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Compare 46 Cottages in Summerland Key with updated reviews, rates, and availability.

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.0 out of 10, Wonderful, (42)
"This is our second year at one of these cottages. We love the complex and the location is great to get to many things. The cottage has everything you would need and is very clean. The host has been great to work with."
The price is SAR 881
SAR 1,664 total
includes taxes & fees
3 Mar - 4 Mar
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
Exterior detail

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.8 out of 10, Excellent, (60)
"Somewhat threadbare but clean and stocked kitchen"
The price is SAR 656
SAR 1,381 total
includes taxes & fees
10 Mar - 11 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cottage with Pool and Boat Dockage just minutes to Key West!
Pool

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

8.6 out of 10, Excellent, (132)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
The price is SAR 750
SAR 1,292 total
includes taxes & fees
23 Feb - 24 Feb
Cottage with Pool and Boat Dockage just minutes to Key West!
Quaint cottage, pool, dockage just minutes to Key West!
Exterior

Quaint cottage, pool, dockage just minutes to Key West!

9.0 out of 10, Wonderful, (132)
"It is what it is, only wish the furniture was not worn out. "
The price is SAR 938
SAR 1,664 total
includes taxes & fees
4 Mar - 5 Mar
Quaint cottage, pool, dockage just minutes to Key West!
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.2 out of 10, Wonderful, (67)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
The price is SAR 938
SAR 1,735 total
includes taxes & fees
5 Mar - 6 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Property grounds

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

10.0 out of 10, Exceptional, (20)
"Our stay was very pleasant. Enjoyed the pool and paddle board courts. The unit was clean and comfortable. Jessica was super easy to reach and extremely responsive. "
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Waterfront Cozy Cottage with Boat Ramp & Dock!
Cozy Cottage dock for fishing, snorkeling, and relaxing.

Waterfront Cozy Cottage with Boat Ramp & Dock!

10.0 out of 10, Exceptional, (54)
"Brother-in-law and I stayed for 3 nights for a quick fishing getaway. The property was perfect for our needs. The property manager was proactive and communicative. He even reached out the day of check-in to let us know an early check-in was available. The property was in a nice quiet area, but just close enough to Kiki's to hear the evening live music from the fantastic pier. Also, within walking distance to Kiki's for a quick bite and a drink after fishing.The property was extremely clean...
Waterfront Cozy Cottage with Boat Ramp & Dock!
Waterfront Home
View from the porch

Waterfront Home

8.8 out of 10, Excellent, (155)
"I wasn't expecting a 140 resort fee due before proceeding past the gate guard. The gate guard's response to my puzzled look was, "You were aware of the resort fee, right?" The fee is likely (at least I hope) embedded in the TOS. Moving on. The property permits pets but walking one's dog is prohibited. The properties are so small that one must walk a dog. Knowing this property was on a canal with open water access, I was not surprised that it needed some TLC. I think, most folks rent this type...
Waterfront Home
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Aerial view

Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)

10.0 out of 10, Exceptional, (11)
"Super cute bungalow surrounded by a beautiful lake. The location was perfect for us and super convenient to Key West! The staff was very friendly and very helpful. After hours check-in was very smooth. We will stay there again when we are in the area!"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Drive to cottages

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.6 out of 10, Excellent, (38)
"Well located to visit Key West as well as other Keys both East and West. House needs some attention. "
The price is SAR 881
SAR 1,664 total
includes taxes & fees
8 Mar - 9 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Canal front, dockage, 2 bedroom, 2 bath
Exterior

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (76)
"Cute house with wonderful features. Covered deck was a nice place to enjoy a book and meal. The open design of the living room and kitchen made the cottage feel big. The Venture Out community is welcoming. It was an excellent atmosphere to walk and bike in a safe space."
Canal front, dockage, 2 bedroom, 2 bath
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Miscellaneous

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

9.8 out of 10, Exceptional, (9)
"We arrived to a spotless cabana! The bed was perfect! Just awesome accommodations that I would definitely book again!!! Highly recommend- it was close to Key West but quiet and relaxing. And our pet stayed with us."
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Riley's Retreat - Venture Out 107

Riley's Retreat - Venture Out 107

8.6 out of 10, Excellent, (7)
"We would stay here again. Very clean. Kitchen well supplied. The beds could be more comfortable, but that could be a preference of bed type. The blinds in the bedrooms did not close completly so if you sleep late the light could be an issue. Itwasnt for us."
Riley's Retreat - Venture Out 107
Direct Oceanfront Cottage-Sunrise View- #2,
Wouldn't you love to start your morning with a beautiful sunrise like this?

