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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Sugarloaf Key

Old Wooden Bridge Resort and Marina
Relax in a cozy seating area with a sofa and small table, and enjoy a fully equipped kitchenette with microwave, coffee maker, and refrigerator.

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (252)
"I love ❤️ this place "
Old Wooden Bridge Resort and Marina
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Enjoy a serene outdoor space surrounded by lush plants and a charming seating area.

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (16)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is AU$494
includes taxes & fees
27 Aug - 28 Aug
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Waterfront Home
Enjoy stunning ocean views from the balcony of this beachfront property, featuring a spacious living area with large windows and comfortable outdoor seating.

Waterfront Home

8.8 out of 10, Excellent, (167)
"Great price great location "
Waterfront Home
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Exterior

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

The price is AU$766
includes taxes & fees
14 Aug - 15 Aug
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Canal front, dockage, 2 bedroom, 2 bath
Relax by the pool surrounded by lush palm trees.

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (85)
"The place was everything as described. Close enough to Key West and beaches that we did not stay home much during the day but nice to have a peaceful place to land in the evenings. Bedrooms and bathrooms were right but served its purpose. Jennifer and Susan were very helpful with check in. Thanks for letting my parents relive their glory days in the Keys. I would stay again if we come back!"
Canal front, dockage, 2 bedroom, 2 bath
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Relax in a serene oasis with a hot tub surrounded by lush tropical plants and a wooden fence.

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

10.0 out of 10, Exceptional, (18)
"Will stay here again "
The price is AU$525
includes taxes & fees
10 Aug - 11 Aug
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Direct Oceanfront Cottage-Sunrise View- #2,
Enjoy a tranquil beachside retreat with access to the calm sea and nearby amenities.

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (186)
"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "
Direct Oceanfront Cottage-Sunrise View- #2,
Conch Republic Consul General's Cottage.-Historic District
Relax by the serene pool surrounded by lush greenery and a charming building.

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (161)
"Cute, charming, clean and quiet. Great location. "
Conch Republic Consul General's Cottage.-Historic District
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Comfortable bedroom with two beds, a wall-mounted TV, and a ceiling fan.

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is AU$496
includes taxes & fees
19 Aug - 20 Aug
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Relax in a secluded outdoor space with a hot tub surrounded by lush tropical plants and trees.

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

9.6 out of 10, Exceptional, (22)
"Loved listening to live music right across the street. Very convenient location. Booze, food, coffee and beach within blocks. "
The price is AU$510
includes taxes & fees
31 Aug - 1 Sept
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Heart of Downtown Key West Cottage With Off-Street Parking
Cozy home with a front porch and garden, perfect for relaxation.

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (133)
"We very much enjoyed our stay at the cottage. Everything you need for a comfortable stay and a location that can't be beat. Also, the off-street parking was a time, money, and sanity saver. Thanks to Marcela and family!"
Heart of Downtown Key West Cottage With Off-Street Parking
OCEAN BREEZE HOUSE Summer Vacation bring the family. Fishing and Lobster season
Relax by the pool surrounded by palm trees and lounge chairs.

OCEAN BREEZE HOUSE Summer Vacation bring the family. Fishing and Lobster season

9.4 out of 10, Exceptional, (28)
"Great private location"
OCEAN BREEZE HOUSE Summer Vacation bring the family. Fishing and Lobster season
waterfront cottage near key west, sleeps 6
Enjoy waterfront views from the balcony of this two-story property, situated along a tranquil canal with a boat docked at the water's edge.

waterfront cottage near key west, sleeps 6

9.4 out of 10, Exceptional, (22)
"This place is exactly as described. The quirkiness was perfect for my husband and I to spend our anniversary. We had a day of rain and it was perfect!and"
waterfront cottage near key west, sleeps 6
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Enjoy a serene atmosphere in this charming house with a covered porch and lush green surroundings.

Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking

9.2 out of 10, Wonderful, (74)
"Really nice property just as the photos had everything we needed, great surroundings with character the pool area was perfect and well kept a very relaxing and friendly environment . The attached history to the Conch Republic was very interesting and maintained. Communications with Roberta were again very easy and in a timely & friendly manner Easy walk to Duval st and other attractions. All in all a great place to stay and would highly recommend "
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Relax by the beachside with picnic tables nestled among palm trees, overlooking a pool area or lounge.

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

9.6 out of 10, Exceptional, (38)
"Property was very clean and well stocked. Perfect location on the water. Would definitely rent again "
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
One Bedroom Cottage House in Old Town Key West by the Hemingway House.
Enjoy a seaside meal at this beachside dining setup, complete with a beautifully set table and elegant centerpiece.

One Bedroom Cottage House in Old Town Key West by the Hemingway House.

One Bedroom Cottage House in Old Town Key West by the Hemingway House.
Cottage with Pool and Dockage, just minutes to Key West
Surrounded by lush greenery, this pool area offers a serene escape.

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (149)
"Good Fishing, Good local eateries. "
The price is AU$739
includes taxes & fees
5 Aug - 6 Aug
Cottage with Pool and Dockage, just minutes to Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Relax on the beach with lounge chairs and enjoy the tranquil ocean views.

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

9.0 out of 10, Wonderful, (49)
"We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
Relax on the beach with lounge chairs and shaded areas under umbrellas, steps from the ocean.

Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex

10.0 out of 10, Exceptional, (196)
"Had another wonderful week at Sea Breeze Cottage. Perfect home, location, amenities, and host. Love going there. "
Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
Find your zen at HIDDEN TREASURE
Relax on the covered patio with a wicker sofa and chairs, surrounded by lush greenery and a grill for outdoor cooking.

Find your zen at HIDDEN TREASURE

3.0 star property
9.6 out of 10, Exceptional, (9)
"The property and location is great! The private deck was awesome. "
Find your zen at HIDDEN TREASURE
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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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.