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

4.94 out of 5 average rating, 268 reviews

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.

4–11 Aug

₹41,836 per night
Guest favourite

Flat in Key West

4.98 out of 5 average rating, 441 reviews

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.

20–27 Jan

₹28,300 per night
Superhost

Guest suite in Key West

4.83 out of 5 average rating, 12 reviews

Conch Republic Studio - Key West Millionaires Row

In the center of prestigious Millionaires Row, Conch Republic Studio is a private, separate rental in the back of the main house with a private entrance. A tranquil getaway for one or a couple in the Historic District. Walk 5 blocks to Duval Street or marina. Only 8 blocks to Hemingway's House and Lighthouse. In the morning enjoy a famous Five Brothers Cuban coffee or sandwich, evenings dine at one of the South's most popular restaurants, Cafe Sole, both just 100 steps away. 1G optic internet!

2–9 Feb

₹14,693 per night

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

Superhost

Cottage in Key West

4.95 out of 5 average rating, 84 reviews

Mango Cottage 2 bedroom 2 bath with private pool

1–8 Oct

₹46,338 per night
Superhost

Home in Key West

5.0 out of 5 average rating, 3 reviews

Charming + Historic Eyebrow Home

24 Feb – 3 Mar

₹45,942 per night
Superhost

Home in Upper Sugarloaf Key

4.86 out of 5 average rating, 43 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

6–13 Aug

₹74,259 per night
Superhost

Home in Key West

4.95 out of 5 average rating, 39 reviews

Southard Comfort ~ Feel The Key West Vibe

11–18 Sep

₹55,996 per night
Guest favourite

Bungalow in Key West

4.99 out of 5 average rating, 76 reviews

Atlantis House's Palm Suite-voted top 25 in USA

14–21 Oct

₹65,102 per night
Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

16–23 Oct

₹9,840 per night
Guest favourite

Home in Key West

5.0 out of 5 average rating, 37 reviews

Gorgeous Romantic Private Villa, Steps from Duval!

6–13 Mar

₹54,146 per night
Guest favourite

Home in Key West

5.0 out of 5 average rating, 13 reviews

Villa Paradiso: A unique mid-town paradise

11–18 May

₹75,195 per night
Guest favourite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

The Gulf Cottage at Marathon Key

8–15 Jun

₹12,420 per night
Guest favourite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Million Dollar View

12–19 Oct

₹65,026 per night
Guest favourite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

9–16 Nov

₹46,665 per night
Guest favourite

Flat in Key West

4.93 out of 5 average rating, 15 reviews

Oceanfront Condo in Key West

10–17 Jul

₹58,013 per night

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

₹834 before taxes and fees

Destinations to explore

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