Holiday Rentals in Key West, FL

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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

Resort-style Amenities And Expansive Pool - Stunning Oceanfront Retreat - Key West, FL
9.6 38 reviews

Resort-style Amenities And Expansive Pool - Stunning Oceanfront Retreat

apartment, Key West
This oceanfront condominium complex is situated directly on 400 feet of coastline, adjacent to Smathers Beach, and is just 2.4 kilometres from Old Town Key West's shops and restaurants.
This family-friendly apartment offers accommodation for four guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, fitness centre, and tennis courts, with a balcony providing ocean views.
121 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.5 26 reviews

121 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
This Old Town Key West property is a short walk from Duval Street and 0.64km from the Atlantic Ocean.
This two-bedroom, two-bathroom house offers 130 square metres of living space, including a private pool, fully equipped kitchen, and accommodates up to six guests; AvantStay services are available.
Spacious Suites And Luxurious Amenities - Charming Cuban Retreat - Key West, FL
9.8 152 reviews

Spacious Suites And Luxurious Amenities - Charming Cuban Retreat

apartment, Key West
This two-bedroom flat is located in a historic Cuban heritage district, just 520 metres from the Southernmost Point and 480 metres from South Beach, with Duval Street's shops and restaurants like Banana Cafe and Origami within a 160-metre walk.
This family-friendly apartment accommodates up to six guests and offers amenities including air conditioning, Wi-Fi, a kitchen with a fridge, microwave, and dishwasher, ensuite bathrooms, a terrace, garden, spa, and tennis court, with parking provided.
93 M² House ∙ 2 Bedrooms ∙ 4 Guests - Key West, FL
10 6 reviews

93 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, Key West
This pet-friendly cottage is situated in Key West's Old Town, just 640 metres from the Historic Seaport and Duval Street, and within walking distance of several restaurants.
Spanning 93 square metres, this property accommodates up to four guests in two bedrooms and a loft, featuring a heated swimming pool on its tropical deck, a well-equipped kitchen with retro appliances, and high-speed 5G internet.

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

Royal Palm Studio At Travelers Palm Inn Key West - Key West, FL
No reviews

Royal Palm Studio At Travelers Palm Inn Key West

studio, Key West
ROYAL PALM STUDIO is centrally located in Key West, Florida, 0.6km from the city centre and an 8-minute walk from South Beach, placing it within easy reach of Mallory Dock and the Key West Aquarium (1.9km).
This self-catering apartment sleeps two guests in one bedroom, boasts a kitchenette with fridge and microwave, a private terrace, and access to an on-site swimming pool and tennis court; free Wi-Fi and parking are also provided.
Poolside Paradise @ Tropical Village By Rent Key - Key West, FL
9.4 18 reviews

Poolside Paradise @ Tropical Village By Rent Key

apartment, Key West
This Key West apartment, a historic 1930s Conch cottage in the Casa Marina neighbourhood, is located a short walk from Duval Street and 0.32 kilometres from Higgs Beach.
This one-bedroom, one-bathroom flat sleeps two guests and features a kitchenette, king-size bed, private patio, and access to a shared pool, gas grill, and laundry facilities; a Smart TV with Roku is also provided.
Newton's Nest ~ Adult Only, 1st Floor 1 Bedroom, 1 Bath Condo W/ Shared Pool! - Key West, FL
10 1 review

Newton's Nest ~ Adult Only, 1st Floor 1 Bedroom, 1 Bath Condo W/ Shared Pool!

apartment, Key West
This Old Town Key West apartment is situated in the Historic District, within walking distance of the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 40 square metre condo offers two bedrooms, one bathroom, sleeping up to two guests, and features a fully equipped kitchen, private sunroom, in-unit laundry, and access to a communal swimming pool and concierge services.
Keys Breeze - Walk To Duval, Private Pool - Key West, FL
10 38 reviews

Keys Breeze - Walk To Duval, Private Pool

apartment, Key West
This Key West Historic District property is located steps from the Key West Butterfly and Nature Conservatory and Duval Street, with South Beach a short 3.2 km drive or cycle away.
This three-bedroom, three-bathroom house offers 114 square metres of living space, a private pool, fully equipped kitchen, and accommodates up to six guests, perfect for exploring the island's attractions.

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

Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking - Key West, FL
8.8 200 reviews

Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking

house, Key West
The Tortuga by Brightwild-Pool, Parking & Pets! is situated in Key West, just over 6km from the famous Duval Street and Mallory Square.
This two-bedroom property, spanning 74 square metres, features a private swimming pool, a hot tub, and a fully equipped kitchen, as well as free parking and Wi-Fi.
Hemingways Atlantic Retreat - Key West, FL
9.2 129 reviews

Hemingways Atlantic Retreat

house, Key West
This apartment is located in Key West, a short walk from Smathers Beach and close to Rest Beach, offering easy access to the island's beautiful beaches and vibrant atmosphere. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment is spacious, with two bedrooms and two bathrooms, ideal for families or groups of up to six guests. It also boasts a range of amenities, including a swimming pool, a Jacuzzi, a fitness center, and a tennis court, ensuring a comfortable and enjoyable stay.
Sky Loft In Key West - Key West, FL
9.5 237 reviews

Sky Loft In Key West

house, Key West
Sky Loft in Key West by Brightwild is centrally located in Key West, a short walk from Simonton Street Beach and South Beach, offering easy access to the island's attractions and nightlife. This property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The one-bedroom apartment is perfect for a family of four, with a spacious 63 square metres of living space. Enjoy a comfortable stay with amenities such as a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, and free Wi-Fi.
Brisa Del Mar By Avantstay - Key West, FL
No reviews

Brisa Del Mar By Avantstay

apartment, Key West
Vacation rental listing. You will be in Key West.
Facilities and services include a dish washer, a kitchen and a swimming pool. Take advantage of the air conditioning in this apartment!

Best Key West, FL holiday rentals with parking

Oceanfront 4-bed 3-bath Home With Pool - Key West, FL
9.4 99 reviews

Oceanfront 4-bed 3-bath Home With Pool

apartment, Key West
This Northside Resort property is conveniently located less than 5 km from Duval Street and Mallory Square, and under 3 km from the Key West Firehouse Museum and Florida Keys beaches.
This eight-guest Key West holiday home boasts four bedrooms, three bathrooms, a private pool and jacuzzi, full kitchen, free Wi-Fi, and a private yard – perfect for families or groups seeking a relaxing escape.
Pool, Laundry, And Grilling Area - Key West, FL
10 11 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.
Poolside Cottage #412 - Key West, FL
9.8 370 reviews

Poolside Cottage #412

house, Key West
This Key West seaside property is situated within 3.2km of the Key West Tropical Forest and Botanical Garden, Fort East Martello Museum and Gallery, and the Key West Art and Historical Society.
This 65 square metre house boasts one bedroom, one bathroom, sleeps six, and includes a fully equipped kitchen, swimming pool, Jacuzzi, and terrace; enjoy ocean views and on-site barbecue facilities.
Hyatt Sunset Harbor 1 Br Luxury Suite - Key West, FL
8.6 582 reviews

Hyatt Sunset Harbor 1 Br Luxury Suite

hotel, 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.
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