Best Short term and Weekly rentals in Key West, FL
9.9 640 reviews
Key West, FL
22/08 – 29/08
£204/nighttotal: £1428 (7 )
Charming Studio In Historic Key West, 5-min Bike Ride To Beach & Bikes Included!
1 2
studio , Key West
This studio apartment is situated in the Cuban district, just a short walk from the best 'con leche' in Key West and a few minutes from all the island's attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The apartment is 42 square metres and features a modern kitchen with an induction cooktop and convection oven. Guests can enjoy free Wi-Fi, digital HD cable, beach chairs, and a shared courtyard for relaxing and storing beach gear.
9.0 144 reviews
Key West, FL
26/10 – 28/10
£321/nighttotal: £642 (2 )
Sunrise Suites Condo With Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
2 4
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 40 reviews
Key West, FL
13/09 – 27/09
£107/nighttotal: £1498 (14 )
Truman Room @ Inn On Fleming~adults Only 2nd Floor Queen & Shared Heated Pool
1 2
B&B , Key West
This Key West apartment, located in Old Town, is two blocks from the Historic Seaport and a short walk from Duval Street, offering easy access to Key West's main attractions. The 15-square-metre (0.015 hectare) self-catering flat comprises one bedroom, one bathroom, sleeps two guests, and includes a swimming pool, garden, concierge service, and free Wi-Fi; bike rentals are available for exploring the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
9.8 46 reviews
Key West, FL
29/12 – 31/12
£627/nighttotal: £1254 (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.
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.
10 25 reviews
Key West, FL
02/07 – 05/07
£473/nighttotal: £1419 (3 )
Palm Garden Retreat With Hot Tub & Prime Key West
1 4
apartment , Key West
This Old Town Key West apartment on White Street is situated six blocks from Duval Street and the Historic Seaport, offering easy access to Key West's attractions. The one-bedroom, one-bathroom flat sleeps four, featuring a king-size bed, sleeper sofa, full kitchen with granite countertops, private hot tub, and access to a shared pool and BBQ area.
9.3 12 reviews
Key West, FL
01/10 – 01/11
£147/nighttotal: £4557 (31 )
La Entrada Rosa ~ Charming 1 Bedroom, 1 Bathroom W/ Loft In Old Town!
1 2
apartment , Key West
This Old Town Key West flat offers a tranquil setting within walking distance of attractions such as the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park. The self-catering apartment features a small kitchen, a porch, a shared laundry, and a flat-screen TV; concierge services include fridge stocking and booking activities, with monthly rentals (minimum 28 nights) available.
9.2 5 reviews
Key West, FL
21/12 – 18/01
£435/nighttotal: £12180 (28 )
Off The Hook - 3 Bedroom / 3 Bathroom W/ Pool & Parking
3 1
apartment , Key West
This three-bedroom, three-bathroom apartment is situated in Key West's New Town, less than 1.6 kilometres from Duval Street, local beaches, and Garrison Bight Marina, offering private gated parking suitable for boat trailers. This 139 square metre holiday home accommodates up to seven guests, featuring a private swimming pool, impact-resistant windows, air conditioning, and a fully equipped kitchen, with beach chairs and towels provided for convenience.
9.6 51 reviews
Key West, FL
29/12 – 27/01
£447/nighttotal: £12963 (29 )
Egret Suite | Bright Retreat, Hot Tubs, Steps From Duval!
1 2
apartment , Key West
The Egret Suite, a Key West holiday cottage, is ideally located in the Historic District, a short walk from Duval Street and close to the Ernest Hemingway Home and Museum. This one-bedroom, one-bathroom self-catering property sleeps four guests and boasts a fully equipped kitchenette, air conditioning, a Jacuzzi, and free Wi-Fi; nearby attractions include Fort Zachary Taylor Historic State Park and South Beach.
9.0 195 reviews
Key West, FL
22/08 – 29/08
£117/nighttotal: £819 (7 )
Summer Special@129\nsun. Thru Wed. Ngts.lodging Only 129. + Extras.
1 2
apartment , Key West
This one-bedroom house in Key West's Historic District is located within a 15-minute walk of Duval Street, the Key West Firehouse Museum, and the Florida Keys Beaches. The property offers a comfortable stay for up to four guests with a fully equipped kitchen, a sofa bed, a dining area, a patio, and a garden, as well as free parking nearby.
9.5 1253 reviews
Key West, FL
24/07 – 25/07
£358/nightfor 1 night
Key West Bed And Breakfast
2 4
B&B , Key West
The Key West Bed and Breakfast is located in a quiet neighbourhood just 1.1 km from Simonton Street Beach and a short walk from the bustling Duval Street. The property consistently receives excellent ratings for location, cleanliness and user experience. This charming guesthouse offers a private patio for relaxing and a fully equipped bathroom with a shower and hairdryer. Guests can enjoy free Wi-Fi, a garden, a swimming pool, a terrace, and parking.
