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?

Leaward Isle Island Retreat , At Mine | Lovely Suite Steps From Duval Street and Flor De Cana ~ Adults Only - Poolview Queen Suite At Azul Mansion are among 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?

Among the Airbnbs in Key West, FL, At Mine | Lovely Suite Steps From Duval Street , At Mine | Key West Suite Steps From Duval Street and Duval Balcony - Street Suite are the most popular ones.

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?

Leaward Isle Island Retreat , At Mine | Lovely Suite Steps From Duval Street and Flor De Cana ~ Adults Only - Poolview Queen Suite At Azul Mansion 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?

The best rentals for families and kids in Key West, FL are Leaward Isle Island Retreat , Key West Villas and Sunset South: First Floor 2 Bedroom 1 Bath Condo At Bayfront Suites & Marina .

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.

Key West, FL Holiday Rentals & Airbnb

10 8 reviews

Key West, FL

21/12 – 18/01

£419/nighttotal: £11732 (28 )

Tropical Properties Vacation Rental - Key West

4 1

apartment , Key West

This Old Town Key West house is ideally located less than 1 km from Duval Street, the Key West Firehouse Museum, and the Ernest Hemingway Home and Museum, and under 2 km from South Beach.
Sleeping eight guests, this property boasts three bedrooms, a sofa bed, two bathrooms, a private pool, a fenced garden with barbecue, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher.

9.7 25 reviews

Key West, FL

02/07 – 07/07

£334/nighttotal: £1670 (5 )

Colony Sunset- Bright And Airy Cottage

1 2

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.

9.5 2 reviews

Key West, FL

22/08 – 29/08

£163/nighttotal: £1141 (7 )

The Mallory Suite At Inn On Fleming Key West!

1 2

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.

Key West, FL

13/09 – 27/09

£231/nighttotal: £3234 (14 )

Casa Atlantica One Bedroom

1 2

apartment , Key West

Casa Atlantica, a Key West apartment, is situated 2km from Key West International Airport and within a few kilometres of beaches such as Rest Beach, Higgs Beach, and Smathers Beach, and attractions including the Ernest Hemingway Home and Museum and Duval Street.
This 86 square metre, one-bedroom flat sleeps three guests and features a fully equipped kitchen with dishwasher, a balcony, free Wi-Fi, and on-site parking, plus a tennis court for guest use.

9.6 394 reviews

Key West, FL

17/10 – 24/10

£619/nighttotal: £4333 (7 )

Pete's East Cottage: Cypress East Cottage Steps From Duval

1 2

cottage , Key West

This charming cottage is situated in Key West's Old Town district, just a short walk from the popular Banana Cafe Restaurant and Coffee and Tea house. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The cottage offers a unique blend of original Key West shotgun home charm and contemporary design elements, creating a spacious and inviting space. Guests can enjoy a private outdoor area, a shared pool with a waterfall, and a loft bedroom with a unique glass railing, offering a stunning view.

9.0 28 reviews

Key West, FL

13/09 – 27/09

£209/nighttotal: £2926 (14 )

The Caroline Suite | 1 Bedroom Condo W/shared Pool

1 2

apartment , Key West

This Key West Historic District flat is less than 1.6km from Duval Street, the Ernest Hemingway Home and Museum, and South Beach, offering easy access to Key West's attractions.
The 33-square-metre self-catering apartment sleeps four, featuring a bedroom, bathroom, kitchen with fridge and microwave, air conditioning, a private pool, and in-unit laundry facilities.

8.3 4147 reviews

Key West, FL

20/06 – 27/06

£494/nighttotal: £3458 (7 )

Beachside Resort & Residences

2 7

resort , Key West

The Key West Marriott Beachside Hotel is located on the beach in Key West, just under 1.2 miles from Key West Airport and a short shuttle ride from the city centre. The hotel has consistently received very good ratings for its location, cleanliness, and overall guest experience.
The hotel offers a range of accommodation options, from comfortable rooms to suites with upgraded amenities. Guests can enjoy a private sandy beach, a swimming pool, a hot tub, a fitness centre, a spa, and a choice of dining options, including a steakhouse and a bar.

9.4 2561 reviews

Key West, FL

25/07 – 27/07

£359/nighttotal: £718 (2 )

Santa Maria Suites Resort

1 3

resort , Key West

The Santa Maria Suites Resort is located just one block from the Atlantic Ocean and Duval Street, placing you right in the heart of Key West's lively atmosphere. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience.
The accommodation offers spacious suites with full kitchens and 48-inch flat-screen TVs, ideal for a comfortable stay. Guests can enjoy a range of amenities including two outdoor heated pools, a spa, a fitness centre, and a restaurant serving Japanese cuisine.

