Search Sugarloaf Key Cottage Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Cottages in Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (257)
"River boat houses, pool, kayak rentals. "
Old Wooden Bridge Resort and Marina

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. "
The price is ¥18,466
¥37,523 total
includes taxes & fees
Aug 27 - Aug 28
Cottage with Pool and Boat Dockage just minutes to Key West!

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

9.0 out of 10, Wonderful, (85)
"My husband and I stayed with our son in the cottage and it was everything we needed. Great location, beautiful pool on the water, and just enough space. "
The price is ¥23,637
¥51,614 total
includes taxes & fees
Aug 27 - Aug 28
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

8.8 out of 10, Excellent, (162)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
The price is ¥19,944
¥39,334 total
includes taxes & fees
Sep 1 - Sep 2
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

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

10.0 out of 10, Exceptional, (19)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location and very nice room"
The price is ¥10,874
¥44,564 total
includes taxes & fees
Aug 27 - Aug 28
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

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

10.0 out of 10, Exceptional, (3)
"This was the perfect cottage for our stay. Very clean, nicely remodeled, great location to everything. It had everything we needed for or stay."
The price is ¥33,239
¥70,302 total
includes taxes & fees
Sep 10 - Sep 11
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

Living Life Dockside

The price is ¥55,543
¥70,421 total
includes taxes & fees
Aug 27 - Aug 28
Living Life Dockside

The Dancing Rooster: 2 Blocks from Duval in Old Town.

10.0 out of 10, Exceptional, (123)
"The property owner and staff do a great job of communicating. House is very clean and worked well for us"
The price is ¥36,933
¥74,900 total
includes taxes & fees
Aug 27 - Aug 28
The Dancing Rooster: 2 Blocks from Duval in Old Town.

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

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is ¥10,874
¥44,564 total
includes taxes & fees
Aug 27 - Aug 28
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

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

9.8 out of 10, Exceptional, (20)
"Will stay here again "
The price is ¥10,932
¥44,804 total
includes taxes & fees
Aug 27 - Aug 28
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

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

9.6 out of 10, Exceptional, (24)
"Loved listening to live music right across the street. Very convenient location. Booze, food, coffee and beach within blocks. "
The price is ¥10,932
¥44,804 total
includes taxes & fees
Aug 27 - Aug 28
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

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

9.8 out of 10, Exceptional, (18)
"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 ¥11,966
¥46,219 total
includes taxes & fees
Sep 8 - Sep 9
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

9.6 out of 10, Exceptional, (18)
"The location was perfect, close enough to walk to anything we needed to get to. The hosts went above and beyond to be helpful and even picked us up from the airport! The room was great and felt very private."
The price is ¥11,966
¥46,219 total
includes taxes & fees
Sep 8 - Sep 9
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sugarloaf Key Hotel Reviews

Find out more about Sugarloaf Key

Find out more about Sugarloaf Key

Sugarloaf Key Cottages information

Number of reviews
1,863
Accommodation
121 Cottages
Lowest Price
¥10,874
Highest Price
¥33,239

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 vacay 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.