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.

Casa Papa Del Mar Ocean Front 1800 Atlantic Spectacular View And Island Charm - Key West, FL
9.5 261 reviews

Casa Papa Del Mar Ocean Front 1800 Atlantic Spectacular View And Island Charm

apartment, Key West
This beachfront apartment is conveniently located a short walk from Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, with Duval Street and Mallory Square just a short drive away. The apartment has received excellent ratings for its cleanliness, location and overall experience.
This two-bedroom apartment offers 139 square metres of space, comfortably accommodating up to six guests. The apartment features a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a sauna, a fitness centre, a tennis court, and parking.
Harbor House Penthouse- A - Key West, FL
10 31 reviews

Harbor House Penthouse- A

apartment, Key West
This Key West City Centre condo, situated in the Historic District, offers easy access to Mallory Square and its renowned sunset celebrations.
This five-bedroom, four-bathroom apartment boasts a spacious 209 square metre floor area, sleeping up to twelve guests and featuring a fully equipped kitchen, high-speed internet, and a large terrace.
Walking On Sunshine By Last Key Realty - Key West, FL
10 1 review

Walking On Sunshine By Last Key Realty

apartment, Key West
Walking on Sunshine, a Key West apartment, is conveniently located 1.9km from Key West International Airport and within a short drive of Rest Beach, Smathers Beach, Higgs Beach, Duval Street, Mallory Square, and the Ernest Hemingway Home and Museum.
This 126 square metre, two-bedroom, two-bathroom flat sleeps up to 11 guests and boasts a fully equipped kitchen, swimming pool, jacuzzi, spa, fitness centre, tennis court, parking, sea views, free Wi-Fi, and an elevator.
3-bedroom House Boat In Tranquil Key West With Ac - Key West, FL
No reviews

3-bedroom House Boat In Tranquil Key West With Ac

apartment, Key West
This pet-friendly houseboat in Key West is located a 6-minute walk from Bayview Park and a 15-minute walk from the Studios of Key West.
This 139 square metre floating home offers accommodation for up to 10 guests with 3 bedrooms, 2.5 bathrooms, a full kitchen, and on-site laundry, plus a barbecue and access to water sports equipment.

Best family friendly Key West, FL holiday rentals

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

Luxury Condo-free Parking,wifi,bikes,big Pool,walk To Restaurants, Beach  Chairs - Key West, FL
9.5 279 reviews

Luxury Condo-free Parking,wifi,bikes,big Pool,walk To Restaurants, Beach Chairs

apartment, Stock Island
This apartment is located on Stock Island, just under 800 metres from Key West and 2.4 kilometres from Key West International Airport, offering a peaceful escape from the hustle and bustle of the city. It has been rated excellent for cleanliness and user experience and very good for location.
The apartment has 102 square metres of living space with two bedrooms and can accommodate up to six guests. It comes with a range of amenities, including a swimming pool, jacuzzi, fitness centre, free bike rentals, and access to a nearby golf course and boat ramp.
Apartment ∙ 8 Bedrooms ∙ 20 Guests - Key West, FL
No reviews

Apartment ∙ 8 Bedrooms ∙ 20 Guests

apartment, Key West
This luxurious eight-bedroom Key West property, situated in the Modern Keys district, offers convenient access to Key Haven and Stock Island boat ramps.
The spacious residence boasts an open-plan design, accommodating up to 20 guests with eight bathrooms, a private pool, grilling area, fully equipped kitchen, high-speed internet, and parking for four vehicles plus a boat trailer.
Apartment ∙ 4 Bedrooms ∙ 12 Guests - Key West, FL
No reviews

Apartment ∙ 4 Bedrooms ∙ 12 Guests

apartment, Key West
Commodore's Cove, a ground-floor apartment in Key West's Old Town, offers easy walking access to numerous attractions.
This four-bedroom, four-bathroom dwelling sleeps twelve guests, boasting a full kitchen with stainless steel appliances, private parking, free Wi-Fi, and a shared garden, plus the option to rent the adjoining Commodore's Compound for larger groups.
Seagull Suite | Inviting Studio, Steps From Duval - Key West, FL
No reviews

Seagull Suite | Inviting Studio, Steps From Duval

apartment, Key West
This one-bedroom flat in Key West is situated a mere 160 metres from the Southernmost Point and 480 metres from South Beach, with Duval Street's shops and restaurants easily accessible on foot.
This pet-friendly studio apartment accommodates four guests with a queen bed and a queen sofa bed, offering a kitchenette, air conditioning, complimentary WiFi, and access to shared hot tubs.

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.

