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Our top choices for Summerland Key cottages

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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
9.0 out of 10, Wonderful, (56 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
The price is ¥38,622
¥71,755 total
includes taxes & fees
Mar 11 - Mar 12
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (166 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is ¥28,089
¥50,541 total
includes taxes & fees
Mar 10 - Mar 11
Cottage with swimming pool and dockage, just minutes to Key West!

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

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (165 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
The price is ¥31,600
¥54,959 total
includes taxes & fees
Mar 12 - Mar 13
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
9.0 out of 10, Wonderful, (93 reviews)
"The place has a lot of potential. There are a few areas that need improvement. Badly cabinet doors are off, missing falling off. The baseboard, especially in the bathroom are very dirty. The registers in the house are rusty some with holes in them even the place just needs a little TLC."
United States
Tim J.
The price is ¥40,027
¥77,470 total
includes taxes & fees
Mar 9 - Mar 10
Canal front, dockage, 2 bedroom, 2 bath

Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,
Little Torch Key
8.6 out of 10, Excellent, (196 reviews)
"Great location"
United States
Kimberly W.
The price is ¥35,111
¥64,391 total
includes taxes & fees
Mar 15 - Mar 16
Direct Oceanfront Cottage-Sunrise View- #2,

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (178 reviews)
"The property needed a deep clean, dirty AC grills, etc. space needs to be updated. It served us well as a "motel" space, but lacked the upkeep and quality for a vacation space."
United States
Lyndon B.
The price is ¥39,013
¥76,173 total
includes taxes & fees
Mar 11 - Mar 12
Waterfront Home

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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.4 out of 10, Very Good, (58 reviews)
"It was like staying at my Grandmom's house--it was clean but bathroom and kitchen cabinet needed some attention. Still, we were very happy with bungalow 12 and would stay there again.We only stayed overnight but the little pool, beach and fire pit would be quite enjoyable had we stayed longer. Great price and very close to Key West. "
United States
joanne
The price is ¥38,622
¥71,442 total
includes taxes & fees
Mar 2 - Mar 3
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (52 reviews)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
The price is ¥38,622
¥71,755 total
includes taxes & fees
Mar 12 - Mar 13
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (91 reviews)
"Nice place to vacation "
United States
Kevin D.
The price is ¥38,622
¥71,755 total
includes taxes & fees
Mar 10 - Mar 11
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (150 reviews)
"Enjoyed the area. Not to far from Key West but far enough there wasn't a crowd"
United States
Donna P.
The price is ¥38,622
¥68,808 total
includes taxes & fees
Mar 10 - Mar 11
Quaint cottage, pool, dockage just minutes to Key West!

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

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (123 reviews)
"host answered our question. Did not know w& d was coin washer and dryer"
United States
Robin D.
The price is ¥35,111
¥64,391 total
includes taxes & fees
Mar 13 - Mar 14
Charming cottages, dockage, pool, just minutes to Key West

Beautiful Cottage & Amenities in Gated Community

Beautiful Cottage & Amenities in Gated Community
Cudjoe Key
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home, perfect for our needs"
United States
Lindsay S.
The price is ¥53,252
¥123,077 total
includes taxes & fees
Mar 4 - Mar 5
Beautiful Cottage & Amenities in Gated Community

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (163 reviews)
"Very convenient to Restaurants & nice drive to Key West"
United States
Kim V.
The price is ¥38,622
¥68,808 total
includes taxes & fees
Mar 14 - Mar 15
Cottage with Pool and Dockage, just minutes to Key West

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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (77 reviews)
"It was a nice location. 30” from Key West. "
United States
Linda N.
The price is ¥38,622
¥71,755 total
includes taxes & fees
Mar 14 - Mar 15
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (28 reviews)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
United States
Patrick M.
The price is ¥77,869
¥136,583 total
includes taxes & fees
Apr 1 - Apr 2
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (305 reviews)
"Great stay in Bug Pine Key! Clean and spacious room, excellent staff and Beautiful views!"
United States
Peter
Old Wooden Bridge Resort and Marina

OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
Old Town Key West
9.6 out of 10, Exceptional, (55 reviews)
"We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!"
United States
Dean H.
The price is ¥46,266
¥113,260 total
includes taxes & fees
Mar 4 - Mar 5
OSPREY STUDIO @ The Colony-Sleeps up to 4

Osprey Suite | Charming Hideaway, Hot Tubs!

Osprey Suite | Charming Hideaway, Hot Tubs!
Old Town Key West
9.8 out of 10, Exceptional, (33 reviews)
"Loved this little place "
United States
Charles N.
The price is ¥43,867
¥97,220 total
includes taxes & fees
Apr 1 - Apr 2
Osprey Suite | Charming Hideaway, Hot Tubs!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Old Town Key West
10.0 out of 10, Exceptional, (33 reviews)
"Very clean and host was available and helpful.The beds were extremely comfortable. Only issue was the height of the beds. We are short people so climbing into bed was more difficult. We would book again!!!!"
United States
Patricia C.
The price is ¥43,867
¥97,220 total
includes taxes & fees
Apr 1 - Apr 2
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Comfortable Cottage with Private Pool & Lovely Garden - Great Location

Comfortable Cottage with Private Pool & Lovely Garden - Great Location
Old Town Key West
8.8 out of 10, Excellent, (122 reviews)
"Great location and a great pool "
United States
J C.
The price is ¥105,334
¥178,958 total
includes taxes & fees
Mar 20 - Mar 21
Comfortable Cottage with Private Pool & Lovely Garden - Great Location
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 Summerland Key Hotel Reviews

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
1,767
Accommodation
59 Cottages
Lowest Price
¥50,541
Highest Price
¥178,958

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between ¥50,541 and ¥178,958 per night. These stays offer a chance to reconnect with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Summerland Key?
Reconnect with nature in one of the 59 cottages waiting for you in Summerland Key. To help you select a stay that's right for you, use our filter tool to search for must-have amenities.
Are there any family-friendly cottages in Summerland Key?
You bet there are! Reserve a room at Old Wooden Bridge Resort And Marina, a top base for enjoying the great outdoors in Summerland Key. This family-friendly cottage has a 2.5-star rating and comes with handy amenities such as a firepit and a picnic area. Once you've checked in and unpacked your suitcase, there are lots of family-friendly attractions to see around Summerland Key. Florida Keys Beaches and Sugarloaf Beach promise fun for all ages.
Why book your cottage in Summerland Key with Expedia?
We think that vacays should be stress-free, so if you're after cottages in Summerland Key at a competitive rate, Expedia has your back. Keep the budget in check and select a thrifty option far from the rush of the city, or splurge on an upscale cottage to spoil your favorite people.
How can I find cheap cottages in Summerland Key?
Expedia is here to help you track down cheap cottages in Summerland Key. To book your perfect stay in a few quick keystrokes, try out our handy filter tool to refine your search results by star rating, budget and amenities.
What is there to do in Summerland Key near my cottage?
The ideal travel accessory is a well-planned itinerary. Florida Keys Beaches is a wonderful place to begin your exploration of Summerland Key.