Summerland Key, FL Cottage Rentals from $253

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

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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

Cudjoe Key

Lawrence L.

$341 nightly

Sep 9 - Sep 10

Total with taxes and fees

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

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

Cudjoe Key

BRIAN S.

$444 nightly

Sep 16 - Sep 17

Total with taxes and fees

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

3. Old Wooden Bridge Resort and Marina

Punta Brisa

Lisa

$225 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Old Town Key West

Richard M.

$577 nightly

Sep 14 - Sep 15

Total with taxes and fees

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

Old Town Key West

Phyllis B.

$521 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

Old Town Key West

Daniel M.

$553 nightly

Sep 30 - Oct 1

Total with taxes and fees

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Top Summerland Key Hotel Reviews

Parmer's Resort

10/10 Excellent

"A typical "keys style" resort that had everything we needed with a kitchen, deck seating, a dock for our boat. Enjoyed the Complimentary coffee. Will be back with the family + dog"

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

10/10 Excellent

"Perfect house for a couples getaway or a small family. Really convenient to just park your boat right outside the back in the canal. Air-conditioning was very good, and the property was very clean. Mel, the host, was easy to communicate with and very accommodating."

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

10/10 Excellent

"We really enjoyed the privacy and safety of the community. We arrived a little early and were able to gain early access. That was not expected. Then we met Julie, who hand delivered us a delicious key-lime pie! Julie was great throughout our whole stay and accommodated all our needs well beyond our expectations. The place was clean, and the kitchen was loaded with everything you would need to prepare dinner/drinks at home. The bikes were a treat. We used them to roam around or when the kids wanted to fish/swim. The balcony is beautiful with a nice sunrise view. The only suggestion i would make is if your'e bringing more then one vehicle, figure out the overflow parking before hand. There is a one vehicle limit that got a bit confusing in the later hours."

Direct Oceanfront Cottage-Sunrise View- #2,

10/10 Excellent

"Delightful cottage. It can get a little warm without central AC but the window units do a pretty good job of cooling it down. The kitchen doesn’t have a unit and had I actually wanted to cook I imagine it might be too hot. But if you’re not planning to cook and just need a nice comfortable space for o relax after a full day on and in the water this is it! We will definitely be looking to come back next year."

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews	723
Accommodation	51 Cottages
Lowest Price	$253
Highest Price	$631

Frequently asked questions

How much do cottages in Summerland Key cost?

Cottages in Summerland Key range between $253 and $631 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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Our top choices for Summerland Key cottages

1. Canal Front home with easy Ocean access