Best Short term and Weekly rentals in Key West, FL
10 2 reviews
Key West, FL
27/06 – 04/07
A$435/nightTotal: A$3045 (7 )
One Bedroom Suite | Beachside Resort
1 3
apartment , Key West
This luxury resort in North Key West, situated on seven acres of waterfront, offers direct Gulf of Mexico views and is located 1.6 kilometres from Duval Street, placing it close to Florida Keys Beaches and Smathers Beach. This one-bedroom, two-bathroom apartment accommodates up to four guests and features a fully equipped kitchen with stainless-steel appliances, a private balcony, access to a heated swimming pool and hot tub, and is conveniently located near attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point.
9.7 1706 reviews
Key West, FL
08/01 – 17/01
A$559/nightTotal: A$5031 (9 )
At Mine | Lovely Suite Steps From Duval Street
1 2
apartment , Key West
This Key West hotel suite is situated on a quiet street, a short walk from Duval Street. The renovated one-bedroom suite sleeps two, offering a queen-sized bed, mini-fridge, microwave, air conditioning, and access to a shared garden, patio, and swimming pool; self check-in is available after 3pm.
This Key West Historic District property is a short 0.8km walk from Key West Cemetery and Duval Street, with the Ernest Hemingway Home and Museum and Florida Keys beaches within a 2.4km radius. The self-catering house boasts a fully equipped kitchen, private garden with barbecue, jacuzzi, and balcony; free Wi-Fi and parking are also included.
10 56 reviews
Key West, FL
01/08 – 08/08
A$2798/nightTotal: A$19586 (7 )
**Queen Of Louisa @ Duval** Home In Old Town & Private Pool + Last Key Services
6 11
apartment , Key West
This Key West Historic District property is situated a short walk from Duval Street and the Key West Butterfly and Nature Conservatory, with South Beach approximately 0.8 km away. This four-bedroom, four-bathroom house offers 146 square metres of space, accommodating up to 12 guests and boasting a private pool, spa, tennis court, and free Wi-Fi; in-house laundry facilities are also available.
9.0 2867 reviews
Key West, FL
29/12 – 31/12
A$912/nightTotal: A$1824 (2 )
The Grand Guesthouse
1 2
B&B , Key West
This adults-only guesthouse is located in Key West, just a 1.6 kilometre walk from Duval Street and the Atlantic Ocean, offering a peaceful retreat close to the island's bustling centre. The accommodation has received excellent ratings for its cleanliness, location and overall experience. Each room features local Caribbean artwork and private entrances, providing a unique and intimate stay. The guesthouse offers amenities like bike rentals, free Wi-Fi, flat-screen cable TVs, iPod docking stations, a continental breakfast, a swimming pool, a garden, and a restaurant and bar.
9.6 180 reviews
Key West, FL
11/07 – 18/07
A$753/nightTotal: A$5271 (7 )
Duval Square Retreat: A Beautiful Condo Steps From The Action
1 4
apartment , Key West
This Key West apartment is ideally located on the quieter end of Duval Street in Old Town, within easy walking distance of shops, restaurants, and the Ernest Hemingway Home Museum. The 115 square metre (1238 square feet) condo boasts two ensuite bedrooms, sleeping up to four guests, a fully equipped kitchen, a private balcony, and access to a shared rooftop pool and parking; all within a short distance of Key West's main attractions.
9.4 18 reviews
Key West, FL
26/10 – 28/10
A$2433/nightTotal: A$4866 (2 )
Harbor Walk Hideaways | Group Compound In Old Town, Pool!
4 4
B&B , Key West
Harborwalk Hideaways, in Key West's Historic Seaport District, offers easy walking access to Mallory Square and Duval Street. This Key West property comprises three cottages sleeping up to 14 guests, each with a kitchenette, queen-size Tempur-Pedic beds, and Smart TVs; shared facilities include a plunge pool and outdoor dining area.
