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

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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

Canal Front home with easy Ocean access
Cudjoe Key
8.8 out of 10, Excellent, (191 reviews)
"Porsche Berry Duty"
United States
Rafael G.
$314 nightly
The price is $352
Nov 26 - Nov 27
Total with taxes and fees
Canal Front home with easy Ocean access
A covered outdoor deck with a sofa and table, overlooking a marina with boats and palm trees.

2. Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (110 reviews)
"Exactly as shown in the pictures and as described. Appreciated the extra location for the boat trailer."
United States
Laurie C.
$461 nightly
The price is $514
Nov 14 - Nov 15
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath
A floating houseboat with a covered deck and seating area, docked at a marina.

3. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (380 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
$201 nightly
The price is $226
Dec 4 - Dec 5
Total with taxes and fees
Old Wooden Bridge Resort and Marina
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

Find your zen at HIDDEN TREASURE
Old Town Key West
9.2 out of 10, Wonderful, (23 reviews)
"Great location, clean and well equipped."
United States
Richard M.
Find your zen at HIDDEN TREASURE
A two-story building with balconies, surrounded by lush greenery and palm trees.

5. The Dancing Rooster: Newly Renovated Key West Retreat, One Block to Duval!

The Dancing Rooster: Newly Renovated Key West Retreat, One Block to Duval!
Old Town Key West
9.8 out of 10, Exceptional, (155 reviews)
"Perfect for what we needed. Close to Duval and all the action."
United States
Jonnye W.
$778 nightly
The price is $871
Nov 12 - Nov 13
Total with taxes and fees
The Dancing Rooster: Newly Renovated Key West Retreat, One Block to Duval!
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.
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Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"very clean and nice!!!"
Avry 2-night trip
Posted 13 hours ago
Sugarloaf Key Hotel at KOA Resort

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
668
Accommodation
49 Cottages
Lowest Price
$226
Highest Price
$871

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between $226 and $871 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 49 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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