Best Short term and Weekly rentals in Key West, FL
9.6 30 reviews
Key West, FL
29/12 – 31/12
A$903/nighttotal: A$1806 (2 )
King Room @ Historic Kw B&b
1 2
B&B , Key West
This Key West guesthouse is conveniently located near Mallory Square and Duval Street, offering easy access to Key West's attractions. The single-bedroom, one-bathroom property sleeps up to three guests and includes air conditioning, a swimming pool, and Wi-Fi; a complimentary breakfast may also be provided.
Key West, FL
29/12 – 27/01
A$426/nighttotal: A$12354 (29 )
Enjoy Your Paradise Stay
1 2
apartment , Key West
This peaceful family-friendly flat is located in a quiet Key West neighbourhood, a short distance from Duval Street and Mallory Square. This accommodation offers a tranquil escape with air conditioning, a swimming pool, a jacuzzi, and a fully equipped kitchen, and can host up to 15 guests.
Key West, FL
08/07 – 09/07
A$505/nightfor 1 night
Nightcap @ Speakeasy Inn Key West!
1 2
B&B , Key West
This detached house is located in Key West, a 4-minute walk from South Beach and 500 metres from the city centre, with the aquarium 18 minutes away on foot. This accommodation for 3 guests offers air conditioning, Wi-Fi, a kitchenette with a fridge and microwave, and a terrace, with sightseeing tours available nearby.
This Key West beachfront apartment is situated less than 3.2km from Duval Street and the Southernmost Point, and under 4.8km from the Ernest Hemingway Home and Museum and Mallory Square. This 139 square metre property sleeps six, boasting three bedrooms, two bathrooms, a fully equipped kitchen, and access to a swimming pool, jacuzzi, sauna, fitness centre, and tennis court.
9.1 233 reviews
Key West, FL
01/08 – 08/08
A$1119/nighttotal: A$7833 (7 )
Commodore Compound
4 11
apartment , Key West
Commodore Compound, a centrally located Key West apartment, is less than 0.8 km from Simonton Street Beach, Mallory Dock, and the Key West Aquarium, and under 5 km from Key West International Airport. This eight-bedroom property, perfect for large groups, boasts a fully equipped kitchen, in-unit laundry, private entrance, Jacuzzi, terrace, garden, parking, and free Wi-Fi; nearby attractions include the Key West Butterfly and Nature Conservatory.
9.8 421 reviews
Key West, FL
01/08 – 08/08
A$3307/nighttotal: A$23149 (7 )
Downtown Retreat - A++ Location W/ Private Heated Pool/hot Tub
6 11
apartment , Key West
This Key West Historic District villa is located steps from the San Carlos Institute and Duval Street, within a 2.4km radius of the Ernest Hemingway Home and Museum and Mallory Square. The property boasts a private pool, spa tub, BBQ grills, a fully equipped kitchen including a fridge and microwave, and allows pets; check-out is at 10:00.
9.9 16 reviews
Key West, FL
01/10 – 01/11
A$197/nighttotal: A$6107 (31 )
Great Old Town Key West Cottage
1 2
apartment , Key West
This charming cottage is situated in Old Town Key West, a short 1 km walk from the White Street Pier and the lively Duval Street. It has received excellent ratings for location, cleanliness, and overall user experience. The cottage offers a comfortable and functional space, ideal for couples or solo travellers. The home is fully equipped with modern amenities, including a kitchen, a washer and dryer, high-speed internet, and a desk for those who need to work remotely.
Key West, FL
29/12 – 27/01
A$574/nighttotal: A$16646 (29 )
Nate's Place In Key West
3 2
apartment , Key West
This Key West flat is situated in the Midtown district, a short walk from White Street and the Florida Keys Beaches, and offers convenient street parking. This three-bedroom, two-bathroom property spans 113 square metres and accommodates up to five guests, featuring a private garden with a hammock and an expansive outdoor deck.
8.9 31 reviews
Key West, FL
23/11 – 29/11
A$1321/nighttotal: A$7926 (6 )
Key West’s Atlantic Sunrise Penthouse – Upgraded C
3 6
apartment , Key West
This apartment is located on Smathers Beach, just 2.4 kilometres from the southernmost point of Duval Street and 4 kilometres from Mallory Square, offering a peaceful retreat from the bustling city centre. The apartment has received very good ratings for user experience, cleanliness and location. The apartment is spacious, with three bedrooms and three bathrooms, spanning 195 square metres and accommodating up to eight guests. It offers a range of amenities, including a swimming pool, jacuzzi, fitness centre, and a private balcony with stunning ocean views.
