Holiday homes & rentals in Key West - HomeToGo base64Hash Holiday homes & rentals in Key West - HomeToGo

Holiday homes & rentals in Key West

Find 5,491 available offers from 15 partners
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Top 15 Recommended holiday lettings in Key West

Find your perfect holiday home, apartment or cottage in Key West from just £86 per night!

House Key West
House ∙ 7 guests ∙ 3 bedrooms

Holiday home with private pool, garden & terrace | City view

Key West, Monroe County, Florida, United States
This Key West house rental features a private heated pool, garden, and balcony, perfect for family getaways with pets welcome.
from £230
per night
Excellent(8 ratings)
from £230
per night
View deal
House Key West
House ∙ 10 guests ∙ 4 bedrooms

Holiday home with BBQ & terrace | Near Southernmost Point | City view

Key West, Monroe County, Florida, United States
This Key West house rental features a kitchen, balcony, and parking, perfect for groups of up to 10 looking for an island getaway.
from £185
per night
Outstanding(35 ratings)
from £185
per night
View deal
House Key West
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with terrace, garden & private pool | Next to Southernmost Point | City view

Key West, Monroe County, Florida, United States
This Key West house rental features a private pool, a garden, and a kitchen, perfect for up to 8 guests looking to unwind.
from £298
per night
Outstanding(16 ratings)
from £298
per night
View deal
House Key West
House ∙ 8 guests ∙ 4 bedrooms

House with barbecue & private pool | Close to Duval Street | City view

Key West, Monroe County, Florida, United States
This Key West house rental features a private heated pool, kitchen, balcony, and parking, welcoming up to 8 guests and pets.
from £406
per night
Outstanding(8 ratings)
from £406
per night
View deal
House Key West
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly house with garden, private pool & BBQ | City view | Pets allowed

Key West, Monroe County, Florida, United States
This Key West house rental features a private heated pool, garden, and balcony, perfect for family fun and pet-friendly relaxation.
from £350
per night
Outstanding(9 ratings)
from £350
per night
View deal
House Key West
House ∙ 12 guests ∙ 5 bedrooms

Fully equipped wonderful holiday home with barbeque, jacuzzi & private pool | Perfect for remote work | Pets are welcome

Key West, Monroe County, Florida, United States
This house rental in Key Haven features a private pool, hot tub, and space for 12, perfect for a memorable getaway.
from £486
per night
Outstanding(2 ratings)
from £486
per night
View deal
House Key West
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented house with barbeque, private pool & terrace | City view | Pets allowed

Key West, Monroe County, Florida, United States
This Key West house rental features a private pool, garden, and kitchen, perfect for families and pets, accommodating up to 8 guests.
from £279
per night
Outstanding(17 ratings)
from £279
per night
View deal
Villa Key West
Villa ∙ 12 guests ∙ 5 bedrooms

Fully equipped villa with jacuzzi, barbecue & private pool | Next to Southernmost Point | Nature view | Close to the beach

Key West, Monroe County, Florida, United States
This villa in Key West features a private heated pool, hot tub, kitchen, garden, and balcony, accommodating up to 12 guests.
from £516
per night
Outstanding(5 ratings)
from £516
per night
View deal
House Key West
House ∙ 8 guests ∙ 3 bedrooms

Holiday home with barbecue, terrace & garden | Nature view

Key West, Monroe County, Florida, United States
This house rental in Key West features a kitchen, garden, and waterside access, accommodating up to 8 guests with parking available.
from £167
per night
Outstanding(5 ratings)
from £167
per night
View deal
House Key West
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, BBQ & jacuzzi | Nature view | Suitable for remote work

Key West, Monroe County, Florida, United States
This Key West house rental accommodates 8 guests and features a private heated pool, hot tub, garden, and a fully equipped kitchen.
from £217
per night
Outstanding(25 ratings)
from £217
per night
View deal
House Key West
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped house with private pool, terrace & garden | Near Southernmost Point | Perfect for remote work | Pet-friendly

Key West, Monroe County, Florida, United States
This Key West house rental features a private pool, garden, and balcony, perfect for families and pets, accommodating up to 8 guests.
from £201
per night
from £201
per night
View deal
House Key West
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped house with private pool, garden & terrace | Close to Mallory Square | City view

Key West, Monroe County, Florida, United States
This Key West house rental features a private pool, garden, and kitchen, perfect for a memorable getaway with friends or family.
from £183
per night
Excellent(18 ratings)
from £183
per night
View deal
House Key West
House ∙ 10 guests ∙ 4 bedrooms

