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Compare 75 Cottages in Lower Sugarloaf Key with updated reviews, rates, and availability.

Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very Good, (169)
"The check was very smooth; everyone friendly and helpful with local suggestions. Location was great! Nice and quiet"
The price is ￥20,164
￥38,316 total
includes taxes & fees
Dec 23 - Dec 24
Old Wooden Bridge Resort and Marina
Conch Republic Consul General's Cottage.-Historic District
Pool

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (149)
"Very clean and well equipped kitchen although we didn’t cook! Quiet neighborhood but not far from everything! Pool was very nice and relaxing!"
Conch Republic Consul General's Cottage.-Historic District
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby

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

8.8 out of 10, Excellent, (55)
"Close to Key West, one of its madness or expensive hotel costs! Two bedrooms. Shared - Boat dock and tiny swimming beach on property, we swam every day in the ocean. Also a swimming pool that seemed to be cleaned regularly. Kitchen is partly stocked - reading instructions helps a lot! "
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
Beach nearby

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

9.0 out of 10, Wonderful, (39)
"The cottage was clean and well appointed. Loved the little porch to sit in late in the evening or drink coffee in early in the morning. Beds were comfy, shower was not as strong as I like (but I'm spoiled by my home one, so . . . ) Only problem we noted was sometimes the toilet would not refill after flushing - simple fix, but kind of annoying. Pool was much smaller than it looked in the picture, though. Really enjoyed our stay and would not hesitate to stay again!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
ISLE BE BACK To The Sunny Keys
Fridge, microwave, oven, stovetop

ISLE BE BACK To The Sunny Keys

9.6 out of 10, Exceptional, (24)
"Rxcellent"
ISLE BE BACK To The Sunny Keys
Waterfront Home
Terrace/patio

Waterfront Home

8.8 out of 10, Excellent, (150)
"Has a nice seawall that can accomodate about a 30 foot boat. Cleaning station for fish was nice also. Actual house unit was older, but nice. We really just used it for cooking our fish and sleeping. The main perks of this place is that it has a seawall on a protected canal to keep a boat, has good channel access to both the oceanside and gulf, and is clean. Marina with boat fuel and boat ramp is in Venture Out neighborhood just a few hundred feet away from this actual unit. Overall a good...
Waterfront Home
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (64)
"The cottage worked great for our sister trip. It was a good halfway point to many of the Key's attractions and was in a nice quieter community. The cottage was cozy and clean, but don't expect a fancy accommodation. The property was right on some water which was really nice."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Riley's Retreat - Venture Out 107
Outdoor dining

Riley's Retreat - Venture Out 107

9.2 out of 10, Wonderful, (5)
"Quiet neighborhood close enough yet far enough from Key West madness "
Riley's Retreat - Venture Out 107
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (214)
"Very clean. Could use some updating such as fresh paint. "
The price is ￥47,675
￥99,428 total
includes taxes & fees
Dec 24 - Dec 25
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Sun loungers, beach towels

THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4

9.6 out of 10, Exceptional, (42)
"This place was a gem. Clean, well kept and charming. The owner was very sweet and helpful."
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Beach nearby

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 price is ￥78,155
￥127,744 total
includes taxes & fees
Jan 16 - Jan 17, 2025
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby

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

8.0 out of 10, Very Good, (31)
"Just as advertised. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Waterfront Cozy Cottage with Boat Ramp & Dock!
Property grounds

Waterfront Cozy Cottage with Boat Ramp & Dock!

10.0 out of 10, Exceptional, (53)
"Cottage was great pier was great too! "
Waterfront Cozy Cottage with Boat Ramp & Dock!
SEA SHELL COTTAGE UNIT #2
Beach

SEA SHELL COTTAGE UNIT #2

9.4 out of 10, Exceptional, (13)
"Hidden Hammock was a gem for sure. Quiet, clean, located near lots of restaurants, stores, and things to do, Manager Hope was very kind and helpful giving us tips where to go, where to eat etc. Property sits on Summerland Key and close to everything North or South of us. I would recommend this place highly. Cheryl Zelsman "
SEA SHELL COTTAGE UNIT #2
PALM COTTAGE
Sun loungers, beach towels

PALM COTTAGE

10.0 out of 10, Exceptional, (28)
"First time we had stayed in Summerland Key. Great place to stay. Close to everything we wanted to do. Due to Hurricane Milton we decided to cut our visit short. Trina and Hope were very accommodating with our needs!! We will be back "
PALM COTTAGE
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Dining

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

3.5 star property
8.0 out of 10, Very Good, (2)
"The living room furniture and mattresses are not the most comfortable. Worn. Mattresses in small bedroom need replacement. Air conditioner does not reach small bedroom. "
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
Beach nearby, beach towels

Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex

10.0 out of 10, Exceptional, (182)
"The property was exactly what we wanted and was clean, comfortable, and extended an unexpected level of privacy. The accommodation was perfect for our trip and the location was excellent. "
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Outdoor dining

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

10.0 out of 10, Exceptional, (203)
"Excellent stay at Tidewater View in Cudjoe Key. Lovely home and amenities. We will be back "
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
Interior

Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only

3.0 star property
10.0 out of 10, Exceptional, (1)
"There are 3 things I would say could and should be better. 1) extra toilet paper. There was only one partial roll in each bathroom and one extra partial roll. 2) no shampoo/conditioner. 3) no directions to the pool. I had to call and find out where it was. For the amount you pay, you’d think those items would be available as there are everywhere else I’ve stayed. "
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Fridge, microwave, oven, stovetop

FL Keys Cottage with Ocean Views - Venture Out Unit 395

8.8 out of 10, Excellent, (3)
"Very clean, comfortable beds. Close to everything we wanted to do!"
FL Keys Cottage with Ocean Views - Venture Out Unit 395
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 Lower Sugarloaf Key

Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very Good, (169)
"The check was very smooth; everyone friendly and helpful with local suggestions. Location was great! Nice and quiet"
The price is ￥20,164
￥38,316 total
includes taxes & fees
Dec 23 - Dec 24
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (105)
"Nice for affordable price "
The price is ￥30,606
￥56,413 total
includes taxes & fees
Jan 9 - Jan 10, 2025
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Beach towels

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (358)
"very clean, was able to park the car and walk to where we wanted to go. I would stay again."
The price is ￥24,853
￥49,414 total
includes taxes & fees
Jan 9 - Jan 10, 2025
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.