9.2 86 reviews
Key West, FL
11/07 – 18/07
A$444/nighttotal: A$3108 (7 )
Summer Discounts-conch Republic Consul Cottage.-pool-historic District-parking
1 4
cottage , Key West
This charming cottage is located in the heart of Key West's Historic District, just a kilometre from the Key West Firehouse Museum and Duval Street, and within a 1.5 kilometre walk of the Florida Keys Beaches and the Ernest Hemingway Home and Museum. It has been rated excellent by previous guests. The cottage has one bedroom and one bathroom and can accommodate up to four guests. Amenities include a swimming pool, a terrace, a garden, and free Wi-Fi, as well as a fully equipped kitchen, a washing machine, and a coffee maker.
8.9 135 reviews
Key West, FL
06/07 – 09/07
A$584/nighttotal: A$1752 (3 )
Sunrise Suites Saint Lucia Suite #201
2 6
apartment , Key West
Sunrise Suites Saint Lucia Suite #201 is located in Key West, Florida, just 1 kilometre from Key West International Airport, 6.4 kilometres from the Southernmost Point and 7.4 kilometres from Ernest Hemingway Home and Museum and Duval Street. The property has received very good user ratings, with excellent ratings for its location and cleanliness. The two-bedroom suite is 74 square metres and can accommodate up to 6 guests. It features a fully equipped kitchen, a private balcony, air conditioning, free Wi-Fi, a swimming pool, a jacuzzi, a tennis court, a fitness centre and parking.
8.9 3111 reviews
Key West, FL
02/07 – 03/07
A$733/nightfor 1 night
Authors Key West Guesthouse
2 5
B&B , Key West
Authors Key West Guesthouse is located in Key West, just under 2km from Higgs Beach and a short walk from Duval Street, the heart of the island's lively nightlife and shopping scene. The guesthouse has received very good ratings for its location, cleanliness, and overall experience. The guesthouse offers a range of amenities including a swimming pool, a Jacuzzi, a garden, and a terrace. Guests can enjoy a continental breakfast, free Wi-Fi, and concierge services to help plan their activities.
Best family friendly Key West, FL Short term rentals
Among the 2380 accommodations in Key West, FL, here are the 4 best family friendly rentals
9.6 344 reviews
Key West, FL
02/07 – 05/07
A$851/nighttotal: A$2553 (3 )
The Bartlum-luxurious Studio
1 4
studio , Key West
This Key West apartment is perfectly situated in the heart of the island, just a short walk from the lively Duval Street and the beautiful Simonton Street Beach. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The apartment offers a comfortable living space for up to four guests, with a separate bedroom for privacy. Amenities include a fully equipped kitchen, air conditioning, a terrace or balcony, and a garden, making it ideal for a relaxing and enjoyable stay.
10 2 reviews
Key West, FL
21/12 – 18/01
A$674/nighttotal: A$18872 (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.
10 2 reviews
Key West, FL
01/10 – 01/11
A$438/nighttotal: A$13578 (31 )
Cozy Spot Next To Duval With Swim Spa - 2bed/2bath
2 2
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.
9.6 117 reviews
Key West, FL
02/07 – 03/07
A$5292/nightfor 1 night
Beautiful Sanctuary Private Island Connected By Bridge To Key West
9 5
apartment , Stock Island
This waterfront property is situated on Stock Island, just a short distance from the Key West Tropical Forest and Botanical Garden and Smathers Beach, offering easy access to the island's attractions. The house has received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay. The spacious nine-bedroom home provides ample room for large groups or families, spanning over 743 square metres. Guests can enjoy a range of amenities, including a private pool and spa tub, a fully equipped kitchen, a tennis court, and a barbecue grill, offering both relaxation and entertainment options.
