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

Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
Key West, FL
26/10 – 28/10
1128 €/nighttotal: 2256 € (2 )

Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 4
apartment , Key West
The Rosé Retreat is a two-unit Key West property ideally located in the downtown area, within easy walking distance of many attractions.
This Key West holiday home offers three bedrooms (two king-size, one double), sleeping up to six guests, two bathrooms, a private pool, and two parking spaces; a fully equipped kitchen and in-unit laundry facilities are also provided.
Beach Paradise In The Keys! Location! Location! 2 Blocks To Duval St - Key West, FL
9.4 51 reviews
Key West, FL
27/06 – 28/06
1122 €/nightfor 1 night

Beach Paradise In The Keys! Location! Location! 2 Blocks To Duval St

2 7
apartment , Key West
This Truman Annex townhome, a newly renovated three-bedroom, three-bathroom property, is situated just 0.32 kilometres from Duval Street and the beach, with Fort Zachary Taylor State Park at the street's end.
This Key West holiday home offers 93 square metres of living space, sleeping up to eight guests and boasting a private courtyard, community pool access, and proximity to numerous watersports including snorkelling, fishing, and sunset cruises.
Key West Beachfront Luxury 2/2 Condo A212 - Key West, FL
10 168 reviews
Key West, FL
05/10 – 19/10
565 €/nighttotal: 7910 € (14 )

Key West Beachfront Luxury 2/2 Condo A212

2 1
apartment , Key West
This Key West beachfront condo offers direct access to Smathers Beach and is located within 5 kilometres of Duval Street and Mallory Square.
The 126-square-metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, private balcony, swimming pool, Jacuzzi, and fitness centre; enjoy tennis and the on-site sauna.
Panoramic 3br/3ba Condo - Direct Beach Ocean Front - Key West, FL
10 129 reviews
Key West, FL
17/10 – 24/10
966 €/nighttotal: 6762 € (7 )

Panoramic 3br/3ba Condo - Direct Beach Ocean Front

3 2
apartment , Key West
This three-bedroom apartment is conveniently located in Midtown Key West, just 3.2 kilometres from the airport and 3.2 kilometres from Mallory Square. It offers a peaceful retreat from the bustling city centre, with easy access to the island's attractions and activities. The apartment has received excellent reviews from previous guests.
The spacious apartment, spanning 204 square metres, comfortably accommodates up to eight guests. It boasts a range of amenities, including a swimming pool, jacuzzi, terrace, garden, sauna, parking, and a fully equipped kitchen. Guests can also enjoy stunning ocean views from the bedrooms, kitchen, and living room.

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

Key West On My Mind - Key West, FL
9.5 144 reviews
Key West, FL
30/12 – 10/01
981 €/nighttotal: 10791 € (11 )

Key West On My Mind

2 5
house , Key West
Key West On My Mind is a two-bedroom apartment situated near Smathers Beach, a 2.6 km walk from the Southernmost Point and 3.2 km from the Ernest Hemingway Home and Museum.
This 126 square metre property boasts a private balcony with sea views, two bathrooms, a fully equipped kitchen, free Wi-Fi, private parking, and access to a swimming pool, jacuzzi, sauna, fitness centre, and tennis court.
Sunrise Suites Resort, Key West Fl U #408 2bdr2bth - Key West, FL
9.4 231 reviews
Key West, FL
02/07 – 03/07
355 €/nightfor 1 night

Sunrise Suites Resort, Key West Fl U #408 2bdr2bth

2 5
apartment , Key West
This apartment is located close to the salt ponds bird sanctuary, just a short distance from Smathers Beach and a couple of miles from Higgs Beach, offering a peaceful setting with easy access to some of Key West's most popular beaches. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The two-bedroom, two-bathroom apartment can accommodate up to six guests, providing ample space for families or groups of friends. It offers a range of amenities, including a swimming pool, Jacuzzi, garden, fitness centre, and a private balcony with panoramic views, ensuring a relaxing and enjoyable stay.
The Margaret Suite - Key West, FL
10 1 review
Key West, FL
13/09 – 27/09
327 €/nighttotal: 4578 € (14 )

The Margaret Suite

1 2
apartment , Key West
The Margaret Suite, a studio flat in Key West, is located 2.57 kilometres from Mallory Dock, Mallory Square, and the Key West Aquarium, and 1.93 kilometres from the Southernmost Point, offering easy access to the Ernest Hemingway Home and Museum, Duval Street, and Rest Beach, with Key West International Airport a mere 1.93 kilometres away.
This 37-square-metre studio apartment accommodates up to five guests and features air conditioning, a kitchen with a fridge and microwave, complimentary on-site parking and WiFi, an outdoor swimming pool, a garden, and a private entrance for a comfortable stay.
Vangogh Studio | Updated, Old Town, Heated Pool - Key West, FL
8.6 48 reviews
Key West, FL
02/09 – 05/09
243 €/nighttotal: 729 € (3 )

Vangogh Studio | Updated, Old Town, Heated Pool

1 2
studio , Key West
Van Gogh Studio, a pet-friendly apartment in Key West's Old Town, Bahama Village neighbourhood, is located blocks from Duval Street and within walking distance of the Ernest Hemingway Home and Museum.
This self-catering studio sleeps two, features a kitchenette with microwave, mini-fridge and Keurig, cable TV, complimentary Wi-Fi, and access to an on-site heated pool, sundeck, and shared laundry facilities.

