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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Our top choices for Key West holiday homes

1. Aug.-Sept. Special@125.lodging Only 129. + extras. From.8-17 to 9-30

Aug.-Sept. Special@125.lodging Only 129. + extras. From.8-17 to 9-30
Old Town Key West
9.0 out of 10, Wonderful, (198 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
The price is NZ$524
includes taxes & fees
31 Aug - 1 Sept
Aug.-Sept. Special@125.lodging Only 129. + extras. From.8-17 to 9-30

2. 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
10.0 out of 10, Exceptional, (21 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is NZ$821
includes taxes & fees
25 Aug - 26 Aug
Road's End | Prime Old Town Location! Updated Home w/ Pool

3. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (68 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$511
includes taxes & fees
25 Aug - 26 Aug
Poolside Cottage #411

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$974
includes taxes & fees
9 Sept - 10 Sept
Luxury two floor apartment in prime location of famous Duval Street

5. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (36 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is NZ$513
includes taxes & fees
23 Aug - 24 Aug
Poolside Cottage #412

6. One Bedroom Suite | Beachside Resort

One Bedroom Suite | Beachside Resort
Key West
10.0 out of 10, Exceptional, (4 reviews)
"Great property, room was amazing!"
United States
Daris Y.
The price is NZ$505
includes taxes & fees
25 Aug - 26 Aug
One Bedroom Suite | Beachside Resort

7. Private Parking, Heated Pool - Sweet Caroline

Private Parking, Heated Pool - Sweet Caroline
Key West Historic District
9.0 out of 10, Wonderful, (32 reviews)
"Parking was easy actually was easy. The location is great easy walking distance to Duval and everything that’s happening in downtown."
United States
Robert B.
The price is NZ$1,065
includes taxes & fees
16 Aug - 17 Aug
Private Parking, Heated Pool - Sweet Caroline

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

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Stock Island
10.0 out of 10, Exceptional, (23 reviews)
"Great place nice and clean easy access to the pool short drive to the beach"
United States
Nathan W.
The price is NZ$1,500
includes taxes & fees
13 Aug - 14 Aug
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

9. 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, (6 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
The price is NZ$1,268
includes taxes & fees
13 Aug - 14 Aug
Casa Havana | Old Town Condo w/ Pool & Balcony

10. Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (4 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
The price is NZ$941
includes taxes & fees
25 Aug - 26 Aug
Slice of Paradise

11. 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, (51 reviews)
"Great location, easy check-in/check-out process, house was clean and spacious, and the host was very communicative!"
United States
Lindsey R.
The price is NZ$1,477
includes taxes & fees
17 Aug - 18 Aug
Sea Esta Suite | Located On Iconic Duval w/ Pool

12. Gone Coastal

Gone Coastal
Stock Island
9.6 out of 10, Exceptional, (22 reviews)
"Great place , clean and close to everything!"
United States
april
The price is NZ$1,025
includes taxes & fees
25 Aug - 26 Aug
Gone Coastal

13. Another Day in Paradise

Another Day in Paradise
Stock Island
9.4 out of 10, Exceptional, (3 reviews)
"Comfortable homey house."
United States
Wendi T.
The price is NZ$1,271
includes taxes & fees
26 Aug - 27 Aug
Another Day in Paradise

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)
"Perfect location! We enjoyed the private back yard with pool. "
United States
Haley G.
The price is NZ$1,492
includes taxes & fees
31 Aug - 1 Sept
Coconut Palm - Steps from Duval with Private Pool

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

Southernmost Retreat | On Duval! With Hot Tub, Patio
Old Town Key West
9.8 out of 10, Exceptional, (32 reviews)
"The location was perfect, lots of shopping, food, and drinks you can walk to! The hosts were so nice, responsive, and accommodating to all of our guests! "
United States
Maggie B.
The price is NZ$1,781
includes taxes & fees
13 Aug - 14 Aug
Southernmost Retreat | On Duval! With Hot Tub, Patio

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

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Key West Historic District
10.0 out of 10, Exceptional, (132 reviews)
"Great little house for a family "
United States
Edward M.
The price is NZ$2,127
includes taxes & fees
9 Sept - 10 Sept
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

17. 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$1,027
includes taxes & fees
18 Aug - 19 Aug
Spacious 3-bedroom townhome on Stock Island with resort style pool.

18. Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (38 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is NZ$1,354
includes taxes & fees
10 Sept - 11 Sept
Paradise found

19. Steps to Duval •Hot tub • Sleeps 6

Steps to Duval •Hot tub • Sleeps 6
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.
Steps to Duval •Hot tub • Sleeps 6

20. Luxurious Island Pearl-Private Pool - 2BD/2Bath

Luxurious Island Pearl-Private Pool - 2BD/2Bath
Key West Historic District
10.0 out of 10, Exceptional, (58 reviews)
"Amazing stay five star!! "
United States
Erica S.
The price is NZ$2,113
includes taxes & fees
2 Sept - 3 Sept
Luxurious Island Pearl-Private Pool - 2BD/2Bath
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

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Key West Holiday Homes information

Number of reviews
806
Accommodation
923 Holiday Homes
Lowest Price
NZ$505
Highest Price
NZ$2,127

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