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Holiday homes in Key West You’ll Love

Top-Rated Key West Holiday homes for Every Budget and Style!

Looking for a holiday home in Key West (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $55.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Key West.

We found 290 Holiday-homes in Key West and the surrounding area (within 20 miles)

Key West Villas in Key West, USA

Key West Villas

Villa in Key West, Florida , 512 Angela Street
Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street.
  • Parking
  • Bar
  • Family rooms
  • Outdoor pool
  • Swimming pool

Exceptional 293 Reviews 9.6

from $246.38 Show details »

Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Pool and Parking in Key West, USA

Admirals Gold Key West - Truman Annex Vi...

Villa in Key West, Florida
Offering water sports facilities, Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Pool and Parking features accommodations in...
  • Spa and wellness centre
  • Swimming Pool

no reviews

from $89.00 Show details »

Rose Lane Villas in Key West, USA

Rose Lane Villas

Villa in Key West, Florida , 511 Eaton Street Check-in Location
Located in Key West, Florida, these villas feature a heated outdoor swimming pool.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 300 Reviews 8.6

from $246.38 Show details »

Southernmost Vistas by Last Key Realty in Key West, USA

Southernmost Vistas by Last Key Realty

Holiday home in Key West, Florida , 1327 Whitehead Street
Southernmost Vistas by Last Key Realty is located in Key West, just a 7-minute walk from Ernest Hemingway Home and Museum and 0.6 miles from Duval Str...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $57.00 Show details »

Dance of the Butterflies by Last Key Realty in Key West, USA

Dance of the Butterflies by Last Key Rea...

Holiday home in Key West, Florida , 1323 Whitehead Street
Dance of the Butterflies by Last Key Realty is located in Key West, just a 7-minute walk from Ernest Hemingway Home and Museum and 0.6 miles from Duva...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $61.00 Show details »

Southernmost View -Pool & Water Views in Key West, USA

Southernmost View -Pool & Water Views

Holiday home in Key West, Florida , Whitehead Street 1315
Just a 7-minute walk from Fort Zachary Taylor State Park Beach and 0.9 miles from Higgs Beach, Southernmost View -Pool & Water Views features accommod...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $96.00 Show details »

Helluva Happy Place in Key West, USA

Helluva Happy Place

Holiday home in Key West, Florida
Helluva Happy Place offers accommodations in Key West, a 11-minute walk from Duval Street and one mile from Mallory Square.

no reviews

from $87.00 Show details »

Spanish Lime Cottage by AvantStay Ideal Old Town Key West Location Month Long Stays Only in Key West, USA

Spanish Lime Cottage by AvantStay Ideal...

Holiday home in Key West, Florida
Spanish Lime Cottage by AvantStay Ideal Old Town Key West Location Month Long Stays Only is located in Key West, just a 9-minute walk from Duval Stree...
  • Parking
  • Pets allowed

no reviews

from $70.00 Show details »

Garden Of Roses - Monthly Rental in Key West, USA

Garden Of Roses - Monthly Rental

Holiday home in Key West, Florida , Key West
Garden Of Roses - Monthly Rental offers accommodations in Key West, a 4-minute walk from Ernest Hemingway Home and Museum and half a mile from Duval S...
  • Pets allowed
  • Fitness centre

no reviews

from $96.00 Show details »

Seagull Suite - Southernmost Sanctuary in Key West, USA

Seagull Suite - Southernmost Sanctuary

Holiday home in Key West, Florida , Simonton Street
Seagull Suite - Southernmost Sanctuary offers accommodations in Key West, a 10-minute walk from Ernest Hemingway Home and Museum and 0.6 miles from Du...
  • Pets allowed

no reviews

from $225.26 Show details »

Ibis Suite - Southernmost Sanctuary in Key West, USA

Ibis Suite - Southernmost Sanctuary

Holiday home in Key West, Florida , 1330 Simonton Street #3
Ibis Suite - Southernmost Sanctuary is located in Key West, just a 10-minute walk from Ernest Hemingway Home and Museum and 0.6 miles from Duval Stree...
  • Pets allowed

Fabulous 5 Reviews 8.6

from $237.72 Show details »

Egret Suite - Southernmost Sanctuary in Key West, USA

Egret Suite - Southernmost Sanctuary

Holiday home in Key West, Florida , 1330 Simonton Street #1
Egret Suite - Southernmost Sanctuary offers accommodations in Key West, a 10-minute walk from Ernest Hemingway Home and Museum and 0.6 miles from Duva...
  • Pets allowed

Exceptional 2 Reviews 10.0

from $237.72 Show details »

Pelican Suite - Southernmost Sanctuary in Key West, USA

Pelican Suite - Southernmost Sanctuary

Holiday home in Key West, Florida , 1330 Simonton Street #5
Pelican Suite - Southernmost Sanctuary offers accommodations in Key West, a 10-minute walk from Ernest Hemingway Home and Museum and 0.6 miles from Du...
  • Pets allowed

