Rockland Key Holiday Rentals

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Our top choices for Rockland Key holiday rentals

8.2 out of 10, Very good, (53)
"Great area. Quiet and comfortable "
United States
nancy c.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.0 out of 10, Wonderful, (160)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
Cottage with swimming pool and dockage, 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."
United States
Andrea S.
The price is HK$1,750
HK$2,943 total
includes taxes & fees
19 Jan - 20 Jan 2026
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is HK$1,523
HK$3,016 total
includes taxes & fees
12 Jan - 13 Jan 2026
Aqua Lodges at Hurricane Hole Marina
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is HK$2,325
HK$4,741 total
includes taxes & fees
10 Jan - 11 Jan 2026
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
3.5 star property
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is HK$4,374
HK$7,982 total
includes taxes & fees
16 Jan - 17 Jan 2026
Atlantic View Luxury Villa with Pool
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is HK$2,325
HK$4,741 total
includes taxes & fees
18 Jan - 19 Jan 2026
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Holiday Home in Upper Sugarloaf Key

Palm - Beach Houses Key West
10.0 out of 10, Exceptional, (14)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
United States
Harvey(Tabb) M.
The price is HK$8,511
HK$15,114 total
includes taxes & fees
14 Jan - 15 Jan 2026
Palm - Beach Houses Key West
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is HK$1,944
HK$3,919 total
includes taxes & fees
4 Jan - 5 Jan 2026
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Holiday Home in Raccoon Key

Capmar House at Lunara Bay
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!!!"
United States
Anonymous traveller
The price is HK$5,435
HK$12,310 total
includes taxes & fees
5 Jan - 6 Jan 2026
Capmar House at Lunara Bay
8.6 out of 10, Excellent, (75)
"Place was everything we needed, would definitely stay again "
United States
James h.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.8 out of 10, Excellent, (65)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is HK$4,192
HK$10,232 total
includes taxes & fees
8 Jan - 9 Jan 2026
One of the very few beach houses with a daily, rental license in the Keys.

Holiday Home in Raccoon Key

Springtide House at Lunara Bay
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
The price is HK$5,435
HK$11,914 total
includes taxes & fees
4 Jan - 5 Jan 2026
Springtide House at Lunara Bay
9.6 out of 10, Exceptional, (88)
"This place really had it all , one of my best stays yet anywhere. "
United States
Charles M.
The price is HK$3,149
HK$6,461 total
includes taxes & fees
1 Jan - 2 Jan 2026
Old Florida Style, wrap around porch, boat basin for dockage, open water
2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
The price is HK$5,280
HK$7,829 total
includes taxes & fees
20 Jan - 21 Jan 2026
Grand Marina Suite by Brightwild Waterfront

Holiday Home in Stock Island

Paradise found
9.8 out of 10, Exceptional, (31)
"The home was perfect. Very well decorated. Clean comfortable,luxurious and well located. We absolutely recommend this home to anyone staying in the Keys. We will certainly return."
United States
Christel M.
Paradise found
10.0 out of 10, Exceptional, (3)
"Beautiful "
United States
Lisa P.
The price is HK$4,082
HK$7,936 total
includes taxes & fees
3 Jan - 4 Jan 2026
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Holiday Home in Raccoon Key

Larkshine House at Lunara Bay
2.0 star property
10.0 out of 10, Exceptional, (7)
"well maintained, clean, easy to access"
United States
Raj P.
The price is HK$9,323
HK$19,203 total
includes taxes & fees
4 Jan - 5 Jan 2026
Larkshine House at Lunara Bay
8.6 out of 10, Excellent, (120)
"Jennifer was very nice and accommodating."
United States
Randy G.
Charming cottages, dockage, pool, just minutes to Key West
9.2 out of 10, Wonderful, (142)
"Really nice location and a beautiful pool. The gym/activities area was not well equipped "
United States
Jennifer H.
The price is HK$7,449
HK$12,286 total
includes taxes & fees
31 Dec - 1 Jan 2026
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
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

Find out more about Rockland Key

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