Best Short term and Weekly rentals in Key West, FL
9.6 249 reviews
Key West, FL
12/11 – 15/11
£567/nighttotal: £1701 (3 )
Key Wes't Best- Upgraded Condo 5 Mins To Smathers Beach Fantastic Value
2 5
apartment , Key West
This beachfront apartment is located just a 15-minute walk from Florida Keys Beaches and Clarence S. Higgs Memorial Beach Park, and within 3 miles of Duval Street and Mallory Square, offering easy access to Key West's attractions. The property has consistently received excellent ratings for cleanliness, location, and overall guest experience. The apartment features two bedrooms and two bathrooms, comfortably accommodating up to six guests. It provides a range of amenities, including a swimming pool, jacuzzi, sauna, fitness centre, tennis court, and a private terrace or balcony, ensuring a relaxing and enjoyable stay.
10 2 reviews
Key West, FL
20/07 – 22/07
£175/nighttotal: £350 (2 )
Hideaway ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
1 1
B&B , Key West
This guesthouse is located directly on Duval Street in Old Town Key West, just 320 meters from the beach and the Southernmost Point, offering immediate access to galleries, restaurants, and bars, and is steeped in Prohibition-era lore. The 23 square meter 'Hideaway' room accommodates two guests with air conditioning, Wi-Fi, a fridge, and microwave, and features outdoor seating and access to a restored wraparound porch, with the property being adults-only and a short distance from the Ernest Hemingway Home and Museum.
9.9 100 reviews
Key West, FL
20/07 – 22/07
£219/nighttotal: £438 (2 )
Tropical Heron Hideaway W/ Hot Tub + Pool
1 1
apartment , Key West
This Key West apartment, ideally located for exploring the island, offers a convenient base for your holiday, although the precise distance to specific attractions such as Mallory Square or Duval Street is not specified. The one-bedroom, one-bathroom flat sleeps four guests and includes a private porch, swimming pool, jacuzzi, and outdoor grill, providing all the essentials for a comfortable Key West stay.
8.4 15 reviews
Key West, FL
27/06 – 04/07
£227/nighttotal: £1589 (7 )
Sunrise 308-2br/2ba Condo Near Beaches With Pool, Parking, Balcony
2 3
apartment , Key West
This Key West seaside apartment, situated 1.9km from Smathers Beach and 1.9km from the Fort Zachary Taylor Historic State Park, offers stunning ocean views. The 74 square metre property boasts three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, swimming pool, jacuzzi, fitness centre, and free Wi-Fi.
9.8 311 reviews
Key West, FL
23/11 – 29/11
£661/nighttotal: £3966 (6 )
Waterfront Dock Pool Condo Near Duval St Pet Ok
1 6
apartment , Key West
This waterfront Key West apartment, situated in the historic downtown area, is approximately 1.6km from Duval Street, the Historic Seaport, and the Hemingway House. The 118 square metre property boasts two bedrooms (king and two queen-size beds), two bathrooms, accommodates six guests, and includes a private boat slip, heated pool access, and a balcony overlooking the harbour.
9.8 38 reviews
Key West, FL
29/12 – 31/12
£626/nighttotal: £1252 (2 )
Luxurious Stay | Snorkeling. Outdoor Pool
1 2
B&B , Key West
This studio apartment is located on Key West's harbour in Old Town, offering easy access to Mallory Square and the Southernmost Point Buoy, historical sites within 500 meters. This accommodation, suitable for two guests, features air conditioning, Wi-Fi, a swimming pool, and is within 100 meters of an on-site bar and restaurant, with rooms up to approximately 37 square meters and a balcony.
9.8 46 reviews
Key West, FL
11/11 – 13/11
£344/nighttotal: £688 (2 )
Duval Corner - Pet Friendly With Balcony
1 2
apartment , Key West
This Key West apartment, situated in the Lower Duval area, is a short walk from the Southernmost Point buoy and the Ernest Hemingway Home. The one-bedroom flat offers a queen-size bed, a queen-size sofa bed, a fully equipped kitchen including a microwave, fridge and freezer, and accommodates up to four guests, with a shared balcony and pet-friendly options for a small additional cleaning fee.
8.6 139 reviews
Key West, FL
05/09 – 19/09
£261/nighttotal: £3654 (14 )
Comfortable Condo With Pool, Private Balcony, & Beach Access
2 4
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.
