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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Summerland Key cottages

Exterior

Cottage in Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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 AED 909
AED 1,689 total
includes taxes & fees
11 Mar - 12 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Cottage in Cudjoe Key

Cottage with swimming pool and dockage, just minutes to 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 AED 661
AED 1,190 total
includes taxes & fees
10 Mar - 11 Mar
Cottage with swimming pool and dockage, just minutes to Key West!
Exterior

Cottage in Cudjoe Key

Private Oceanfront Cottage with dockage, pool 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 AED 744
AED 1,294 total
includes taxes & fees
12 Mar - 13 Mar
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Outdoor dining

Cottage in Cudjoe Key

Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, (93 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 AED 942
AED 1,823 total
includes taxes & fees
9 Mar - 10 Mar
Canal front, dockage, 2 bedroom, 2 bath
Property grounds

Cottage in Little Torch Key

Direct Oceanfront Cottage-Sunrise View- #2,
8.6 out of 10, Excellent, (196 reviews)
"Great location"
United States
Kimberly W.
The price is AED 826
AED 1,516 total
includes taxes & fees
15 Mar - 16 Mar
Direct Oceanfront Cottage-Sunrise View- #2,
Outdoor dining

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 AED 918
AED 1,793 total
includes taxes & fees
11 Mar - 12 Mar
Waterfront Home
Exterior

Cottage in Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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 AED 909
AED 1,682 total
includes taxes & fees
2 Mar - 3 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Cottage in Cudjoe Key

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 AED 909
AED 1,689 total
includes taxes & fees
12 Mar - 13 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Cottage in Cudjoe Key

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 AED 909
AED 1,689 total
includes taxes & fees
10 Mar - 11 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Cottage in Cudjoe Key

Quaint cottage, pool, dockage just minutes to 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.
The price is AED 909
AED 1,620 total
includes taxes & fees
14 Mar - 15 Mar
Quaint cottage, pool, dockage just minutes to Key West!
Exterior

Cottage in Cudjoe Key

Charming cottages, dockage, pool, 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.
The price is AED 826
AED 1,516 total
includes taxes & fees
13 Mar - 14 Mar
Charming cottages, dockage, pool, just minutes to Key West
Exterior

Cottage in Cudjoe Key

Cottage with Pool and Dockage, just minutes to Key West
9.2 out of 10, Wonderful, (163 reviews)
"Very convenient to Restaurants & nice drive to Key West"
United States
Kim V.
The price is AED 909
AED 1,620 total
includes taxes & fees
14 Mar - 15 Mar
Cottage with Pool and Dockage, just minutes to Key West
Outdoor pool, a heated pool

Cottage in Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from 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 AED 909
AED 1,689 total
includes taxes & fees
14 Mar - 15 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Cottage in Cudjoe Key

Beautiful Cottage & Amenities in Gated Community
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home, perfect for our needs"
United States
Lindsay S.
The price is AED 1,253
AED 2,897 total
includes taxes & fees
4 Mar - 5 Mar
Beautiful Cottage & Amenities in Gated Community
Exterior

Cottage in Punta Brisa

Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, (304 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
Terrace/patio

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 AED 1,145
AED 2,736 total
includes taxes & fees
4 Mar - 5 Mar
OSPREY STUDIO @ The Colony-Sleeps up to 4
1 bedroom, WiFi

Cottage in Old Town Key West

Osprey Suite | Charming Hideaway, Hot Tubs!
9.8 out of 10, Exceptional, (32 reviews)
"Loved this little place "
United States
Charles N.
The price is AED 1,126
AED 2,426 total
includes taxes & fees
3 Mar - 4 Mar
Osprey Suite | Charming Hideaway, Hot Tubs!
1 bedroom, WiFi

Cottage in Old Town Key West

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
The price is AED 1,056
AED 2,328 total
includes taxes & fees
4 Mar - 5 Mar
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Outdoor dining

Cottage in Old Town Key West

HIDDEN OASIS 3 blocks from Duval
9.6 out of 10, Exceptional, (100 reviews)
"Loved the location of the cottage "
United States
Betty B.
The price is AED 1,870
AED 3,658 total
includes taxes & fees
14 Mar - 15 Mar
HIDDEN OASIS 3 blocks from Duval
Exterior

Cottage in Old Town Key West

Find your zen at HIDDEN TREASURE
8.8 out of 10, Excellent, (12 reviews)
"Great place to stay! "
United States
sarah R.
Find your zen at HIDDEN TREASURE
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

Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"The room was clean the staff was amazing!! The Tiki Bar and food were great! The resort was perfect! "
Darla 4-night trip
Posted 4 days ago
Looe Key Reef Resort

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between AED 1,190 and AED 3,658 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.