Holiday Rentals in Key West, FL

4265 available vacation rental offers

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Key West, FL holiday rentals
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Best Holiday rentals and Airbnb offers 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

Kingfish Keep | Lively Escape On Duval! Balcony! - Key West, FL
No reviews

Kingfish Keep | Lively Escape On Duval! Balcony!

apartment, Key West
This Pescado Penthouse apartment is located directly on Duval Street in Key West's historic district, a mere 300 meters from the beach and the Southernmost Point.
This family-friendly flat accommodates up to four guests, offering a kitchenette with a microwave, fridge, and stove, along with air conditioning and complimentary WiFi, and is suitable for group rentals as part of the larger Pescado Penthouse.
Shared Pool & Parking - The Cottage At James House - Key West, FL
No reviews

Shared Pool & Parking - The Cottage At James House

bungalow, Key West
This detached cottage offers a prime downtown Key West location, just a short walk from Duval Street and the Historic Seaport, placing you within 500 metres of attractions such as Fury Water Adventures and Mallory Square's Sunset Celebration. This pet-friendly accommodation, suitable for three guests, features a fully equipped kitchen, air conditioning, and access to a shared swimming pool at the Curry Mansion Inn, with a private parking spot provided.
Spacious Deck And Ample Pool - Charming Vacation Hideaway - Key West, FL
No reviews

Spacious Deck And Ample Pool - Charming Vacation Hideaway

house, Key West
This four-bedroom, three-and-a-half-bathroom detached house is located just 160 metres from Duval Street, offering convenient access to the Southernmost Point and Atlantic beaches.
This family-friendly property sleeps up to ten guests and features air conditioning, Wi-Fi, a kitchen equipped with a fridge, microwave oven, and dishwasher, a swimming pool, a terrace, a garden, a spa, a tennis court, and parking.
Tropical Landscaping And Private Deck - Charming Coastal Escape - Key West, FL
No reviews

Tropical Landscaping And Private Deck - Charming Coastal Escape

cottage, Key West
Hidden Treasure, a secluded conch cottage, is situated amongst tropical landscaping and a private pond, offering a tranquil retreat within walking distance of Key West's attractions, approximately 800 meters from Duval Street. This family-friendly holiday home accommodates up to six guests with two king bedrooms and a queen sofa bed, featuring a full kitchen, air conditioning, a swimming pool, spa, tennis court, and a private deck with covered dining.

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

Southern Palms - Key West, FL
9.0 585 reviews

Southern Palms

house, Key West
This apartment is located in the heart of Key West, just 1.8 kilometres from South Beach and less than 1.6 kilometres from Fort Zachary Taylor State Park Beach. It has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment is well-equipped and offers a comfortable stay. It features a fully equipped kitchen, a private terrace, and access to a swimming pool, jacuzzi, sauna, and parking.
Dog-friendly Condo With Pool, Hot Tub, Balcony, Central Ac, W/d, & Fitness Room - Key West, FL
8.8 125 reviews

Dog-friendly Condo With Pool, Hot Tub, Balcony, Central Ac, W/d, & Fitness Room

apartment, Key West
This two-bedroom flat in Key West's Sunrise Suites Resort is situated by the sea, offering views of the Salt Ponds Preserve from its balcony, and is less than 1 kilometre from the Southernmost Point and the Ernest Hemingway Home and Museum.
This 74 square metre apartment accommodates up to six guests, featuring air conditioning, a kitchen with a fridge, microwave, and dishwasher, and access to shared amenities including a swimming pool and hot tub, with a fitness room and tennis court also available at the resort.
Heated Rooftop Pool, Gated Parking - Casa Caribe - Key West, FL
9.4 51 reviews

Heated Rooftop Pool, Gated Parking - Casa Caribe

apartment, Key West
This two-storey townhouse, situated on the quieter end of Duval Street at its junction with Truman Avenue, Key West, offers easy access (within 1.6km) to the Southernmost Point and downtown attractions.
The property boasts two en-suite bedrooms, sleeping up to six guests, and features a private hot tub, a shared rooftop pool with Duval Street views, and a fully equipped kitchen including a fridge, freezer, microwave, and a washer/dryer; off-street parking is also provided.
Poolside Hide-away @ Palm Gardens Offered By Rent Key West Vacations - Key West, FL
10 2 reviews