Holiday home with private pool, garden & jacuzzi | City view

Key West, Monroe County, Florida, United States
This Key West house rental features a private pool, hot tub, garden, and beach access, perfect for families and pets alike.
from £400
per night
Excellent(18 ratings)
from £400
per night
View deal
Cottage Key West
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage with barbeque, heated pool & terrace | Close to Southernmost Point | Nature view

Key West, Monroe County, Florida, United States
This Key West cottage features a heated pool, kitchen, and pet-friendly amenities, perfect for a family getaway.
from £86
per night
Excellent(5 ratings)
from £86
per night
View deal
Condo Key West
Condo ∙ 6 guests ∙ 2 bedrooms

Flat with sauna, barbecue & heated pool | Near West Martello Tower | Nature view

Key West, Monroe County, Florida, United States
This Key West condo features beach access, a heated pool, hot tub, and a balcony, perfect for a memorable getaway.
from £140
per night
Outstanding(28 ratings)
from £140
per night
View deal

Holiday lettings and apartments with air conditioning

House  Key West
from £239 per night
House ∙ 6 guests ∙ 2 bedrooms

Fully equipped charming house with BBQ, jacuzzi & terrace | Nature view | Perfect for remote work | Pets allowed

4.6
Excellent(95 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
View deal
House  Key West
from £216 per night
House ∙ 8 guests ∙ 3 bedrooms

Holiday home with garden, private pool & BBQ | Close to West Martello Tower

4.8
Outstanding(8 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
View deal
House  Key West
from £115 per night
House ∙ 8 guests ∙ 2 bedrooms

Holiday home with barbeque, terrace & private pool | Near West Martello Tower | Nature view

5.0
Outstanding(29 ratings)
Key West, Monroe County, Florida, United States
Air conditioning
View deal
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Best holiday homes with a patio or terrace

House  Key West
from £238 per night
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped charming holiday home with barbecue, terrace & garden

4.6
Excellent(36 ratings)
Key West, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Key West
from £148 per night
House ∙ 6 guests ∙ 2 bedrooms

House with private pool, barbecue & jacuzzi | Near Southernmost Point | City view | Perfect for remote work

5.0
Outstanding(11 ratings)
Key West, Monroe County, Florida, United States
Balcony/Patio
View deal
Cottage  Key West
from £161 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage with garden, terrace & heated pool | Close to Mallory Square | City view | Perfect for remote work

5.0
Outstanding(253 ratings)
Key West, Monroe County, Florida, United States
Balcony/Patio
View deal
See all offers

Holiday cottages, homes & apartments with sauna

Condo  Key West
from £495 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Fully equipped wonderful condo with barbecue, sauna & garden | Near Mallory Square

4.8
Outstanding(120 ratings)
Key West, Monroe County, Florida, United States
Sauna
View deal
Condo  Key West
from £134 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped flat with barbecue, sauna & terrace | Next to West Martello Tower | Nature view | Next to the beach

4.8
Outstanding(18 ratings)
Key West, Monroe County, Florida, United States
Sauna
View deal
Condo  Key West
from £357 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped pleasant condo with hot tub, sauna & heated pool | Next to the beach

4.5
Excellent(2 ratings)
Key West, Monroe County, Florida, United States
Sauna
View deal
See all offers

Budget-friendly Holiday Homes in Key West

Find Fantastic yet Cheap Lettings

House Key West
from £253 per night
House ∙ 9 guests ∙ 3 bedrooms

Family-friendly nice house with garden, terrace & BBQ | Suitable for remote work | Pet-friendly

5.0
Outstanding(6 ratings)
Key West, Monroe County, Florida, United States
View deal
Condo Key West
from £249 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Flat with terrace, heated pool & garden | Near Southernmost Point

Key West, Monroe County, Florida, United States
View deal
House Key West
from £197 per night
House ∙ 5 guests ∙ 4 bedrooms

Holiday home with heated pool, barbecue & garden | Close to Duval Street | City view | Suitable for remote work

4.8
Outstanding(10 ratings)
Key West, Monroe County, Florida, United States
View deal

Top-Rated Lettings and Properties in Key West

Book Holiday Letting Offers with the Highest User Rating

House Key West
from £380 per night
House ∙ 8 guests ∙ 3 bedrooms

Family-friendly nice house with terrace, barbecue & hot tub | City view | Perfect for remote work | Pets allowed

4.9
Outstanding(17 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
from £167 per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped lovely holiday home with private pool, barbeque & hot tub | Close to West Martello Tower | Nature view | Dogs allowed

4.5
Excellent(8 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
from £447 per night
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with private pool & BBQ

5.0
Outstanding(7 ratings)
Key West, Monroe County, Florida, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Key West

How are reviews collected?
Molly B.
Guest verified by HomeToGo

Check-in was a bit touchy, as the office was locked & unoccupied, despite the fact that the hours stated on the door said it should be open. Got that resolved. Condo unit was PERFECT! Beds were very comfortable! We loved the back deck & spent much time there! Staff was very friendly & accomodating!