9.0 104 reviews
Key West, FL
12/11 – 15/11
£489/nighttotal: £1467 (3 )
Bermuda Retreat-waterfront 2br 2ba Condo W/ Pool & Boat Slip
2 5
apartment , Key West
This Key West apartment is situated just a mile from Duval Street and across the road from Bayview Park, offering a peaceful retreat close to the heart of the action. It has consistently received excellent ratings for its cleanliness, location, and overall experience. The apartment is spacious, with a floor area of 113 square metres, and can comfortably accommodate up to eight guests. Amenities include a private balcony with water views, a fully equipped kitchen, a swimming pool, a garden, and parking, making it ideal for families or groups looking for a relaxing and enjoyable stay.
9.7 7 reviews
Key West, FL
29/12 – 31/12
£558/nighttotal: £1116 (2 )
Beachfront Key West + Free Breakfast, Bar & Pool
1 2
B&B , Key West
This studio apartment is situated in Historic Old Town, Key West, on the Atlantic Coast, offering easy access to the Southernmost Point Buoy, Key West Lighthouse Museum, and Mallory Square, all within a short walk. This guesthouse accommodates two guests and features a king-size bed, a sitting area, a coffee maker, and access to resort amenities including three heated swimming pools, two private beaches, and a fitness centre.
10 4 reviews
Key West, FL
05/09 – 19/09
£268/nighttotal: £3752 (14 )
The Roost
1 4
apartment , Key West
This three-bedroom, two-bathroom flat is situated in Key West's historic district, offering a peaceful neighbourhood setting next to St. Mary Star of the Sea, with a short 500-metre walk to Duval Street. This apartment accommodates up to six guests and features private balconies off each bedroom, original Miami Dade pine floors and walls, high ceilings, an indoor washer and dryer, and a Jacuzzi, with beach towels provided.
9.4 113 reviews
Key West, FL
12/11 – 15/11
£398/nighttotal: £1194 (3 )
Key West Condo Close To The Ocean. 1 Mile To Smathers & 3 Miles To Duval St.
2 5
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.
Best Key West, FL short term rentals with a balcony
10 5 reviews
Key West, FL
21/12 – 18/01
£589/nighttotal: £16492 (28 )
Newly-built, Dog-friendly Home With Shared Pool - Walk To Beach & Dining
3 1
apartment , Key West
This Old Town Key West flat is situated one block from Duval Street, within easy walking distance of dining, shops, galleries, and beaches, with the Ernest Hemingway Home and Museum nearby and Fort Zachary Taylor State Park 1.6 kilometres away. This 130 square metre residence accommodates up to six guests across three bedrooms and three bathrooms, offering a shared swimming pool, a private washer/dryer, off-street parking, and a 30lb weight limit for dog-friendly stays, subject to a mandatory 28-night minimum.
10 2 reviews
Key West, FL
11/07 – 18/07
£237/nighttotal: £1659 (7 )
One Bedroom Suite | Beachside Resort
1 4
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.
Key West, FL
11/07 – 18/07
£411/nighttotal: £2877 (7 )
**Havana Especial @ Duval Street** Cottage & Pool + Last Key Services
2 4
apartment , Key West
This two-bedroom cottage is located on Duval Street in Old Town Key West, a short walk from the Southernmost Point and Hemingway House, and includes a rare private parking space. This property accommodates up to four guests with two en-suite bedrooms, a fully equipped kitchen, a rear courtyard with a barbecue, and a front porch, all complemented by Five-Star Guest Services from Last Key Realty.
10 123 reviews
Key West, FL
20/07 – 22/07
£963/nighttotal: £1926 (2 )
Bottoms Up Bungalow - Perfect 2 Bed/2 Bath Private Pool
2 1
apartment , Key West
Bottom's Up Bungalow is situated in the Key West Historic District, just under 1.6 kilometres from Duval Street, the beaches, and the marina. This charming property has received excellent user ratings, making it a popular choice for travellers. The bungalow has 2 bedrooms and 2 bathrooms, spanning 114 square metres and accommodating up to 6 guests. It offers a range of amenities, including a private pool, a spa, a terrace, and a garden, providing a relaxing and enjoyable stay.
Explore Family-Friendly Holiday Rentals in Key West, FL
Kid-friendly short-term lets in Key West, FL with family-friendly amenities make your holiday stress-free.
