Summerland Key Cottages ￥44,108

View To Old Bahia Honda Bridge, Part Of The Florida Keys Overseas Heritage Trails, From West Summerland Key On A Sunny Autumn Day With A Clear Blue Sky And A Few Clouds

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In two weeks

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Our top choices for Summerland Key cottages

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

Cudjoe Key

Kasey M.

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

Cudjoe Key

Anthony

￥59,866 total

includes taxes & fees

Jun 15 - Jun 16

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Cudjoe Key

Bryan M.

￥66,347 total

includes taxes & fees

Jun 14 - Jun 15

Waterfront Home

Cudjoe Key

Karen H.

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Cudjoe Key

Shari H.

￥103,274 total

includes taxes & fees

Jun 14 - Jun 15

Beautiful Cottage & Amenities in Gated Community

Cudjoe Key

Lindsay S.

￥142,223 total

includes taxes & fees

Jul 4 - Jul 5

Old Wooden Bridge Resort and Marina

Punta Brisa

Sofia

￥44,108 total

includes taxes & fees

Jun 18 - Jun 19

OSPREY STUDIO @ The Colony-Sleeps up to 4

Old Town Key West

Donald

￥105,719 total

includes taxes & fees

Jun 19 - Jun 20

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Top Summerland Key Hotel Reviews

Parmer's Resort

10/10 Excellent

"Parmer’s Resort on Little Torch Key is the kind of place you go when you truly want to slow down and unwind—but still have everything you need within reach. The property has a classic“old Florida” charm that is not flashy or overdone—instead, it feels cozy, laid-back, and genuinely welcoming. Parmer's has that homey, relaxed vibe that makes it easy to settle in, unplug, and enjoy the simple pleasures of the Keys. It’s the perfect setting if you’re looking to escape the hustle and just breathe for a while. It’s tucked away in a quiet spot, giving you that “away-from-it-all” feeling, yet you’re still just a short drive from great food and local favorites. Places like Kiki’s, Square Grouper, and Tonio’s are all nearby, and there’s even a fun little taco spot a few miles down the road that’s worth checking out. The amenities really add to the experience without feeling overwhelming. There’s a small private beach where you can relax by the water, plus bicycles, kayaks, and stand-up paddleboards available so you can explore at your own pace. It’s easy to fill your day with outdoor activities—or do nothing at all, which is just as enjoyable here. [parmersresort.com] Another highlight is the daily breakfast, which is such a nice touch. Having that ready each morning makes the stay even more convenient. We will be back!!!"

Sugarloaf Key Hotel at KOA Resort

6/10 Okay

"The hotel was VERY clean and well-appointed as hotel kitchenettes go. Everything was new and well maintained. Some curiosities. ZERO closet space. So, for an extended stay facility you mostly had to live out of your suitcase. No ceiling fans. They did provide a floor fan. Biggest issue for us as we only stayed 2 nights, was the shower. It was very roomy with a rainfall head and a wall shower head, but the floor was literally as slippery as wet ice! They did provide a small shower mat that we felt was insufficient in size. If you stepped off the mat, you risked a fall. The bed mattresses were poor at best. Lots of outdoor "toys" and water activities. The grounds were immaculate. We would go back."

Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out

8/10 Good

"The property is on a beautiful view of water, and the communication by the host was excellent. Distance from Key West was good and allowed you to be a little outside of the fray. Three pieces of constructive feedback. We stay a lot in Vrbo‘s and the general expectation is that there is sufficient things like toilet paper, paper towel, dishwasher detergent and coffee pods for a Keurig machine that is there. These were not included, other than a starter roll of TP and paper towel. While it apparently says that in the listing, we didn’t catch it because we have grown accustomed to just having it stocked. Given the price, that would be a simple audition and would make a big difference. Labeling the three remotes in the living room, would’ve been helpful. We never could figure out the TV. And last, the golf cart is a big bonus, especially when you have aging people with you. However, the golf cart is in bad shape, it’s old and the brake needs to be fixed. Other than that, it was worth the stay."

SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!

8/10 Good

"The bed was overly soft. Making sleeping a challenge. The area and the pool were great. I never did find the beach with in a 6 minute walk. Room was clean could use a comfortable chair to sit in. All in all it was a great place to stay."

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews	929
Accommodation	55 Cottages
Lowest Price	￥44,108
Highest Price	￥142,223

Frequently asked questions

How much do cottages in Summerland Key cost?

Cottages in Summerland Key range between ￥44,108 and ￥142,223 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 55 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 favorite 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.

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Summerland Key cottages

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

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