Reviewed on 18/02/2024 | Group
Condo Key West
from £227 per night
Condo ∙ 6 guests ∙ 1 bedroom
4.1
Very good(810 ratings)
Key West, Monroe County, Florida, United States
View deal
Cynthia F.
Guest verified by HomeToGo

Our 8 night stay at coconut Mallory was a 10/10. The room was just what we expected. Clean, very attractive landscaping, it was so nice to eat our self-prepared meals on our own little porch area. The kitchen was stocked with all of the cooking essentials we needed. A/c was cold The pools were perfect. Staff was awesome. We will definitely be coming back to this location.

Reviewed on 02/06/2023 | Couple
Condo Key West
from £176 per night
Condo ∙ 2 guests ∙ 1 bedroom
4.1
Very good(809 ratings)
Key West, Monroe County, Florida, United States
View deal

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Find your dream stay

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Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Key West

  • Pool (4,428)
  • Air conditioning (5,329)
  • WiFi (5,125)
  • Parking (389)
  • Balcony/patio (2,757)
  • Kitchen (3,778)
  • TV (5,089)
  • Washing machine (3,175)
  • Grill (1,868)
  • No pets (3,624)
  • Garden (2,354)
  • Dishwasher (2,383)

More than two-thirds of the holiday rentals provide a pool, which makes Key West a great destination for travellers looking to spend their holidays poolside. More hotel room offer a pool than condo. On average, hotel room with pools in Key West can welcome 8 holidaymakers and have an average cost of £589 a night. Among these offers, nearly half are within 2 kilometres of water.

Price and Availability Index for Key West

Click on any bar to see price and availability information

Holiday Letting Price Information in Key West

We analysed holiday cottage, home and apartment prices to create a graph showing the average nightly price in Key West. Prices during one week in December (26/12 – 02/01) go up to £841 per night, which is the highest average price in the next 12 months. On average, the most interesting prices are in one week in September (12/09 – 19/09), when the average price is only £505 per night.

Rental availability information in Key West

This graph shows the holiday letting availability rate for the upcoming year. The most challenging week to find a letting in the next twelve months is in March (27/03 – 03/04). On the other hand, the week with the most available offers is in July (04/07 – 11/07).

Choose a Key West Holiday Letting for an Unforgettable Beach Holiday

Key West is the place to go if you're looking for a beach holiday with all the benefits of a city break. It is ideal for any type of stay, from a weekend escape to a long-term holiday. Relish a quiet seaside break and stay in a Key West holiday letting . Key West has it all, from tranquil seaside nooks to lively entertainment.

What are the best activities for families in Key West?

Travelling with Children

Travelling with kids? Key West has something for everyone, young or old. Visit Key West Nature Preserve Park, where you can enjoy nature walks and hikes through lush mangrove forest.

The Key West Marine Park is great for swimming and snorkeling, and is protected by buoys, making it safe for younger adventurers. Astro City is a popular playground located across from Higgs Beach, while Florida Keys Eco-Discovery Centre features interactive displays about reefs and mangroves.

What are the top sights in Key West?

History and More

Apart from diving, swimming, snorkelling and water-based activities, there is plenty to see on land. Visit the Old Town and Fort Zachary Taylor. The latter is a historic state park that is now used as a venue for events such as Civil War reenactments.

Stop at Mallory Square, a plaza known for its ’Sunset Celebration’. People gather here not only to view arts and crafts, eat from food carts or enjoy street performances, but also to watch the awe-inspiring sunset. The New Town, which is on the east side of the island, features malls, shopping centers, schools and residential zones.

Another famous attraction in Key West is the replica of a buoy made from concrete located at South and Whitehead Streets, which marks the ’southernmost point’ of the Continental USA.

What are the must-see attractions in Key West?

Uncover Key West Island gems

Fort Zachary Taylor Historic State Park

Known simply as Fort Taylor or Fort Zach, this park is centred around a Civil War-era fort. Visitors can enjoy cycling, swimming, snorkeling and fishing here. Grab a bite at the open-air Cayo Hueso Café.

Harry S. Truman Little White House

The winter White House for former president Harry S. Truman is a great place to learn about Key West's history. Local guides add colour to the experience with their anecdotes.

The Ernest Hemingway Home and Museum

Learn about the literary icon's numerous romantic relationships, friendships and writings through a guided tour of his erstwhile residence.

