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Our top choices for Lower Sugarloaf Key holiday 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, (281)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
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 5.426.819 ₫
10.518.905 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Aqua Lodges at Hurricane Hole Marina

Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations
3.0 star property
Key West
8.2 out of 10, Very good, (821)
"The staff goes above and beyond very, very warm and nice people"
United States
erik
Coconut Mallory Resort And Marina By Kees Vacations

The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
The Grenada Suite Pool View Private Balcony

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 14.811.187 ₫
27.030.418 ₫ total
includes taxes & fees
16 Jan - 17 Jan 2026
Atlantic View Luxury Villa with Pool

Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
The price is 26.043.992 ₫
34.565.691 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Coconut Mallory Marina and Resort Condo

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
The price is 30.254.319 ₫
44.568.508 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Contra House Key West

The Grand Turk by Brightwild Sunset View Pool

The Grand Turk by Brightwild Sunset View Pool
2.0 star property
Key West
The Grand Turk by Brightwild Sunset View Pool

The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
The price is 15.444.009 ₫
22.173.333 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
The Bartlum Luxury Studio In Prime Location

New Coastal Rose - Bright Loft With High Ceilings

New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
Key West Historic District
New Coastal Rose - Bright Loft With High Ceilings

Mesa House Uno by Brightwild Perfect Location

Mesa House Uno by Brightwild Perfect Location
2.0 star property
Key West Historic District
The price is 18.033.575 ₫
25.086.595 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Mesa House Uno by Brightwild Perfect Location

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 12.330.632 ₫
16.111.412 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Island View 1BR Residence With Balcony

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
The price is 17.848.673 ₫
26.478.189 ₫ total
includes taxes & fees
20 Jan - 21 Jan 2026
Grand Marina Suite by Brightwild Waterfront

Poolside Suite by Brightwild Pvt Pool Parking

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
Old Town Key West
The price is 14.241.911 ₫
23.220.387 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Poolside Suite by Brightwild Pvt Pool Parking

New The Cottage at James House

New The Cottage at James House
2.0 star property
Key West Historic District
8.0 out of 10, Very good, (2)
"The best thing about this property is location. Short walk to everything - short walk to Sloppy Joes. It is overpriced for the accommodations but you pay for location. "
United States
Pamela
The price is 14.303.467 ₫
19.290.616 ₫ total
includes taxes & fees
20 Jan - 21 Jan 2026
New The Cottage at James House

Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking
2.0 star property
Old Town Key West
The price is 13.564.655 ₫
23.738.805 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Sea Breeze by Brightwild Off-street Parking

Duval Dream Loft by Brightwild Right on Duval

Duval Dream Loft by Brightwild Right on Duval
2.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1)
The price is 29.932.613 ₫
42.472.034 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Duval Dream Loft by Brightwild Right on Duval

Cloud Suite on Duval Luxury Condo Epic Location

Cloud Suite on Duval Luxury Condo Epic Location
2.0 star property
Old Town Key West
The price is 25.709.354 ₫
37.720.869 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Cloud Suite on Duval Luxury Condo Epic Location

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is 10.789.391 ₫
20.935.910 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Starlight Serenity - Hideaway w Stunning Views

Sunnyside Up by Brightwild Pool Parking

Sunnyside Up by Brightwild Pool Parking
3.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1)
The price is 26.757.445 ₫
37.300.363 ₫ total
includes taxes & fees
20 Jan - 21 Jan 2026
Sunnyside Up by Brightwild Pool Parking
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