Poolside Hide-away @ Palm Gardens Offered By Rent Key West Vacations

apartment, Key West
This Key West apartment, a first-floor condo in the Historic District, is situated six blocks (approximately 0.96 km) from Duval Street and the Historic Seaport.
The 42-square-metre (452 sq ft) one-bedroom flat sleeps four, boasting a full kitchen with granite countertops, a private hot tub, in-unit laundry, and access to Palm Gardens' pool and BBQ area.

Frequently asked questions about holiday rentals in Key West, FL

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

    Key West is bursting with things to see and do, but you shouldn't miss the iconic Southernmost Point buoy, the Ernest Hemingway Home and Museum, and a sunset at Mallory Square.
  • What are the best Airbnb and vacation rentals in Key West, FL?

    Leaward Isle Island Retreat, At Mine | Lovely Suite Steps From Duval Street and Ambrosia ~ Adults Only - Poolside King Room In Azul Mansion are the most popular Airbnb and vacation rentals in Key West, FL among travelers.

  • 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 the heart of Key West, with plenty of historic architecture, shops, and restaurants. For a quieter stay, consider the more residential areas of New Town or the Truman Annex.
  • 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 see local marine life, while the Butterfly Conservatory is a colourful and educational experience. The Key West Historic Seaport is also a popular choice, with boat tours and interactive exhibits.
  • What are the best vacation 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?

    Peak season in Key West runs from December to April, so booking your vacation rental well in advance is essential. If you're looking for better deals, consider travelling during the shoulder seasons of 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. If you're a music lover, the Key West Songwriters Festival in May is a must-see. The Key West Food and Wine Festival in January is another popular event.
  • 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 Location In Down Town Key West W/ 2 Pools - Huge Private Roof Deck & Parking.

  • 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?

    Strolling along Duval Street is free and a great way to soak up the atmosphere. You can also enjoy the free sunset celebrations at Mallory Square or explore the historic Fort Zachary Taylor State Park.
  • What are the best restaurants with local dishes in Key West, FL?

    For authentic Key West cuisine, try the Blue Heaven restaurant, known for its fresh seafood and laid-back atmosphere. The Hogfish Bar & Grill is another popular choice, serving up classic Key West fare.
  • Are there pet-friendly attractions in Key West, FL?

    Many restaurants and shops in Key West are pet-friendly. The Key West Butterfly and Nature Conservatory welcomes well-behaved dogs on a leash. You can also enjoy a walk with your furry friend along the beach at Higgs Beach.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals often offer more space and privacy than a hotel room, and can be a more cost-effective option for families or groups. Many rentals also have unique features like private patios or balconies.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular destination for watersports like fishing, sailing, and kayaking. The Key West Yacht Club offers a variety of sailing and boating activities. For those who prefer land-based activities, the Key West Golf Club offers a challenging 18-hole course.

Popular destinations

Best Key West, FL holiday rentals with a balcony

Key West Condo Close To The Ocean. 1 Mile To Smathers & 3 Miles To Duval St. - Key West, FL
9.2 115 reviews

Key West Condo Close To The Ocean. 1 Mile To Smathers & 3 Miles To Duval St.

apartment, Key West
This two-bedroom apartment, ideal for families or groups of up to six, is located in Key West, just 2 kilometres from the Fort East Martello Museum and Gallery and 3 kilometres from Smathers Beach.
The 74 square metre apartment offers a fully equipped kitchen, a private balcony, a swimming pool, a fitness centre and a jacuzzi, perfect for a relaxing getaway.
Stay At Sunrise Suites 203! - Key West, FL
9.2 122 reviews

Stay At Sunrise Suites 203!

