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

Discover Holiday Rentals by the Sea in Key West, FL

Plan a relaxing coastal trip at shoreside holiday rentals in Key West, FL, located a brief distance from regional boardwalks.

Seventh Heaven~waterfront 5 Br, 4 Ba Townhome With Pool, Elevator & Dockage! - Key West, FL
9.8 17 reviews

Seventh Heaven~waterfront 5 Br, 4 Ba Townhome With Pool, Elevator & Dockage!

apartment, Key West
This Key West waterfront property, a conch-style house in the Meadows neighbourhood overlooking Garrison Bight Marina, offers easy access to Old Town's attractions, including the Ernest Hemingway Home and Museum and the Southernmost Point.
The 317 square metre (3,412 square feet) residence boasts five bedrooms, four bathrooms, sleeps twelve guests, and features a private heated pool (seasonal), private dockage for boats up to 30 feet, a lift, multiple balconies with marina views, and a concierge service arranging local activities.
Breezy Bungalow | Close 2 Zachary Taylor State Park & Beach | Month-long Stays - Key West, FL
9.4 35 reviews

Breezy Bungalow | Close 2 Zachary Taylor State Park & Beach | Month-long Stays

apartment, Key West
This charming house is located in Old Town Key West, just 1 kilometre from Duval Street and the Ernest Hemingway Home and Museum. It has received excellent user and location ratings and a very good cleanliness rating.
This 2-bedroom house can accommodate up to 4 guests. It is equipped with free Wi-Fi, a balcony, and a fully equipped kitchen, including a dishwasher. You can also enjoy the convenience of air conditioning, a swimming pool, a garden, and parking.
Harbor House Suite A - Key West, FL
10 3 reviews

Harbor House Suite A

house, Key West
Harbor House Suite A offers four-bedroom, four-bathroom self-catering accommodation in Key West's historic district, a few steps from Mallory Square and a 0.6km stroll from Simonton Street Beach.
This 218 square metre property sleeps 23 guests and boasts a fully equipped kitchen including a fridge, microwave, and dishwasher, air conditioning, free Wi-Fi, and private entrance; its proximity to Key West International Airport (5km) adds to its convenience.
Wonderful Condo In Key West W/free Wifi, Lanai, A/c, Shared Hot Tub & Pool - Key West, FL
9.0 8 reviews

Wonderful Condo In Key West W/free Wifi, Lanai, A/c, Shared Hot Tub & Pool

apartment, Key West
This Key West condo is located by the sea, a short 200-metre walk from Smathers Beach and close to Southernmost Point and the Ernest Hemingway Home and Museum.
This 130 square metre apartment sleeps up to 8 guests and features 3 bedrooms, 2 bathrooms, a fully equipped kitchen, private balcony, and access to a shared swimming pool and tennis court.

Best family friendly Key West, FL holiday rentals

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

45 M² House ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
9.2 18 reviews

45 M² House ∙ 1 Bedroom ∙ 4 Guests

house, Key West
This Old Town Key West cottage, in The Colony Suites gated community, is situated two blocks from Duval Street.
The 45-square-metre property offers a loft-style bedroom, a bathroom, a sleeper sofa accommodating four guests, a private backyard with a propane BBQ, and access to a shared pool and coin-operated laundry facilities; AvantStay services are also available.
Waterfront Oasis With Heated Pool And Tiki Bar - Stunning Coastal Retreat - Key West, FL
No reviews

Waterfront Oasis With Heated Pool And Tiki Bar - Stunning Coastal Retreat

apartment, Key West
This 2nd-floor corner waterfront condominium in Key West's Pelican Landing community is situated approximately 1.6 kilometres from Duval Street and a 10-minute drive from Key West International Airport (EYW).
This pet-friendly flat offers two bedrooms and two bathrooms, accommodating up to six guests with a maximum occupancy of eight, and features unobstructed marina and pool views, a private balcony with direct pool access, an included private boat slip, and access to a heated community pool and tiki area.
Waterfront Dock And Heated Pool - Stunning Tropical Escape - Key West, FL
No reviews

