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

Search Summerland Key Cottages

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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 £381
includes taxes & fees
2 Oct - 3 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, (373 reviews)
"Nice place"
United States
abhimanyu
The price is £183
includes taxes & fees
27 Sept - 28 Sept
Old Wooden Bridge Resort and Marina
A cozy outdoor patio area with a wooden deck, a white table, and a cushioned seating area.

3. 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)
"We had such a great time on our visit. The place was exactly like the only photos and we enjoyed the pool, the area and the other visiters. Beautiful Old Town feel!"
United States
Debra S.
OSPREY STUDIO @ The Colony-Sleeps up to 4
A two-story building with balconies, surrounded by lush greenery and palm trees.

4. 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, (35 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 £574
includes taxes & fees
3 Oct - 4 Oct
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
A building with a white exterior, a brick pathway, and lush greenery including palm trees and flowering plants.

5. 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 £418
includes taxes & fees
29 Sept - 30 Sept
Get your ISLAND STLYE on!
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

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.

7. 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.
The price is £470
includes taxes & fees
30 Sept - 1 Oct
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.
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

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

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

10/10 Excellent
"Our three-night stay at this exceptional waterfront retreat was nothing short of extraordinary. Set against sweeping open-water views, the property offers that rare combination of effortless comfort, understated elegance, and a truly idyllic setting.From the moment we arrived, the home felt like a private escape designed for relaxation. The interiors were inviting and beautifully maintained, while the waterfront setting provided a spectacular backdrop throughout our stay. Mornings overlooking the water and quiet evenings by the dock were among the many memorable moments.The private dock and golf cart elevated the experience even further, making it wonderfully easy to explore the community and enjoy everything the resort has to offer. Every detail seemed to encourage slowing down, savoring the surroundings, and simply enjoying being there.Although we stayed only three nights, the experience felt wonderfully restorative—and we found ourselves wishing we had booked a much longer stay. This is the kind of place where the pace immediately changes, the views become part of the experience, and a short getaway feels like a true escape.Beautifully situated, exceptionally comfortable, and surrounded by breathtaking waterfront scenery, this home is a destination in itself. We would return without hesitation and look forward to our next visit. A truly memorable stay in a spectacular setting. Host Mel is wonderful and very attentive."
Ammad H. 3-night trip
Posted 1 hour ago
Waterfront 2BR, Dock,Golf Cart, trailer parking,Open Water Views Venture Out 320

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
628
Accommodation
51 Cottages
Lowest Price
£183
Highest Price
£574

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between £183 and £574 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?
Settle in at Old Wooden Bridge Resort And Marina and make your family visit to Summerland Key an easy one. This family-friendly cottage has a 2.5-star rating and conveniences like a picnic area and a firepit. After checking in and kicking back together in your home away from home, it's time to head out and visit some of the local sights. No Name Key and Florida Keys Beaches are popular family-friendly attractions in Summerland Key.
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 favourite 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.