Holiday Homes in Key West
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Our top choices for Key West holiday homes
Poolside Cottage #412
Poolside Cottage #412Key West
9.2 out of 10, Wonderful, (28)
"The property and our place was really nice. Would definitely stay again. "
Sarah M.
The price is NZ$654
includes taxes & fees
7 Jan - 8 Jan 2026
Very Low Rates. See dates below avail. PreXmas spec@ And 10% Off wkly stays
Very Low Rates. See dates below avail. PreXmas spec@ And 10% Off wkly staysOld Town Key West
9.0 out of 10, Wonderful, (180)
"We had such a delightful time staying here! While the space is small, it was absolutely perfect for two people. Everything was clean, comfortable, and conveniently located. We really enjoyed our time in Key West and would definitely stay here again!
"
ALISHA
The price is NZ$880
includes taxes & fees
16 Jan - 17 Jan 2026
10.0 out of 10, Exceptional, (1)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
Karen
The price is NZ$3,309
includes taxes & fees
20 Jan - 21 Jan 2026
Poolside Cottage #411
Poolside Cottage #411Key West
9.8 out of 10, Exceptional, (53)
"Perfect for our family! Recommend 10/10!"
Melissa F.
The price is NZ$941
includes taxes & fees
3 Jan - 4 Jan 2026
Road’s End | Prime Old Town Location! Modern Updates, Shared Pool!
Road’s End | Prime Old Town Location! Modern Updates, Shared Pool!Old Town Key West
The price is NZ$913
includes taxes & fees
6 Jan - 7 Jan 2026
The Shellstone House at Solaire Lunara Bay
The Shellstone House at Solaire Lunara BayRaccoon Key
The price is NZ$4,559
includes taxes & fees
4 Jan - 5 Jan 2026
Capmar House at Lunara Bay
Capmar House at Lunara BayRaccoon Key
9.8 out of 10, Exceptional, (29)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
Anonymous traveller
The price is NZ$2,713
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious 3-bedroom townhome on Stock Island with resort style pool.
Spacious 3-bedroom townhome on Stock Island with resort style pool.Stock Island
The price is NZ$900
includes taxes & fees
10 Jan - 11 Jan 2026
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.
Top Key West Hotel Reviews
Winslow's Bungalows - Key West Historic Inns
10/10 Excellent
Find out more about Key West
Key West Holiday Homes information
Number of reviews | 364 |
|---|---|
Accommodation | 1043 Holiday Homes |
Lowest Price | NZ$654 |
Highest Price | NZ$5,714 |
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- Smathers Beach
- Southernmost Point
- Key West Cemetery
- Clarence S. Higgs Memorial Beach Park
- Mel Fisher Maritime Museum
- Mallory Square
- Fort Zachary Taylor Historic State Park
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