key West - Key West, FL
9.2 2442 reviews

The Perry Hotel & Marina Key West

resort, Stock Island
The Perry Hotel & Marina Key West is located on Stock Island, just 8km from Key West's Old Town and 5km from Key West International Airport. It has excellent user ratings, with particularly high marks for cleanliness and location.
The hotel has a waterfront setting with two pools and direct marina access. Guests can enjoy a range of amenities, including restaurants, a spa, a fitness centre, tennis courts, and complimentary shuttle service to Old Town.
121 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.5 26 reviews

121 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
This Old Town Key West property is a short walk from Duval Street and 0.64km from the Atlantic Ocean.
This two-bedroom, two-bathroom house offers 130 square metres of living space, including a private pool, fully equipped kitchen, and accommodates up to six guests; AvantStay services are available.
Apartment ∙ 3 Bedrooms ∙ 8 Guests - Key West, FL
9.0 2 reviews

Apartment ∙ 3 Bedrooms ∙ 8 Guests

apartment, Key West
This three-bedroom apartment is situated in Beachside Key West, just a short distance from Duval Street and its attractions.
The apartment offers private parking with electric charging stations, a fully equipped kitchen, a spacious living area with a queen sleeper sofa, and a private balcony, comfortably accommodating up to eight guests.

Best Key West, FL holiday rentals with a pool

Among the 3183 accommodations in Key West, FL, here are the 4 best rentals with a pool

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.
Sea Esta Suite | Located On Iconic Duval W/ Pool - Key West, FL
10 5 reviews

Sea Esta Suite | Located On Iconic Duval W/ Pool

house, Key West
Sea Esta Suite, a two-storey townhouse on Duval Street in Key West, is situated on the 1000 block, a short walk (less than 0.8km) from the Southernmost Point buoy.
This Key West holiday home offers two king bedrooms each with an en-suite bathroom, plus a queen-size sofa bed, accommodating up to six guests; amenities include a private garage, a shared rooftop pool, a newly renovated kitchen with modern appliances, and a private washer/dryer.
Anchor Drop Modern Elegance Upgrades Throughout Views Of Atlantic Ocean - Key West, FL
9.7 311 reviews

Anchor Drop Modern Elegance Upgrades Throughout Views Of Atlantic Ocean

apartment, Key West
This two-bedroom apartment in Beachside, Key West is just a 15-minute walk from the Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, and within a short drive of Duval Street and Mallory Square. The property has received excellent ratings for location, cleanliness and user experience.
The 126 square metre apartment comfortably sleeps six guests and features a fully equipped kitchen, a terrace, a garden, a swimming pool, a Jacuzzi, a sauna, a fitness centre and a tennis court. Guests will also enjoy access to parking, air conditioning and internet.
Casa Serendipity At Old Town - Key West, FL
10 50 reviews

Casa Serendipity At Old Town

house, Key West
This charming Key West cottage is situated in Old Town, just a short walk from Duval Street, the Historic Seaport, and a selection of restaurants and bars. The cottage has received excellent ratings for location, cleanliness, and overall user experience.
The three-bedroom cottage comfortably sleeps six guests and features a fully-equipped kitchen, a private pool, and a spacious outdoor living area with a propane grill. Guests can enjoy the Key West sunshine by relaxing on the porch or by the pool, or explore the surrounding area on foot.

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

The Flight Deck - 3 Bedroom / 3 Bathroom With Shared Pool & Fitness Center! - Key West, FL
9.4 17 reviews

The Flight Deck - 3 Bedroom / 3 Bathroom With Shared Pool & Fitness Center!

apartment, Key West
This three-bedroom townhouse is situated in the Coral Hammock Community on Stock Island, just 6.4 kilometres from the centre of Key West.
The property offers a private escape with a garden, a swimming pool, and a terrace, perfect for families or groups of up to six guests.
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.
Direct Ocean View From Your Condo-no Contact Check-in - Key West, FL
9.4 178 reviews

Direct Ocean View From Your Condo-no Contact Check-in

apartment, Key West
This Key West condo is ideally situated just steps from Smathers Beach and within 4.8 kilometres of Duval Street and Mallory Square.
The 109-square-metre apartment features two bedrooms, two bathrooms, sleeps six guests, and boasts a private balcony, swimming pool, Jacuzzi, tennis court, and parking; barbecue grills are available for guest use.
The Rigby House - Pool, One Block From Duval St - Key West, FL
10 15 reviews

The Rigby House - Pool, One Block From Duval St

apartment, Key West
This Key West Historic District property is situated a short walk from Papa's Pilar Rum Distillery and Duval Street, and within 0.9 km of Mallory Square and the Ernest Hemingway Home and Museum.
This six-bedroom, seven-bathroom house offers 232 square metres of living space, accommodating up to 12 guests and boasting a private pool, fully equipped kitchen, and balcony; nearby attractions include beaches and the Florida Keys.

Best Key West, FL holiday rentals with parking

Breezy Retreat - Key West, FL
9.0 1 review

Breezy Retreat

house, Key West
Breezy Retreat, a Key West house, is centrally located, less than 0.8km from South Beach, Higgs Beach, and the Ernest Hemingway Home and Museum.
This 145 square metre property sleeps seven guests across two bedrooms and two bathrooms, boasting a private pool, terrace, free Wi-Fi, and parking – a rare find in Key West – plus access to a fitness centre and tennis court.
Spectacular Ocean View Amazing Quality- Massage Ch - Key West, FL
10 57 reviews

Spectacular Ocean View Amazing Quality- Massage Ch

apartment, Key West
This luxurious Key West penthouse, situated in the 1800 Atlantic Complex near Duval Street, offers breathtaking direct ocean views and is conveniently located for exploring the island's attractions.
The two-bedroom, two-bathroom apartment sleeps six, boasting a king and twin beds, a queen sofa bed, a gourmet kitchen, 80-inch smart TV with Sonos sound, a zero-gravity massage chair and access to extensive complex amenities including an Olympic-size swimming pool, Jacuzzi, and tennis courts.
Key West's Best - Key West, FL
9.4 6 reviews

Key West's Best

house, Key West
This Key West holiday home is ideally located near Smathers, Rest, and Higgs Beaches, approximately 2.6 km from the Southernmost Point and 3.2 km from the Ernest Hemingway Home and Museum, with Key West International Airport just 1.9 km away.
The two-bedroom, two-bathroom property sleeps up to 11 guests and boasts a private balcony with ocean views, a swimming pool, Jacuzzi, sauna, fitness centre, tennis court, and well-equipped kitchen; nearby activities include exploring the beaches and visiting local attractions.
~Poinciana Garden~ Casual 1st Floor Duplex 2 Blocks From Duval Street! - Key West, FL
9.6 388 reviews

~Poinciana Garden~ Casual 1st Floor Duplex 2 Blocks From Duval Street!

apartment, Key West
This Key West Historic District property is a short 0.8km walk from Key West Cemetery and Duval Street, with the Ernest Hemingway Home and Museum and Florida Keys beaches within a 2.4km radius.
The self-catering house boasts a fully equipped kitchen, private garden with barbecue, jacuzzi, and balcony; free Wi-Fi and parking are also included.
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