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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
8.2 out of 10, Very Good, (54 reviews)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is AED 744
AED 1,455 total
includes taxes & fees
15 Jan - 16 Jan
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, (155 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 AED 643
AED 1,165 total
includes taxes & fees
15 Jan - 16 Jan
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 AED 918
AED 1,619 total
includes taxes & fees
23 Jan - 24 Jan
Quaint cottage, pool, dockage just minutes to Key West!

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (175 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is AED 735
AED 1,542 total
includes taxes & fees
26 Jan - 27 Jan
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.
Private Oceanfront Cottage with 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
8.6 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 AED 826
AED 1,578 total
includes taxes & fees
19 Jan - 20 Jan
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
9.0 out of 10, Wonderful, (89 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.
Canal front, dockage, 2 bedroom, 2 bath

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 AED 983
AED 2,522 total
includes taxes & fees
27 Jan - 28 Jan
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, (161 reviews)
"We love our little cudjoe key hideaway"
United States
Mary H.
The price is AED 918
AED 1,619 total
includes taxes & fees
23 Jan - 24 Jan
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 AED 735
AED 1,376 total
includes taxes & fees
15 Jan - 16 Jan
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
8.6 out of 10, Excellent, (75 reviews)
"Place was everything we needed, would definitely stay again "
United States
James h.
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, (286 reviews)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
Old Wooden Bridge Resort and Marina

Living Life Dockside

Living Life Dockside
Stock Island
The price is AED 1,388
AED 2,085 total
includes taxes & fees
15 Jan - 16 Jan
Living Life Dockside

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

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.8 out of 10, Exceptional, (36 reviews)
"Good place to stay loved it"
United States
Charles I.
The price is AED 1,017
AED 2,141 total
includes taxes & fees
19 Jan - 20 Jan
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

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

The Dancing Rooster: 2 Blocks from Duval in Old Town.
Old Town Key West
9.8 out of 10, Exceptional, (135 reviews)
"Great place to stay"
United States
JEFFREY Z.
The price is AED 2,075
AED 3,329 total
includes taxes & fees
1 Feb - 2 Feb
The Dancing Rooster: 2 Blocks from Duval in Old Town.

Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
3.0 star property
Old Town Key West
8.8 out of 10, Excellent, (11 reviews)
"Great place to stay! "
United States
sarah R.
The price is AED 1,914
AED 3,743 total
includes taxes & fees
2 Feb - 3 Feb
Find your zen at HIDDEN TREASURE

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 AED 1,017
AED 2,130 total
includes taxes & fees
21 Jan - 22 Jan
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

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, (29 reviews)
"It was very cozy to be in after running around in all the chaos of the streets all day"
United States
Sabrina L.
The price is AED 1,076
AED 2,224 total
includes taxes & fees
26 Jan - 27 Jan
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

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 AED 1,017
AED 2,141 total
includes taxes & fees
19 Jan - 20 Jan
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

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.
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

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between AED 1,165 and AED 3,743 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.
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.