Compare Vacation Rentals & Airbnb in Key West, FL

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Key West, FL vacation rentals
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4265 Rentals and Airbnb in Key West, FL

Best family friendly Key West, FL vacation rentals

Among the 4265 accommodations in Key West, FL, here are the 4 best family friendly rentals

The Mesa House - One Block From Duval St - Key West, FL
No reviews

The Mesa House - One Block From Duval St

house, Key West
This residence, located in Old Town Key West, offers oceanfront proximity with easy beach access and is situated just 50 metres from Duval Street and a short walk to the Key West Seaport.
This family-friendly dwelling sleeps up to 10 guests, featuring three bedrooms, two bathrooms, two full kitchens, air conditioning, free WiFi, and a private washer and dryer.
Private Heated Pool & Near Duval - The Curry House - Key West, FL
No reviews

Private Heated Pool & Near Duval - The Curry House

house, Key West
Curry House, a historic guesthouse in Old Town Key West, is situated within 500 metres of Duval Street and 300 metres of the waterfront, offering convenient access to the Historic Seaport and numerous attractions.
This three-storey residence provides accommodation for up to 18 guests, featuring nine uniquely decorated rooms, each with a mini-fridge, cable TV, and complimentary WiFi, alongside a private heated swimming pool and a fenced patio for secure bicycle storage.
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.
Knowles Main House With Pool - Key West, FL
9.8 34 reviews

Knowles Main House With Pool

apartment, Key West
This Key West property enjoys a central location, offering easy access to the island's attractions, although precise distances to specific landmarks aren't specified.
The five-bedroom, four-bathroom house sleeps ten guests, boasting a private pool, rooftop deck, and convenient driveway parking for two cars; each bedroom includes a private bathroom, ensuring maximum privacy for large groups.

Best Key West, FL vacation rentals with a pool

Among the 4265 accommodations in Key West, FL, here are the 4 best rentals with a pool

Waterfront Dock Pool Condo Near Duval St Pet Ok - Key West, FL
9.8 330 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.
The Mallory Suite At Inn On Fleming Key West! - Key West, FL
9.5 2 reviews

The Mallory Suite At Inn On Fleming Key West!

house, Key West
The Mallory Suite is a centrally located Key West apartment, 1.6km from Mallory Square, 0.9km from the city centre, and a 16-minute walk from Simonton Street Beach.
This 20 square metre self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a swimming pool, tennis court, parking, and Wi-Fi.
The Margaret Suite - Key West, FL
10 5 reviews

The Margaret Suite

apartment, Key West
This studio apartment, located in Key West's Historic District, offers proximity to Mallory Square, the Key West Historic Seaport, the Ernest Hemingway Home and Museum, and Fort Zachary Taylor State Park, all within a short walk.
This 46 square meter self-contained accommodation, ideal for up to three guests, features a queen bed and a sofa bed, a compact kitchenette with a fridge and microwave, air conditioning, and access to shared amenities including a swimming pool and on-site laundry, with first-come, first-serve off-street parking available.
The Margaret Suite - Key West, FL
9.2 10 reviews

The Margaret Suite

apartment, Key West
The Margaret Suite, a studio apartment, is located in Old Town Key West, placing it within the historic Bayview House and close to local attractions.
This updated holiday flat accommodates up to four guests, featuring an open-concept layout with vaulted ceilings, coastal finishes, air conditioning, Wi-Fi, a kitchen with a fridge and microwave, and access to a swimming pool, parking, and is approximately 1.6 kilometres from the nearest beach.

Frequently Asked Questions about vacation rentals in Key West, FL

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

    You've got to see the sunset at Mallory Square, it's a real Key West institution. And don't forget to visit the Ernest Hemingway Home and Museum, it's a fascinating place to learn about the famous author's life in Key West.
  • What are the best Airbnb and vacation 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 great choice, it's right in the heart of everything, with lots of restaurants, shops, and attractions. If you're looking for something a bit quieter, try the historic Bahama Village, it's got a more laid-back vibe.
  • 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 big hit with kids, they've got all sorts of fascinating sea creatures. The Butterfly Conservatory is another great option, with hundreds of beautiful butterflies fluttering around you.
  • 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?

    You'll want to book well in advance, especially if you're travelling during peak season, which is from December to April. If you're looking for a bit more flexibility, try booking in the shoulder seasons, 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 Key West Food and Wine Festival is a big one, with lots of food and drink tastings. The Hemingway Days Festival is another great option, celebrating the life and work of Ernest Hemingway. If you're here in October, don't miss Fantasy Fest, it's a wild and colourful celebration.
  • 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 Southernmost Sanctuary.

  • 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, it's full of shops, bars, and restaurants. You can also visit the Key West Cemetery, it's a fascinating place to wander around and learn about the history of Key West. And don't forget to check out the free sunset celebrations at Mallory Square.
  • What are the best restaurants with local dishes in Key West, FL?

