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

Apartment ∙ 6 Bedrooms ∙ 16 Guests - Key West, FL
No reviews

Apartment ∙ 6 Bedrooms ∙ 16 Guests

apartment, Key West
Catchlight House, a six-bedroom Key West property situated in a gated community near Key Haven and Stock Island, offers convenient access to boat ramps and water activities.
This spacious Key West dwelling sleeps sixteen guests, boasting six en-suite king bedrooms, a private washer/dryer, and free gym access at FYT, alongside driveway parking for two cars and a boat trailer; pet-friendly (up to two, 18kg max, £15/night per pet).
Casa De Cuba A Beach House - Cuban Flair Steps From Duval - Key West, FL
10 111 reviews

Casa De Cuba A Beach House - Cuban Flair Steps From Duval

apartment, Key West
This Key West holiday home is ideally situated in Old Town, a short walk from Duval Street and the City Zoo Gallery, with the Ernest Hemingway Home and Museum and South Beach within 1.6km.
The three-bedroom property sleeps six, boasting a private pool, fenced garden, fully equipped kitchen including a dishwasher, and free Wi-Fi; gas grills are available for al fresco dining.
Valhalla - Southernmost Oasis - Key West, FL
No reviews

Valhalla - Southernmost Oasis

house, Key West
This Southernmost Oasis holiday let in Key West is situated a 4-minute walk from South Beach and 3.06 kilometres from Key West International Airport.
This 84 square metre holiday home offers accommodation for up to 7 guests with 2 bedrooms and 2 bathrooms, featuring a heated swimming pool, a fully equipped kitchen with a dishwasher and washing machine, air conditioning, and complimentary WiFi.
The Salty Sunshine Of Key West - Key West, FL
9.4 96 reviews

The Salty Sunshine Of Key West

boat, Key West
The Salty Sunshine is moored in a sheltered bay just a short distance from Key West's lively downtown area, offering a peaceful escape from the bustling city. This location provides easy access to the island's shops, restaurants, and bars, while still offering a sense of tranquility and privacy.
The vessel offers two bedrooms, each with a queen-sized bed, comfortably accommodating up to six guests. The Salty Sunshine is equipped with a kitchen featuring a fridge and microwave, a hot shower, and a sofa bed in the living room, ensuring a comfortable stay.

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

Pool, Laundry, And Grilling Area - Key West, FL
9.8 10 reviews

Pool, Laundry, And Grilling Area

apartment, Key West
This Old Town Key West apartment, situated in the historic Cuban district, is minutes from Duval Street and within walking distance of many attractions, including the second oldest saltwater tide pool in Key West.
This one-bedroom, one-bathroom self-catering unit sleeps two guests and features a private master suite with garden access, a Florida room with kitchenette and outdoor grill, a heated Jacuzzi tub, and shared access to a pool and garden; nearby amenities include a convenience store and Cuban coffee shop.
Kw Canalfront 3br: Htd Pool, Boat Tie-up, Pet Ok - Key West, FL
9.3 9 reviews

Kw Canalfront 3br: Htd Pool, Boat Tie-up, Pet Ok

apartment, Key West
This private Key West residence offers 66 feet of canal frontage with dockage, providing direct access to the Atlantic and Gulf, and is a short cycle of less than 1 kilometre to Key West's beaches, waterfront dining, Old Town, and Mallory Square.
This three-bedroom, one-and-a-half-bathroom holiday home accommodates up to six guests, featuring air conditioning, a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, a swimming pool, garden, parking, and high-speed Wi-Fi, with a boat ramp located just 100 metres away.
Oceanview At 1800 Atlantic, Short Walk To Smathers Beach Wish Island Paradise - Key West, FL
9.4 30 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.
Oceanfront Oasis - Key West, FL
8.7 3 reviews

Oceanfront Oasis

house, Key West
This Key West oceanfront property, situated in the La Brisa neighbourhood, is a short 1.9 km from the Southernmost Point and 2.3 km from the Ernest Hemingway Home.
This 111 square metre house boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private balcony, swimming pool, sauna, fitness centre, and tennis court; nearby Smathers Beach is an eight-minute walk away.