9.2 45 reviews
Key West, FL
12/11 – 15/11
A$759/nightTotal: A$2277 (3 )
Two-bedroom, Two-bath Condo Close To The Ocean. Full Kitchen, Living R & Balcony
3 5
apartment , Key West
This two-bedroom Key West apartment is located within a 3km radius of the Fort East Martello Museum and Gallery, Key West Art and Historical Society, and Key West Tropical Forest and Botanical Garden, with Smathers Beach and Lower Keys Medical Center within 5km. The 74 square metre apartment features a fully equipped kitchen, a private balcony, and a swimming pool, comfortably accommodating up to six guests.
9.0 144 reviews
Key West, FL
06/07 – 09/07
A$614/nightTotal: A$1842 (3 )
Sunrise Suites Condo With Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
2 6
apartment , Key West
This Key West condo is situated on the eastern side of the island, offering proximity to Smathers Beach and within eight kilometres of popular attractions like Southernmost Point and the Ernest Hemingway Home and Museum. This two-bedroom, two-bathroom apartment spans 72 square metres, accommodating up to six guests with amenities including a kitchen, air conditioning, WiFi, a swimming pool, jacuzzi, and private parking.
9.8 238 reviews
Key West, FL
06/01 – 08/01
A$1603/nightTotal: A$3206 (2 )
Rooftop Penthouse
2 5
apartment , Key West
This house is located in Old Town Key West, just a short walk from Duval Street and the San Carlos Institute, and within 15 minutes of the Ernest Hemingway Home and Museum and the Florida Keys Beaches. The property has received excellent ratings for location, cleanliness, and overall experience. This two-bedroom house offers 167 square metres of space and can comfortably accommodate up to six guests. You'll find a fully equipped kitchen, a terrace, a garden, and laundry facilities, along with air conditioning and free Wi-Fi.
9.6 148 reviews
Key West, FL
20/07 – 27/07
A$609/nightTotal: A$4263 (7 )
~ Casablanca Too ~Chicly Updated Home With Hot Tub In A Quiet Location.
1 1
apartment , Key West
Casablanca Too is a duplex located in a residential neighbourhood on the edge of Historic Old Town, just 1.5 kilometres from Duval Street and a 5-minute bike ride from Higgs Beach. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. The duplex features a spacious 57 square metre layout with one bedroom, one bathroom, and can accommodate up to two guests. Amenities include a private hot tub, a fully equipped kitchen, a washer and dryer, a garden, parking, and internet access.
9.8 118 reviews
Key West, FL
11/11 – 14/11
A$1092/nightTotal: A$3276 (3 )
Waterfront Condo Free Slip & Pool 2b2b In Key West
1 4
apartment , Key West
This Key West condo, situated on Garrison Bight Marina, offers direct marina views and is a short cycle ride (approximately 1-2 km) from Duval Street and a short walk from Bayview Park. Sleeping up to six guests, this two-bedroom, two-bathroom apartment boasts a fully equipped kitchen, shared swimming pool, garden, parking and excellent guest ratings; enjoy tennis and basketball at the nearby park.
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
9.9 273 reviews
Key West, FL
12/11 – 15/11
A$675/nightTotal: A$2025 (3 )
Fully Renovated Condo With Private Balcony, Shared Pool, Hot Tub And Parking
2 5
apartment , Key West
This two-bedroom apartment is located in Key West, within 3 km of the Fort East Martello Museum and Gallery, the Key West Art and Historical Society, and the Key West Tropical Forest and Botanical Garden. The apartment boasts a fully equipped kitchen, a private balcony, and access to a swimming pool, a Jacuzzi, a fitness centre, and a spa, making it an ideal choice for families or groups of up to six guests.
