Key West, FL Short term rentals

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Key West, FL short term rentals
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Best Short term and Weekly rentals in Key West, FL

Best Key West, FL short term rentals with a balcony

Newly-built, Dog-friendly Home With Shared Pool - Walk To Beach & Dining - Key West, FL
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.
One Bedroom Suite | Beachside Resort - Key West, FL
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.
**Havana Especial @ Duval Street** Cottage & Pool + Last Key Services - Key West, FL
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.
Bottoms Up Bungalow - Perfect  2 Bed/2 Bath Private Pool - Key West, FL
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.

Apartment ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
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.
Waterfront Condo Free Slip & Pool 2b2b In Key West - Key West, FL
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.
Oceanview At 1800 Atlantic, Short Walk To Smathers Beach Wish Island Paradise - Key West, FL
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.
Two-bedroom, Two-bath Condo Close To The Ocean. Full Kitchen, Living R & Balcony - Key West, FL
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.

Cocktails & Dreams: Modern 2nd Floor Condo, Steps From Duval St, Seaport, Waterpark, Beach & Pool! - Key West, FL
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

Eyebrow Suite Eyebrow House - Key West, FL
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.
Honeymoon Banyan Suite Near Higgs Beach - Key West, FL
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.
Heated Rooftop Pool, Gated Parking - Casa Caribe - Key West, FL
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.
2 Bedroom 1 Bath Condo At Bayfront Suites & Marina - Cleaning Fee Included - Key West, FL
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

The Curry Classic | Main Mansion King - Key West, FL
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
205e La Brisa-2br 2ba Beachfront Condo W/parking, Shared Pool, Grills - Key West, FL
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
Henry's Piece Of Paradise On The Ocean In Key West - Weekly / Nightly - Key West, FL
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
**Set Sail @ Coconut Mallory** Condo + Last Key Services - Key West, FL
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.

Apartment ∙ 6 Bedrooms ∙ 12 Guests - Key West, FL
Key West, FL
01/08 – 08/08
£2867/nighttotal: £20069 (7 )

Apartment ∙ 6 Bedrooms ∙ 12 Guests

6 11
apartment , Key West
Night Watch @ Speakeasy Inn Key West! - Key West, FL
Key West, FL
30/10 – 04/11
£312/nighttotal: £1560 (5 )

Night Watch @ Speakeasy Inn Key West!

1 2
B&B , Key West
Old Town Suites - Key West, FL
8.7 756 reviews
Key West, FL
24/07 – 25/07
£579/nightfor 1 night

Old Town Suites

2 4
B&B , Key West
Poolside Suite With Direct Pool Access - Key West, FL
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.

Pool View Two Bedroom Residence - Key West, FL
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
Dog-friendly Key West Cottage With Private Hot Tub & Unbeatable Location - Key West, FL
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
Poolside Cottage #411 - Key West, FL
9.7 342 reviews
Key West, FL
11/11 – 13/11
£253/nighttotal: £506 (2 )

Poolside Cottage #411

1 2
apartment , Key West
Luxury Key West Compound With Pool, Guest Cottage, And Walkable Access To Duval - Key West, FL
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

4 1
apartment , Key West
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