Search Summerland Key Cottages

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

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, (54)
"It was a nice Key West cottage with beautiful views of Cudjoe Bay."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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, (26)
"Very comfortable low key rental. The house was clean and setup perfectly for what we needed. The pool was very warm more like an oversized hot tub but it was still nice to hang out in after a day out. Loved the outdoor shower! Will definitely keep this on our list of places to stay for our next trip down!"
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.
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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, (27)
"This place was nice. The pool situation was a little awkward as it does appear to be mainly for the bigger house as other reviews stated. The gas grill which is beneath the main house by the pool is communal. The main reason I gave this a 4 was because the smoke alarms in the rental did not have any batteries. Everything else was as described."
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
Waterfront Home
Exterior
Waterfront Home
8.8 out of 10, Excellent, (141)
"Would definitely come back!!!!"
Waterfront Home
SEA SHELL COTTAGE UNIT #2
Beach
SEA SHELL COTTAGE UNIT #2
9.4 out of 10, Exceptional, (8)
"If you don’t need a water view this compound is perfect for what I needed. Very well maintained grounds with brick pavers on all driveways and courtyards. I stayed in a one bedroom with kitchenette with ample areas for my small boat. I will be back."
SEA SHELL COTTAGE UNIT #2
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)
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, (35)
"As advertised. It was to hot to use the pool. The air conditioning went out, but the owner was very responsive with accommodating us and having the AC repaired. A central location to many activities in the Keys."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Blue Mind - Venture Out Unit 225
Property grounds
Blue Mind - Venture Out Unit 225
9.6 out of 10, Exceptional, (64)
"nice place 3rd time there"
Blue Mind - Venture Out Unit 225
**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
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, (39)
"Ww stayed for 6 nights as our first time in the Keys. The property is very well manicured with everything you'll need. We had a small issue with one cottage that was quickly rectified by the owners. Hope Nd Glenn were terrific! Not sure if we'll ever return to the Keys, but we highly recommend The Hidden Hammick to anyone visiting the area."
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, (66)
"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
8.8 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
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
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)
Riley's Retreat - Venture Out 107
Property grounds
Riley's Retreat - Venture Out 107
9.4 out of 10, Exceptional, (3)
"As advertised. Very clean and well furnished with everything you need!"
Riley's Retreat - Venture Out 107
water at your back door
Exterior
water at your back door
8.8 out of 10, Excellent, (30)
"Overall Great Stay. Excellent Host and the property was great. Would highly recommend it."
water at your back door
"Venture Out" into the Sun & Sea. Cozy cottage near the water!
Property grounds
"Venture Out" into the Sun & Sea. Cozy cottage near the water!
"Venture Out" into the Sun & Sea. Cozy cottage near the water!
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
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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

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (187)
"Very cute house! I didn't want to leave. Had plenty of everything. I definitely will stay there again. I have recommennded this house to several people after returning from our trip. The house had really nice & big washer & dryer. Was nice to come home with a suitcase of clean clothes rather than a hamper of dirty clothes. I took my teenager son & his friend & they enjoyed the bikes & kayaks. They also made friends with a couple other teenagers at the pool the first night we were there. Pool is...
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (204)
"Beautiful and quiet location. Close to Key West yet just far enough to be away from the crowds. Family thoroughly enjoyed it. Everything is as pictured and immaculately clean, truly a gem. Melanie was friendly, always available and always responsive."
The price is $300
$381 total
includes taxes & fees
Jun 18 - Jun 19
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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, (54)
"It was a nice Key West cottage with beautiful views of Cudjoe Bay."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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.

Summerland Key Cottages information

Number of reviews
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 Cottages
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Highest Price

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.

Recent reviews of Summerland Key hotels
Expedia verified reviews

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

5/5 Excellent
"My family and i stayed at this property during Memorial day weekend. The rooms are amazing!! very clean and spacious. the pool was very nice, and they had live music and drinks. we had an issue during check-in where my card was accidentally charged twice, but the staff was very responsive and were able to issue me a refund upon my return. I would definitely recommend this hotel to any and everyone, we are actually looking to book for labor day.."
A verified traveler stayed at Sugarloaf Key Hotel at KOA Resort
Posted 1 day ago
Sugarloaf Key Hotel at KOA Resort