8.1 843 reviews
Key West, FL
04/09 – 07/09
A$575/nightTotal: A$1725 (3 )
Kona Kai Oasis
1 2
B&B , Key West
This guest house is centrally located in Key West's Old Town, 4 blocks from the beach and 2 blocks from Duval Street's dining scene, and 2.4 kilometres from Fort Zachary Taylor Historic State Park. The property offers rooms with microwaves and refrigerators, complimentary WiFi, a swimming pool, barbecue facilities, and on-site bicycle hire for exploring the area.
10 206 reviews
Key West, FL
08/01 – 17/01
A$1012/nightTotal: A$9108 (9 )
Casa Caribe Beautiful Tropical 2 Bedroom Sleeps 6
2 2
apartment , Stock Island
This Stock Island family home, situated less than 1.6km from the Key West Tropical Forest and Botanical Garden, Clark Maxwell Environmental Habitat, and Tennessee Williams Fine Arts Center, offers convenient access to local attractions and amenities. This two-bedroom, three-bathroom property sleeps six guests and boasts a swimming pool, spa, fitness centre, and fully equipped kitchen including a dishwasher, alongside a terrace, garden, and parking; ideal for family holidays in the Lower Keys.
10 2 reviews
Key West, FL
03/07 – 05/07
A$2126/nightTotal: A$4252 (2 )
Apartment ∙ 2 Bedrooms ∙ 9 Guests
2 2
apartment , Key West
This Key West apartment, ideally situated for exploring the island's attractions, offers convenient access to various transport options. The two-bedroom, two-bathroom flat sleeps eight guests, features a private patio with shared pool access, and includes a fully equipped kitchen, washer/dryer, and smart TVs.
Best Key West, FL short term rentals with a balcony
9.8 7 reviews
Key West, FL
29/12 – 31/12
A$1363/nightTotal: A$2726 (2 )
The Curry Poolside | Ground Floor King
1 2
apartment , Key West
This Key West apartment, situated in the Historic District, is less than 0.5km from Duval Street and within walking distance of Mallory Square and the Mel Fisher Maritime Museum. The one-bedroom, one-bathroom flat sleeps two guests and offers a shared heated pool, on-site parking (subject to availability), and in-room amenities including a mini-fridge and laundry facilities.
9.7 220 reviews
Key West, FL
29/12 – 27/01
A$1314/nightTotal: A$38106 (29 )
Waterfront Condo With Dock, Pool, Downtown Key West Near Duval
2 2
apartment , Key West
This waterfront apartment in historic Downtown Key West offers a private boat slip (maximum 12 metres long, 4 metres wide, 5.5 metres clearance) and is less than 1.6km from Duval Street, the Historic Seaport, and the Hemingway House. The 118 square metre, two-bedroom, two-bathroom flat sleeps six, boasts a private balcony overlooking the harbour and pool, includes a fully equipped kitchen, in-suite laundry, and access to an on-site heated pool, tiki bar, and secure keyless entry; a golf cart is also provided.
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.
9.8 227 reviews
Key West, FL
29/12 – 27/01
A$1499/nightTotal: A$43471 (29 )
Atlantic Breeze ~ 2b/2ba Renovated Retreat W/ Pool, Fitness Area & Beach!
2 2
apartment , Key West
This apartment is located in a quiet, gated waterfront community in Key West, just a short distance from the airport, beaches, restaurants, and Duval Street. It has received excellent user ratings, making it a popular choice for travellers. The property is a two-bedroom, two-bathroom apartment that can accommodate up to six guests. You can enjoy a range of amenities, including a swimming pool, jacuzzi, terrace, garden, sauna, and concierge service, as well as a fully equipped kitchen.
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
10 15 reviews
Key West, FL
28/06 – 02/07
A$452/nightTotal: A$1808 (4 )
Key West Beach House
1 4
apartment , Key West
This Key West condominium offers direct access to a private beach and is situated approximately 4.8 kilometres from the Historic Seaport District, Duval Street, Mallory Square, and Sunset Pier. This property features two bedrooms and two bathrooms, accommodating up to six guests with a full kitchen, living area, balcony, and sleeper sofa, complemented by a zero-entry heated swimming pool, hot tub, and complimentary on-site kayaking.