8.1 844 reviews
Key West, FL
26/10 – 28/10
£407/nighttotal: £814 (2 )
Kona Kai Oasis
2 4
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.
Best Key West, FL short term rentals with a balcony
9.8 194 reviews
Key West, FL
22/08 – 29/08
£230/nighttotal: £1610 (7 )
The Conch House Heritage Inn
1 2
B&B , Key West
The Conch House Heritage Inn is located in Key West, just under half a kilometre from the Ernest Hemingway Home and Museum and less than two kilometres from Duval Street. The B&B has received excellent ratings for location, cleanliness, and overall user experience. The inn is an adult-only establishment, offering a peaceful retreat for couples. Guests can enjoy a range of amenities, including a swimming pool, a spa, and complimentary breakfast and mimosas.
10 3 reviews
Key West, FL
14/10 – 16/10
£172/nighttotal: £344 (2 )
Nightcap ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
1 2
B&B , Key West
This guesthouse, located in Old Town Key West, is situated in the historic district just 500 meters from the beach and the Southernmost Point, with Duval Street's attractions a few steps away. The 20 square meter Nightcap room accommodates two guests and features a queen bed, a stocked kitchenette with a fridge and microwave, air conditioning, outdoor seating overlooking Duval Street, and access to an on-site rum bar.
9.6 148 reviews
Key West, FL
22/08 – 29/08
£306/nighttotal: £2142 (7 )
~ Casablanca Too ~Chicly Updated Home With Hot Tub In A Quiet Location.
1 2
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.
9.6 141 reviews
Key West, FL
05/09 – 19/09
£378/nighttotal: £5292 (14 )
Henry's Piece Of Paradise On The Ocean In Key West - Weekly / Nightly
2 4
apartment , Key West
This beachfront Key West condo is situated less than 5km from Duval Street and Mallory Square, offering easy access to Key West's nightlife, sunset celebrations, and Florida Keys Beaches, and a 15-minute drive from Clarence S. Higgs Memorial Beach Park and the Key West AIDS Memorial. The 125 square metre property boasts two bedrooms, two bathrooms, a fully equipped kitchen, private balcony, in-unit laundry, and access to a swimming pool, jacuzzi, sauna, fitness centre, and tennis court; perfect for couples or small families seeking a luxurious Key West getaway.
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.
Key West, FL
02/07 – 05/07
£773/nighttotal: £2319 (3 )
Apartment ∙ 2 Bedrooms ∙ 6 Guests
2 4
apartment , Key West
The Mesa House, Dos, a two-bedroom Key West apartment, is located in Old Town, close to Simonton Street and within easy walking distance of many attractions. This self-catering suite sleeps six, offering a king bed, two twin beds, a queen-size sofa bed, full kitchen with oven and stove, washer/dryer, two cable TVs, free Wi-Fi, air conditioning, and a terrace/balcony plus garden and parking.
Key West, FL
01/10 – 01/11
£149/nighttotal: £4619 (31 )
Condo ∙ 2 Bedrooms ∙ 4 Guests
2 2
apartment , Key West
This two-bedroom, two-bathroom condominium is located in the 1800 Atlantic district of Key West, offering direct beach access just 100 metres from the sandy sunning beach and within easy reach of the island's attractions. This fully furnished residence accommodates up to four guests and features resort-style amenities including an Olympic-sized swimming pool, gym, fitness centre, three tennis courts, and an oversized private balcony with partial ocean views, alongside in-unit laundry and one assigned covered parking space.
9.6 1209 reviews
Key West, FL
26/10 – 28/10
£612/nighttotal: £1224 (2 )
Key West Villas
2 4
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.
8.7 756 reviews
Key West, FL
24/07 – 25/07
£579/nightfor 1 night
Old Town Suites
2 4
B&B , Key West
Old Town Suites is in Key West's Old Town district, just a short walk from the Ernest Hemingway Home and Museum and Duval Street, the island's main thoroughfare. This B&B has consistently received excellent ratings for its location, cleanliness, and overall experience. Each apartment at Old Town Suites comes with a fully equipped kitchen and modern amenities, allowing guests to enjoy a comfortable and independent stay. Guests can also enjoy the property's garden, terrace, and on-site restaurant and bar.
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.