9.5 2 reviews

Key West, FL

02/09 – 05/09

£288/nighttotal: £864 (3 )

The Cornish Suite At Inn On Fleming Key West!

2 2

house , Key West

THE CORNISH SUITE at the Inn on Fleming Key West is centrally located, less than 1.6km from Mallory Square and Duval Street, and a short walk from Simonton Street Beach.
This 31 square metre self-catering property sleeps four guests in two bedrooms and one bathroom, and offers free Wi-Fi, on-site parking, a swimming pool, and a terrace; nearby attractions include the Ernest Hemingway Home and Museum and Key West International Airport (3km).

9.2 322 reviews

Key West, FL

14/10 – 16/10

£157/nighttotal: £314 (2 )

Signature King At Beachside Resort

1 2

apartment , Key West

Beachside Resort & Residences, a guesthouse in Key West, Florida, boasts a seven-acre beachfront location on the Gulf of Mexico, offering easy access to Key West's attractions.
This self-catering unit features a king-size bed, private bathroom, and access to a resort pool, hot tub, fitness centre, and on-site restaurants including Tavern N Town and Chicken Walk, accommodating up to two guests.

9.9 14 reviews

Key West, FL

13/09 – 27/09

£150/nighttotal: £2100 (14 )

Ibis Suite | Bright Hideaway, Hot Tubs, Near Duval

1 2

apartment , Key West

The Ibis Suite is located a short walk from Duval Street in Key West, Florida, one block from the Southernmost Point buoy and three blocks from South Beach.
This pet-friendly apartment sleeps four guests in two queen-size beds, and features a kitchenette with fridge, freezer, and microwave, plus a shared hot tub and laundry facilities; contactless check-in is available.

8.4 1350 reviews

Key West, FL

27/06 – 28/06

£1441/nightfor 1 night

The Reach Key West, Curio Collection By Hilton

2 7

resort , Key West

The Reach Key West, Curio Collection by Hilton is located in Old Town, Key West, just 1.5 kilometres from Duval Street, a lively area with a wide selection of restaurants, shops, and nightlife. The resort has received very good ratings for both its location and overall experience, with good marks for cleanliness.
This hotel offers a range of rooms, including suites and studios, all with private balconies offering views of the ocean or the town. Guests can enjoy a private beach, a swimming pool, a spa, a fitness centre, and a variety of activities like scuba diving, snorkelling, and deep-sea fishing.

Best family friendly Key West, FL holiday rentals

Among the 3183 accommodations in Key West, FL, here are the 4 best family friendly rentals

9.5 2 reviews

Key West, FL

21/12 – 18/01

£354/nighttotal: £9912 (28 )

Reynolds Paradise

1 1

apartment , Key West

This charming house is situated in Old Town Key West, just under a kilometre from Duval Street and the Key West Firehouse Museum. It enjoys an excellent location rating, with guests praising its proximity to local attractions and the beach.
The house has two bedrooms and can accommodate up to six guests. It is fully equipped with modern amenities, including a kitchen with a dishwasher, a private garden, and a jacuzzi for relaxation.

9.5 30 reviews

Key West, FL

02/07 – 07/07

£784/nighttotal: £3920 (5 )

127 M² House ∙ 2 Bedrooms ∙ 6 Guests

2 2

house , Key West

This Old Town Key West property is situated just one block from Duval Street's entertainment and four blocks from the Atlantic Ocean.
This two-bedroom, two-bathroom house boasts 137 square metres of living space, featuring an open-plan layout with Key West décor, a private pool (with optional heating, subject to seasonal availability), a lush tropical garden including an orchid house, and parking; it comfortably sleeps six guests.

10 5 reviews

Key West, FL

20/06 – 27/06

£265/nighttotal: £1855 (7 )

Apartment ∙ 1 Bedroom ∙ 4 Guests

1 1

apartment , Key West

This Key West condo is situated within a resort offering convenient access to Duval Street's attractions via a complimentary shuttle service.
The one-bedroom apartment, sleeping up to four guests, boasts a king-size bed, queen-size sleeper sofa, fully equipped kitchen with stainless steel appliances, en-suite bathroom with whirlpool tub, private balcony with resort pool views, and a private washer/dryer.

Key West, FL

25/07 – 27/07

£463/nighttotal: £926 (2 )

Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 3

apartment , Key West

This Key West apartment, conveniently located near Key West International Airport, offers easy access to the island's attractions whilst enjoying tranquil salt marsh views.
The two-bedroom, two-bathroom flat sleeps six guests comfortably, featuring a fully equipped kitchen, in-unit laundry, private balcony, and guaranteed parking; nearby attractions include the airport.

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.

