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 kitchen with a refrigerator, stove, and two bar stools.

1. Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30

Old Town Key West

Jeanine

HK$2,247 total

includes taxes & fees

31 Aug - 1 Sept

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

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

Old Town Key West

Mike T.

HK$3,765 total

includes taxes & fees

25 Aug - 26 Aug

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$2,397 total

includes taxes & fees

26 Aug - 27 Aug

An aerial view of a beach with clear turquoise waters, a sandy shore, and a cluster of umbrellas.

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

Old Town Key West

Gregory L.

HK$4,663 total

includes taxes & fees

24 Aug - 25 Aug

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

5. Poolside Cottage #412

Key West

Julia M.

HK$2,389 total

includes taxes & fees

1 Sept - 2 Sept

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

6. One Bedroom Suite | Beachside Resort

Key West

Mike C.

HK$2,271 total

includes taxes & fees

23 Aug - 24 Aug

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

7. Private Parking, Heated Pool - Sweet Caroline

Key West Historic District

Robert B.

HK$4,927 total

includes taxes & fees

1 Sept - 2 Sept

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

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

Old Town Key West

Kim T.

HK$5,810 total

includes taxes & fees

7 Sept - 8 Sept

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

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

Old Town Key West

Lindsey R.

HK$6,809 total

includes taxes & fees

6 Sept - 7 Sept

A covered outdoor seating area with wicker furniture and a white table, overlooking a large tree and lush greenery.

10. TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

Stock Island

Nathan W.

HK$7,109 total

includes taxes & fees

25 Aug - 26 Aug

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

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

Stock Island

Samantha P.

HK$4,460 total

includes taxes & fees

21 Aug - 22 Aug

A clear swimming pool with lounge chairs and palm trees.

12. Another Day in Paradise

Stock Island

Wendi T.

HK$4,600 total

includes taxes & fees

21 Aug - 22 Aug

13. Slice of Paradise

Stock Island

Cathy S.

HK$4,397 total

includes taxes & fees

23 Aug - 24 Aug

A patio area with wicker furniture and a grill.

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

Old Town Key West

Maggie B.

HK$8,066 total

includes taxes & fees

23 Aug - 24 Aug

15. Coconut Palm - Steps from Duval with Private Pool

Old Town Key West

Jim B.

HK$7,088 total

includes taxes & fees

23 Aug - 24 Aug

A clear swimming pool surrounded by palm trees and lounge chairs.

16. Paradise found

Stock Island

Robert B.

HK$5,171 total

includes taxes & fees

1 Sept - 2 Sept

A swimming pool with a wooden deck, a covered patio area, and a building with large windows and a covered porch.

17. BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

Key West Historic District

Jennifer B.

HK$9,843 total

includes taxes & fees

9 Sept - 10 Sept

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

18. Atlantis House Suites

Midtown

Aaron J.

HK$6,222 total

includes taxes & fees

26 Aug - 27 Aug

A white building with blue shutters, surrounded by lush greenery and a brick pathway.

19. Passover Cottage | Private Pool & Ideal Key West Location

Old Town Key West

john w.

HK$7,503 total

includes taxes & fees

8 Sept - 9 Sept

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

20. Gone Coastal

Stock Island

april

HK$4,747 total

includes taxes & fees

21 Aug - 22 Aug

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Top Key West Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

8/10 Good

"Some of the house keepers didn’t speak English which was occasionally a problem for us and other guests.Also, it would be nice if they had drinks and snacks available 24 hours because the marketplace closes too early and low a bit lacking. Once the marketplace closes closes you’re stuck with the bar or restaurant but who wants to order a pizza when all you want us some popcorn? Besides that, the place is beautiful and very well maintained. We had an enjoyable experience."

Hyatt Vacation Club at Windward Pointe, Key West

8/10 Good

"The property was nice, well maintained and the pool was fantastic. The grill/restaurant is fine for basic poolside food and the drinks are strong. The only negative with the property is location. There’s really nothing within walking distance and Old Town is a 10 minute drive away. The only reason we might not stay here again is to be closer to Old Town."

Blue Flamingo Resort Key West

10/10 Excellent

"This place was really nice. It was very clean and quiet. The staff is very helpful and friendly. We enjoyed the outdoor pools, food and bar. There is lots of activities outside to do with your family and friends. We didn’t have a problem at all while we stayed there. I would definitely stay there again if we go back to Key West. This is the best place I have stayed at."

La Concha Key West, Autograph Collection

10/10 Excellent

"We had a wonderful stay at La Concha Hotel in Key West! The location on Duval Street was one of the biggest highlights..it was within perfect walking distance of so many of Key West’s attractions, restaurants, bars, and things to do, which made exploring the area incredibly convenient. Having onsite parking was also a huge benefit, especially in Key West where parking can be difficult to find. The hotel bar was excellent, and the staff throughout the hotel were incredibly friendly and welcoming. Overall, La Concha was a great choice for a Key West stay, especially if you want to be right in the heart of everything!"

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