    For a taste of Key West, try the conch fritters at The Waterfront Brewery. If you're looking for something a bit fancier, head to Latitudes for their award-winning seafood. And for a taste of Cuban cuisine, check out El Siboney.
  • What are the best walking or cycling routes in Key West, FL?

    The Truman Waterfront is a great place for a walk or cycle, with beautiful views of the harbour. For a longer ride, try the scenic route along the Overseas Highway, it's a stunning drive with views of the ocean and the Keys.
  • Are there pet-friendly attractions in Key West, FL?

    Yes, there are plenty of pet-friendly attractions in Key West. You can take your dog to the beach at Higgs Beach, or for a walk along the Truman Waterfront. Many restaurants and shops also welcome well-behaved dogs.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than hotels, and they're often a more affordable option. You'll also have access to a kitchen, so you can save money by cooking some of your own meals.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is a popular spot for watersports, with plenty of opportunities for fishing, sailing, and kayaking. You can also find golf courses, tennis courts, and a fitness centre.

Popular destinations

Best Key West, FL vacation rentals with a balcony

Poinciana Garden~ Casual 1st Floor Duplex - Key West, FL
9.6 393 reviews

Poinciana Garden~ Casual 1st Floor Duplex

apartment, Key West
This Key West Historic District property is a short 0.8km walk from Key West Cemetery and Duval Street, with the Ernest Hemingway Home and Museum and Florida Keys beaches within a 2.4km radius.
The self-catering house boasts a fully equipped kitchen, private garden with barbecue, jacuzzi, and balcony; free Wi-Fi and parking are also included.
Atlantic Paradise By Avantstay - Key West, FL
9.4 140 reviews

Atlantic Paradise By Avantstay

house, Key West
This charming two-bedroom holiday home is located just a short walk from Smathers Beach, Key West's most popular beach, and within easy reach of other nearby beaches. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The property boasts a spacious 126 square metres of living space and can comfortably accommodate up to six guests. A range of amenities are provided, including a fully equipped kitchen, a private balcony, a shared pool and hot tub, and free Wi-Fi and parking.
Thompson Island  Usa !!  Your Key West Retreat !! - Key West, FL
9.6 125 reviews

Thompson Island Usa !! Your Key West Retreat !!

apartment, Stock Island
This waterfront property is situated on Stock Island, just a short distance from the Key West Tropical Forest and Botanical Garden and Smathers Beach, offering easy access to the island's attractions. The house has received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The spacious nine-bedroom home provides ample room for large groups or families, spanning over 743 square metres. Guests can enjoy a range of amenities, including a private pool and spa tub, a fully equipped kitchen, a tennis court, and a barbecue grill, offering both relaxation and entertainment options.
Beachfront 2bdr Condo, Pool & Hot Tub W/ Ocean Views | Papaya Place By Avantstay - Key West, FL
No reviews

Beachfront 2bdr Condo, Pool & Hot Tub W/ Ocean Views | Papaya Place By Avantstay

house, Key West
This Key West condo, located at 1800 Atlantic Condominiums, is situated 2.4 kilometres from downtown Key West and within walking distance of Smathers Beach.
This family-friendly apartment accommodates up to six guests and offers two bedrooms, two bathrooms, a full kitchen, and a balcony, with complex amenities including a shared BBQ area, a heated swimming pool, Jacuzzi, tennis courts, and a fitness centre.

Best Key West, FL vacation rentals with parking

One Bedroom Suite | Beachside Resort - Key West, FL
9.6 107 reviews

One Bedroom Suite | Beachside Resort

apartment, Key West
This Key West Beachside Resort condo, situated directly on the Gulf of Mexico, offers stunning Gulf views from its private balcony.
The one-bedroom apartment, sleeping up to four guests with a king bed and queen sleeper sofa, boasts a fully equipped kitchen, private washer/dryer, and access to a heated pool, hot tub, fitness centre, and on-site marina; bookable sandbar or sunset cruises enhance your stay.
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).
Sunny Condo With Wifi, Hot Tub, Pool & Tennis - Key West, FL
9.4 122 reviews

Sunny Condo With Wifi, Hot Tub, Pool & Tennis

apartment, Key West
This Key West condo is located on the eastern side of the island, approximately 6.4 kilometres from downtown attractions such as the Hemingway House and Southernmost Point, and is also conveniently situated near Key West International Airport and Smathers Beach.
This 72 square metre apartment offers two bedrooms, two bathrooms, and accommodation for up to four guests, featuring a private balcony, air conditioning, a kitchen equipped with a fridge, microwave, and dishwasher, and access to a shared swimming pool, hot tub, and fitness room.
Two Bedroom Residence - Key West, FL
9.4 152 reviews

Two Bedroom Residence

apartment, Key West
This luxurious two-bedroom Key West condo boasts stunning Gulf of Mexico views from its private balcony, situated on a seven-acre beachfront property with direct marina access.
The 2-bedroom apartment, sleeping up to six guests, features a full kitchen with stainless-steel appliances, in-unit laundry, and access to a heated pool, hot tub, Tavern N Town restaurant, and the resort's marina offering boat rentals and watersports via Brightwild Adventures.
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