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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Sugarloaf Key vacation rentals

House | 2 bedrooms, Internet

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 NT$13,524
NT$26,567 total
includes taxes & fees
Aug 12 - Aug 13
Starlight Serenity - Hideaway w Stunning Views
1 Bedroom Aqualodge # 6 Tarpon | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (353 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is NT$3,738
NT$8,734 total
includes taxes & fees
Aug 7 - Aug 8
Old Wooden Bridge Resort and Marina
Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (192 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
The price is NT$3,656
NT$9,509 total
includes taxes & fees
Jul 16 - Jul 17
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

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

8/10 Good
"We went on a girls trip and stayed at the villa, the view is beautiful. the rooms are spacious and accommodating. The pool with the view was perfect. But when we walked in the place it was pretty hot, I let the staff know and they sent a technician right away. However at night we noticed that the living room area was cool but the bedrooms were pretty warm. We had two bedrooms and I thought it was only my room so I called the front desk only the security was available but was able to give me a table fan. Next day I found out both of the rooms were hot and called front desk at night again but no one was answering. All four of us really loved this place but couldn’t sleep comfortably because of the room temperature at night."
nazma 2-night trip
Posted 7 hours ago
Hyatt Vacation Club at Windward Pointe, Key West

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