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

113 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.1 21 reviews

113 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
This Duval Square holiday home is situated on Duval Street in Key West's Old Town, a short walk from restaurants and bars, and within a couple of kilometres of Key West's beaches.
This two-storey property offers 113 square metres of living space, sleeping up to six guests in two en-suite bedrooms plus a sofa bed, and boasts a private pool, parking, and a well-equipped kitchen.
Breezy Retreat - 2bd/2bath - Windward Park - Pool - 5min Walk To Duval! - Key West, FL
10 26 reviews

Breezy Retreat - 2bd/2bath - Windward Park - Pool - 5min Walk To Duval!

apartment, Key West
This Key West Historic District property is a short walk from the Tennessee Williams Key West Exhibit and Duval Street, and within 1 km of the Ernest Hemingway Home and Museum and Florida Keys beaches.
This 145-square-metre house, sleeping four guests in two bedrooms and two bathrooms, boasts a private fenced yard, swimming pool, tennis court, and concierge service, offering a luxurious Key West getaway.
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.
Sunnyside Up - Shared Pool - Key West, FL
9.6 14 reviews

Sunnyside Up - Shared Pool

apartment, Key West
This Key West Historic District flat is a short walk from the Key West Firehouse Museum and Duval Street, and under 1.6 km from South Beach and the Southernmost Point.
This 108-square-metre self-catering apartment sleeps six, boasting two bedrooms, two bathrooms, a terrace, a garden, a swimming pool, and free internet access.

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

Waterfront Dock Pool Downtown Near Duval Pet - Key West, FL
9.4 11 reviews

Waterfront Dock Pool Downtown Near Duval Pet

apartment, Key West
This waterfront condominium in Key West's Meadows district offers direct harbour views and is situated less than 1 kilometre from Duval Street, the Historic Seaport, and Hemingway House.
This 111 square metre, two-bedroom, two-bathroom flat accommodates up to eight guests and features a private boat slip, a shared heated swimming pool, and on-site parking, with one dog up to 11 kg permitted.
Doubletree By Hilton Grand Key Resort - Key West, FL
8.3 1864 reviews

Doubletree By Hilton Grand Key Resort

resort, Key West
The Doubletree By Hilton Grand Key Resort offers a convenient base on the outskirts of historic Old Town Key West, just a 2-minute drive from Key West International Airport, Duval Street, and Old Town, with a complimentary shuttle service to these key areas and Smathers Beach.
This resort features a swimming pool with a poolside tiki bar, on-site dining at Palm Haven Restaurant and Sanctuary Lounge, and guest rooms equipped with flat-screen TVs and mini-refrigerators, with select rooms offering balconies and sofa beds, alongside bicycle rentals and a fitness centre.
Heated Pool, Epic Location - Honeybun Hideaway - Key West, FL
No reviews

Heated Pool, Epic Location - Honeybun Hideaway

apartment, Key West
This studio flat is located in Key West's central downtown district, 50 metres from Duval Street and steps from the historic seaport, offering easy access to Mallory Square, the Fury's tours departure point, and the Shipwreck and Mel Fisher Maritime Museums.
This pet-friendly apartment accommodates two guests and includes a fridge, microwave, and air conditioning, with access to a shared outdoor swimming pool and dining area, perfect for exploring the nearby bars and restaurants.
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.

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

Spectacular Ocean View Amazing Quality- Massage Chair. Newly Renovated - Key West, FL
10 37 reviews

Spectacular Ocean View Amazing Quality- Massage Chair. Newly Renovated

apartment, Key West
This Key West beachfront apartment is situated less than 3.2km from Duval Street and the Southernmost Point, and under 4.8km from the Ernest Hemingway Home and Museum and Mallory Square.
This 139 square metre property sleeps six, boasting three bedrooms, two bathrooms, a fully equipped kitchen, and access to a swimming pool, jacuzzi, sauna, fitness centre, and tennis court.
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.
Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
9.3 152 reviews

Sunrise 103-2br/2ba Condo Near Beaches With Pool, Parking, Balcony

apartment, Key West
This two-bedroom Sunrise Suites condo offers a convenient location in Key West, a short drive from the downtown area and close to Smathers Beach.
The apartment, sleeping up to four comfortably (with a sofa bed for children), boasts two bathrooms, a private balcony, in-unit laundry, and access to a shared pool and jacuzzi within the complex; guaranteed parking is also provided.
Ibis Bay Resort - Key West, FL
8.0 3815 reviews

Ibis Bay Resort

resort, Key West
Ibis Bay Beach Resort is a Key West hotel situated on the north side, offering a tranquil escape yet within 5km of attractions such as Duval Street, Mallory Square, and Regal Key West.
This family-friendly hotel boasts a private beach, an outdoor pool, and convenient access to a marina for water sports, plus on-site amenities including a restaurant, bar, and room service.

Best Key West, FL holiday rentals with parking

**Suite Sanctuary** Oceanfront Condo & Pool + Last Key White Glove Service... - Key West, FL
10 33 reviews

**Suite Sanctuary** Oceanfront Condo & Pool + Last Key White Glove Service...

apartment, Key West
This beachfront Key West condo is situated near Duval Street, Mallory Square, and Smathers Beach, all within a 4.8km radius.
The two-bedroom, two-bathroom apartment sleeps six, offering a fully equipped kitchen, private balcony, and access to a swimming pool, Jacuzzi, sauna, spa, fitness centre, and tennis court; free Wi-Fi is also included.
~Vista Fresco~ Oceanside Condominiums With Resort-style Amenities - Key West, FL
9.6 151 reviews

~Vista Fresco~ Oceanside Condominiums With Resort-style Amenities

apartment, Key West
This two-bedroom apartment is located on 1800 Atlantic in Key West, just east of Smathers Beach, the island's largest beach. The property has excellent user, location, and cleanliness ratings.
The apartment is 122 square metres and can accommodate up to six guests. It offers a range of amenities including a swimming pool, a jacuzzi, a sauna, a spa, a fitness centre, and a garden.
Sundial  Luxurious 2 Bedroom Ocean View Condominiu - Key West, FL
9.8 32 reviews

Sundial Luxurious 2 Bedroom Ocean View Condominiu

apartment, Key West
This luxurious Key West condominium, situated within the 1800 Atlantic Condominiums complex, offers direct Atlantic Ocean views and is a short 1.6km bike ride from Duval Street.
The two-bedroom, two-bathroom apartment sleeps six guests and boasts a spacious balcony, fully equipped kitchen with stainless steel appliances, access to a resort-style pool, spa, and tennis/racquetball courts, plus high-speed internet and smart TVs.
St Croix - Downtown 4x4 Waterfront Penthouse Pool Dock Pet - Key West, FL
9.2 10 reviews

St Croix - Downtown 4x4 Waterfront Penthouse Pool Dock Pet

house, Key West
This Key West penthouse, located 1.8km from the Ernest Hemingway Home and Museum and Duval Street, and 1.9km from Key West International Airport, offers stunning sea views and easy access to popular beaches like Rest Beach, South Beach, and Higgs Beach.
This 186 square metre property boasts four bedrooms, four bathrooms, a private dock, swimming pool, and parking, comfortably accommodating up to 19 guests and featuring a fully equipped kitchen.
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