Best Key West, FL short term rentals with a balcony
9.8 14 reviews
Key West, FL
24/07 – 25/07
A$1329/nightfor 1 night
Sombreroreef Light Suite
1 4
apartment , Key West
This Key West Historic District flat is ideally located just steps from Duval Street and the Ernest Hemingway Home and Museum, with Southernmost Point and beaches within a 1.6km radius. The 48 square metre property comprises two bedrooms, one bathroom, and sleeps four, boasting a fully equipped kitchen, private fenced yard, on-site parking, and a balcony; a washing machine is also provided for added convenience.
9.4 113 reviews
Key West, FL
28/06 – 02/07
A$529/nighttotal: A$2116 (4 )
Key West Condo Close To The Ocean. 1 Mile To Smathers & 3 Miles To Duval St.
2 4
apartment , Key West
This two-bedroom apartment, ideal for families or groups of up to six, is located in Key West, just 2 kilometres from the Fort East Martello Museum and Gallery and 3 kilometres from Smathers Beach. The 74 square metre apartment offers a fully equipped kitchen, a private balcony, a swimming pool, a fitness centre and a jacuzzi, perfect for a relaxing getaway.
Key West, FL
24/07 – 25/07
A$932/nightfor 1 night
Ocean Front Suite | Beachside Resort
1 4
apartment , Key West
This one-bedroom flat offers a luxury resort setting on seven acres in north Key West, overlooking the Gulf of Mexico and situated just 1.6 kilometres from Duval Street attractions. Guests can enjoy a private balcony with sea views, a fully-equipped kitchen with stainless-steel appliances, and access to a heated resort pool and hot tub, with on-site dining and shuttle services also available.
Key West, FL
24/07 – 25/07
A$1039/nightfor 1 night
Ocean Front Suite With Direct Beach Access
1 4
apartment , Key West
This condominium is located on the northern edge of Key West, directly on the beach, offering a 10-minute drive to Duval Street and proximity to the Ernest Hemingway Home and Museum and the Southernmost Point. This one-bedroom, two-bathroom apartment accommodates up to four guests, featuring direct sandy beach access via a private spiral staircase, a fully equipped kitchen with stainless-steel appliances, a king bed, a queen sleeper sofa, a private balcony, and resort amenities including a heated swimming pool, hot tub, and a fitness centre with sea views.
Frequently asked questions about short term rentals in Key West, FL
What kind of weather can travelers expect in Key West, FL?
Key West has a tropical climate, so expect sunshine and warm temperatures year-round. The average temperature is around 25 degrees Celsius, and it rarely dips below 15 degrees Celsius even in the winter. You'll get plenty of sunshine, and the humidity is high.
What are the best short term rentals in Key West, FL?
What are the most popular festivals and events in Key West, FL?
The Fantasy Fest in October is a huge party with parades and costumes, and it's a real highlight. The Key West Songwriters Festival in May is a great event for music lovers, and the Hemingway Days celebration in July is a fun way to celebrate the famous author's life.
What are the best short term rentals with a pool in Key West, FL?
Are there any famous stadiums or sports arenas in Key West, FL?
Key West doesn't have any major stadiums or sports arenas. It's more of a laid-back, relaxed island, not a big sports hub. But you can find plenty of opportunities to enjoy water sports like fishing, kayaking, and sailing.
What are the best short term rentals with a jacuzzi in Key West, FL?
What notable natural landmarks are near Key West, FL?
The Dry Tortugas National Park is a beautiful group of islands about 110 kilometres west of Key West. You can go snorkeling or diving there, and it's home to a historic fort. The Florida Keys National Marine Sanctuary is another great place to explore the underwater world.
What are the best short term rentals for families and kids in Key West, FL?
What part of Key West, FL is ideal for finding lodging?
Old Town is the heart of Key West and has plenty of hotels and guesthouses, but it can be a bit pricey. The area around Duval Street is bustling, and you'll find lots of restaurants, bars, and shops there. If you want something quieter, try the more residential areas like New Town or the Truman Annex.
Destinations nearby
Best Key West, FL short term rentals with a kitchen
9.0 42 reviews
Key West, FL
20/07 – 27/07
A$741/nighttotal: A$5187 (7 )
205e La Brisa-2br 2ba Beachfront Condo W/parking, Shared Pool, Grills
2 1
apartment , Key West
This Key West beachfront condo offers direct access to Smathers Beach and is 2.7km from Duval Street, providing convenient proximity to Key West's attractions and beaches. The 108-square-metre apartment features two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, private balcony, in-unit laundry, and access to a swimming pool, tennis court, and barbecue grills.
