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

Apartment ∙ 2 Bedrooms ∙ 8 Guests - Key West, FL
10 1 review

Apartment ∙ 2 Bedrooms ∙ 8 Guests

apartment, Key West
This Key West apartment, situated in the downtown area with a balcony overlooking Duval Street, offers easy walking access to numerous attractions.
The two-bedroom, one-bathroom dwelling sleeps eight guests, featuring a fully equipped kitchen with a stove, refrigerator, dishwasher, and Keurig coffee machine, plus a washer/dryer, and free Wi-Fi.
Keys Breeze - Walk To Duval, Private Pool - Key West, FL
No reviews

Keys Breeze - Walk To Duval, Private Pool

house, Key West
This renovated island dwelling is located in the southern district of Key West, a mere 300 meters from the Southernmost Point and within walking distance of Duval Street, the Key West Lighthouse, and the Hemingway Home and Museum.
This family-friendly property accommodates up to six guests across three bedrooms and two bathrooms, featuring a private swimming pool, a fully equipped kitchen with stainless-steel appliances, air conditioning, and high-speed internet, perfect for year-round enjoyment and entertaining.
Hyatt Centric Key West Resort & Spa - Key West, FL
8.7 2726 reviews

Hyatt Centric Key West Resort & Spa

resort, Key West
The Hyatt Centric Key West Resort & Spa is situated on Key West Island, just a short walk from the lively Duval Street, known for its nightlife and restaurants. The resort has received very good user ratings, with excellent marks for location and very good ratings for cleanliness.
The hotel has a waterfront location with a swimming pool, a jacuzzi and a spa. Guests can enjoy a range of activities, including relaxing by the pool, exploring the surrounding area via jet ski, scuba diving, snorkelling, and island tours, as well as dining at two on-site restaurants.
Sky Suites Retreat - Balcony Overlooking Duval - Key West, FL
No reviews

Sky Suites Retreat - Balcony Overlooking Duval

apartment, Key West
This elevated second-story loft, situated on the 700 block of Duval Street, offers immediate walking access to Key West's notable dining establishments such as Martin's and Moondog Cafe, as well as the historic Hemingway House, all within 500 metres.
This duplex accommodation, designed for up to 12 guests across two connected lofts with four bedrooms and four and a half bathrooms, features vaulted ceilings, modern decor, private balconies, two fully equipped kitchens, and off-street parking for one compact vehicle.

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

Salvador's Seclusion | Cozy Studio Retreat W/ Heated Pool - Key West, FL
8.8 56 reviews

Salvador's Seclusion | Cozy Studio Retreat W/ Heated Pool

studio, Key West
This Old Town Key West flat is situated a short walk from Florida Keys beaches and Duval Street, within 1.6km of the Southernmost Point and South Beach.
The one-bedroom, one-bathroom apartment sleeps two, offering a private patio, in-unit laundry, a pool, and essential kitchen appliances; nearby attractions include the Ernest Hemingway Home and Museum.
Pool, Laundry, And Grilling Area - Key West, FL
10 1 review

Pool, Laundry, And Grilling Area

apartment, Key West
This Old Town Key West flat, situated two blocks from Duval Street, is close to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
The one-bedroom, one-bathroom apartment sleeps two guests and boasts a king-size bed, full kitchen with dishwasher, private deck with pool and waterfall, and a luxurious jacuzzi tub; nearby amenities include a convenience store and Cuban coffee shop.
Blue Moonshine On The Atlantic - Key West, FL
9.5 2 reviews

Blue Moonshine On The Atlantic

house, Key West
Blue Moonshine on the Atlantic, a Key West property, is located 2.6 km from the Southernmost Point and 3.2 km from the Ernest Hemingway Home and Museum.
This 130-square-metre house boasts two bedrooms, two bathrooms, a hot tub, and sleeps up to 11 guests, offering a fully equipped kitchen, swimming pool, jacuzzi, sauna, fitness centre, tennis court, and ocean views from a private balcony, with free Wi-Fi and proximity to Smathers, Rest, and Higgs Beach.
Your Condo By The Beach With Ocean View - Key West, FL
10 169 reviews

Your Condo By The Beach With Ocean View

apartment, Key West
This oceanfront Key West apartment in the LaBrisa Condominiums is situated near Smathers Beach, approximately 1.6 kilometres from Duval Street and Old Town's attractions.
The one-bedroom, one-bathroom condo sleeps two, boasting a king-size bed, fully equipped kitchen with dishwasher, private terrace, swimming pool, jacuzzi, free Wi-Fi, covered parking, and a washer/dryer; final cleaning is included.

