Summerland Key Cottages

A coastal road with a beach on one side and a marina with boats on the other.

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Our top choices for Summerland Key cottages

A balcony with white chairs and a table, overlooking a canal with houses and palm trees.

1. Canal Front home with easy Ocean access

Cudjoe Key

Lawrence L.

includes taxes & fees

9 Sept - 10 Sept

A balcony with a view of the sea and a distant shoreline.

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

Cudjoe Key

Marisa F.

includes taxes & fees

16 Sept - 17 Sept

A floating houseboat with a covered deck and seating area, docked at a marina.

3. Old Wooden Bridge Resort and Marina

Punta Brisa

Lisa

includes taxes & fees

27 Sept - 28 Sept

A small, single-story building with a white exterior and a metal roof, surrounded by lush greenery and a paved patio area.

4. Find your zen at HIDDEN TREASURE

Old Town Key West

Richard M.

includes taxes & fees

14 Sept - 15 Sept

A two-story building with balconies, surrounded by lush greenery and palm trees.

5. NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

Old Town Key West

Pauline B.

includes taxes & fees

23 Sept - 24 Sept

A patio with a grill, yellow chairs, and a table under a blue umbrella, surrounded by a wooden deck and a lattice fence.

6. HIDDEN OASIS 3 blocks from Duval

Old Town Key West

Daniel M.

includes taxes & fees

30 Sept - 1 Oct

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Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"Very good"

Waterfront 2BR, Dock,Golf Cart, trailer parking,Open Water Views Venture Out 320

10/10 Excellent

"Perfect house for a couples getaway or a small family. Really convenient to just park your boat right outside the back in the canal. Air-conditioning was very good, and the property was very clean. Mel, the host, was easy to communicate with and very accommodating."

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

10/10 Excellent

"We really enjoyed the privacy and safety of the community. We arrived a little early and were able to gain early access. That was not expected. Then we met Julie, who hand delivered us a delicious key-lime pie! Julie was great throughout our whole stay and accommodated all our needs well beyond our expectations. The place was clean, and the kitchen was loaded with everything you would need to prepare dinner/drinks at home. The bikes were a treat. We used them to roam around or when the kids wanted to fish/swim. The balcony is beautiful with a nice sunrise view. The only suggestion i would make is if your'e bringing more then one vehicle, figure out the overflow parking before hand. There is a one vehicle limit that got a bit confusing in the later hours."

Direct Oceanfront Cottage-Sunrise View- #2,

10/10 Excellent

"Delightful cottage. It can get a little warm without central AC but the window units do a pretty good job of cooling it down. The kitchen doesn’t have a unit and had I actually wanted to cook I imagine it might be too hot. But if you’re not planning to cook and just need a nice comfortable space for o relax after a full day on and in the water this is it! We will definitely be looking to come back next year."

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews	724
Accommodation	48 Cottages
Lowest Price	NZ$411
Highest Price	NZ$1,058

Frequently asked questions

How much do cottages in Summerland Key cost?

Cottages in Summerland Key range between NZ$411 and NZ$1,058 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 48 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.

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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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Summerland Key cottages

1. Canal Front home with easy Ocean access