Key West, FL
27/06 – 04/07
A$586/nightTotal: A$4102 (7 )
A Zephyr Suite Cuban Club
1 2
apartment , Key West
This one-bedroom flat offers a prime location in Key West, situated just 400 metres from the city centre and a short walk to the Ernest Hemingway Home and Museum and Southernmost Point. This apartment accommodates up to seven guests and features a fully equipped kitchen, air conditioning, a balcony with an outdoor dining area, and access to a spa and fitness centre, with parking also available.
9.8 241 reviews
Key West, FL
14/10 – 16/10
A$522/nightTotal: A$1044 (2 )
Duval St Apartment W/ Balcony W/parking Adult Only
1 2
B&B , Key West
This Old Town Key West flat overlooks Duval Street, offering immediate access to restaurants, live music venues, and historical sites. The one-bedroom, one-bathroom apartment sleeps three, boasting a private balcony, a fully equipped kitchen including a full-size fridge-freezer, complimentary continental breakfast, a heated swimming pool, and individually controlled air conditioning; Wi-Fi and digital HD cable TV are also included.
9.4 134 reviews
Key West, FL
26/10 – 28/10
A$776/nightTotal: A$1552 (2 )
Sunrise Suites Condo W/ Balcony, Pool & Hot Tub, Tennis & Covered Parking
2 4
apartment , Key West
This two-bedroom condo, part of the Sunrise Suites Resort on Key West's eastern side, is located approximately 8 kilometres from the historic downtown area, offering convenient access to attractions such as the Southernmost Point and the Ernest Hemingway Home and Museum, as well as Smathers Beach and the Key West Tropical Forest and Botanical Garden. This 72 square metre apartment accommodates up to six guests, featuring air conditioning, a kitchen with a fridge, microwave, and dishwasher, a private balcony, and access to a shared swimming pool and hot tub, with family dogs welcome for an additional fee and covered parking provided.
Best Key West, FL short term rentals with laundry available
9.6 14 reviews
Key West, FL
24/07 – 25/07
A$681/nightfor 1 night
Pelican Suite | Cozy Cottage, Hot Tubs, Close To D
1 4
apartment , Key West
Pelican Suite is a one-bedroom cottage located just off Duval Street in Key West, within a 0.8 km walk of the iconic Southernmost Point and South Beach. This pet-friendly property offers two queen beds, a kitchenette, cable TV, and complimentary Wi-Fi, perfect for a comfortable stay for up to four guests.
9.4 167 reviews
Key West, FL
27/06 – 04/07
A$557/nightTotal: A$3899 (7 )
Heart Of Old Town Key West
2 3
apartment , Key West
This Key West apartment is ideally located one block from Duval Street and a short walk from the beach, offering easy access to all the island's attractions. Sleeping four guests, this newly renovated flat boasts two bedrooms, one bathroom, a simple kitchen with fridge and microwave, air conditioning, and complimentary concierge service; a garden is also available for guests' use.
9.5 142 reviews
Key West, FL
27/06 – 04/07
A$611/nightTotal: A$4277 (7 )
Two Bedroom Residence
1 3
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.
9.8 30 reviews
Key West, FL
23/11 – 29/11
A$1339/nightTotal: A$8034 (6 )
**Suite Sanctuary @ The Beach** Oceanfront Condo & Pool + Last Key Services...
3 6
apartment , Key West
This beachfront Key West condo is situated near Duval Street, Mallory Square, and Smathers Beach, all within a 4.8km radius. The two-bedroom, two-bathroom apartment sleeps six, offering a fully equipped kitchen, private balcony, and access to a swimming pool, Jacuzzi, sauna, spa, fitness centre, and tennis court; free Wi-Fi is also included.