10 2 reviews
Key West, FL
11/07 – 18/07
£280/nighttotal: £1960 (7 )
Apartment ∙ 2 Bedrooms ∙ 6 Guests
2 4
apartment , Key West
This Key West apartment, situated near Key West International Airport, offers convenient access to the island's attractions. Sleeping up to six guests, this two-bedroom, two-bathroom second-floor suite features a king and queen bedroom, a queen sofa bed, private balcony, in-unit laundry, and designated parking; amenities include a swimming pool, garden, and free Wi-Fi.
9.8 118 reviews
Key West, FL
12/11 – 15/11
£620/nighttotal: £1860 (3 )
Waterfront Condo Free Slip & Pool 2b2b In Key West
1 5
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.
9.4 27 reviews
Key West, FL
30/10 – 04/11
£490/nighttotal: £2450 (5 )
Oceanview At 1800 Atlantic, Short Walk To Smathers Beach Wish Island Paradise
2 2
apartment , Key West
This Beachside, Key West condo is conveniently located near Florida Keys Beaches, offering easy access to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park. The 122 square metre apartment features two bedrooms (king and twin beds), two bathrooms, a full kitchen, and a 12-metre private balcony with ocean views; it sleeps six and boasts access to an Olympic-sized pool, jacuzzi, tennis courts, and other amenities within the 1800 Atlantic complex.
9.2 45 reviews
Key West, FL
06/01 – 08/01
£453/nighttotal: £906 (2 )
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.
Frequently asked questions about short term rentals in Key West, FL
Which top landmarks you shouldn't miss in Key West, FL?
You've got to see the Southernmost Point Buoy, it's the most southerly point in the continental US. Then there's the Ernest Hemingway Home and Museum, a beautiful house with lots of six-toed cats. And don't forget Mallory Square, it's a lively spot to watch the sunset.
What are the best 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 warm temperatures year-round. It's usually sunny and humid, with an average temperature around 25 degrees Celsius. The rainy season runs from May to October, but even then, showers are usually short and intense.
What are the best short term rentals with a pool in Key West, FL?
What are the most popular festivals and events in Key West, FL?
Key West is famous for its lively festivals. The Fantasy Fest in October is a big one, with parades and parties. The Hemingway Days in July celebrates Ernest Hemingway with a look-alike contest and other events. And the Key West Food and Wine Festival in January is a great way to sample local cuisine.
What are the best short term rentals with a jacuzzi in Key West, FL?
Are there any famous stadiums or sports arenas in Key West, FL?
Key West doesn't have any major sports stadiums or arenas. It's more of a laid-back island town, focused on its beaches and unique atmosphere. But you can find plenty of places to play some casual beach volleyball or go for a swim.
What are the best short term rentals for families and kids in Key West, FL?
What notable natural landmarks are near Key West, FL?
Just a short boat trip from Key West is the Dry Tortugas National Park, home to Fort Jefferson, a massive brick fort. It's a great place to snorkel and see the coral reefs. And if you're looking for a bit of history, you can visit the Key West Lighthouse, built in 1848.
What part of Key West, FL is ideal for finding lodging?
Old Town is a popular spot, with lots of historic buildings and restaurants. The area around Duval Street is lively and full of shops and bars. If you prefer something quieter, you can try the area around Smathers Beach, which is less crowded and more relaxed.
Destinations nearby
Find the Best Seaside Short-Term Rentals in Key West, FL
Anchor your next coastal holiday at comfortable shoreside short-term rentals in Key West, FL near the waterfront.
9.9 64 reviews
Key West, FL
11/07 – 18/07
£434/nighttotal: £3038 (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 a kitchen
9.5 2 reviews
Key West, FL
11/07 – 18/07
£363/nighttotal: £2541 (7 )
Eyebrow Suite Eyebrow House
2 4
apartment , Key West
This Key West apartment, centrally located less than 0.2km from Duval Street, offers easy access to South Beach (8-minute walk), Fort Zachary Taylor State Park Beach (10-minute walk), and Higgs Beach (19-minute walk), placing you near Key West's major attractions and historical sites. The 70 square metre self-catering flat comprises two bedrooms, one bathroom, and sleeps seven, boasting a fully equipped kitchen, in-unit laundry, free Wi-Fi, satellite TV, a swimming pool, jacuzzi, and tennis court.