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (170)
"The location and views are great. It was a comfortable stay. There were some deferred maintenance items which were shared with the property manager. Completion of these items will greatly enhance the experience at the property and make it a '10' rating."
The price is SAR 844
SAR 1,536 total
includes taxes & fees
23 Mar - 24 Mar
Direct Oceanfront Cottage-Sunrise View- #2,
Cottage with swimming pool and dockage, just minutes to Key West!
Property grounds

Cottage with swimming pool and dockage, just minutes to Key West!

9.0 out of 10, Wonderful, (139)
"It was a very cute and small place to stay. My husband and I are very tall and felt a little cramped in the bathroom otherwise our stay was great. Check in and out was simple. "
The price is SAR 750
SAR 1,277 total
includes taxes & fees
25 Mar - 26 Mar
Cottage with swimming pool and dockage, just minutes to Key West!
Cottage with Pool and Dockage, just minutes to Key West
Exterior

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (133)
"We enjoyed our stay, would stay again. Communication was excellent. Property is just as pictured. Great location, great value for the price. Could use a little freshening up, light bulb in laundry room, etc."
The price is SAR 1,031
SAR 1,785 total
includes taxes & fees
2 Mar - 3 Mar
Cottage with Pool and Dockage, just minutes to Key West
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Exterior

Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

9.8 out of 10, Exceptional, (12)
"Great spot. Very quiet and clean. "
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior detail

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.0 out of 10, Very Good, (33)
"This property is clean and adequate. Close to the lower keys, and easy to get to the upper keys and back. The listing indicates that there is a washer and dryer; however, these are coin-operated and in a different part of the compound, not in the unit. There has been road work done in the area, so the driveway was not easy to find by using the directions listed. All-in-all, not bad!"
The price is SAR 656
SAR 1,381 total
includes taxes & fees
24 Feb - 25 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Embrace tropical living at TURTLE COVE VIEWS...

**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool

9.4 out of 10, Exceptional, (30)
"The house was beautiful and right on the water! We didn't bring a boat so just sitting and having coffee every morning and night was awesome!! We did see several roaches in the kitchen but even in our own house of Florida we know all about them. The only part was we were getting ready to leave and packing our vehicle we left our four fishing rods right next to our vehicle and they were stolen. They really hurt us because 2 of them were custom and had names on them. Not sure who took them but we...
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK
Ocean Breeze House Sleeps 7. Two bedrooms two bathrooms

OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK

9.2 out of 10, Wonderful, (19)
"We stayed here with one other couple. Nice, modestly updated property, comfy bed (we had the bedroom with two queens), great billiard room and screen porch. Sipped coffee on screen porch and watched sky turn pink. While there, they helped us line up a great charter boat to sandbars, promptly fixed a minor plumbing issue, and were appropriately attentive. We only cooked breakfast in the kitchen and it was moderately equipped and fine for our purposes. Pool and amenity. Definitely recommend!"
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCK
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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Other property types in Summerland Key

Charming cottages, dockage, pool, just minutes to Key West
Property grounds

Charming cottages, dockage, pool, just minutes to Key West

8.6 out of 10, Excellent, (106)
"Drove From CLE to The Keys with my dog and enjoyed the quietness of the property. 30 an hour from Key West. Great rate. Would recommend. "
The price is SAR 844
SAR 1,547 total
includes taxes & fees
26 Feb - 27 Feb
Charming cottages, dockage, pool, just minutes to Key West
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (194)
"We loved the house! Thank you for being so flexible with us. We thought the second bedroom had 2 beds when we booked online but it only has 1."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Direct Oceanfront Cottage-Sunrise View- #2,
Wouldn't you love to start your morning with a beautiful sunrise like this?

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (170)
"The location and views are great. It was a comfortable stay. There were some deferred maintenance items which were shared with the property manager. Completion of these items will greatly enhance the experience at the property and make it a '10' rating."
The price is SAR 844
SAR 1,536 total
includes taxes & fees
23 Mar - 24 Mar
Direct Oceanfront Cottage-Sunrise View- #2,
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.

Frequently asked questions

How much do cottages in Summerland Key cost?
You’ll pay between SAR 656 and SAR 1,031 per night for cottages in Summerland Key. Whatever your budget, a wonderful stay is only a click away on Expedia. 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?
Lock in your vacation dates and then choose from 46 cottages in Summerland Key. Yearning for a place where you can surround yourself with nature? Expedia will help you find the ideal escape in a few simple clicks.
Why book your cottage in Summerland Key with Expedia?
Reserving a cottage in Summerland Key is as easy as working out your travel dates and picking an ideal place for a vacation in nature. From high-end retreats to affordable properties and cottages that have amenities like a kitchenette, Expedia has something for all styles and tastes. As for irresistible deals? We’ve got them too!
How can I find cheap cottages in Summerland Key?
With Expedia’s user-friendly filter tool, comparing cheap cottages in Summerland Key is easy. To discover stays that’ll make your bank balance smile, refine your search results by star rating, amenities and budget.