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

Holiday Homes in Key West

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (24 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
Road's End | Prime Old Town Location! Updated Home w/ Pool
A patio area with a fountain, seating, and umbrellas.

2. Andros Suite | Perfect Location with Pool!

Andros Suite | Perfect Location with Pool!
Old Town Key West
10.0 out of 10, Exceptional, (4 reviews)
"Great little place 1 block off Duval. A nice quiet oasis from everything a street away. Moon Dog restaurant is around the block and was great for breakfast and dinner. Great kitchen! The mattress upstairs could use a firmer replacement IMHO…overall very good spot!"
United States
Robert J.
Andros Suite | Perfect Location with Pool!
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

3. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (70 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is NZ$536
includes taxes & fees
27 Sept - 28 Sept
Poolside Cottage #411
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

Luxury two floor apartment in prime location of famous Duval Street
Old Town Key West
9.6 out of 10, Exceptional, (103 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
United States
Gregory L.
The price is NZ$1,050
includes taxes & fees
28 Sept - 29 Sept
Luxury two floor apartment in prime location of famous Duval Street
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

Casa Havana | Old Town Condo w/ Pool & Balcony
Old Town Key West
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
Casa Havana | Old Town Condo w/ Pool & Balcony
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

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (53 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is NZ$1,303
includes taxes & fees
2 Oct - 3 Oct
Sea Esta Suite | Located On Iconic Duval w/ Pool
A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

7. One Bedroom Suite | Beachside Resort

One Bedroom Suite | Beachside Resort
Key West
10.0 out of 10, Exceptional, (7 reviews)
"Great property, room was amazing!"
United States
Daris Y.
The price is NZ$465
includes taxes & fees
27 Sept - 28 Sept
One Bedroom Suite | Beachside Resort
A wooden deck with a large tree, outdoor seating, and a marina in the background.

8. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is NZ$565
includes taxes & fees
10 Oct - 11 Oct
Poolside Cottage #412
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

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is NZ$920
includes taxes & fees
28 Sept - 29 Sept
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A patio area with wicker furniture and a grill.

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

Southernmost Retreat | On Duval! With Hot Tub, Patio
Old Town Key West
9.6 out of 10, Exceptional, (33 reviews)
"Awesome place great location communication with host was great would stay here again next time I’m in key west."
United States
Drew L.
The price is NZ$1,646
includes taxes & fees
28 Sept - 29 Sept
Southernmost Retreat | On Duval! With Hot Tub, Patio
A pool area with a hot tub, outdoor seating, and a wooden fence with pool rules posted.

11. Private Parking, Heated Pool - Sweet Caroline

Private Parking, Heated Pool - Sweet Caroline
Key West Historic District
9.0 out of 10, Wonderful, (32 reviews)
"Amazing home and location! So close to Duval and all the fun places. I highly recommend staying here. Very comfy, clean and convenient."
United States
Susana C.
Private Parking, Heated Pool - Sweet Caroline
A wooden deck with two lounge chairs and a gazebo surrounded by lush greenery.

12. Atlantis House Suites

Atlantis House Suites
Midtown
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place to stay ! Located just close enough and just far away enough . Highly recommended "
United States
Aaron J.
Atlantis House Suites
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

Hemingway's Neighbor: Hot Tub, Sundeck, Old Town
Old Town Key West
9.8 out of 10, Exceptional, (18 reviews)
"Perfect location parking is a plus and being put friendly as a plus"
United States
Kat B.
The price is NZ$1,135
includes taxes & fees
28 Sept - 29 Sept
Hemingway's Neighbor: Hot Tub, Sundeck, Old Town
A backyard with a swimming pool, lounge chairs, and a wooden fence.

14. Coconut Palm - Steps from Duval with Private Pool

Coconut Palm - Steps from Duval with Private Pool
Old Town Key West
9.0 out of 10, Wonderful, (39 reviews)
"Great Property Excellent location "
United States
Jim B.
The price is NZ$2,212
includes taxes & fees
27 Oct - 28 Oct
Coconut Palm - Steps from Duval with Private Pool
A hallway with closed louvered doors, a wall-mounted light fixture, and a framed tropical-themed artwork.

15. Duval Vibes • Pool • 10 Guests

Duval Vibes • Pool • 10 Guests
Old Town Key West
10.0 out of 10, Exceptional, (16 reviews)
"Everything was clean and tidy, had trouble opening the door and the host was there to help with answering the questions I had. Super fun place to stay or even to relax"
United States
Grace K.
Duval Vibes • Pool • 10 Guests
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.

Spacious 3-bedroom townhome on Stock Island with resort style pool.
Stock Island
10.0 out of 10, Exceptional, (7 reviews)
"Perfect for our family trip to Key West. Great location and we enjoyed the pool and nearby restaurants. Easy check in and check out process and clear, timely communication with the owner. "
United States
Samantha P.
The price is NZ$987
includes taxes & fees
6 Oct - 7 Oct
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A backyard with a swimming pool, wooden deck, and a covered patio area.

17. Conch Cove | Private Oasis with Heated Pool!

Conch Cove | Private Oasis with Heated Pool!
Old Town Key West
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful spot and outstanding property management company. "
United States
Jessica B.
Conch Cove | Private Oasis with Heated Pool!
A clear swimming pool with lounge chairs and palm trees.

18. Another Day in Paradise

Another Day in Paradise
Stock Island
9.6 out of 10, Exceptional, (4 reviews)
"It was perfect for what we were looking for"
United States
Megan A.
Another Day in Paradise
A modern living room with a white sofa, blue chairs, and a kitchen in the background.

19. Harbor House Penthouse- B

Harbor House Penthouse- B
Key West Historic District
9.8 out of 10, Exceptional, (18 reviews)
"Great location "
United States
Shawn G.
The price is NZ$2,143
includes taxes & fees
30 Sept - 1 Oct
Harbor House Penthouse- B
A covered outdoor patio with a pool, seating area, and lush greenery.

20. Coconut Palm by Brightwild Island Home w Pool

Coconut Palm by Brightwild Island Home w Pool
2.0 star property
Old Town Key West
The price is NZ$1,741
includes taxes & fees
5 Oct - 6 Oct
Coconut Palm by Brightwild Island Home w Pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Key West Hotel Reviews

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Genial"
Yisel 1-night trip
Posted less than an hour ago
Blue Flamingo Resort Key West

Find out more about Key West

Key West Holiday Homes information

Number of reviews
653
Accommodation
916 Holiday Homes
Lowest Price
NZ$465
Highest Price
NZ$2,212

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