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Featured Cottages in Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (176)
"It is very quite. There is a bridge near to the cabin. "
The price is AU$396
includes taxes & fees
26 Jan - 27 Jan
Old Wooden Bridge Resort and Marina

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (131)
"Stayed here for a few nights during a multi stop trip to Florida. The location is perfect for accessing the best of the lower keys. We brought our kayaks and launched right from the property for a great paddle. Easy drive to Bahia Honda for some beach time and more paddling. Also a great jumping off location for spending a nice long day in Key West. Beautiful sunrise from this property as well. Would stay again. "
Cottage with Pool and Boat Dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!

9.0 out of 10, Wonderful, (131)
"Overall rating of good. Lovely, updated kitchen and bathroom, the shower was fabulous. It had a great area for the dogs, the beds were comfortable, but the living room needs a lot of work. It wasn’t comfortable to sit and relax to watch tv. The remote for the tv was missing and the cable remote wasn’t working so that was challenging. We finally fixed it. The blinds were torn, and you can hear your neighbors conversations. The location was good and it was clean. Not sure we would stay there...
Quaint cottage, pool, dockage just minutes to Key West!

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

9.8 out of 10, Exceptional, (9)
"We arrived to a spotless cabana! The bed was perfect! Just awesome accommodations that I would definitely book again!!! Highly recommend- it was close to Key West but quiet and relaxing. And our pet stayed with us."
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

Waterfront Home

8.8 out of 10, Excellent, (154)
"I wasn't expecting a 140 resort fee due before proceeding past the gate guard. The gate guard's response to my puzzled look was, "You were aware of the resort fee, right?" The fee is likely (at least I hope) embedded in the TOS. Moving on. The property permits pets but walking one's dog is prohibited. The properties are so small that one must walk a dog. Knowing this property was on a canal with open water access, I was not surprised that it needed some TLC. I think, most folks rent this type...
Waterfront Home

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (74)
"My husband loved fishing everyday and I enjoyed reading.The place was in a perfect location and had most of the comforts of home. There was no cleaning table for the fish big inconvenience and no light available. My issue is the lack of shade on the porch on the comfortable couch. It’s way too hot"
Canal front, dockage, 2 bedroom, 2 bath

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

10.0 out of 10, Exceptional, (16)
"We were very happy with our stay at this property! It was perfect for a couple! A lot of the properties I looked at were two bedrooms and much more expensive. I was happy to find this one. The gated community was awesome and friendly. The communication with the manager was prompt and helpful. I read some of the reviews complaining about all the "rules". We had ZERO problems with all the rules in the Venture Out Community. It was so quiet and everyone was friendly. We will definitely...
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

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

9.2 out of 10, Wonderful, (66)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
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

8.6 out of 10, Excellent, (37)
"Well located to visit Key West as well as other Keys both East and West. House needs some attention. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Riley's Retreat - Venture Out 107

8.8 out of 10, Excellent, (6)
"Quiet neighborhood close enough yet far enough from Key West madness "
Riley's Retreat - Venture Out 107

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (168)
"Quaint little (actually spacious) cottage on waterfront. Easy access and enough off the beaten path where your solitude isnt interrupted. Gorgeous sunrise view. It was nice to have in-house washer/dryer. My only suggestion would be to add an outlet plug with USB ports. Bang for buck it was well worth it!"
Direct Oceanfront Cottage-Sunrise View- #2,

Cottage with swimming pool and dockage, just minutes to Key West!

9.0 out of 10, Wonderful, (136)
"Property kept clean. Very quiet. Close to my family"
Cottage with swimming pool and dockage, just minutes to Key West!

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (150)
"My aunts, mom and I had a great stay. The rooms were spacious, allowing plenty of space for the 5 of us to spread out. Roberta and the owner were very kind. I am hoping to get my husband to come back for a visit with me. "
Conch Republic Consul General's Cottage.-Historic District

Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

9.8 out of 10, Exceptional, (11)
"Quiet. Spacious room that appeared fairly new decor and fixtures. Nice shower. Not alot of outdoor space around bungalow, but rest of property walkable."
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

The Dancing Rooster: 2 Blocks from Duval in Old Town.

10.0 out of 10, Exceptional, (108)
"Our 3 bedroom, 2 bathroom bungalow accommodated the 5 of us perfectly. Kitchen had all that we needed, space to sit outside, and so close to the action on Duval St. "
The Dancing Rooster: 2 Blocks from Duval in Old Town.

Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)

10.0 out of 10, Exceptional, (5)
"Took my grandmother on her bucket list trip. Great location and set up for myself, my mom and grandmother!"
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)

Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex

10.0 out of 10, Exceptional, (185)
"Loved our stay , perfect layout with everything we needed. Quiet location in Truman Annex. Hope to stay next year! "
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex

**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

10.0 out of 10, Exceptional, (204)
"Stunning views. Very clean. Loved it all!!!"
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool

9.4 out of 10, Exceptional, (30)
"The house was beautiful and right on the water! We didn't bring a boat so just sitting and having coffee every morning and night was awesome!! We did see several roaches in the kitchen but even in our own house of Florida we know all about them. The only part was we were getting ready to leave and packing our vehicle we left our four fishing rods right next to our vehicle and they were stolen. They really hurt us because 2 of them were custom and had names on them. Not sure who took them but we...
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool

ISLE BE BACK To The Sunny Keys

9.6 out of 10, Exceptional, (24)
"Rxcellent"
ISLE BE BACK To The Sunny Keys
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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Other property types in Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (176)
"It is very quite. There is a bridge near to the cabin. "
The price is AU$396
includes taxes & fees
26 Jan - 27 Jan
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (110)
"Family had a great time "
The price is AU$602
includes taxes & fees
20 Jan - 21 Jan
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (361)
"Fun little place with a great pool. Ken was very helpful in all aspects. Highly recommended. Be aware its a small place but very comfortable."
The price is AU$558
includes taxes & fees
3 Feb - 4 Feb
Steps from Duval, Pool on Site & Bikes Included!
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.

Frequently asked questions

What is there to do in Sugarloaf Key near my cottage?
Once you’ve settled into your hotel, head out and explore the fun things Sugarloaf Key has to offer. Florida Keys Beaches is a top attraction to add to your to-do list.