Key West Vacation Homes

A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

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Our top choices for Key West holiday homes

A building with a red door, a covered porch, and a bamboo plant in the foreground.

1. Road's End | Prime Old Town Location! Updated Home w/ Pool

Old Town Key West

Mike T.

HK$3,328 total

includes taxes & fees

27 Oct - 28 Oct

A patio area with a fountain, seating, and umbrellas.

2. Andros Suite | Perfect Location with Pool!

Old Town Key West

Robert J.

HK$3,312 total

includes taxes & fees

2 Oct - 3 Oct

A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

3. Poolside Cottage #411

Key West

Jennifer W.

HK$2,288 total

includes taxes & fees

28 Sept - 29 Sept

An aerial view of a beach with clear turquoise waters, a sandy shore, and a dense forested area.

4. Luxury two floor apartment in prime location of famous Duval Street

Old Town Key West

Gregory L.

HK$4,383 total

includes taxes & fees

28 Sept - 29 Sept

A covered porch with a table and chairs, a view of the street, and a building with a balcony.

5. Casa Havana | Old Town Condo w/ Pool & Balcony

Old Town Key West

Kim T.

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

6. Sea Esta Suite | Located On Iconic Duval w/ Pool

Old Town Key West

Rick H.

HK$5,473 total

includes taxes & fees

2 Oct - 3 Oct

A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

7. One Bedroom Suite | Beachside Resort

Key West

Daris Y.

HK$2,504 total

includes taxes & fees

2 Oct - 3 Oct

A wooden deck with a large tree, outdoor seating, and a marina in the background.

8. Poolside Cottage #412

Key West

Julia M.

HK$2,423 total

includes taxes & fees

10 Oct - 11 Oct

A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

9. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Stock Island

Linda

HK$3,843 total

includes taxes & fees

28 Sept - 29 Sept

A patio area with wicker furniture and a grill.

10. Southernmost Retreat | On Duval! With Hot Tub, Patio

Old Town Key West

Drew L.

HK$6,989 total

includes taxes & fees

28 Sept - 29 Sept

A pool area with a hot tub, outdoor seating, and a wooden fence with pool rules posted.

11. Private Parking, Heated Pool - Sweet Caroline

Key West Historic District

Susana C.

HK$6,532 total

includes taxes & fees

2 Oct - 3 Oct

A wooden deck with two lounge chairs and a gazebo surrounded by lush greenery.

12. Atlantis House Suites

Midtown

Aaron J.

HK$5,334 total

includes taxes & fees

1 Oct - 2 Oct

A bed with a white quilt and two pillows, one with a floral pattern. There are two wooden nightstands with lamps, and a painting on the wall.

13. Hemingway's Neighbor: Hot Tub, Sundeck, Old Town

Old Town Key West

Kat B.

HK$4,837 total

includes taxes & fees

27 Sept - 28 Sept

A backyard with a swimming pool, lounge chairs, and a wooden fence.

14. Coconut Palm - Steps from Duval with Private Pool

Old Town Key West

Jim B.

HK$9,189 total

includes taxes & fees

27 Oct - 28 Oct

A hallway with closed louvered doors, a wall-mounted light fixture, and a framed tropical-themed artwork.

15. Duval Vibes • Pool • 10 Guests

Old Town Key West

Grace K.

A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

16. Spacious 3-bedroom townhome on Stock Island with resort style pool.

Stock Island

Samantha P.

HK$4,250 total

includes taxes & fees

6 Oct - 7 Oct

A backyard with a swimming pool, wooden deck, and a covered patio area.

17. Conch Cove | Private Oasis with Heated Pool!

Old Town Key West

Jessica B.

HK$8,888 total

includes taxes & fees

4 Oct - 5 Oct

A clear swimming pool with lounge chairs and palm trees.

18. Another Day in Paradise

Stock Island

Megan A.

HK$4,367 total

includes taxes & fees

4 Oct - 5 Oct

A modern living room with a white sofa, blue chairs, and a kitchen in the background.

19. Harbor House Penthouse- B

Key West Historic District

Shawn G.

HK$8,914 total

includes taxes & fees

2 Oct - 3 Oct

A covered outdoor patio with a pool, seating area, and lush greenery.

20. Coconut Palm by Brightwild Island Home w Pool

Old Town Key West

HK$7,883 total

includes taxes & fees

27 Sept - 28 Sept

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Top Key West Hotel Reviews

Blue Flamingo Resort Key West

10/10 Excellent

"The Blue Flamingo was clean. The staff was kind and helpful. Anything we needed was handled very well."

Ibis Bay Beach Resort

8/10 Good

"If your looking for an a good resort for a value price this is your place. It is full of character!! The staff is friendly, even let us check in early. Beautiful location on the water with lots of outdoor space, just to lounge around. Loved all the hammocks. Do yourself a favor and pay a little extra for a water view room super cute porch that leads out to a secluded beach with hammocks and loungers."

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"From before we arrived we already knew we chose the right place to stay! We had questions about parking our motorcycle on property and there was no hesitation to share information and also connect with us. The staff is great. We are recommending this location and properties to friends and family. Next time we’re in town, 100% this will be the place we stay. Location is great and the property is fun to explore. Thank you all for making our stay memorable!"

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