Dry Tortugas National Park

Seventy miles from Key West, this secluded park is home to Fort Jefferson, wild birds, coral reefs and marine life. It's the ideal location for a camping excursion.

Key West Butterfly and Nature Conservatory

Kids in particular will love this conservatory where nearly 60 species of butterflies thrive in a climate-controlled, glass-enclosed habitat.

Information about holiday rentals in Key West

🏡 Holiday homes available 5,491 rentals
🌙 Nightly prices from £86
⭐ Popular amenities Pool, Air conditioning and Internet
🐾 Pet friendly rentals 1,822 properties
🏊 Holiday rentals with pools 4,261 properties

Frequently Asked Questions

What is the average nightly price for a holiday home in Key West?

The average starting price for a holiday cottage or rental in Key West is £86 per night. Prices vary depending on the type of holiday let, season, and amenities. Use HomeToGo to compare deals and find the best value for your trip.

How many holiday homes are available to rent in Key West? And what are the most popular types of holiday lets?

There are 5,491 holiday apartments from 15 providers on offer in Key West. Holiday homes in Key West often include spacious house rentals and condos. They’re ideal whether you’re planning a romantic escape or a group getaway. HomeToGo makes it easy to find a holiday home that fits your needs.

What is the most searched holiday rental amenity in Key West?

When choosing a holiday home in Key West, consider looking for a place with Pool, Air conditioning, or Internet, which are the three most popular amenities for this destination.

Do you offer holiday homes with a swimming pool in Key West?

Yes, 78% of holiday homes in Key West come with a swimming pool. Enjoy your own private swim spot by browsing one of the 4,261 properties with a pool available. Browse poolside holiday rentals on HomeToGo, starting from around £589.

What is the best time of year to travel to Key West?

Sun lovers should visit Key West in July and August to enjoy the warmest weather.

How do I find discounts on holiday rentals in Key West?

You can find fabulous discounts on holiday homes in Key West with the nightly price of accommodation beginning at £86 - and HomeToGo has introduced plenty of filters that mean it's a piece of cake to uncover some awesome offers. When considering different dates for your holiday, you can use HomeToGo's flexible dates technology to quickly locate low-price timings and get discounts of up to 10%. Moreover, HomeToGo's 'distance from' filter enables you to discover hidden gem holiday homes in lower-price, under-the-radar locales that are just as close to your desired destination, whether that's a beach, lake, ski region or city centre. Book early to get the benefits of the greatest variety of options and top discounts - and do so without worries by clicking on HomeToGo's 'free cancellation' filter when you search.

What are the advantages of finding a holiday letting in Key West with HomeToGo?

From increased privacy away from the crowds to plenty of room to enjoy with your family, friends or partner, holiday lets in Key West offer a wide range of benefits. HomeToGo surfaces genuine ratings from verified visitors, and searching is safe, simple, and stress-free - so with 5,491 lettings from 15 providers in the region, you're bound to find the ideal holiday home with all of the amenities to suit you in Key West.

Do you offer holiday accommodation for couples in Key West?

Absolutely – you’ll find plenty of cosy, well-rated holiday lettings in Key West perfect for two. Whether you’re after seclusion or a city break, there’s something for every type of trip. Let HomeToGo help you plan your next romantic break.

Can I book a waterfront holiday rental in Key West?

You can book one of 5488 waterfront holiday homes in Key West for a truly scenic break. Staying close to the water is ideal for scenic views and a relaxing atmosphere. Use HomeToGo’s "Near the water" filter to find your perfect waterfront holiday let.

Why should I book my holiday rental with HomeToGo?

HomeToGo brings together over 15 million holiday rentals from trusted providers, so you can find the best deal in one place. With smart filters, tailored recommendations and a Best Price Guarantee, booking is simple and stress-free. Book with confidence and enjoy support every step of the way.

Can I find family-friendly holiday lettings in Key West?

You’ll find family-ready holiday rentals in Key West that cater to groups. Many come with space for large groups and practical features like kitchens and gardens. Start your search with HomeToGo for a stress-free getaway.

Can I cancel my holiday rental booking for free?

Free cancellation is available on lots of holiday homes, depending on the provider. Just make sure to check the property's policy before booking.

Is it possible to rent a holiday home for a weekend getaway in Key West?

Short stays are absolutely possible in Key West, including weekends. Many homes offer short stays without long commitments. Discover your ideal holiday home with ease on HomeToGo.

Are there any last-minute holiday rental deals in Key West?

There are plenty of last-minute holiday homes in Key West available at reduced prices. These can be a great way to save up to 10% on spontaneous getaways. Check often and book quickly to grab the best offers.

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