10 2 reviews

Key West, FL

21/12 – 18/01

£333/nighttotal: £9324 (28 )

Cozy Spot Next To Duval With Swim Spa - 2bed/2bath

2 1

apartment , Key West

This Key West Historic District flat is located half a block from Duval Street, less than 0.3 kilometres from the Ernest Hemingway Home and Museum, and close to Mallory Square and the Southernmost Point buoy.
The two-bedroom, two-bathroom apartment sleeps six, features a full kitchen with dishwasher, a shared swimming pool, and is available for monthly rentals, offering easy access to numerous restaurants and shops.

9.5 86 reviews

Key West, FL

20/06 – 27/06

£231/nighttotal: £1617 (7 )

Poolside Suite With Direct Pool Access

1 2

apartment , Key West

This luxurious Key West apartment, at the Beachside Resort on the Gulf of Mexico, offers direct access to a resort pool and is within easy reach of the award-winning Tavern N Town restaurant.
The one-bedroom, one-bathroom flat sleeps four, boasts a king-size bed, fully equipped kitchen with stainless steel appliances, private balcony with pool views, a stackable washer/dryer, and access to resort amenities including a heated pool, hot tub, and fitness centre.

9.0 3 reviews

Key West, FL

22/08 – 29/08

£230/nighttotal: £1610 (7 )

The Geiger Suite At Inn On Fleming Key West!

2 2

house , Key West

THE GEIGER SUITE at the Inn on Fleming Key West offers a central location, a short walk from Simonton Street Beach and the Ernest Hemingway Home and Museum, and under 3.2km from Key West International Airport.
This self-catering property boasts a 32 square metre floor area, comprising two bedrooms, one bathroom, and accommodating up to four guests, with amenities including a swimming pool, tennis court, free parking, and Wi-Fi.

8.8 188 reviews

Key West, FL

17/10 – 24/10

£443/nighttotal: £3101 (7 )

Sandpiper On The Ocean

2 2

house , Key West

Sandpiper on the Ocean, a Key West apartment, offers superb beachfront proximity, being a 4-minute walk from Smathers Beach and within 2.6km of the Southernmost Point and Ernest Hemingway Home.
This two-bedroom, two-bathroom flat sleeps families or groups, boasting a fully equipped kitchen, private balcony with ocean views, on-site parking, a swimming pool, Jacuzzi, and complimentary Wi-Fi; tour organisation services are also available.

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?
Leaward Isle Island Retreat, At Mine | Lovely Suite Steps From Duval Street and Flor De Cana ~ Adults Only - Poolview Queen Suite At Azul Mansion are among 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?
Among the Airbnbs in Key West, FL, At Mine | Lovely Suite Steps From Duval Street, At Mine | Key West Suite Steps From Duval Street and Duval Balcony - Street Suite are the most popular ones.
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?
Leaward Isle Island Retreat, At Mine | Lovely Suite Steps From Duval Street and Flor De Cana ~ Adults Only - Poolview Queen Suite At Azul Mansion 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?
The best rentals for families and kids in Key West, FL are Leaward Isle Island Retreat, Key West Villas and Sunset South: First Floor 2 Bedroom 1 Bath Condo At Bayfront Suites & Marina.
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.

Destinations nearby

Best Key West, FL holiday rentals with a balcony

9.6 198 reviews

Key West, FL

02/09 – 05/09

£343/nighttotal: £1029 (3 )

Poolside Breeze Retreat

2 2

house , Key West

This apartment is located in Key West, just a short walk from Smathers Beach and Rest Beach, with Higgs Beach also within easy reach. The property has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This two-bedroom, two-bathroom flat spans 126 square metres and comfortably accommodates six guests. The apartment offers a range of amenities, including a fully equipped kitchen, a private balcony with sea views, a swimming pool, a Jacuzzi, a fitness centre, a tennis court, and free parking.

8.8 162 reviews

Key West, FL

14/10 – 16/10

£257/nighttotal: £514 (2 )

Elegant Condo With Entertainment & Private Parking - Great Central Location

1 2

apartment , Key West

This one-bedroom flat is centrally located in downtown Key West, offering an easy walk to Duval Street's entertainment and nearby beaches, and is situated within 0.5 kilometres of the Ernest Hemingway Home and Museum.
This 47 square metre condo accommodates up to four guests and provides private parking, free WiFi, and air conditioning, with water activities such as jet skiing and kayaking available nearby.

9.8 8 reviews

Key West, FL

20/06 – 27/06

£1050/nighttotal: £7350 (7 )

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

5 7

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.