9.8 44 reviews
Key West, FL
04/09 – 07/09
£244/nighttotal: £732 (3 )
Honeymoon Banyan Suite Near Higgs Beach
1 2
apartment , Key West
This Key West apartment, near Higgs Beach and White Street Pier, is a 10-minute (approx. 6.4 km) drive from Duval Street and the waterfront. The self-catering suite, sleeping two, features a king-size bed, kitchenette with microwave and fridge, and access to a shared garden, outdoor grill, and complimentary bicycles; the option to rent a second suite for larger groups is also available.
9.5 44 reviews
Key West, FL
27/06 – 04/07
£474/nighttotal: £3318 (7 )
Heated Rooftop Pool, Gated Parking - Casa Caribe
1 3
apartment , Key West
This two-storey townhouse, situated on the quieter end of Duval Street at its junction with Truman Avenue, Key West, offers easy access (within 1.6km) to the Southernmost Point and downtown attractions. The property boasts two en-suite bedrooms, sleeping up to six guests, and features a private hot tub, a shared rooftop pool with Duval Street views, and a fully equipped kitchen including a fridge, freezer, microwave, and a washer/dryer; off-street parking is also provided.
9.6 803 reviews
Key West, FL
05/09 – 19/09
£295/nighttotal: £4130 (14 )
2 Bedroom 1 Bath Condo At Bayfront Suites & Marina - Cleaning Fee Included
2 4
apartment , Key West
This apartment is located in the Meadows district of Key West, just a short walk from Duval Street, the Hemingway Home, and the beaches. It has consistently received excellent ratings for its location, cleanliness, and overall user experience. The apartment itself offers a comfortable and well-equipped space for your stay. Guests can enjoy a range of amenities including a swimming pool, tennis court, fitness centre, and a restaurant, as well as a private balcony and a fully equipped kitchen.
Best Key West, FL short term rentals with laundry available
8.4 7 reviews
Key West, FL
27/06 – 04/07
£175/nighttotal: £1225 (7 )
The Curry Classic | Main Mansion King
1 2
apartment , Key West
9.0 42 reviews
Key West, FL
13/09 – 27/09
£274/nighttotal: £3836 (14 )
205e La Brisa-2br 2ba Beachfront Condo W/parking, Shared Pool, Grills
2 2
apartment , Key West
9.6 143 reviews
Key West, FL
11/11 – 14/11
£486/nighttotal: £1458 (3 )
Henry's Piece Of Paradise On The Ocean In Key West - Weekly / Nightly
2 4
apartment , Key West
9.8 137 reviews
Key West, FL
12/11 – 15/11
£497/nighttotal: £1491 (3 )
**Set Sail @ Coconut Mallory** Condo + Last Key Services
3 5
apartment , Key West
Discover Short-Term Rentals with Parking in Key West, FL
Park up and enjoy the coast and local beaches. These short-term lets in Key West, FL come with a free car park on-site.
Key West, FL
01/08 – 08/08
£2867/nighttotal: £20069 (7 )
Apartment ∙ 6 Bedrooms ∙ 12 Guests
6 11
apartment , Key West
Key West, FL
30/10 – 04/11
£312/nighttotal: £1560 (5 )
Night Watch @ Speakeasy Inn Key West!
1 2
B&B , Key West
8.7 756 reviews
Key West, FL
24/07 – 25/07
£579/nightfor 1 night
Old Town Suites
2 4
B&B , Key West
9.5 86 reviews
Key West, FL
11/11 – 13/11
£284/nighttotal: £568 (2 )
Poolside Suite With Direct Pool Access
1 2
apartment , Key West
Top Holiday Lets with a Jacuzzi in Key West, FL
These short-term lets near the water in Key West, FL come with a hot tub or jacuzzi, ideal for a private hot tub soak after a.
9.2 25 reviews
Key West, FL
26/10 – 28/10
£484/nighttotal: £968 (2 )
Pool View Two Bedroom Residence
2 4
apartment , Key West
9.0 185 reviews
Key West, FL
26/10 – 28/10
£522/nighttotal: £1044 (2 )
Dog-friendly Key West Cottage With Private Hot Tub & Unbeatable Location
3 4
apartment , Key West
9.7 342 reviews
Key West, FL
11/11 – 13/11
£253/nighttotal: £506 (2 )
Poolside Cottage #411
1 2
apartment , Key West
10 6 reviews
Key West, FL
21/12 – 18/01
£860/nighttotal: £24080 (28 )
Luxury Key West Compound With Pool, Guest Cottage, And Walkable Access To Duval