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

Atlantic Hideaway- Key West - Key West, FL
9.6 86 reviews

Atlantic Hideaway- Key West

apartment, Key West
This Key West apartment, situated in the Beachside neighbourhood, is one kilometre from Key West International Airport and three kilometres from Duval Street.
The 122-square-metre, two-bedroom, two-bathroom property in the 1800 Atlantic condo complex sleeps six, boasting a private lanai, access to two pools, a spa, and a fully equipped kitchen; beach chairs and towels are provided.
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.
High Tide In Key West - Key West, FL
9.0 202 reviews

High Tide In Key West

house, Key West
This Key West apartment, ideally located 2 km from the Ernest Hemingway Home and Museum and 2.6 km from the Southernmost Point buoy, offers easy access to Key West International Airport (1.9 km).
The two-bedroom, two-bathroom flat provides self-catering facilities including a fully equipped kitchen, free Wi-Fi, private parking, and access to a swimming pool, Jacuzzi, fitness centre, tennis court, and sauna; it comfortably sleeps four guests and is close to Smathers Beach, Rest Beach, and Higgs Beach.
Apartment ∙ 4 Bedrooms ∙ 16 Guests - Key West, FL
No reviews

Apartment ∙ 4 Bedrooms ∙ 16 Guests

apartment, Key West
This Duval Street duplex, situated in the heart of Key West's Old Town, offers easy walking access to numerous attractions.
Sleeping up to 18 guests in four bedrooms and two bathrooms across two adjacent historic lofts, this Key West property boasts fully equipped kitchens, a terrace overlooking Duval Street, a garden, and a washer/dryer in each unit; free Wi-Fi is also provided.

Best Key West, FL holiday rentals with parking

Colony Sunset- Bright And Airy Cottage - Key West, FL
9.6 31 reviews

Colony Sunset- Bright And Airy Cottage

apartment, Key West
This charming Key West cottage is situated in the historic Old Town district, just a short stroll from Duval Street, the island's lively hub. The property has received excellent ratings for its location, cleanliness, and overall experience, ensuring a pleasant stay.
The cottage offers a spacious living area with a king-sized bed, accommodating up to four guests. It features a fully equipped kitchen, a private deck, and access to a shared pool, providing everything you need for a relaxing and enjoyable Key West getaway.
Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock - Key West, FL
9.4 11 reviews

Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock

house, Key West
This Key West waterfront condo is situated approximately 1.8km from both the Ernest Hemingway Home and Museum and Duval Street, and 1.9km from Key West International Airport.
The 121 square metre property boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private dock, swimming pool, garden, and free Wi-Fi; self-catering is facilitated by a fully equipped kitchen.
Sept Special@119.lodging + With 5 Night Stay 5th Night Free Lodging! - Key West, FL
9.0 198 reviews

Sept Special@119.lodging + With 5 Night Stay 5th Night Free Lodging!

apartment, Key West
This one-bedroom house in Key West's Historic District is located within a 15-minute walk of Duval Street, the Key West Firehouse Museum, and the Florida Keys Beaches.
The property offers a comfortable stay for up to four guests with a fully equipped kitchen, a sofa bed, a dining area, a patio, and a garden, as well as free parking nearby.
"Hemingway" 1 Bedroom At Leo's - Key West, FL
9.7 65 reviews

"Hemingway" 1 Bedroom At Leo's

apartment, Stock Island
This Stock Island apartment, situated two blocks from the Key West entrance, offers easy access to Key West's attractions via bicycle, scooter, or golf cart.
The one-bedroom flat, located within Leo's RV Park, sleeps two guests and includes a kitchen with fridge and microwave, air conditioning, parking, and access to on-site recreational facilities such as ping pong, chess, and billiards, plus relaxing Tiki Huts.
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