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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
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 ¥35,667
¥68,084 total
includes taxes & fees
Jan 26 - Jan 27
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (157 reviews)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
United States
Richard S.
The price is ¥27,741
¥50,132 total
includes taxes & fees
Jan 31 - Feb 1
Cottage with Pool and Boat Dockage just minutes to 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, (147 reviews)
"great location, we are return visitors & will be back!"
United States
Shannon W.
The price is ¥39,630
¥69,234 total
includes taxes & fees
Jan 24 - Jan 25
Quaint cottage, pool, dockage just minutes to Key West!

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (176 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is ¥28,534
¥62,993 total
includes taxes & fees
Jan 29 - Jan 30
Waterfront Home

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 ¥35,667
¥59,366 total
includes taxes & fees
Feb 8 - Feb 9
Private Oceanfront Cottage with 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 ¥65,746
¥141,059 total
includes taxes & fees
Jan 27 - Jan 28
Beautiful Cottage & Amenities in Gated Community

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
9.0 out of 10, Wonderful, (92 reviews)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
The price is ¥40,660
¥77,427 total
includes taxes & fees
Feb 1 - Feb 2
Canal front, dockage, 2 bedroom, 2 bath

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, (54 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
The price is ¥39,234
¥71,147 total
includes taxes & fees
Feb 2 - Feb 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, (76 reviews)
"Place was everything we needed, would definitely stay again "
United States
James h.
The price is ¥39,234
¥71,623 total
includes taxes & fees
Feb 6 - Feb 7
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, (162 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is ¥31,704
¥53,799 total
includes taxes & fees
Feb 15 - Feb 16
Cottage with swimming pool and dockage, just minutes to Key West!

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, (161 reviews)
"Very nice and quiet! "
United States
Lura H.
The price is ¥39,630
¥70,343 total
includes taxes & fees
Jan 27 - Jan 28
Cottage with Pool and 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, (121 reviews)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
United States
ANJANA
The price is ¥31,704
¥60,000 total
includes taxes & fees
Jan 25 - Jan 26
Charming cottages, dockage, pool, 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
8.8 out of 10, Excellent, (90 reviews)
"Nice place to vacation "
United States
Kevin D.
The price is ¥39,234
¥72,732 total
includes taxes & fees
Feb 5 - Feb 6
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (292 reviews)
"Everything was great"
United States
Isabella
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, (54 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 ¥45,288
¥113,287 total
includes taxes & fees
Feb 3 - Feb 4
OSPREY STUDIO @ The Colony-Sleeps up to 4

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

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Old Town Key West
9.8 out of 10, Exceptional, (29 reviews)
"Loved this little place "
United States
Charles N.
The price is ¥41,849
¥89,568 total
includes taxes & fees
Jan 29 - Jan 30
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

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

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Old Town Key West
9.8 out of 10, Exceptional, (23 reviews)
"Great little place, perfect for southernmost area."
United States
Lee G.
The price is ¥41,849
¥88,617 total
includes taxes & fees
Jan 25 - Jan 26
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

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

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Old Town Key West
9.6 out of 10, Exceptional, (27 reviews)
"Safe location. Clean room and comfortable beds."
United States
Billie W.
The price is ¥55,958
¥109,072 total
includes taxes & fees
Feb 4 - Feb 5
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

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

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Old Town Key West
10.0 out of 10, Exceptional, (31 reviews)
"Clean room, amazing location, the host was very communicative and helpful. They had a car service ready to pick us up at the airport which was phenomenal. "
United States
Lauren S.
The price is ¥55,958
¥109,072 total
includes taxes & fees
Feb 1 - Feb 2
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

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

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Old Town Key West
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
The price is ¥41,849
¥89,568 total
includes taxes & fees
Jan 27 - Jan 28
Pelican Suite | Cozy Cottage, Hot Tubs, Close to 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.
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Top Summerland Key Hotel Reviews

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
1,893
Accommodation
59 Cottages
Lowest Price
¥50,132
Highest Price
¥141,059

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between ¥50,132 and ¥141,059 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.