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

Search Summerland Key Cottage Accommodations

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

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 AU$671
includes taxes & fees
27 Oct - 28 Oct
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 AU$348
includes taxes & fees
18 Oct - 19 Oct
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 AU$1,007
includes taxes & fees
9 Nov - 10 Nov
Get your ISLAND STLYE on!
A two-story building with balconies, surrounded by lush greenery and palm trees.

4. 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, (152 reviews)
"Perfect for what we needed. Close to Duval and all the action."
United States
Jonnye W.
The price is AU$1,165
includes taxes & fees
20 Oct - 21 Oct
The Dancing Rooster: Newly Renovated Key West Retreat, One Block to Duval!
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.
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 AU$1,279
includes taxes & fees
9 Nov - 10 Nov
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

Parmer's Resort

Parmer's Resort

10/10 Excellent
"I've stayed at Parmers several times and anytime I'm in the Keys Parmers is where I stay. Staff is excellent."
Ken 2-night trip
Posted 15 hours ago
Parmer's Resort

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
702
Accommodation
51 Cottages
Lowest Price
AU$348
Highest Price
AU$1,279

Frequently asked questions

How much do cottages in Summerland Key cost?
You can expect to pay between AU$348 and AU$1,279 per night for cottages in Summerland Key. Whatever your budget, an awesome stay is just clicks away on Expedia. This price was 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?
Surround yourself with nature in one of the 51 cottages available in Summerland Key. To help you reserve a place that's right for you, take advantage of our filters to search for amenities or perks you need.
What is there to do in Summerland Key near my cottage?
You'll find plenty of superb things to do in Summerland Key. Discover well-known attractions like Florida Keys Beaches, Sugarloaf Beach and Big Pine Key Flea Market. Blue Hole, Cook Island and Upper Sugarloaf Sound are other must-see's.