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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Summerland Key cottages

Exterior

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 £338
includes taxes & fees
8 Feb - 9 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

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, (165 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is £238
includes taxes & fees
15 Feb - 16 Feb
Cottage with swimming pool and dockage, just minutes to Key West!
Outdoor dining

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (177 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is £353
includes taxes & fees
22 Feb - 23 Feb
Waterfront Home
Exterior

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, (55 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
The price is £338
includes taxes & fees
18 Feb - 19 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Outdoor pool, a heated pool

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, (77 reviews)
"Place was everything we needed, would definitely stay again "
United States
James h.
The price is £338
includes taxes & fees
11 Feb - 12 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

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, (163 reviews)
"Very convenient to Restaurants & nice drive to Key West"
United States
Kim V.
The price is £326
includes taxes & fees
12 Feb - 13 Feb
Cottage with Pool and Dockage, just minutes to Key West
Exterior

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 £826
includes taxes & fees
28 Feb - 1 Mar
Beautiful Cottage & Amenities in Gated Community
Exterior

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 £334
includes taxes & fees
23 Feb - 24 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

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, (122 reviews)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
United States
ANJANA
The price is £298
includes taxes & fees
15 Feb - 16 Feb
Charming cottages, dockage, pool, just minutes to Key West
Exterior

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (299 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

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 £534
includes taxes & fees
11 Feb - 12 Feb
OSPREY STUDIO @ The Colony-Sleeps up to 4
1 bedroom, free WiFi, bed sheets

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, (39 reviews)
"Great place!!! Private with but still in the middle of everything. 5+ stars will be back in November!!!"
United States
Rob
The price is £449
includes taxes & fees
8 Feb - 9 Feb
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Exterior

Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
Old Town Key West
8.8 out of 10, Excellent, (12 reviews)
"Great place to stay! "
United States
sarah R.
The price is £791
includes taxes & fees
11 Feb - 12 Feb
Find your zen at HIDDEN TREASURE
Terrace/patio

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 £509
includes taxes & fees
10 Feb - 11 Feb
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
1 bedroom, WiFi

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Old Town Key West
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
The price is £452
includes taxes & fees
9 Feb - 10 Feb
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
1 bedroom, WiFi

Osprey Suite | Charming Hideaway, Hot Tubs!

Osprey Suite | Charming Hideaway, Hot Tubs!
Old Town Key West
9.8 out of 10, Exceptional, (30 reviews)
"Loved this little place "
United States
Charles N.
The price is £515
includes taxes & fees
3 Mar - 4 Mar
Osprey Suite | Charming Hideaway, Hot Tubs!
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

Parmer's Resort

Parmer's Resort

10/10 Excellent
"The rooms were very clean! Views were beautiful. Pool was heated the cool days we were there. The breakfast was good and fresh. Loved the afternoon tea, hot chocolate, and coffee selections. Staff were very welcoming!"
Karen 1-night trip
Posted 2 days ago
Parmer's Resort

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
1,357
Accommodation
59 Cottages
Lowest Price
£238
Highest Price
£826

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between £238 and £826 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?
Settle in at Old Wooden Bridge Resort And Marina and make your family visit to Summerland Key an easy one. This family-friendly cottage has a 2.5-star rating and conveniences like a picnic area and a firepit. After checking in and kicking back together in your home away from home, it's time to head out and visit some of the local sights. No Name Key and Florida Keys Beaches are popular family-friendly attractions in Summerland Key.
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.