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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 and around

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

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (254)
"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, (19)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is €296
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

10.0 out of 10, Exceptional, (1)
"Easy walk to everything! Comfortable stay. "
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 €295
includes taxes & fees
10 Aug - 11 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 €294
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, (23)
"Loved listening to live music right across the street. Very convenient location. Booze, food, coffee and beach within blocks. "
The price is €295
includes taxes & fees
17 Aug - 18 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
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, (72)
"Very nice quiet place for your lower key vacation. Nice accommodations and easy drive to Key West and Islamorada and several state parks. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Charming cottages, dockage, pool, just minutes to Key West
Fridge, microwave, oven, stovetop

Charming cottages, dockage, pool, just minutes to Key West

8.6 out of 10, Excellent, (118)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
The price is €280
includes taxes & fees
8 Aug - 9 Aug
Charming cottages, dockage, pool, just minutes to Key West
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Exterior

**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…

10.0 out of 10, Exceptional, (139)
"great location wish we could use pool!!! lovely stay"
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
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
waterfront cottage near key west, sleeps 6
Marina

waterfront cottage near key west, sleeps 6

9.4 out of 10, Exceptional, (23)
"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
**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
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Terrace/patio

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

9.8 out of 10, Exceptional, (17)
"Super location on quiet end of Duval. Easy access to restaurants, pubs, beach, etc. Check-in super easy. Take advantage of the shuttle. Room is simple, but all you need for a quick trip - bed, bath, fridge. "
The price is €296
includes taxes & fees
5 Aug - 6 Aug
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (144)
"We had a nice stay at the cottages. Location worked well for our fishing excursions and access across the street to old RT 1 to walk the dogs. "
Cottage with Pool and Boat Dockage just minutes to Key West!
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, (150)
"Good Fishing, Good local eateries. "
The price is €421
includes taxes & fees
5 Aug - 6 Aug
Cottage with Pool and Dockage, just minutes to Key West
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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Our stay was great the place was very clean also children friendly environment had a lots of games, the staff was great and we had a lot of fun."
Glenroy 2-night trip
Posted 1 day ago
Blue Flamingo Resort Key West

Frequently asked questions

Why book your cottage in Sugarloaf Key with Expedia?
Expedia has some excellent cottages in Sugarloaf Key, so start planning for a memorable holiday close to nature. If you have a set budget, click on how much you want to spend and the preferred star rating of your property. Or, make your way to the filters to search for cottages with a pool or free WiFi. We'll help you find the perfect place whatever your style of travel or plans.
How can I find cheap cottages in Sugarloaf Key?
A great way to find cheap cottages in Sugarloaf Key is with Expedia's convenient filter tool. Narrow your search by budget, star rating and amenities to grab awesome rates in just a few clicks.
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.