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

Search Summerland Key Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Summerland Key cottages

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

1. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (33 reviews)
"This place was great! As advertised. It is located within a resort community, so it is safe with lots of amenities. "
United States
BRIAN S.
The price is ￥36,931
￥74,006 total
includes taxes & fees
Oct 15 - Oct 16
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
A floating houseboat with a covered deck and seating area, docked at a marina.

2. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (374 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
The price is ￥14,098
￥38,128 total
includes taxes & fees
Oct 26 - Oct 27
Old Wooden Bridge Resort and Marina
A building with a white exterior, a brick pathway, and lush greenery including palm trees and flowering plants.

3. 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.
The price is ￥42,070
￥112,092 total
includes taxes & fees
Nov 9 - Nov 10
Get your ISLAND STLYE on!
A two-story building with balconies, surrounded by lush greenery and palm trees.

4. 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, (152 reviews)
"Perfect for what we needed. Close to Duval and all the action."
United States
Jonnye W.
The price is ￥79,170
￥126,553 total
includes taxes & fees
Oct 20 - Oct 21
The Dancing Rooster: 2 Blocks from Duval in Old Town.
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

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
10.0 out of 10, Exceptional, (36 reviews)
"The location of jolly rooster was great, and we managed to get parking right outside. Very clean property. Host was very responsive to emails while we were there. Would definitely book again"
United States
Pauline B.
The price is ￥79,320
￥129,173 total
includes taxes & fees
Oct 25 - Oct 26
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
A small, single-story building with a white exterior and a metal roof, surrounded by lush greenery and a paved patio area.

6. 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.
The price is ￥50,875
￥123,768 total
includes taxes & fees
Oct 27 - Oct 28
Find your zen at HIDDEN TREASURE
A cozy outdoor patio area with a wooden deck, a white table, and a cushioned seating area.

7. OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
Old Town Key West
9.4 out of 10, Exceptional, (63 reviews)
"The place is very clean and AC works great. Access to pool was super convenient. Pool is very nice. Landscaping is tropical and tidy."
United States
Juan B.
OSPREY STUDIO @ The Colony-Sleeps up to 4
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Summerland Key Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

8/10 Good
"Balcony"
Martin 1-night trip
Posted 9 hours ago
Sugar Loaf Lodge

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
702
Accommodation
51 Cottages
Lowest Price
￥38,128
Highest Price
￥129,173

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between ￥38,128 and ￥129,173 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.