Summerland Key Vacation Homes

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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Our top choices for Summerland Key holiday homes

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Cudjoe Key

April W.

HK$5,044 total

includes taxes & fees

1 Jul - 2 Jul

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key

John S.

HK$4,669 total

includes taxes & fees

28 Jun - 29 Jun

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Cudjoe Key

jim b.

HK$4,606 total

includes taxes & fees

25 Jun - 26 Jun

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Cudjoe Key

Alisa M.

HK$4,753 total

includes taxes & fees

26 Jun - 27 Jun

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

David T.

HK$4,201 total

includes taxes & fees

26 Jun - 27 Jun

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Cudjoe Key

Cheryl V.

HK$4,412 total

includes taxes & fees

8 Jul - 9 Jul

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Cudjoe Key

Tammy G.

HK$4,798 total

includes taxes & fees

21 Jun - 22 Jun

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Cudjoe Key

Phani U.

HK$4,869 total

includes taxes & fees

28 Jun - 29 Jun

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Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"Love it here!"

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking

8/10 Good

"Very clean and nice home. Host was quick to respond. There was a lot of seaweed which made it difficult to take our boat in/out. We had to manually pull/push it to avoid seaweed getting into the engine. The community pool is very nice and well maintained."

SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster

10/10 Excellent

"Had a great 5 night stay wish it was longer. Very clean and well appointed. Tonios was amazing. Great coffee and sandwiches at 5 brothers just down the street Pool was perfect for my morning laps. Definitely would rent again"

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!!!"

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."

Old Florida Style, wrap around porch, boat basin for dockage, open water

10/10 Excellent

"What a gem! This house was perfect for our family’s first trip to the Keys. The location was amazing and provided the type of privacy I wanted. Little Torch Key is beautiful with easy access to lots of activities and attractions. The host was great and easy to work with. I would definitely book this spot again!"

Find out more about Summerland Key