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.
Eyw Getaway - Key West, FL
10 85 reviews

Eyw Getaway

apartment, Key West
This Sunrise Suites condo is situated 1.6km from Key West International Airport, 2.4km from the beach, and 5.6km from Duval Street.
The two-bedroom, two-bathroom apartment sleeps six guests and boasts a fully equipped kitchen, in-unit laundry, a private balcony with sunset views, and access to a heated pool, hot tub, tennis court, and fitness centre; free on-site parking is also provided.
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.
Ambrosia At Azul Mansion Key West - Key West, FL
8.0 2 reviews

Ambrosia At Azul Mansion Key West

house, Key West
Ambrosia at Azul Mansion, a Key West apartment, is centrally located less than 0.6km from the city centre, a 12-minute walk from South Beach, and within 1.9km of Duval Street, the Ernest Hemingway Home and Museum, and Mallory Dock.
This self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes free Wi-Fi, on-site parking, a swimming pool, and a terrace; nearby attractions include the beaches and various Key West sights.

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.

Casa Key West-pool & Free Parking - Key West, FL
No reviews

Casa Key West-pool & Free Parking

house, Key West
Holiday house. You will be located in Key West.
Services and facilities: a swimming pool, a terrace and free parking. This house also has air conditioning!
Waterfront Home In Key Cove Landings - Key West, FL
9.6 203 reviews

Waterfront Home In Key Cove Landings

apartment, Key West
This Key West house is located in Northside Resort, just under 5km from Duval Street and Mallory Square, offering easy access to the island's attractions. The property has received excellent ratings for location, cleanliness and overall user experience.
The house has 4 bedrooms and covers 218 square metres. Guests can enjoy a private pool, a fully equipped kitchen, a terrace, a garden, and a barbecue grill, perfect for relaxing and enjoying the Key West sunshine.
Aug.-sept. Special@125.lodging Only 129. + Extras. From.8-17 To 9-30 - Key West, FL
9.0 198 reviews

Aug.-sept. Special@125.lodging Only 129. + Extras. From.8-17 To 9-30

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.
Comfortable Condo With Pool, Private Balcony, & Beach Access - Key West, FL
8.6 140 reviews

Comfortable Condo With Pool, Private Balcony, & Beach Access

apartment, Key West
This Key West condo offers a prime waterfront position in the Beachside district, providing direct access to the Florida Keys Overseas Heritage Trail and situated 800 metres from Smathers Beach and Indigenous Park, 3.2 kilometres from the Ernest Hemingway Home and Museum, and less than 4.8 kilometres from Mallory Square.
This spacious 126 square metre apartment, accommodating up to six guests, features two bedrooms and two bathrooms, along with central air conditioning, a full kitchen, private washer and dryer, three cable televisions, complimentary WiFi, and a private balcony with seating.

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.

High Tide In Key West - Key West, FL
9.0 207 reviews

High Tide In Key West

house, Key West

Best Key West, FL holiday rentals with a balcony

Pool View Two Bedroom Residence - Key West, FL
9.6 4 reviews

Pool View Two Bedroom Residence

apartment, Key West
Chicken Run At Custom House Inn | Unbeatable Location! - Key West, FL
9.8 11 reviews

Chicken Run At Custom House Inn | Unbeatable Location!

apartment, Key West
Kate's Krawl Off Duval ~ 1 Br/1 Ba Private Home/outdoor Deck/steps To Duval! - Key West, FL
9.6 93 reviews

Kate's Krawl Off Duval ~ 1 Br/1 Ba Private Home/outdoor Deck/steps To Duval!

apartment, Key West
La Brisa - Ocean Views Across From Smathers Beach - Key West, FL
10 197 reviews

La Brisa - Ocean Views Across From Smathers Beach

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.

Sparkling Community Pool And Cozy Living Space - Charming Retreat - Key West, FL
No reviews

Sparkling Community Pool And Cozy Living Space - Charming Retreat

apartment, Key West
Harbor House Penthouse- B - Key West, FL
9.5 6 reviews

Harbor House Penthouse- B

house, Key West
Conch Cove | Private Oasis With Heated Pool! - Key West, FL
9.4 29 reviews

Conch Cove | Private Oasis With Heated Pool!

apartment, Key West
Abaco - Large Waterfront 2x2 End Unit With Boat Slip - Key West, FL
8.8 5 reviews

Abaco - Large Waterfront 2x2 End Unit With Boat Slip

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.

Anchor Drop Key West - Key West, FL
No reviews

Anchor Drop Key West

house, Key West
Beachside Resort & Residences - Key West, FL
8.2 4442 reviews

Beachside Resort & Residences

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

One Bedroom Suite | Beachside Resort

apartment, Key West
Caribbean Conch 5 Minutes To Smathers Beach & 10 Minute Bike Downtown - Value - Key West, FL
9.2 158 reviews

Caribbean Conch 5 Minutes To Smathers Beach & 10 Minute Bike Downtown - Value

apartment, 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.

Duval Balcony Spanky's Retreat - Key West, FL
9.8 893 reviews

Duval Balcony Spanky's Retreat

apartment, Key West
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