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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

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
8.2 out of 10, Very good, (54 reviews)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is €347
includes taxes & fees
20 Jan - 21 Jan
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Outdoor dining

Cottage in Cudjoe Key

Waterfront Home
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 €343
includes taxes & fees
19 Jan - 20 Jan
Waterfront Home
Exterior

Cottage in Cudjoe Key

Cottage with Pool and Boat Dockage just minutes to Key West!
8.6 out of 10, Excellent, (156 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 €271
includes taxes & fees
21 Jan - 22 Jan
Cottage with Pool and Boat Dockage 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, (161 reviews)
"We love our little cudjoe key hideaway"
United States
Mary H.
The price is €381
includes taxes & fees
25 Jan - 26 Jan
Cottage with Pool and Dockage, just minutes to 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 €371
includes taxes & fees
19 Jan - 20 Jan
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Outdoor dining

Cottage in Cudjoe Key

Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, (90 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 €456
includes taxes & fees
1 Feb - 2 Feb
Canal front, dockage, 2 bedroom, 2 bath
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 €590
includes taxes & fees
27 Jan - 28 Jan
Beautiful Cottage & Amenities in Gated Community
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, (76 reviews)
"Place was everything we needed, would definitely stay again "
United States
James h.
The price is €372
includes taxes & fees
18 Jan - 19 Jan
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, (147 reviews)
"great location, we are return visitors & will be back!"
United States
Shannon W.
The price is €391
includes taxes & fees
27 Jan - 28 Jan
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, (121 reviews)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
United States
ANJANA
The price is €328
includes taxes & fees
20 Jan - 21 Jan
Charming cottages, dockage, pool, just minutes to Key West
Exterior

Cottage in Punta Brisa

Old Wooden Bridge Resort and Marina
2.5 star property
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
Outdoor dining

Cottage in Stock Island

Living Life Dockside
The price is €536
includes taxes & fees
18 Jan - 19 Jan
Living Life Dockside
Terrace/patio

Cottage in Old Town Key West

OSPREY STUDIO @ The Colony-Sleeps up to 4
2.0 star property
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 €685
includes taxes & fees
3 Feb - 4 Feb
OSPREY STUDIO @ The Colony-Sleeps up to 4
Terrace/patio

Cottage in Old Town Key West

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
9.8 out of 10, Exceptional, (23 reviews)
"Great little place, perfect for southernmost area."
United States
Lee G.
The price is €485
includes taxes & fees
21 Jan - 22 Jan
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Exterior

Cottage in Old Town Key West

The Dancing Rooster: 2 Blocks from Duval in Old Town.
9.8 out of 10, Exceptional, (135 reviews)
"Great place to stay"
United States
JEFFREY Z.
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Property grounds

Cottage in Old Town Key West

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
9.8 out of 10, Exceptional, (36 reviews)
"Good place to stay loved it"
United States
Charles I.
The price is €483
includes taxes & fees
19 Jan - 20 Jan
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Property grounds

Cottage in Old Town Key West

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
9.8 out of 10, Exceptional, (29 reviews)
"Loved this little place "
United States
Charles N.
The price is €483
includes taxes & fees
19 Jan - 20 Jan
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Terrace/patio

Cottage in Old Town Key West

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
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 €494
includes taxes & fees
26 Jan - 27 Jan
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Exterior

Cottage in Old Town Key West

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
The price is €483
includes taxes & fees
19 Jan - 20 Jan
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Terrace/patio

Cottage in Old Town Key West

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
9.6 out of 10, Exceptional, (27 reviews)
"Bar across street wonderful they didn’t clean room staff talked to great with anything you needed court yard could have been better maintained overall would go back and stay there "
United States
Richele
The price is €516
includes taxes & fees
25 Jan - 26 Jan
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from 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

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"The rooms were great. The bunk bed mattresses could be better but after a long day the kids didn’t mind them. The room was clean and tons of room. If you want water views ask for 2nd floor and for sunrise views ask for north building. The drinks at the bar are great and the kids loved the beach and pool area. The location is great for trips to Bahia Honda and key west. Would definitely stay here again. "
Benjamin 5-night trip
Posted 5 days ago
Sugarloaf Key Hotel at KOA Resort

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
1,635
Accommodation
59 Cottages
Lowest Price
€271
Highest Price
€685

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between €271 and €685 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.