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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Summerland Key cottages

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

1. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (373 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
$225 nightly
The price is $253
Sep 29 - Sep 30
Total with taxes and fees
Old Wooden Bridge Resort and Marina
A building with a white exterior, a brick pathway, and lush greenery including palm trees and flowering plants.

2. Get your ISLAND STLYE on!

Get your ISLAND STLYE on!
Old Town Key West
9.6 out of 10, Exceptional, (84 reviews)
"Good location. Provided everything that was listed. The unit was very clean."
United States
Mary S.
$480 nightly
The price is $526
Sep 29 - Sep 30
Total with taxes and fees
Get your ISLAND STLYE on!
A two-story building with balconies, surrounded by lush greenery and palm trees.

3. The Dancing Rooster: 2 Blocks from Duval in Old Town.

The Dancing Rooster: 2 Blocks from Duval in Old Town.
Old Town Key West
9.8 out of 10, Exceptional, (151 reviews)
"Perfect for what we needed. Close to Duval and all the action."
United States
Jonnye W.
$693 nightly
The price is $774
Oct 20 - Oct 21
Total with taxes and fees
The Dancing Rooster: 2 Blocks from Duval in Old Town.
A patio with a grill, yellow chairs, and a table under a blue umbrella, surrounded by a wooden deck and a lattice fence.

4. HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
Old Town Key West
9.6 out of 10, Exceptional, (103 reviews)
"All around amazing place! Location was perfect! "
United States
Daniel M.
HIDDEN OASIS 3 blocks from Duval
A small, single-story building with a white exterior and a metal roof, surrounded by lush greenery and a paved patio area.

5. Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
Old Town Key West
9.2 out of 10, Wonderful, (22 reviews)
"Great location, clean and well equipped."
United States
Richard M.
$555 nightly
The price is $610
Sep 30 - Oct 1
Total with taxes and fees
Find your zen at HIDDEN TREASURE
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

Looe Key Reef Resort

Looe Key Reef Resort

8/10 Good
"Great place to stay while fishing."
Shavelle 1-night trip
Posted 5 hours ago
Looe Key Reef Resort

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
711
Accommodation
51 Cottages
Lowest Price
$253
Highest Price
$774

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between $253 and $774 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 51 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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