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.

Hyatt Sunset Harbour Resort-prime Location On Key West!! - Key West, FL
8.6 589 reviews

Hyatt Sunset Harbour Resort-prime Location On Key West!!

resort, 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.
Poolside Cottage #411 - Key West, FL
9.8 237 reviews

Poolside Cottage #411

house, Key West
This Key West cottage, part of the Coconut Mallory Resort & Marina, enjoys a secluded waterfront location 4km from Smathers Beach and 5.6km from Duval Street.
Sleeping six, this self-catering property boasts a queen bed, pull-out queen sofa bed, and Murphy bed, plus a fully equipped kitchen, shared laundry facilities, and access to resort amenities including a pool, hot tub, and Gumbo's bar & grill.
Comfortable Condo With Pool, Private Balcony, & Beach Access - Key West, FL
8.6 141 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.
Boat Slip - Waterfront Condo - Key West Pool - Key West, FL
No reviews

Boat Slip - Waterfront Condo - Key West Pool

apartment, Key West
This waterfront condominium is situated in the Meadows district of Key West, approximately 1.6 kilometres from Duval Street and the Historic Seaport, with Bayview Park directly adjacent.
This 103 square metre apartment offers two bedrooms and two bathrooms, comfortably sleeping up to six guests with a maximum occupancy of eight, and features a private balcony, a communal heated swimming pool, a boat slip, and is pet-friendly for one dog up to 11.3 kilograms.

Best family friendly Key West, FL holiday rentals

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

Key West Villas - Key West, FL
9.8 808 reviews

Key West Villas

house, Key West
This charming house is situated in Old Town Key West, just a minute's walk from Duval Street and within a 10-minute walk of The Southernmost Point, the Ernest Hemingway Home and Museum, and Mallory Square. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The house offers spacious rooms with private bathrooms, small refrigerators, and microwaves, while apartments offer fully-equipped kitchens and seating areas. Guests can enjoy a heated pool, daily continental breakfast, free Wi-Fi, a guest launderette, and even rent bicycles to explore the charming streets of Key West.
Apartment ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
No reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Key West
This one-bedroom apartment is located within a resort complex in Key West, just a short distance from Duval Street and the attractions of Old Town. The apartment boasts a private balcony with pool views, a fully equipped kitchen, and a whirlpool tub, perfect for relaxing after a day of exploring the island.
Crawl To Duval W/ Hot Tub - Key West, FL
8.6 6 reviews

Crawl To Duval W/ Hot Tub

house, Key West
This Key West holiday home is centrally located, a 0.4km walk from South Beach and Fort Zachary Taylor State Park Beach, and less than 0.3km from the city centre.
This two-bedroom property offers 84 square metres of space, sleeping up to 11 guests and boasting a private hot tub, fully equipped kitchen, and free parking; nearby attractions include Higgs Beach, the Ernest Hemingway Home and Museum, and Duval Street.
122 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.4 20 reviews

122 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
This Key West condo is situated near Smather's Beach, a short walk from the beach and approximately 2.4 kilometres from Key West's downtown area, offering easy access to shops, restaurants and bars.
This 122 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a private balcony, swimming pool, Jacuzzi, fitness centre, and free Wi-Fi; shared amenities such as tennis courts are also available within the complex.

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.

**The Osprey's Nest** Condo & Pool + Last Key White Glove Service... - Key West, FL
9.4 39 reviews

**The Osprey's Nest** Condo & Pool + Last Key White Glove Service...

apartment, Key West
This Key West seaside apartment, situated 1.9km from Smathers Beach and 1.9km from the Fort East Martello Museum, offers stunning ocean views.
The 74 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, private balcony, free Wi-Fi, plus access to a swimming pool, jacuzzi, fitness centre, and tennis court.
Orchid Suite @ The Old Town Villas, Steps From - Key West, FL
9.5 109 reviews

Orchid Suite @ The Old Town Villas, Steps From

apartment, Key West
This bi-level suite is located in a prime Key West district, providing easy access to local attractions and situated conveniently within the city.
This stylish apartment sleeps up to four guests, featuring two distinct upstairs sleeping areas with queen beds, a downstairs living space with air conditioning and entertainment systems, and includes amenities such as Wi-Fi, a kitchen with essential appliances, and a swimming pool, with pets welcome.
Ibis Bay Resort - Key West, FL
8.0 3815 reviews

Ibis Bay Resort

resort, Key West
Ibis Bay Beach Resort is a Key West hotel situated on the north side, offering a tranquil escape yet within 5km of attractions such as Duval Street, Mallory Square, and Regal Key West.
This family-friendly hotel boasts a private beach, an outdoor pool, and convenient access to a marina for water sports, plus on-site amenities including a restaurant, bar, and room service.
Papaya Place By Avantstay - Key West, FL
9.0 109 reviews

Papaya Place By Avantstay

house, Key West
Papaya Place by AvantStay is a short walk from Smathers Beach in Key West, offering easy access to the beach and nearby attractions. The property has received very good user ratings, with excellent scores for location and cleanliness.
The two-bedroom house, spanning 122 square metres, provides ample space for a comfortable stay. Guests can enjoy a range of amenities, including a private balcony, a shared pool and hot tub, a fully equipped kitchen, free parking, air conditioning, and access to a fitness centre and tennis court.