Waterfront Dock And Heated Pool - Stunning Tropical Escape

apartment, Key West
This waterfront condominium in Key West's Pelican Landing offers direct access to the water, complete with a private boat slip, dockage, and fish cleaning station, situated approximately 1.6 kilometres from Duval Street, the Historic Seaport, and Hemingway House, and a short distance from Higgs and Smathers beaches.
This 111 square metre apartment accommodates up to eight guests with two bedrooms and two bathrooms, featuring a full kitchen, dining area, living room, private balcony, air conditioning, on-site parking, a heated swimming pool, and BBQ grills, and permits one dog up to 11.3 kilograms for a pet fee.
Panoramic 3br/3ba Condo - Direct Beach Ocean Front - Key West, FL
10 132 reviews

Panoramic 3br/3ba Condo - Direct Beach Ocean Front

apartment, Key West
This three-bedroom apartment is conveniently located in Midtown Key West, just 3.2 kilometres from the airport and 3.2 kilometres from Mallory Square. It offers a peaceful retreat from the bustling city centre, with easy access to the island's attractions and activities. The apartment has received excellent reviews from previous guests.
The spacious apartment, spanning 204 square metres, comfortably accommodates up to eight guests. It boasts a range of amenities, including a swimming pool, jacuzzi, terrace, garden, sauna, parking, and a fully equipped kitchen. Guests can also enjoy stunning ocean views from the bedrooms, kitchen, and living room.

Frequently asked questions about holiday rentals in Key West, FL

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

    You simply have to visit the Southernmost Point Buoy, it's the most photographed spot in Key West! And don't miss Mallory Square, which comes alive in the evenings with street performers and the famous sunset celebration.
  • 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 the heart of Key West, with charming streets, historic buildings, and plenty of restaurants and shops. It's a great choice for a vacation rental, but be prepared for a bit of noise, as it's a lively area.
  • 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 local marine life, and the Butterfly Conservatory is a magical experience for all ages. The Key West Historic Seaport is also a good option, with boat tours and a museum.
  • 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?

    Key West is a popular destination year-round, but the best time to book a vacation rental is during the shoulder seasons, from April to May and September to October. You'll find better deals and fewer crowds during these months.
  • 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 Fantasy Fest in October is a wild and colourful celebration, and the Hemingway Days in July honours the famous author with a literary festival and a look-alike contest. There's also the Key West Songwriters Festival in May.
  • 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?

    Stroll along Duval Street and soak up the atmosphere, enjoy a picnic at Higgs Beach, or take a walk around Fort Zachary Taylor Historic State Park. You can also find free concerts and events at various locations throughout the city.
  • What are the best restaurants with local dishes in Key West, FL?

    For a taste of Key West, try the conch fritters at the Blue Heaven restaurant or the seafood at the Waterfront Brewery. The Hogfish Bar and Grill also has a great selection of local dishes.
  • What are the best walking or cycling routes in Key West, FL?

    The Key West Historic Seaport is a great place to start a walking tour, and you can explore the charming streets of Old Town. For cycling, the scenic route along the Overseas Highway is popular, offering stunning views of the ocean.
  • Are there pet-friendly attractions in Key West, FL?

    Many of the beaches in Key West are dog-friendly, including Higgs Beach and Smathers Beach. You can also find pet-friendly restaurants and shops throughout the city.
  • What are the benefits of choosing a vacation rental in Key West, FL?

    Vacation rentals offer more space and privacy than hotel rooms, and they often come with amenities like kitchens and laundry facilities. They can also be a more affordable option, especially for larger groups or families.
  • What are the top sports attractions and facilities in Key West, FL?

