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

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.
Cozy Studio With Shared Porch And Bbq Grill - Charming Hideaway - Key West, FL
No reviews

Cozy Studio With Shared Porch And Bbq Grill - Charming Hideaway

apartment, Key West
This private studio apartment, part of the Conch Republic Cottages group rental property, is situated a short distance from Duval Street's entertainment district.
The studio accommodates two guests and features a kitchenette, air conditioning, Wi-Fi, and access to shared outdoor amenities including a garden and barbecue grill.
Apartment ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
10 3 reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Key West
This one-bedroom apartment is located in Key West, just a short distance from the famous Duval Street and its attractions.
The apartment features a king-size bed, a double vanity en-suite bathroom with a whirlpool tub, a fully equipped kitchen with stainless steel appliances, a private balcony, and a private washer and dryer.
Commodore's Cove - One Block From Duval St - Key West, FL
No reviews

Commodore's Cove - One Block From Duval St

apartment, Key West
This first-floor condo on Simonton Street offers a prime Key West location, just 100 metres from Duval Street and conveniently situated between Downtown and the Historic Seaport, providing easy access to Mallory Square and the Shipwreck and Mel Fisher Maritime Museums.
This pet-friendly apartment accommodates up to 12 guests across four bedrooms, each with an en suite bathroom and flat-screen TV, and features a fully equipped kitchen, complimentary WiFi, air conditioning, and one private parking space for compact vehicles.

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

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.
Waterfront Dock Pool Penthouse Near Duval St - Key West, FL
9.8 529 reviews

Waterfront Dock Pool Penthouse Near Duval St

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.
Hidden Oasis 3 Blocks From Duval - Key West, FL
9.6 102 reviews

Hidden Oasis 3 Blocks From Duval

cottage, Key West
This charming cottage is situated just a short walk from Duval Street, Key West Cemetery, and the waterfront, offering easy access to the island's vibrant attractions and the beautiful ocean. It has received excellent reviews from previous guests, highlighting its convenient location and comfortable amenities.
The cottage spans 47 square meters and comfortably accommodates up to four guests in one bedroom and one bathroom. It features a private terrace, shared pool access, a barbecue area, a fully equipped kitchen, laundry facilities, and parking, ensuring a relaxing and enjoyable stay.
Sky Loft In Key West - Key West, FL
No reviews

Sky Loft In Key West

house, Key West
Holiday rental listing. This accommodation is located in Key West.
Services and facilities include an iron, a washing machine and a terrace. This house is ideal for families.

Frequently asked questions about holiday rentals in Key West, FL

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

    You absolutely must visit the Southernmost Point of the Continental US, a landmark in Key West. If you're a history buff, the Ernest Hemingway Home and Museum is a must-see. And don't forget to take a sunset cruise to enjoy the stunning views of the Florida Keys.
  • 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, vibrant nightlife, and proximity to attractions. If you prefer a more relaxed vibe, consider the quieter neighbourhoods of New Town or the Sunset Key. But if you're looking for a more affordable option, you can find some great deals in the Stock Island neighbourhood.
  • 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 great place to learn about the marine life of the Florida Keys. The Butterfly Conservatory is also a popular choice, with its beautiful butterflies and exotic plants. For a fun day out, visit the Key West Waterfront and enjoy the various water activities on offer, such as kayaking and paddle boarding.
  • 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?

    The best time to book a vacation rental in Key West is during the shoulder seasons, from April to May and September to October. You'll avoid the crowds and enjoy more affordable prices. But if you're looking for a more lively experience, the peak season from December to April is when the island comes alive with festivals and events.
  • 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 Key West Hemingway Days festival in July is a must-see, with its literary readings, fishing tournaments, and a look-alike contest. The Fantasy Fest in October is a colourful and lively celebration with parades, parties, and costumes. If you're looking for something more relaxed, the Key West Sunset Celebration is a beautiful way to end the day.
  • What are the best rentals or Airbnbs with a jacuzzi in Key West, FL?

    The best holiday 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 Duval Street and soak up the atmosphere. Visit the Key West Historic Seaport and explore the historic ships and boats. And don't forget to enjoy the free concerts and events held at the various parks and squares around the island.
  • What are the best restaurants with local dishes in Key West, FL?

    For fresh seafood, try The Stoned Crab or The Blue Heaven. For a taste of Key West's history, visit The Cuban Coffee Queen. And if you're looking for something a little more upscale, try The Restaurant at the Ocean Key Resort.
  • What are the best walking or cycling routes in Key West, FL?

    The Key West Greenway is a great option for a scenic walk or bike ride. It stretches for about 10 kilometres and passes by some of the island's most beautiful spots. You can also take a walk or bike ride along the historic Duval Street, stopping to enjoy the shops and restaurants along the way.
  • Are there pet-friendly attractions in Key West, FL?