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.

Kwss403 Sunrise Suites Tierra Bomba Suite #403 - Key West, FL
9.0 280 reviews

Kwss403 Sunrise Suites Tierra Bomba Suite #403

house, Key West
Sunrise Suites Tierra Bomba Suite #403 is located in Key West, Florida, just a short distance from Key West International Airport and a few miles from the Southernmost Point, making it a convenient base for exploring the island. The apartment has been rated very good for its overall experience, and excellent for its location and cleanliness.
The two-bedroom apartment is spacious, with a floor area of 74 square metres and a capacity for up to six guests. The property offers a range of amenities, including a swimming pool, jacuzzi, fitness centre, tennis court, and parking, as well as a fully equipped kitchen and a terrace or balcony for enjoying the Key West sunshine.
J Ferrara - Updated Studio, Pool, Walk To Duval St - Key West, FL
8.9 27 reviews

J Ferrara - Updated Studio, Pool, Walk To Duval St

apartment, Key West
This Key West studio flat is situated in historic Bahama Village, 0.4 km from Duval Street, 1.6 km from Fort Zachary Taylor State Park, and 3.2 km from Smathers Beach.
The self-catering unit sleeps two, features artwork by James Ferrara, includes a kitchenette with microwave and fridge, and offers access to a shared swimming pool and parking.
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.
~ Petite Maison ~ 2 King Ensuite Bedrooms On A Quiet Lane Near Duval Street. - Key West, FL
9.9 470 reviews

~ Petite Maison ~ 2 King Ensuite Bedrooms On A Quiet Lane Near Duval Street.

apartment, Key West
This Key West house, situated on the southern end of Duval Street, is within walking distance of cafes, nightclubs, the Southernmost Point buoy, and the Key West Butterfly and Nature Conservatory.
The property offers four ensuite bedrooms sleeping up to eight guests, a private saline pool (seasonally heated for a fee), a modern kitchen with stainless steel appliances, and a dog is allowed (up to 25 lbs, with restrictions).

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.

Charming Key West By The Sea - Key West, FL
9.7 24 reviews

Charming Key West By The Sea

apartment, Key West

Best Key West, FL holiday rentals with a balcony

The Green Hour | 5br Casa Marina Estate W/ Private Pool & Outdoor Kitchen - Key West, FL
10 52 reviews

The Green Hour | 5br Casa Marina Estate W/ Private Pool & Outdoor Kitchen

apartment, Key West
**Belle Of The Beach @ Casa East** Beach House + Last Key White Glove Service... - Key West, FL
10 87 reviews

**Belle Of The Beach @ Casa East** Beach House + Last Key White Glove Service...

apartment, Key West
Welcome To Poseidon Too - A Newly, Completely Renovated Condo @ Sunrise Suites! - Key West, FL
10 25 reviews

Welcome To Poseidon Too - A Newly, Completely Renovated Condo @ Sunrise Suites!

apartment, Key West
Southern Palms - Key West, FL
No reviews

Southern Palms

house, 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.

**Duke Of Catherine @ Duval** Home & Hot Tub + Last Key White Glove Service... - Key West, FL
10 42 reviews

**Duke Of Catherine @ Duval** Home & Hot Tub + Last Key White Glove Service...

apartment, Key West
Paradise Place By Avantstay Key West Old Town Condo W/ Shared Pool - Key West, FL
No reviews

Paradise Place By Avantstay Key West Old Town Condo W/ Shared Pool

apartment, Key West
Carey's Corner | Updated Studio With Heated Pool - Key West, FL
8.6 47 reviews

Carey's Corner | Updated Studio With Heated Pool

studio, Key West
13 M² Apartment ∙ 1 Bedroom ∙ 2 Guests - Key West, FL
No reviews

13 M² Apartment ∙ 1 Bedroom ∙ 2 Guests

apartment, 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.

Dog-friendly Key West Cottage With Private Hot Tub & Unbeatable Location - Key West, FL
9.0 187 reviews

Dog-friendly Key West Cottage With Private Hot Tub & Unbeatable Location

apartment, Key West
Kwss210 Sunrise Suites Bonaire Suite #210 - Key West, FL
8.7 128 reviews

Kwss210 Sunrise Suites Bonaire Suite #210

apartment, Key West
The Grande Vista - Key West, FL
9.1 203 reviews

The Grande Vista

house, Key West
Kwss112 Sunrise Suites Cozumel Suite #112 - Key West, FL
8.7 208 reviews

Kwss112 Sunrise Suites Cozumel Suite #112

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.

The Elizabeth Suite | 1 Bedroom Condo, Shared Pool - Key West, FL
9.6 11 reviews

The Elizabeth Suite | 1 Bedroom Condo, Shared Pool

apartment, Key West
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