A waterfront with a pier, calm water, and houses with palm trees in the background.

Sugarloaf Key Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Sugarloaf Key vacation rentals

A wooden deck with a hanging hammock and a view of a green landscape.

1. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is ₩460,347
₩980,114 total
includes taxes & fees
Dec 1 - Dec 2
Starlight Serenity - Hideaway w Stunning Views
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

2. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (379 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
The price is ₩154,875
₩361,826 total
includes taxes & fees
Nov 3 - Nov 4
Old Wooden Bridge Resort and Marina
A row of floating houses with balconies, connected by walkways, on calm water.

3. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (201 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ₩142,870
₩389,159 total
includes taxes & fees
Nov 3 - Nov 4
Aqua Lodges at Hurricane Hole Marina
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 Sugarloaf Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"We had a quick stay. Everything was clean and staff was nice. We needed to find a quiet work area for the next day and the evening/night staff was not informed or able to help us out. So instead that guest had to leave early. Other than that all was good. Jenn was very helpful in getting us a golf cart and giving recommendations. Fun activities."
Cindy 2-night trip
Posted less than an hour ago
Southernmost Beach Resort and Guesthouses

Find out more about Sugarloaf Key

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