    Key West is known for its watersports, with opportunities for fishing, sailing, kayaking, and diving. There are also several golf courses and tennis courts in the area, as well as the Key West Yacht Club.

Popular destinations

Compare Self-Catering Holiday Rentals with a Swimming Pool in Key West, FL

Pool access at your holiday rental in Key West, FL provides the perfect complement to a day by the water. Find your ideal stay here.

Tropical Vineyard At The Truman Annex In Key West - Key West, FL
9.2 53 reviews

Tropical Vineyard At The Truman Annex In Key West

apartment, Key West
This apartment is located in the Truman Annex district of Old Town Key West, just 0.4 kilometres from Duval Street and 0.4 kilometres from Fort Zachary Taylor State Park, offering easy access to both the lively nightlife and the serene beach. It has received excellent user ratings, making it a popular choice for travellers.
The apartment has a floor area of 54 square metres, with one bedroom and one bathroom, comfortably accommodating up to four guests. It features modern amenities including a fully equipped kitchen, a large balcony, a swimming pool, and parking, providing a comfortable and convenient stay.
Tropical Paradise Key West - Key West, FL
9.4 192 reviews

Tropical Paradise Key West

house, Key West
This apartment is located just 400 metres from Smathers Beach in Key West, offering a convenient location for enjoying the island's beautiful beaches. The apartment has consistently received excellent ratings for its cleanliness, location, and overall user experience.
The property is a spacious two-bedroom apartment with a floor area of 126 square metres, comfortably accommodating up to six guests. This self-catering apartment boasts a range of amenities and features, including a fully equipped kitchen, a private balcony with sea views, a swimming pool, a jacuzzi, a fitness centre, and free parking.
Parrot Perch By Avantstay - Key West, FL
8.9 46 reviews

Parrot Perch By Avantstay

house, Key West
This Key West Old Town property is conveniently located less than 1 km from the Ernest Hemingway Home and Museum, half a kilometre from the Key West Aquarium, and a 2 km walk from Fort Zachary Taylor State Park Beach.
This self-catering house boasts a fully equipped kitchen, private parking (a Key West rarity), a shared swimming pool, and a patio ideal for al fresco dining; it offers free Wi-Fi and accommodates families.
Kwss210 Sunrise Suites Bonaire Suite #210 - Key West, FL
8.7 245 reviews

Kwss210 Sunrise Suites Bonaire Suite #210

apartment, Key West
Sunrise Suites Bonaire Suite #210 is a two-bedroom Key West apartment, conveniently located 1 kilometre from Key West International Airport and within a short drive of attractions such as the Southernmost Point (6.4 km), Ernest Hemingway Home and Museum (7.4 km), Duval Street (7.4 km), and Mallory Square (8 km).
This 72 square metre self-catering flat offers two bathrooms, a private balcony, a fully equipped kitchen, in-unit laundry facilities, and access to a swimming pool, hot tub, fitness centre, and tennis court; sleeping up to four guests.

Top-Rated Self-Catering Holiday Rentals with Free Parking in Key West, FL

A car park at your holiday rental in Key West, FL makes reaching the coast and local beaches easy every day with no extra faff.

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.
The Blue Flamingo Resort Key West - Key West, FL
No reviews

The Blue Flamingo Resort Key West

resort, Key West
The Blue Flamingo Resort Key West is located 5 kilometres from Key West's city centre, offering easy access to attractions such as the Key West Tropical Forest and Botanical Garden and the Lower Keys Medical Centre.
This resort provides a variety of amenities, including indoor and outdoor swimming pools, a fitness centre, a bar, a restaurant, and family-friendly facilities, with the Blue Flamingo Resort Key West offer including live entertainment and happy hour access.
Rose Lane Villas - Key West, FL
9.2 579 reviews