9.2 151 reviews

Key West, FL

20/06 – 27/06

£360/nighttotal: £2520 (7 )

Ocean Hideaway On The Atlantic

2 2

house , Key West

Ocean Hideaway on the Atlantic, a Key West apartment, is situated near Smathers Beach, approximately 2.6 km from the Southernmost Point and 3.2 km from the Ernest Hemingway Home.
This 126 square metre self-catering flat boasts two bedrooms, two bathrooms, a living room, and a fully equipped kitchen, plus amenities including a swimming pool, jacuzzi, and tennis court; free Wi-Fi and on-site parking are also provided.

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.

8.8 216 reviews

Key West, FL

14/10 – 16/10

£228/nighttotal: £456 (2 )

Watch Sunsets From Your Deck, Shared Pool/hot Tub - Perfect For The Whole Family

2 2

apartment , Key West

This two-bedroom condo, situated on Key West's eastern edge, offers west-facing views ideal for watching the sunset and is located a few kilometres from Key West International Airport and the downtown area's attractions.
This 72-square-meter apartment accommodates up to four guests and features a private balcony with ocean views, a fully equipped kitchen, air conditioning, on-site swimming pool, jacuzzi, exercise room, and is dog-friendly.

9.9 34 reviews

Key West, FL

20/06 – 27/06

£285/nighttotal: £1995 (7 )

Soul Of Duval At Duval Street

2 2

apartment , Key West

This Key West apartment, situated on the 600 block of Duval Street, is a half block from Duval Street's main attractions, offering easy walking access to landmarks such as the Southernmost Point and Hemingway House.
The two-bedroom, one-bathroom flat sleeps four guests and boasts a fully equipped kitchen with luxury appliances, a private balcony overlooking the promenade, in-unit laundry facilities, and dedicated gated parking—a rare find in Key West's Old Town.

9.1 18 reviews

Key West, FL

24/07 – 25/07

£981/nightfor 1 night

Eleuthera - 2x2 Fully Updated Old Town Waterfront Corner Condo

2 4

house , Key West

This Key West condo, situated in Old Town, is a 17-minute walk from Rest Beach, 1.6 km from Higgs Beach, and 1.9 km from Key West International Airport, offering easy access to South Beach, the Ernest Hemingway Home and Museum, and Duval Street.
The 121-square-metre property features two bedrooms, two bathrooms, sleeps up to ten guests, includes a fully equipped kitchen, swimming pool, free Wi-Fi, on-site parking, and free bicycle use.

9.8 103 reviews

Key West, FL

17/10 – 24/10

£521/nighttotal: £3647 (7 )

Key West's Crown Jewel

2 2

apartment , Key West

This luxurious Key West penthouse, situated in the 1800 Atlantic Condominium development, offers direct access to Smather's Beach and is 2.4 kilometres from Key West's Old Town, providing easy access to shops, restaurants, and attractions.
The 121-square-metre property boasts two king-size bedrooms, two bathrooms, a fully equipped kitchen, and a stunning 10.7-metre balcony with breathtaking ocean views; it comfortably sleeps six guests and includes access to a swimming pool, jacuzzi, fitness centre, and reserved parking.

Holiday Rentals in Key West, FL

Best Holiday rentals and Airbnb offers in Key West, FL

Tropical Properties Vacation Rental - Key West

Colony Sunset- Bright And Airy Cottage

The Mallory Suite At Inn On Fleming Key West!

Casa Atlantica One Bedroom

Pete's East Cottage: Cypress East Cottage Steps From Duval

The Caroline Suite | 1 Bedroom Condo W/shared Pool

Beachside Resort & Residences

Santa Maria Suites Resort

The Cornish Suite At Inn On Fleming Key West!

Signature King At Beachside Resort

Ibis Suite | Bright Hideaway, Hot Tubs, Near Duval

The Reach Key West, Curio Collection By Hilton

Best family friendly Key West, FL holiday rentals

Reynolds Paradise

127 M² House ∙ 2 Bedrooms ∙ 6 Guests

Apartment ∙ 1 Bedroom ∙ 4 Guests

Apartment ∙ 2 Bedrooms ∙ 6 Guests

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

Cozy Spot Next To Duval With Swim Spa - 2bed/2bath

Poolside Suite With Direct Pool Access

The Geiger Suite At Inn On Fleming Key West!

Sandpiper On The Ocean

Frequently asked questions about holiday rentals in Key West, FL

Destinations nearby

Best Key West, FL holiday rentals with a balcony

Poolside Breeze Retreat

Elegant Condo With Entertainment & Private Parking - Great Central Location

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

Ocean Hideaway On The Atlantic

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

Watch Sunsets From Your Deck, Shared Pool/hot Tub - Perfect For The Whole Family

Soul Of Duval At Duval Street

Eleuthera - 2x2 Fully Updated Old Town Waterfront Corner Condo

Key West's Crown Jewel