10 6 reviews
Key West, FL
21/12 – 18/01
A$657/nighttotal: A$18396 (28 )
Sea-nic View ~ 2 Br/2ba Water-front Views, Pool Access And Dockage!
2 1
apartment , Key West
This oceanfront Key West condo, situated in New Town near Garrison Bight Marina, offers easy access to attractions such as the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park. The 97 square metre (1044 square foot) property boasts three bedrooms, two bathrooms, sleeps six, and includes a private 8.5 metre boat slip, a heated pool, and concierge services; monthly rentals (minimum 28 nights) are available.
9.6 90 reviews
Key West, FL
11/07 – 18/07
A$408/nighttotal: A$2856 (7 )
One Bedroom Suite | Beachside Resort
1 4
apartment , Key West
This Key West Beachside Resort condo, situated directly on the Gulf of Mexico, offers stunning Gulf views from its private balcony. The one-bedroom apartment, sleeping up to four guests with a king bed and queen sleeper sofa, boasts a fully equipped kitchen, private washer/dryer, and access to a heated pool, hot tub, fitness centre, and on-site marina; bookable sandbar or sunset cruises enhance your stay.
9.9 64 reviews
Key West, FL
11/07 – 18/07
A$828/nighttotal: A$5796 (7 )
Cocktails & Dreams: Modern 2nd Floor Condo, Steps From Duval St, Seaport, Waterpark, Beach & Pool!
2 4
apartment , Key West
This Old Town Key West flat is less than 1 km from Duval Street, the Ernest Hemingway Home and Museum, and We Cycle Key West, and within 2.4 km of Fort Zachary Taylor Historic State Park and Mallory Square. The 63 square metre apartment sleeps four, offering two bedrooms, one bathroom, a fully equipped kitchen including dishwasher, in-unit laundry, cable TV, and a terrace; plus, a swimming pool and parking are available.
Best Key West, FL short term rentals with laundry available
Key West, FL
29/12 – 27/01
A$560/nighttotal: A$16240 (29 )
Blue Horizon Hideaway
3 2
apartment , Key West
This waterfront holiday home is located in Key West's Northside Resort area, a 6-minute drive from Duval Street and a 12-minute walk from Regal Key West. This spacious 130 m² residence offers 3 bedrooms and 2.5 bathrooms, a fully equipped kitchen, in-unit laundry, a communal swimming pool, and a private terrace, with parking and internet provided.
9.8 12 reviews
Key West, FL
01/10 – 01/11
A$487/nighttotal: A$15097 (31 )
Quiet Conch House In Historic District
4 2
apartment , Key West
This Key West house rental is ideally located in Old Town, less than 1.6km from Key West Cemetery, Duval Street, and the Ernest Hemingway Home and Museum, with beaches within a 2.4km radius. The 130 square metre property boasts four bedrooms, two bathrooms, sleeping up to eight guests, and features a fully equipped kitchen, laundry facilities, private balcony, and free Wi-Fi.
9.8 233 reviews
Key West, FL
11/07 – 18/07
A$609/nighttotal: A$4263 (7 )
**The Mellow Macaw** Cozy Condo Near Duval + Last Key Services...
2 4
apartment , Key West
This Key West apartment is ideally located in Old Town, a short walk from Duval Street and the City Zoo Gallery, with the Ernest Hemingway Home and Museum and beaches within a 6.4km radius. The 68 square metre property offers two bedrooms, one bathroom, sleeps six guests, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, and access to a garden, spa, and parking.
9.8 272 reviews
Key West, FL
11/07 – 18/07
A$554/nighttotal: A$3878 (7 )
**Suzy's Parrot Perch @ Old Town** Cozy 2nd Floor Condo + Last Key Services...
2 4
apartment , Key West
This Key West Historic District flat is situated a short walk from the City Zoo Gallery and Duval Street, with the Ernest Hemingway Home and Museum and Florida Keys beaches within 1.6km. The 74 square metre property comprises two bedrooms, one bathroom, and sleeps six, boasting a fully equipped kitchen, terrace, garden access, a spa, tennis court, and free Wi-Fi.