Rose Lane Villas

house, Key West
These villas are situated on Duval Street in Key West, just a short walk from the Key West Aquarium and a mile from the Southernmost Point, putting you right in the heart of the action. The villas have received excellent ratings for location, cleanliness, and user experience.
The properties offer a range of features including fully equipped kitchens, private balconies, flat-screen TVs, free Wi-Fi, and parking. The heated outdoor pool provides a welcome respite from the Florida sun, while the proximity to local attractions makes exploring the island easy.
The Whitehead Room At Inn On Fleming Key West! - Key West, FL
9.0 1 review

The Whitehead Room At Inn On Fleming Key West!

house, Key West
THE WHITEHEAD ROOM at the Inn on Fleming Key West is centrally located, 1km from the city centre, a 17-minute walk from the Ernest Hemingway Home and Museum, and 1.6km from Mallory Square.
This self-catering apartment offers 15 square metres of accommodation, sleeping two guests in one bedroom and one bathroom, and includes a swimming pool, free Wi-Fi, and on-site parking.

Luxury Holiday Rentals in Key West, FL

Comfort, quality and a prime location; each luxury holiday rental or Airbnb in Key West, FL is selected with your relaxation in mind.

The Grande Vista - Key West, FL
9.1 203 reviews

The Grande Vista

house, Key West

Best Key West, FL holiday rentals with a balcony

Poolside Paradise Tropical Village - Key West, FL
No reviews

Poolside Paradise Tropical Village

apartment, Key West
Duval's Duet On Duval - Key West, FL
9.3 334 reviews

Duval's Duet On Duval

apartment, Key West
Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom - Key West, FL
8.0 4 reviews

Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom

house, Key West
Sunrise 308-2br/2ba Condo Near Beaches With Pool, Parking, Balcony - Key West, FL
8.6 16 reviews

Sunrise 308-2br/2ba Condo Near Beaches With Pool, Parking, Balcony

apartment, Key West

Explore Pet-Friendly Holiday Rentals in Key West, FL

These dog-friendly holiday rentals in Key West, FL feature outdoor showers and access to pet-welcoming beaches.

Private Luxury Suite, Hot Tub, Half Block To Duval - Key West, FL
No reviews

Private Luxury Suite, Hot Tub, Half Block To Duval

apartment, Key West
Two Rustic Cottages With Private Hot Tubs & Private Parking - Dogs Ok - Key West, FL
9.2 101 reviews

Two Rustic Cottages With Private Hot Tubs & Private Parking - Dogs Ok

cabin, Key West
Road's End | Prime Old Town Location! Updated Home W/ Pool - Key West, FL
10 22 reviews

Road's End | Prime Old Town Location! Updated Home W/ Pool

apartment, Key West
Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-friendly - Key West, FL
9.9 16 reviews

Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-friendly

house, Key West

Choose the Right Holiday Rentals with a Hot Tub in Key West, FL

A holiday rental or Airbnb with a hot tub near the water in Key West, FL is ideal for a private evening soak.

Sunshine Suite Condo  Enjoy Outdoor Hot Tub & Pool - Key West, FL
9.4 508 reviews

Sunshine Suite Condo Enjoy Outdoor Hot Tub & Pool

apartment, Key West
Sunrise Suites Resort, Key West Fl U #408 2bdr2bth - Key West, FL
9.5 240 reviews

Sunrise Suites Resort, Key West Fl U #408 2bdr2bth

apartment, Key West
Living The Dream Key West Style - Key West, FL
10 62 reviews

Living The Dream Key West Style

houseboat, Stock Island
Beachside Resort & Residences - Key West, FL
8.2 4442 reviews

Beachside Resort & Residences

resort, Key West

Browse Holiday Rentals with a Spa in Key West, FL

Discover spa and spa bath access at these holiday rentals near the water in Key West, FL for waterside wellness at its best.

Ricky's Retreat - Truman @ Duval | Ideal Getaway! - Key West, FL
9.8 39 reviews

Ricky's Retreat - Truman @ Duval | Ideal Getaway!

apartment, Key West
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