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

Waterfront Home
Exterior
Waterfront Home
8.8 out of 10, Excellent, (141)
"Would definitely come back!!!!"
Waterfront Home
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath
9.2 out of 10, Wonderful, (63)
"Resorts was great love the pool and water....home was clean nice bedrooms and baths really small but we just sleep in them. Deck was great. To be in early morning watching sun rise..."
Canal front, dockage, 2 bedroom, 2 bath
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.2 out of 10, Very Good, (26)
"Cottage is very nice, old but well maintained. Entrance difficult to find."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Sun loungers, beach towels
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
9.6 out of 10, Exceptional, (38)
"Relaxed property away from the hub of key west. Access to everything the keys has to offer with your own little slice of heaven at the end of day. Excellent host and communication. Already planning next years trip!!"
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
SEA SHELL COTTAGE UNIT #2
Beach
SEA SHELL COTTAGE UNIT #2
9.2 out of 10, Wonderful, (7)
"Nice, quiet, relaxing, reasonably priced with a lovely pool outside our door!"
SEA SHELL COTTAGE UNIT #2
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.8 out of 10, Excellent, (51)
"The grounds are good. The pools were clean and plenty of deck and dock space. The cottage itself needs help. It needed general maintenance on it. It needs caulking in the bathroom. It needs weather strips around door as it is not tight. There was not enough hand towels and there are no oven mitts in the kitchen. The exhaust fan has been taken out. The ceiling fan in one room only works on high. The ac vents and exhaust fan in the bathroom needs cleaning. We were happy about the porch except the...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Property grounds
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
10.0 out of 10, Exceptional, (2)
"This is a nice property. The accommodations were large enough for my family. The indoor space was clean and nicely appointed. The outdoor space was ok. Due to how close the units are together you are right next to your neighbors car when sitting on the patio. The location is about 20 miles from Key West allowing for easy day trips while resting in a quieter location. I would definitely stay here again."
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Property grounds
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
9.8 out of 10, Exceptional, (6)
"This was a great place to settle on our trip to Key West. Quiet, accommodating, home-like."
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Property grounds
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
10.0 out of 10, Exceptional, (9)
"Perfect size for a couple. New and clean, couldn’t be happier, thanks!"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Blue Lobster Lodge - Venture Out #543
Fridge, microwave, dishwasher, coffee/tea maker
Blue Lobster Lodge - Venture Out #543
9.0 out of 10, Wonderful, (6)
"Great amenities and location."
Blue Lobster Lodge - Venture Out #543
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
Sun loungers, beach towels
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
10.0 out of 10, Exceptional, (25)
"Easy from start to finish! Lovely cottage in very central location in the Florida Keys. Hope was the highlight of the trip, truly the “hostess with the mostest.” She checked in daily, offered great tips for restaurants and activities. Loved everything about the property: quiet, the outdoor shower, the beds, the pool, Lulu, and the freshest seafood! Would definitely recommend."
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
A heated pool
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
10.0 out of 10, Exceptional, (14)
"Excellent concept. Loved this unit. Very clean. Only had one small glitch when checking in because I don't text. The lady who manages the unit was exceptional. Wished I could find employees like her."
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, (52)
"Perfect location."
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
Beach
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, (34)
"This property is super cute. Convenient for being close to Key West without the price of Key West. We VERY much enjoyed our 3 night stay. Our property (#15) had a little grill outside so we were able to cookout one night of our stay. Make sure you stop at Publix or Winn Dixie before getting there it is a litle trek to get to grocery store. I would also suggest bringing a few extra bath towels, our cottage only had 3 and 4 adults. Most things you would need, pots, pans, silverware, cups, coffee...
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
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.0 out of 10, Wonderful, (33)
"Really nice place! Love how close it is to Key West. A little difficult to find because roads arent marked. Pool needed some attention. Affordable! Will definitely be back."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
Property grounds
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
9.8 out of 10, Exceptional, (19)
"This was the perfect place to rent for a boat It was clean and had everything we needed"
The price is $299
$630 total
includes taxes & fees
May 22 - May 23
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Outdoor pool, a heated pool
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
9.0 out of 10, Wonderful, (6)
"Clean. Comfortable. Great location. We will be staying again."
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Property grounds
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
9.6 out of 10, Exceptional, (28)
"Great location and beautiful views!"
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Fridge, microwave, oven, stovetop
FL Keys Cottage with Ocean Views - Venture Out Unit 395
8.0 out of 10, Very Good, (2)
"Great location and nice park amenities. Kids really liked the Venture Out pool."
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Property grounds
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
9.8 out of 10, Exceptional, (7)
"We stayed here as a family of 4, so cute, clean and quiet! Loved it!"
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Don't see what you're looking for?
See all available properties in Summerland Key
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.

Other property types in Summerland Key

Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath
9.2 out of 10, Wonderful, (63)
"Resorts was great love the pool and water....home was clean nice bedrooms and baths really small but we just sleep in them. Deck was great. To be in early morning watching sun rise..."
Canal front, dockage, 2 bedroom, 2 bath
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Outdoor dining
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.2 out of 10, Wonderful, (174)
"Great location, 23 miles to Key West. View from deck is breathtaking."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Waterfront Home
Exterior
Waterfront Home
8.8 out of 10, Excellent, (141)
"Would definitely come back!!!!"
Waterfront Home
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 can expect to pay between and per night for cottages in Summerland Key. Whatever your budget, an awesome stay is just clicks away on Expedia. This price was 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?
Surround yourself with nature in one of the cottages available in Summerland Key. To help you reserve a place that’s right for you, take advantage of our filters to search for amenities or perks you need.
Why book your cottage in Summerland Key with Expedia?
Expedia has some great cottages in Summerland Key, so get set for an unforgettable stay on nature’s doorstep. If you have a certain budget, click on how much you’re willing to spend and the star rating of your property. Or take advantage of our filters to search for cottages with a pool or a hot tub. We’ll help you find the right fit whatever your plans or style of travel.
How can I find cheap cottages in Summerland Key?
With Expedia’s convenient filter tool, locating cheap cottages in Summerland Key couldn’t be simpler. To discover accommodations that’ll make your wallet happy, narrow down your search by budget, amenities and star rating.
What is there to do in Summerland Key near my cottage?
You’ll find plenty of superb things to do in Summerland Key. Discover well-known attractions like Florida Keys Beaches, Sugarloaf Beach and Big Pine Key Flea Market. Blue Hole, Cook Island and Upper Sugarloaf Sound are other must-see’s.