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Our top choices for Summerland Key cottages

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 €390
includes taxes & fees
11 Mar - 12 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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 €271
includes taxes & fees
10 Mar - 11 Mar
Cottage with swimming pool and dockage, just minutes to Key West!
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 €296
includes taxes & fees
12 Mar - 13 Mar
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
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 €417
includes taxes & fees
9 Mar - 10 Mar
Canal front, dockage, 2 bedroom, 2 bath
8.6 out of 10, Excellent, (196 reviews)
"Great location"
United States
Kimberly W.
The price is €346
includes taxes & fees
15 Mar - 16 Mar
Direct Oceanfront Cottage-Sunrise View- #2,

Cottage in Cudjoe Key

Waterfront Home
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 €415
includes taxes & fees
11 Mar - 12 Mar
Waterfront Home
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 €386
includes taxes & fees
4 Mar - 5 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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 €386
includes taxes & fees
12 Mar - 13 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.8 out of 10, Excellent, (91 reviews)
"Nice place to vacation "
United States
Kevin D.
The price is €386
includes taxes & fees
10 Mar - 11 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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.
Quaint cottage, pool, dockage just minutes to Key West!
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.
Charming cottages, dockage, pool, just minutes to Key West
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home, perfect for our needs"
United States
Lindsay S.
The price is €673
includes taxes & fees
4 Mar - 5 Mar
Beautiful Cottage & Amenities in Gated Community
9.2 out of 10, Wonderful, (163 reviews)
"Very convenient to Restaurants & nice drive to Key West"
United States
Kim V.
The price is €370
includes taxes & fees
14 Mar - 15 Mar
Cottage with Pool and Dockage, just minutes to Key West
8.6 out of 10, Excellent, (77 reviews)
"It was a nice location. 30” from Key West. "
United States
Linda N.
The price is €386
includes taxes & fees
14 Mar - 15 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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.
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
2.5 star property
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

Cottage in Old Town Key West

OSPREY STUDIO @ The Colony-Sleeps up to 4
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 €609
includes taxes & fees
4 Mar - 5 Mar
OSPREY STUDIO @ The Colony-Sleeps up to 4
9.8 out of 10, Exceptional, (33 reviews)
"Loved this little place "
United States
Charles N.
The price is €527
includes taxes & fees
1 Apr - 2 Apr
Osprey Suite | Charming Hideaway, Hot Tubs!
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 €527
includes taxes & fees
1 Apr - 2 Apr
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
8.8 out of 10, Excellent, (122 reviews)
"Great location and a great pool "
United States
J C.
The price is €973
includes taxes & fees
20 Mar - 21 Mar
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
€271
Highest Price
€973

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between €271 and €973 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 favourite 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.