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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

Browse Select Sugarloaf Key Cottages

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
8.6 out of 10, Excellent, (252)
"I love ❤️ this place "
Old Wooden Bridge Resort and Marina
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Terrace/patio

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 £249
includes taxes & fees
5 Aug - 6 Aug
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Waterfront Home
Terrace/patio

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

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool

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!
Terrace/patio

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

10.0 out of 10, Exceptional, (18)
"Will stay here again "
The price is £244
includes taxes & fees
3 Aug - 4 Aug
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

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
Pool

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!
1 bedroom, free WiFi, bed sheets

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 £247
includes taxes & fees
12 Aug - 13 Aug
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Terrace/patio

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 £244
includes taxes & fees
3 Aug - 4 Aug
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Heart of Downtown Key West Cottage With Off-Street Parking
Exterior

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
Pool

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
Marina

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
Terrace/patio

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
Outdoor dining

**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.
Outdoor dining

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
Pool

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 £364
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
Beach nearby

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
Beach nearby, beach towels

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
Outdoor dining

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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Top Sugarloaf Key Hotel Reviews

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"This is our second time visiting The Perry, and albeit we were sad to find out our favorite couple at the front desk had left, we still enjoyed every minute! All the staff is very amicable and serviceable - including the bartenders at the Salty Oyster!! Happy hour (4-6pm) is fantastic - 50% off drinks and 25% off food, btw!! Our room was impeccable when we checked in, and the stay was just a breeze. We will be coming back to stay in our next trip to Key West!! "
Daniela 3-night trip
Posted 12 hours ago
The Perry Hotel & Marina Key West

Frequently asked questions

Why book your cottage in Sugarloaf Key with Expedia?
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How can I find cheap cottages in Sugarloaf Key?
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What is there to do in Sugarloaf Key near my cottage?
After you've unpacked your things and settled in, set out and explore the wonderful things Sugarloaf Key has to offer. Florida Keys Beaches is a great attraction to add to your must-do list.