Search Lower Sugarloaf Key Cottage Rentals

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Compare 76 Cottages in Lower Sugarloaf Key with updated reviews, rates, and availability.

Old Wooden Bridge Resort and Marina
2.5 star property
8.4 out of 10, Very Good, (161)
"The houseboat was a delight. Super comfortable and a full kitchen. Very dog-friendly. The woman who checked us in was super nice, and the salt-water pool felt great!"
The price is ¥20,034
¥38,069 total
includes taxes & fees
Nov 24 - Nov 25
Old Wooden Bridge Resort and Marina
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 ¥25,003
¥67,788 total
includes taxes & fees
Nov 26 - Nov 27
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Southernmost Retreat: 2 Blocks from Duval in Old Town.
10.0 out of 10, Exceptional, (106)
"Key West after fantasy week we had a great time manager always got right back to us"
The price is ¥77,650
¥128,006 total
includes taxes & fees
Nov 24 - Nov 25
Southernmost Retreat: 2 Blocks from Duval in Old Town.
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
8.0 out of 10, Very Good, (29)
"Just as advertised. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
10.0 out of 10, Exceptional, (179)
"The property is great location. Nice and clean. We really enjoyed stay. Pillows would be the only negative feedback. Need some softer ones."
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
9.2 out of 10, Wonderful, (69)
"This quaint little bungalow has everything you need. We walked about 21 miles overall during our 8 day stay but we were able to see so many amazing things. We went fishing, went on a sunset cruise, walked to several of the museums. We were Awed by the rich history. I think we actually ate our way through Key West and still had a few meals in the bungalow. Oh did I mention the almost private pool. We loved that, after a long day walking we would come back and soak in the pool for a while. We...
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
waterfront cottage near key west, sleeps 6
9.4 out of 10, Exceptional, (16)
"We had a great stay! Other than the weather, everything was perfect! We had plans to dock our boat up at the house but it was too windy to take the boat out. We still enjoyed the patio and grilled out one night! We took showers across the street at the camp restrooms bc there were four of us and we would’ve ran out of hot water but that was no problem. We enjoyed our stay!"
waterfront cottage near key west, sleeps 6
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, (62)
"We are old Florida Keys visitors and past residents. We were delighted with the accommodations, pool and view.We are planning our next stay...same time, same place minus the two days of Helene.Will have to make arraignments for a recliner to be delivered for my wifes sleeping and sitting comfort.Our first night was Sept 20 not the 19th as indicated in error. We stayed 9 nights.Thanks again for the great stay!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Blue Mind - Venture Out Unit 225
9.4 out of 10, Exceptional, (66)
"nice place 3rd time there"
Blue Mind - Venture Out Unit 225
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
10.0 out of 10, Exceptional, (200)
"Great little place on the water especially if you are bringing a boat. The house was perfect! It was my birthday and our host Charity even got me a birthday cake and card. We will definitely be back!! "
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Waterfront Cozy Cottage with Boat Ramp & Dock!
10.0 out of 10, Exceptional, (51)
"I really enjoyed it there we / my 12 year old and I . Took out charters everyday that we were there . They will pick you up from your dock ! We will be back .. Great experience!"
Waterfront Cozy Cottage with Boat Ramp & Dock!
SEA SHELL COTTAGE UNIT #2
9.2 out of 10, Wonderful, (11)
"We thoroughly enjoyed our stay here, the room we rented was perfect for us it definitely has an old school vibe. The pool was nice on the hot summer days but they were going through a bit of a crab invasion while we were there. But that was no big deal for us. Hope was super nice and have a bunch of suggestions for things to do and places to eat while down there. Ask in all we had a great time and will try to return in the future."
SEA SHELL COTTAGE UNIT #2
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.8 out of 10, Excellent, (53)
"The grounds are good. The pools were clean and plenty of deck and dock space. The cottage itself needs help. It needed general maintenance on it. It needs caulking in the bathroom. It needs weather strips around door as it is not tight. There was not enough hand towels and there are no oven mitts in the kitchen. The exhaust fan has been taken out. The ceiling fan in one room only works on high. The ac vents and exhaust fan in the bathroom needs cleaning. We were happy about the porch except the...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK
9.4 out of 10, Exceptional, (15)
"We loved the area Hope wad great and wr had a great time!"
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
10.0 out of 10, Exceptional, (206)
"The house was perfect in every way for us….. 2 married couples. The communication with property manager was beyond superb. Although a few steps from Duval, was a very quiet location. Highly recommend. "
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
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!
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
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
9.6 out of 10, Exceptional, (40)
"The property was just as it was listed as, very clean and very inviting. We loved that it was so quiet! We will definitely go back again!"
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
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
2.5 star property
8.4 out of 10, Very Good, (161)
"The houseboat was a delight. Super comfortable and a full kitchen. Very dog-friendly. The woman who checked us in was super nice, and the salt-water pool felt great!"
The price is ¥20,034
¥38,069 total
includes taxes & fees
Nov 24 - Nov 25
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (104)
"Nice for affordable price "
The price is ¥20,826
¥45,270 total
includes taxes & fees
Dec 3 - Dec 4
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
9.6 out of 10, Exceptional, (356)
"We walked most everywhere and loved the Southernmost Beach Bar! Eating at Moon Dog Cafe was so spectacular that we ate there 3 times in 2 days! This place is all it says it is. Simply perfect. "
The price is ¥15,375
¥37,060 total
includes taxes & fees
Dec 2 - Dec 3
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.