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

Two-bedroom, Two-bath Condo Close To The Ocean. Full Kitchen, Living R & Balcony - Key West, FL
9.2 47 reviews

Two-bedroom, Two-bath Condo Close To The Ocean. Full Kitchen, Living R & Balcony

apartment, Key West
This two-bedroom Key West apartment is located within a 3km radius of the Fort East Martello Museum and Gallery, Key West Art and Historical Society, and Key West Tropical Forest and Botanical Garden, with Smathers Beach and Lower Keys Medical Center within 5km.
The 74 square metre apartment features a fully equipped kitchen, a private balcony, and a swimming pool, comfortably accommodating up to six guests.
Tropical Getaway With Pool & Sundeck - 1 Block To Duval St, 2 Blocks To Beach - Key West, FL
9.2 95 reviews

Tropical Getaway With Pool & Sundeck - 1 Block To Duval St, 2 Blocks To Beach

apartment, Key West
This studio flat is located in Old Town Key West, 200 metres from the southernmost beach and 100 metres from Duval Street, with the Ernest Hemingway Home and Museum and the Key West Lighthouse within walking distance.
This 37 square metre studio accommodation accommodates up to four guests and features a kitchenette with a fridge and microwave, air conditioning, WiFi, a private outdoor seating area, and access to a shared courtyard with a swimming pool and bar.
**Suite Sanctuary @ The Beach** Oceanfront Condo & Pool + Last Key Services... - Key West, FL
10 31 reviews

**Suite Sanctuary @ The Beach** Oceanfront Condo & Pool + Last Key Services...

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.
Spacious Waterfront 4 Bedroom Home - Key West, FL
9.6 97 reviews

Spacious Waterfront 4 Bedroom Home

apartment, Key West
This four-bedroom house is located in Northside Resort, just three miles from Duval Street, Mallory Square, and The Unitarian Universalist Fellowship of Key West. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The 368 square metre house can accommodate up to eight guests, offering plenty of space for families or groups of friends. Amenities include a private pool, Jacuzzi, terrace, garden, and concierge services, along with a fully equipped kitchen, free Wi-Fi, and parking.

Best Key West, FL holiday rentals with parking

The Butterfly Nest | Newly Updated W/ Shared Pool - Key West, FL
9.8 45 reviews

The Butterfly Nest | Newly Updated W/ Shared Pool

apartment, Key West
Butterfly Nest, in the Sunrise Suites complex on Key West's south-east side, is situated 1.6km from the beach and a ten-minute drive from Duval Street.
This 74 square metre condo sleeps six, offering three bedrooms, two bathrooms, a fully equipped kitchen, private balcony, and shared access to a heated pool, hot tub, and tennis court; pet-friendly (up to two pets, 18kg maximum, £16/night/pet).
Casa Mar With Private Heated Pool & Dock Key West - Key West, FL
10 7 reviews

Casa Mar With Private Heated Pool & Dock Key West

house, Key West
This Key West waterfront property, situated on the Riviera Canal, offers direct Gulf and ocean access via a 50ft seawall and is ideally located for exploring the island.
The 213-square-metre (2300 sq ft) dwelling boasts a spacious layout with three bedrooms, two bathrooms, sleeping up to twelve guests, a private dock, and a dedicated game room featuring ping-pong, foosball, basketball, and board games.
Waterfront Dock Pool Condo Near Duval St Pet Ok - Key West, FL
9.8 320 reviews

Waterfront Dock Pool Condo Near Duval St Pet Ok

apartment, Key West
This waterfront Key West apartment, situated in the historic downtown area, is approximately 1.6km from Duval Street, the Historic Seaport, and the Hemingway House.
The 118 square metre property boasts two bedrooms (king and two queen-size beds), two bathrooms, accommodates six guests, and includes a private boat slip, heated pool access, and a balcony overlooking the harbour.
Just Chillin' Out On The Ocean: 1/2 Off Charters! - Key West, FL
9.6 49 reviews

Just Chillin' Out On The Ocean: 1/2 Off Charters!

boat, Key West
This luxury yacht is anchored off the coast of Key West, Florida, offering unparalleled access to the island's attractions.
The vessel boasts two queen-sized bedrooms, two bathrooms, and accommodates four guests, featuring a full kitchen, high-speed internet, and a covered patio; daily breakfast and a complimentary shuttle to Key West are included.
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