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.

Destinations nearby

Best Key West, FL holiday rentals with a balcony

Ocean Views! <Br>i Didnt Do It Too - Key West, FL
9.8 58 reviews
Key West, FL
20/06 – 27/06
457 €/nighttotal: 3199 € (7 )

Ocean Views! <Br>i Didnt Do It Too

2 2
houseboat , Stock Island
This barge is situated on Stock Island in Key West, close to Robbie's and the Key West Golf Club, offering a peaceful waterfront location. It has consistently received excellent ratings for user experience, location, and cleanliness.
The barge features two bedrooms, comfortably accommodating up to six guests. It is equipped with a full kitchen, a spacious rooftop deck with stunning views, and modern amenities like a washer and dryer, dishwasher, and air conditioning, as well as access to kayaking, paddleboarding, and boating.
Apartment ∙ 2 Bedrooms ∙ 9 Guests - Key West, FL
10 2 reviews
Key West, FL
24/07 – 28/07
931 €/nighttotal: 3724 € (4 )

Apartment ∙ 2 Bedrooms ∙ 9 Guests

2 7
apartment , Key West
This Key West apartment, ideally situated for exploring the island's attractions, offers convenient access to various transport options.
The two-bedroom, two-bathroom flat sleeps eight guests, features a private patio with shared pool access, and includes a fully equipped kitchen, washer/dryer, and smart TVs.
Apartment ∙ 2 Bedrooms ∙ 8 Guests - Key West, FL
Key West, FL
24/07 – 28/07
897 €/nighttotal: 3588 € (4 )

Apartment ∙ 2 Bedrooms ∙ 8 Guests

2 7
apartment , Key West
This two-bedroom Key West condo, sleeping up to ten guests, is ideally located on Duval Street, offering easy walking access to numerous attractions in the heart of the city.
The property features a king-size bed, two further king-size beds in a loft, two sofa beds, a fully equipped kitchen including a fridge, microwave, and stove, a private balcony overlooking Duval Street, and a private washer/dryer; parking is available nearby.
The Collins On Duval - Key West, FL
9.3 502 reviews
Key West, FL
02/07 – 03/07
1117 €/nightfor 1 night

The Collins On Duval

2 5
apartment , Key West
The Collins on Duval by Brightwild is located in the heart of Key West, just 1.6km from Simonton Street Beach and 1.1km from South Beach, offering easy access to Duval Street and its shops and restaurants. This apartment has excellent user, location and cleanliness ratings.
This two-bedroom flat provides ample space for families or groups of friends. The apartment offers modern amenities such as air conditioning, free Wi-Fi, a kitchen with a fridge, microwave, and dishwasher, as well as a patio for outdoor relaxation.

Best Key West, FL holiday rentals with parking

Poolside Paradise Tropical Village - Key West, FL
Key West, FL
21/12 – 18/01
419 €/nighttotal: 11732 € (28 )

Poolside Paradise Tropical Village

1 1
apartment , Key West
Poolside Paradise Tropical Village offers a Key West apartment, conveniently located 2.2km from the Ernest Hemingway Home and Museum and under 1.5km from Duval Street, close to South Beach and other attractions.
This 31-square-metre flat features one bedroom, one bathroom, sleeps three, and includes a private balcony, swimming pool access, tennis court, parking, Wi-Fi, and a fully equipped kitchen with a microwave and fridge.
Waterfront Dock Pool Penthouse Near Duval St - Key West, FL
9.8 498 reviews
Key West, FL
27/06 – 28/06
1731 €/nightfor 1 night

Waterfront Dock Pool Penthouse Near Duval St

4 7
apartment , Key West
This Key West penthouse condo, located in the historic downtown area less than 1.6km from Duval Street and close to attractions such as the Historic Seaport and Hemingway House, offers breathtaking waterfront views.
The 172 square metre property boasts four bedrooms, four bathrooms, sleeping up to sixteen guests, and includes a private boat slip (up to 35ft), a heated pool, and a full kitchen; on-site amenities also include a tiki bar & grill and bike rentals.
Caribbean Conch 5 Minutes To Smathers Beach & 10 Minute Bike Downtown - Value - Key West, FL
9.2 151 reviews
Key West, FL
22/08 – 29/08
313 €/nighttotal: 2191 € (7 )

Caribbean Conch 5 Minutes To Smathers Beach & 10 Minute Bike Downtown - Value

2 2
apartment , Key West
This two-bedroom apartment is situated in Beachside, Key West, just a 15-minute walk from the beautiful Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, and within 2 miles of Duval Street and Southernmost Point. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment is comfortably furnished and features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. Enjoy the on-site amenities, including a swimming pool, jacuzzi, terrace, garden, sauna, fitness centre, tennis court, and parking.
Completely Renovated Condo With Pool, Hot Tub, & Private Patio - Free Parking - Key West, FL
9.0 138 reviews
Key West, FL
20/06 – 27/06
495 €/nighttotal: 3465 € (7 )

Completely Renovated Condo With Pool, Hot Tub, & Private Patio - Free Parking

2 2
apartment , Key West
This Key West condominium is located by the sea, a short drive from Key West International Airport and near Southernmost Point and the Ernest Hemingway Home and Museum.
This 72 square metre flat offers 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests, featuring a renovated interior, a fully-equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, and parking, with nearby access to Smathers Beach and water activities.
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