9.0 2 reviews
Key West, FL
23/06 – 24/06
£217/nightfor 1 night
After Hours ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
1 2
B&B , Key West
This guesthouse is situated in Old Town Key West, a few hundred metres from the beach and the Southernmost Point, placing it close to major landmarks like the Ernest Hemingway Home and Museum and directly on Duval Street, offering easy access to galleries, restaurants, and bars. This adults-only B&B, with a history tied to rum-running, features a celebrated Rum Bar with a global selection, a stocked kitchenette in the 'After Hours' room, tropical decor, and an upstairs wraparound porch providing a prime spot for people-watching, accommodating two guests with one bedroom and one bathroom.
Best Key West, FL short term rentals with a kitchen
9.7 50 reviews
Key West, FL
11/07 – 18/07
£439/nighttotal: £3073 (7 )
Waterfront Dock Pool Downtown Near Duval Pet
1 4
apartment , Key West
This Key West waterfront condo, situated in the historic Downtown district, is less than 1.6km from Duval Street, the Historic Seaport, and the Hemingway House. The 118 square metre, two-bedroom, two-bathroom apartment sleeps up to six guests, boasting a private boat slip (maximum 12 metres long, 4 metres wide, and 5.5 metres high), a private elevator, a heated pool, and a large balcony overlooking the harbour.
10 3 reviews
Key West, FL
22/08 – 29/08
£154/nighttotal: £1078 (7 )
Night Watch ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
1 2
B&B , Key West
This guesthouse is located directly on Duval Street in Old Town Key West, a historic district two blocks from the beach and the Southernmost Point, offering immediate access to galleries, restaurants, and bars. The 'Night Watch' room, a 22 square metre space for two guests, features a stocked kitchenette with a fridge and microwave, air conditioning, and Wi-Fi, with outdoor seating on a restored wraparound porch overlooking Duval Street.
10 76 reviews
Key West, FL
31/07 – 02/08
£348/nighttotal: £696 (2 )
Eyw Getaway
1 2
apartment , Key West
This Sunrise Suites condo is situated 1.6km from Key West International Airport, 2.4km from the beach, and 5.6km from Duval Street. The two-bedroom, two-bathroom apartment sleeps six guests and boasts a fully equipped kitchen, in-unit laundry, a private balcony with sunset views, and access to a heated pool, hot tub, tennis court, and fitness centre; free on-site parking is also provided.
10 4 reviews
Key West, FL
21/12 – 18/01
£144/nighttotal: £4032 (28 )
Charming Cottage In Old Town
1 1
apartment , Key West
This Key West cottage, conveniently located in [Insert specific Key West neighbourhood or proximity to a landmark, e.g., near Duval Street], offers easy access to the island's attractions. The 1-bedroom, 1-bathroom self-catering property sleeps 2 guests and includes a private deck, 8 x 24ft heated pool, in-unit laundry, and free Wi-Fi; its size exceeds that of a typical Key West holiday home.
Best Key West, FL short term rentals with laundry available
8.8 3 reviews
Key West, FL
29/12 – 27/01
£242/nighttotal: £7018 (29 )
Cabin Fever ~ First Floor 1 Bedroom, 1 Bathroom With Full Kitchen And Pool!
1 2
apartment , Key West
9.2 17 reviews
Key West, FL
05/09 – 19/09
£305/nighttotal: £4270 (14 )
Key West Oceanfront Escape With Pool, Balcony & Steps From Smathers Beach
3 4
apartment , Key West
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
9.2 16 reviews
Key West, FL
29/12 – 31/12
£801/nighttotal: £1602 (2 )
The Curry Poolside | Ground Floor Two Queens
1 2
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
21/12 – 18/01
£389/nighttotal: £10892 (28 )
Monthly Rental-old Town One Level Home W/ Shared, Heated Pool, Parking, A/c,heat
1 1
apartment , Key West
Key West, FL
29/12 – 27/01
£279/nighttotal: £8091 (29 )
Shared Pool + Backyard Lounge | Charming Cottage | Steps To Waterfront Dining
2 2
apartment , Key West
Key West, FL
27/06 – 04/07
£312/nighttotal: £2184 (7 )
A Zephyr Suite Cuban Club
1 2
apartment , Key West
9.7 319 reviews
Key West, FL
06/07 – 09/07
£426/nighttotal: £1278 (3 )
Waterfront 2br | Pool | Key West | Pet Ok
2 6
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.
8.8 124 reviews
Key West, FL
26/10 – 28/10
£342/nighttotal: £684 (2 )
Cozy Dog-friendly Condo W/ Shared Pool, Hot Tub, Private Deck & Parking
2 4
apartment , Key West
Key West, FL
01/10 – 01/11
£351/nighttotal: £10881 (31 )
Charming 3-bedroom House In Old Town Key West With Wifi, Ac, Spa And Parking
