Search Cottages in Sugarloaf Key

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare Cottages in Sugarloaf Key with updated reviews, rates, and availability.

Old Wooden Bridge Resort and Marina
Exterior

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very Good, (178)
"Unique hotel with early communication from the owners. Definitely not a quiet location as we heard lots of loud marina-related boat noises all night. A great place to sleep with ear plugs. The shower was quite small and challenging to warm (like an RV shower). All showers were lukewarm. Also, there are very limited dining options nearby, so vacationers to the keys who are not cooking their meals on-site daily will likely be driving to Key West (30 miles away) a good deal of their time here."
The price is AED 474
AED 900 total
includes taxes & fees
26 Jan - 27 Jan
Old Wooden Bridge Resort and Marina
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

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

9.0 out of 10, Wonderful, (40)
"This is our second year at one of these cottages. We love the complex and the location is great to get to many things. The cottage has everything you would need and is very clean. The host has been great to work with."
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
Exterior detail

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

8.8 out of 10, Excellent, (57)
"Spent Monday through Friday enjoying the peace and tranquility of this beautiful location. We brought a 22 foot center console with us and had no problems launching at the onsite boat ramp or tying up to the dock. Had to pay particular attention to the tides for fishing excursions as the immediate waters are very shallow. The cabin was adequately appointed for our needs and clean upon our arrival. The pool was also spotless and there were plenty of chairs/lounges for sitting pool and/or...
The price is AED 1,010
AED 1,817 total
includes taxes & fees
19 Feb - 20 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cottage with Pool and Boat Dockage just minutes to Key West!
Pool

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!
Exterior

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...
The price is AED 826
AED 1,516 total
includes taxes & fees
21 Feb - 22 Feb
Quaint cottage, pool, dockage just minutes to Key West!
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Miscellaneous

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
View from the porch

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...
The price is AED 918
AED 1,789 total
includes taxes & fees
21 Feb - 22 Feb
Waterfront Home
Canal front, dockage, 2 bedroom, 2 bath
Exterior

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"
The price is AED 1,047
AED 1,945 total
includes taxes & fees
25 Jan - 26 Jan
Canal front, dockage, 2 bedroom, 2 bath
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Main Entrance off Street - Peaceful and Quiet!

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.
Waterfront Cozy Cottage with Boat Ramp & Dock!
Cozy Cottage dock for fishing, snorkeling, and relaxing.

Waterfront Cozy Cottage with Boat Ramp & Dock!

10.0 out of 10, Exceptional, (54)
"Brother-in-law and I stayed for 3 nights for a quick fishing getaway. The property was perfect for our needs. The property manager was proactive and communicative. He even reached out the day of check-in to let us know an early check-in was available. The property was in a nice quiet area, but just close enough to Kiki's to hear the evening live music from the fantastic pier. Also, within walking distance to Kiki's for a quick bite and a drink after fishing.The property was extremely clean...
Waterfront Cozy Cottage with Boat Ramp & Dock!
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Aerial view

Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)

10.0 out of 10, Exceptional, (11)
"Super cute bungalow surrounded by a beautiful lake. The location was perfect for us and super convenient to Key West! The staff was very friendly and very helpful. After hours check-in was very smooth. We will stay there again when we are in the area!"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Property grounds

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
Exterior

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

9.2 out of 10, Wonderful, (67)
"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
Drive to cottages

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

Riley's Retreat - Venture Out 107

8.6 out of 10, Excellent, (7)
"Quiet neighborhood close enough yet far enough from Key West madness "
Riley's Retreat - Venture Out 107
Direct Oceanfront Cottage-Sunrise View- #2,
Wouldn't you love to start your morning with a beautiful sunrise like this?

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (169)
"It was kind of exciting. the cops showed up on the property and on the next door property to the North, there was a tree of stolen bouys and a stolen crab trap. It was quiet. there was a bit of a flood when it rained but within a day or 2 the water was gone. we had trouble opening the slider on the deck and I think there was moisture in the door. Hopefully we left it pretty clean. we had to be at the airport by 6:30. thank you, it was a wonderful stay. Patty "
Direct Oceanfront Cottage-Sunrise View- #2,
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (215)
"Very clean. Could use some updating such as fresh paint. "
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Cottage with swimming pool and dockage, just minutes to Key West!
Property grounds

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"
The price is AED 551
AED 1,047 total
includes taxes & fees
3 Feb - 4 Feb
Cottage with swimming pool and dockage, just minutes to Key West!
Cottage with Pool and Dockage, just minutes to Key West
Exterior

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (127)
"Perfect spot to chill with friends, enjoy the views, and the pool is beautiful."
The price is AED 588
AED 1,210 total
includes taxes & fees
27 Jan - 28 Jan
Cottage with Pool and Dockage, just minutes to Key West
Conch Republic Consul General's Cottage.-Historic District
Conch Republic Style Swimming Pool.

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
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.
Don't see what you're looking for?
See all available properties in Sugarloaf Key
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Sugarloaf Key

Old Wooden Bridge Resort and Marina
Exterior

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very Good, (178)
"Unique hotel with early communication from the owners. Definitely not a quiet location as we heard lots of loud marina-related boat noises all night. A great place to sleep with ear plugs. The shower was quite small and challenging to warm (like an RV shower). All showers were lukewarm. Also, there are very limited dining options nearby, so vacationers to the keys who are not cooking their meals on-site daily will likely be driving to Key West (30 miles away) a good deal of their time here."
The price is AED 474
AED 900 total
includes taxes & fees
26 Jan - 27 Jan
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Exterior

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (112)
"We loved staying on the houseboat."
The price is AED 559
AED 1,145 total
includes taxes & fees
28 Jan - 29 Jan
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Pool

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 AED 657
AED 1,255 total
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

Why book your cottage in Sugarloaf Key with Expedia?
Expedia has some terrific cottages in Sugarloaf Key, so get ready for an unforgettable stay on nature’s doorstep. If you’re sticking to a budget, select how much you want to spend and your preferred property star rating. Or, use our filters to search for cottages with a hot tub or a kitchen. We’ll help you find the perfect digs whatever your bank balance or plans.
How can I find cheap cottages in Sugarloaf Key?
The simplest way to track down cheap cottages in Sugarloaf Key is with Expedia’s useful filter tool. Narrow down your search results by amenities, star rating and budget to snag awesome prices in just a few clicks.