apartment, Key West
This Key West condo is situated 1.9 km from Smathers Beach and 1.9 km from the Fort East Martello Museum and Gallery, with other attractions such as the Key West Art & Historical Society within a 3.2 km radius.
This 74 square metre, two-bedroom, two-bathroom apartment sleeps six, offering a fully equipped kitchen, private balcony, in-unit laundry, swimming pool, jacuzzi, fitness centre and spa access.
The Reach Key West, Curio Collection By Hilton - Key West, FL
8.4 1395 reviews

The Reach Key West, Curio Collection By Hilton

resort, Key West
The Reach Key West, Curio Collection by Hilton is located in Old Town, Key West, just 1.5 kilometres from Duval Street, a lively area with a wide selection of restaurants, shops, and nightlife. The resort has received very good ratings for both its location and overall experience, with good marks for cleanliness.
This hotel offers a range of rooms, including suites and studios, all with private balconies offering views of the ocean or the town. Guests can enjoy a private beach, a swimming pool, a spa, a fitness centre, and a variety of activities like scuba diving, snorkelling, and deep-sea fishing.
Heated Rooftop Pool, Gated Parking - Casa Caribe - Key West, FL
8.8 28 reviews

Heated Rooftop Pool, Gated Parking - Casa Caribe

apartment, Key West
This Key West apartment, a two-storey townhouse in the Historic District, is situated steps from the Southernmost Point buoy and a short 1.6km walk from Key West's downtown attractions on Duval Street.
The 116 square metre property boasts a spacious layout with two bedrooms, three bathrooms, and sleeps six, including a queen sofa bed, plus a private deck, rooftop pool access, in-unit laundry, and off-street parking.

Best Key West, FL holiday rentals with parking

Contra House -Luxury Home With Pool - Key West, FL
9.6 29 reviews

Contra House -Luxury Home With Pool

house, Key West
This Key West property, a luxurious four-bedroom house, is centrally located, a short walk from South Beach and less than 1.6km from Simonton Street Beach, placing you minutes from Duval Street, the Ernest Hemingway Home and Museum, and the Southernmost Point.
The 227 square metre dwelling boasts a private pool, a fully equipped kitchen, and can comfortably accommodate up to twelve guests, offering free Wi-Fi and air conditioning.
Casa Atlantica Studio Condo On The Ocean Key West - Key West, FL
9.2 223 reviews

Casa Atlantica Studio Condo On The Ocean Key West

house, Key West
Casa Atlantica, a waterfront apartment in Key West, is situated steps from White Street Pier and Higgs Beach, a short cycle ride (approximately 2 kilometres) from Duval Street and the Historic District.
This 64-square-metre studio flat offers a king-sized bed, a fully equipped kitchen including a fridge, microwave, and dishwasher, a private patio with ocean views, and accommodates two guests; shared laundry facilities and limited on-street parking are available.
Casa Key West-pool & Free Parking - Key West, FL
9.1 221 reviews

Casa Key West-pool & Free Parking

house, Key West
Villa Coastal by Brightwild-Pool & Free Parking is located just a short walk from Duval Street and the Southernmost Point in Key West, placing you right in the heart of the action. This property has received excellent ratings for location, cleanliness and overall user experience.
This three-bedroom villa offers plenty of space for families or groups of friends. The property includes a private pool, free parking, air conditioning, a dishwasher, and a full kitchen, making it a comfortable and convenient base for exploring Key West.
Abbey's Attic - Truman @ Duval | Cozy Getaway - Key West, FL
10 14 reviews

Abbey's Attic - Truman @ Duval | Cozy Getaway

apartment, Key West
This Key West studio apartment enjoys a prime location near the intersection of Truman Avenue and Duval Street, a short walk from Duval Street and just 0.16 kilometres from the Key West Lighthouse.
The self-catering unit, sleeping two guests, offers a kitchenette with a mini-fridge and microwave, air conditioning, free Wi-Fi, and cable TV; its central location provides easy access to restaurants, nightlife, and attractions including the Ernest Hemingway Home and Museum.
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