Good 1 Reviews 7.0

from $237.72 Show details »

Heron Suite - Southernmost Sanctuary in Key West, USA

Heron Suite - Southernmost Sanctuary

Holiday home in Key West, Florida , 1330 Simonton Street #2
Heron Suite - Southernmost Sanctuary is located in Key West, just a 10-minute walk from Ernest Hemingway Home and Museum and 0.6 miles from Duval Stre...
  • Pets allowed

Exceptional 1 Reviews 10.0

from $264.65 Show details »

Southernmost Sanctuary All in Key West, USA

Southernmost Sanctuary All

Holiday home in Key West, Florida , 1330 Simonton Street All
Southernmost Sanctuary All offers accommodations in Key West, a 10-minute walk from Ernest Hemingway Home and Museum and 0.6 miles from Duval Street.

no reviews

from $2.317.30 Show details »

Bahamian Blues by Last Key Realty in Key West, USA

Bahamian Blues by Last Key Realty

Holiday home in Key West, Florida , 302 Amelia Street
Bahamian Blues by Last Key Realty is located in Key West, just a 5-minute walk from Ernest Hemingway Home and Museum and half a mile from Duval Street...
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $82.00 Show details »

Sugarpoppy Cottage by Last Key Realty in Key West, USA

Sugarpoppy Cottage by Last Key Realty

Holiday home in Key West, Florida , 412 Louisa Street
Sugarpoppy Cottage by Last Key Realty is located in Key West, just a 5-minute walk from Ernest Hemingway Home and Museum and half a mile from Duval St...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $57.00 Show details »

Southernmost Hospitality V by Last Key Realty in Key West, USA

Southernmost Hospitality V by Last Key R...

Holiday home in Key West, Florida , 1224 Duval St
A 8-minute walk from Fort Zachary Taylor State Park Beach in Key West, Southernmost Hospitality V by Last Key Realty features accommodations with acce...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $1.346.44 Show details »

Key West Cockadoodle Cottage on Duval in Key West, USA

Key West Cockadoodle Cottage on Duval

Holiday home in Key West, Florida
Providing water sports facilities and free Wifi, Key West Cockadoodle Cottage on Duval provides accommodations in the center of Key West.
  • Spa and wellness centre

no reviews

from $73.00 Show details »

Twice as Nice on Duval Street in Key West, USA

Twice as Nice on Duval Street

Holiday home in Key West, Florida
Offering water sports facilities, Twice as Nice on Duval Street features accommodations in the center of Key West.
  • Spa and wellness centre

no reviews

from $90.00 Show details »

Casa Suite Casa by Last Key Realty in Key West, USA

Casa Suite Casa by Last Key Realty

Holiday home in Key West, Florida , 731 Waddell Street
A 7-minute walk from South Beach in Key West, Casa Suite Casa by Last Key Realty features accommodations with access to spa facilities.
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $99.00 Show details »

The Polynesian House byLast Key Realty in Key West, USA

The Polynesian House byLast Key Realty

Holiday home in Key West, Florida , 1415 Alberta Street
The Polynesian House byLast Key Realty offers accommodations in Key West, a 14-minute walk from Ernest Hemingway Home and Museum and 0.9 miles from Du...
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $55.00 Show details »

Havana Moon over Duval - Key West Cottage w Pool in Key West, USA

Havana Moon over Duval - Key West Cottag...

Holiday home in Key West, Florida
Offering water sports facilities and free Wifi, Havana Moon over Duval - Key West Cottage w Pool offers accommodations in the center of Key West.
  • Spa and wellness centre

no reviews

from $88.00 Show details »

Salvadors Seclusion in Key West, USA

Salvadors Seclusion

Holiday home in Key West, Florida , 1016 Howe St #4
Salvadors Seclusion is located in Key West, just a 7-minute walk from Southernmost Point and half a mile from Duval Street.
  • Pets allowed
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Pleasant 7 Reviews 6.2

from $167.78 Show details »

Andys Attic in Key West, USA

Andys Attic

Holiday home in Key West, Florida , 1016 Howe St #12
Andys Attic offers accommodations in Key West, a 7-minute walk from Southernmost Point and half a mile from Duval Street.
  • Pets allowed
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $190.39 Show details »

Number of Holiday homes in Key West 290
Number of guest ratings 86,662
Average price per night $74.00
Lowest price per night $55,00
Highest price per night $91,00

Top 10 Cheapest Holiday-homes in Key West

Discover the Cheapest Holiday-homes in Key West – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Key West

Check out the Most Booked Holiday-homes in Key West – Based on Guest Popularity.

Holiday homes in Key West (Florida), comfortable and familiar

Staying in a holiday or vacation home in Key West can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Key West for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Key West should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com