    Yes, many attractions in Key West are pet-friendly, including the Key West Historic Seaport, the Key West Aquarium, and the Butterfly Conservatory. Many restaurants and shops also welcome well-behaved dogs. Just be sure to check with the individual establishment for their pet policy.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than a hotel room. They often come with amenities such as a kitchen, laundry facilities, and a private balcony or patio. You can also find vacation rentals in a variety of locations, from the heart of Old Town to the quieter neighbourhoods on the outskirts of the island.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a great place for water sports, with opportunities for swimming, kayaking, paddleboarding, and fishing. The Key West Waterfront is a popular spot for these activities. For golfers, there is the Key West Golf Club, which offers a challenging 18-hole course with stunning views of the ocean.

Popular destinations

Best Key West, FL holiday rentals with a balcony

Waterfront Dock Pool Key West Near Duval - Key West, FL
9.7 268 reviews

Waterfront Dock Pool Key West Near Duval

apartment, Key West
This waterfront Key West condo, situated in the historic Downtown district, is conveniently located approximately 1.6 kilometres from Duval Street, the Historic Seaport, and the Hemingway House.
The 112 square metre apartment features two bedrooms (king and two queen-size beds), two bathrooms, a full kitchen, and a large balcony with direct pool and dock access; it sleeps six guests and includes a private boat slip (up to 12 metres).
Apartment ∙ 6 Bedrooms ∙ 12 Guests - Key West, FL
No reviews

Apartment ∙ 6 Bedrooms ∙ 12 Guests

apartment, Key West
This six-bedroom Key West house, situated in the downtown area, offers easy walking access to numerous attractions.
Sleeping up to twelve guests, the property boasts a fully equipped kitchen with stainless steel appliances, a terrace, garden, parking for two vehicles, and an electric vehicle charger; six bathrooms and plush bedding complete this comfortable family-friendly dwelling.
Henry's Penthouse On The Ocean In Key West  - Weekly / Nightly Rentals - Key West, FL
9.6 100 reviews

Henry's Penthouse On The Ocean In Key West - Weekly / Nightly Rentals

apartment, Key West
This beachfront Key West condo is located less than 5 kilometres from Duval Street, Mallory Square, and Florida Keys Beaches, and within a 15-minute drive of Clarence S. Higgs Memorial Beach Park and the Key West AIDS Memorial.
This 125 square metre apartment offers two bedrooms, two bathrooms, sleeps five guests, and boasts a private balcony, swimming pool, Jacuzzi, and free Wi-Fi, plus access to a fitness centre, tennis court, and sauna.
Newly Furnished Suite With Pool, Hot Tub, Tennis, Balcony, Parking - Dog Ok - Key West, FL
8.6 124 reviews

Newly Furnished Suite With Pool, Hot Tub, Tennis, Balcony, Parking - Dog Ok

apartment, Key West
This two-bedroom flat, located in the Sunrise Suites resort community on Key West's eastern side, offers an oceanfront setting with easy access to Smathers Beach and Ernest Hemingway's former home, approximately 1.6 kilometres away.
Boasting 72 square meters of living space, this accommodation accommodates up to six guests and features a private balcony, air conditioning, a swimming pool, jacuzzi, and allows one dog, with convenient private parking available.

Best Key West, FL holiday rentals with parking

Cloud Suite On Duval - Key West, FL
9.7 369 reviews

Cloud Suite On Duval

apartment, Key West
Sky Suites Retreat, a centrally located Key West apartment, is a short walk (less than 1km) from the Ernest Hemingway Home and Museum, South Beach, and Duval Street.
This four-bedroom dwelling offers guests a fully equipped kitchen, private patio, in-unit laundry, free Wi-Fi, and parking, ideal for families or groups.
Hyatt Sunset Harbour Resort-prime Location On Key West!! - Key West, FL
8.6 589 reviews

Hyatt Sunset Harbour Resort-prime Location On Key West!!

resort, Key West
The Hyatt Residence Club Key West, Sunset Harbor is situated in Key West, a short walk from Mallory Square and the Key West Aquarium, making it a convenient base for exploring this lively island. The hotel is rated 4 stars and has received very good user reviews for its location, cleanliness, and overall experience.
This resort offers a comfortable and modern setting for your stay. Amenities include a swimming pool, a Jacuzzi, a terrace, a garden, a sauna, a spa, a fitness centre, and parking.
Gated Parking, Heated Pool  - Villa Positano - Key West, FL
9.2 57 reviews

Gated Parking, Heated Pool - Villa Positano

apartment, Key West
This Duval Square condo, situated at the junction of Truman Avenue and Duval Street in Key West, offers a prime location less than a kilometre from the town's centre and its attractions.
This two-bedroom, two-bathroom apartment sleeps six, boasting a rooftop pool, private hot tub, open-plan kitchen, and in-unit laundry facilities, all within easy walking distance of restaurants and bars on Duval Street.
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.
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