Holiday rentals in Key West

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Top-rated holiday rentals in Key West

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.
13–20 Dec
₹36,788 per night
4.94 out of 5 average rating, 267 reviews
Guest favourite
Flat in Key West
Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.
22–29 Jan
₹24,458 per night
4.97 out of 5 average rating, 439 reviews
Superhost
Holiday home in Key West
Historic Cigar House. 3rd floor Suite W/Kitchen
This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.
6–13 Jan
₹29,314 per night
4.88 out of 5 average rating, 223 reviews

Popular amenities for Key West holiday rentals

Stay near Key West's top sights

Duval Street62 locals recommend
Mallory Square100 locals recommend
Key West Butterfly and Nature Conservatory56 locals recommend
Fort Zachary Taylor Historic State Park47 locals recommend
Higgs Beach21 locals recommend
Sebago Watersports6 locals recommend

Other great holiday rentals in Key West

Guest favourite
Apartment in Key West
Hidden Beach Duplex, Best Place in Key West
17–24 Nov
₹50,367 per night
4.99 out of 5 average rating, 83 reviews
Superhost
Houseboat in Key West
The Crystalmarine Suite – Rustic Luxury on the Sea
31 Oct – 7 Nov
₹37,723 per night
4.9 out of 5 average rating, 31 reviews
Guest favourite
Bungalow in Key West
Atlantis House's Palm Suite-voted top 25 in USA
5–12 Aug
₹48,348 per night
4.99 out of 5 average rating, 75 reviews
Guest favourite
Home in Key West
Gorgeous Romantic Private Villa, Steps from Duval!
22 Feb – 1 Mar
₹55,056 per night
5.0 out of 5 average rating, 36 reviews
Superhost
Home in Upper Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse
11–18 Jan
₹64,192 per night
4.86 out of 5 average rating, 42 reviews
Superhost
Flat in Key West
Cozy Little Cottage @ KW Vacation
3–10 Oct
₹28,728 per night
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Key West
Oceanfront Condo in Key West
5–12 Dec
₹50,219 per night
4.93 out of 5 average rating, 14 reviews
Guest favourite
Cottage in Key West
Mango Cottage 2 bedroom 2 bath with private pool
8–15 Oct
₹79,776 per night
4.95 out of 5 average rating, 84 reviews
Superhost
Apartment in Key West
Ocean front 1BR/1BA Suite w/ kitchen & living rm
4–11 Jan
₹28,330 per night
4.83 out of 5 average rating, 36 reviews
Guest favourite
Apartment in Key West
Spectacular Ocean View Amazing quality- Massage Ch
20–27 May
₹58,759 per night
5.0 out of 5 average rating, 10 reviews
Guest favourite
Apartment in Key West
*Come to my Deck for a time you won't Forget!
24–31 Oct
₹32,558 per night
4.99 out of 5 average rating, 76 reviews
Superhost
Tiny home in Big Pine Key
Breezy pines 28 foot 5th wheel trailer .
3–10 Oct
₹8,316 per night
4.8 out of 5 average rating, 88 reviews

Quick stats about holiday rentals in Key West

Total rentals

1.8T properties

Rentals with a pool

1.2T properties have a pool

Pet-friendly rentals

490 properties allow pets

Family-friendly rentals

1.1T properties are a good fit for families

Total number of reviews

52T reviews

Nightly prices starting at

₹829 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West