Vacation rentals in Key West

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Top-rated vacation 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.
Nov. 24 – Dec. 1
$784 CAD per night
4.94 out of 5 average rating, 267 reviews
Guest favourite
Apartment 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.
Dec. 1 – 8
$485 CAD per night
4.97 out of 5 average rating, 439 reviews
Superhost
Vacation 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.
Nov. 15 – 22
$624 CAD per night
4.88 out of 5 average rating, 223 reviews

Popular amenities for Key West vacation 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 vacation rentals in Key West

Guest favourite
Townhouse in Key West
Stunning Townhouse * Full kitchen! * Sleeps 6
Nov. 14 – 21
$1,015 CAD per night
4.96 out of 5 average rating, 223 reviews
Guest favourite
Condo in Key West
Hidden Beach Duplex, Best Place in Key West
Nov. 17 – 24
$1,000 CAD per night
4.99 out of 5 average rating, 83 reviews
Superhost
Houseboat in Key West
The Crystalmarine Suite – Rustic Luxury on the Sea
Aug. 19 – 26
$749 CAD 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
Aug. 4 – 11
$995 CAD per night
4.99 out of 5 average rating, 75 reviews
Guest favourite
Condo in Key West
*Come to my Deck for a time you won't Forget!
Oct. 24 – 31
$717 CAD per night
4.99 out of 5 average rating, 76 reviews
Guest favourite
Cottage in Key West
Mango Cottage 2 bedroom 2 bath with private pool
Jul. 14 – 21
$1,288 CAD per night
4.95 out of 5 average rating, 84 reviews
Guest favourite
Cottage in Key West
Casa Serendipity @ Old Town - Private Home & Pool
Sep. 29 – Oct. 6
$1,095 CAD per night
5.0 out of 5 average rating, 26 reviews
Superhost
Home in Upper Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse
Feb. 12 – 19
$1,497 CAD per night
4.86 out of 5 average rating, 42 reviews
Guest favourite
Home in Key West
Gorgeous Romantic Private Villa, Steps from Duval!
Jul. 5 – 12
$859 CAD per night
5.0 out of 5 average rating, 36 reviews
Superhost
Condo in Key West
Ocean Front Studio private Sandy Beach in Key West
Dec. 7 – 14
$646 CAD per night
4.89 out of 5 average rating, 72 reviews
Guest favourite
Boat in Key West
Cozy Houseboat “Wild One”
Jun. 20 – 27
$397 CAD per night
5.0 out of 5 average rating, 61 reviews
Guest favourite
Apartment in Key West
Oceanfront Condo in Key West
Jun. 16 – 23
$1,050 CAD per night
4.93 out of 5 average rating, 14 reviews

Quick stats about vacation rentals in Key West

Total rentals

1.8K properties

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

490 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

52K reviews

Nightly prices starting at

$14 CAD before taxes and fees

Destinations to explore

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