Rockland Key Holiday Rentals
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Our top choices for Rockland Key holiday rentals
Cottage in Cudjoe Key
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West8.2 out of 10, Very good, (53)
"Great area. Quiet and comfortable "
nancy c.
Cottage in Cudjoe Key
Cottage with swimming pool and dockage, just minutes to Key West!9.0 out of 10, Wonderful, (160)
"Everything was there that I needed. Very nice area for my dog."
Terry
Cottage in Cudjoe Key
Private Oceanfront Cottage with dockage, pool just minutes to Key West!8.6 out of 10, Excellent, (164)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
Andrea S.
The price is HK$1,750
HK$2,943 total
includes taxes & fees
19 Jan - 20 Jan 2026
Houseboat in Stock Island
Aqua Lodges at Hurricane Hole Marina8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
William
The price is HK$1,523
HK$3,016 total
includes taxes & fees
12 Jan - 13 Jan 2026
Holiday Home in Cudjoe Key
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS9.4 out of 10, Exceptional, (101)
"Great location. "
Davian k.
The price is HK$2,325
HK$4,741 total
includes taxes & fees
10 Jan - 11 Jan 2026
Villa in Summerland Key
Atlantic View Luxury Villa with Pool10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
Preetam
The price is HK$4,374
HK$7,982 total
includes taxes & fees
16 Jan - 17 Jan 2026
Holiday Home in Cudjoe Key
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
Ubaldo G.
The price is HK$2,325
HK$4,741 total
includes taxes & fees
18 Jan - 19 Jan 2026
Holiday Home in Upper Sugarloaf Key
Palm - Beach Houses Key West10.0 out of 10, Exceptional, (14)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
Harvey(Tabb) M.
The price is HK$8,511
HK$15,114 total
includes taxes & fees
14 Jan - 15 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.
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Top Rockland Key Hotel Reviews
Havana Cabana at Key West
10/10 Excellent
Find out more about Rockland Key
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