Lower Sugarloaf Key Vacation Rentals

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Our top choices for Lower Sugarloaf Key vacation rentals

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (278)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is ¥17,510
¥45,762 total
includes taxes & fees
Dec 14 - Dec 15
Aqua Lodges at Hurricane Hole Marina

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (52)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
The price is ¥20,991
¥49,329 total
includes taxes & fees
Dec 14 - Dec 15
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
9.0 out of 10, Wonderful, (88)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
The price is ¥24,540
¥57,505 total
includes taxes & fees
Dec 15 - Dec 16
Canal front, dockage, 2 bedroom, 2 bath

DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is ¥23,168
¥67,483 total
includes taxes & fees
Dec 15 - Dec 16
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (120)
"Jennifer was very nice and accommodating."
United States
Randy G.
The price is ¥24,878
¥51,234 total
includes taxes & fees
Dec 23 - Dec 24
Charming cottages, dockage, pool, just minutes to Key West

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
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 ¥78,717
¥142,978 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Atlantic View Luxury Villa with Pool

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
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 ¥38,873
¥78,834 total
includes taxes & fees
Dec 15 - Dec 16
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (2)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is ¥43,308
¥61,945 total
includes taxes & fees
Dec 17 - Dec 18
Island View 1BR Residence With Balcony

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (121)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
The price is ¥31,487
¥80,146 total
includes taxes & fees
Dec 17 - Dec 18
Kelly's Kabin - Adorable Private Summerland Key Cottage

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
2.5 star property
Cudjoe Key
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is ¥36,735
¥101,036 total
includes taxes & fees
Dec 15 - Dec 16
Island Time #110 Ocean Views - Cudjoe Key

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
Meadows
10.0 out of 10, Exceptional, (17)
"Really enjoyed the accommodations. "
United States
Timothy
The price is ¥18,037
¥67,270 total
includes taxes & fees
Dec 16 - Dec 17
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
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 ¥38,797
¥87,176 total
includes taxes & fees
Dec 14 - Dec 15
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.2 out of 10, Very Good, (50)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is ¥20,991
¥49,174 total
includes taxes & fees
Dec 16 - Dec 17
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (90)
"Nice place to vacation "
United States
Kevin D.
The price is ¥24,540
¥53,843 total
includes taxes & fees
Dec 14 - Dec 15
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (155)
"The property was excellent. The location was perfect. Quiet and relaxing. "
United States
Jonathan K.
The price is ¥38,484
¥87,765 total
includes taxes & fees
Dec 15 - Dec 16
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
Old Town Key West
8.4 out of 10, Very Good, (319)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is ¥39,718
¥49,931 total
includes taxes & fees
Dec 16 - Dec 17
Hyatt Vacation Club at Sunset Harbor, Key West

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.8 out of 10, Exceptional, (33)
"Good place to stay loved it"
United States
Charles I.
The price is ¥22,125
¥61,791 total
includes taxes & fees
Dec 20 - Dec 21
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cutthroat Harbor Estates
8.4 out of 10, Very Good, (118)
"Great experience "
United States
Peyton S.
The price is ¥35,057
¥83,534 total
includes taxes & fees
Dec 15 - Dec 16
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (75)
"It was ok for what we needed. Needs some repairs though."
United States
Craig M.
The price is ¥21,034
¥49,430 total
includes taxes & fees
Dec 14 - Dec 15
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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 Lower Sugarloaf Key Hotel Reviews

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