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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Cottages in Longboat Key

FANTASTIC COTTAGE- SLEEPS 8! - LONGBOAT KEY FL - ENTIRE WEEK OF 3/29 - 4/5 2025
Terrace/patio

FANTASTIC COTTAGE- SLEEPS 8! - LONGBOAT KEY FL - ENTIRE WEEK OF 3/29 - 4/5 2025

10.0 out of 10, Exceptional, (2)
"Every person I dealt with from the day I found this on VRBO was wonderful! Susan was great and the staff at Little Gull was amazing—so friendly and helpful. The cottage (7) was absolutely perfect! It had everything we could possibly have wanted. The big front porch was awesome—loved sitting out there in the morning having my coffee and enjoying the view of the Gulf. We met several other guests—most of whom had been going there for years. Everyone was super friendly and gave us ideas of the best...
FANTASTIC COTTAGE- SLEEPS 8! - LONGBOAT KEY FL - ENTIRE WEEK OF 3/29 - 4/5 2025
Perfect cottage! Million dollar views
Beach

Perfect cottage! Million dollar views

10.0 out of 10, Exceptional, (1)
"Loved this place can't say anything bad. Hope to return at some point. Beautiful lil cottage on the bay! Thank you Joan for getting the ESPN added to the TV!"
Perfect cottage! Million dollar views
Gulf-Front Charm with Old Florida Soul-2BR Cottage
Beach

Gulf-Front Charm with Old Florida Soul-2BR Cottage

Gulf-Front Charm with Old Florida Soul-2BR Cottage
Longboat Key Cottage: Extended Stays Welcome!
Beach nearby

Longboat Key Cottage: Extended Stays Welcome!

Longboat Key Cottage: Extended Stays Welcome!
Charming Bayside 1BR Cottage
Beach

Charming Bayside 1BR Cottage

Charming Bayside 1BR Cottage
2BR Cottage Gulf Side of Property, Resort Amenities
Beach

2BR Cottage Gulf Side of Property, Resort Amenities

2BR Cottage Gulf Side of Property, Resort Amenities
2BR Cottage Bayside Time for Relaxation
Fridge, microwave, oven, coffee/tea maker

2BR Cottage Bayside Time for Relaxation

2BR Cottage Bayside Time for Relaxation
2BR Cottage Bay Views Bayside
Fridge, microwave, oven, stovetop

2BR Cottage Bay Views Bayside

2BR Cottage Bay Views Bayside
2BR Cottage Bayside Close to the Pool
Fridge, microwave, oven, coffee/tea maker

2BR Cottage Bayside Close to the Pool

10.0 out of 10, Exceptional, (1)
"Beautiful spot, along the bay and the beach. The condo was relaxing and lovely. Recommend!"
2BR Cottage Bayside Close to the Pool
2BR Cottage Bayside of Property, Full Resort Amenities
Beach

2BR Cottage Bayside of Property, Full Resort Amenities

2BR Cottage Bayside of Property, Full Resort Amenities
Little Gull 2BR Cottage with Ultimate Views of the Famous Sunsets
Beach

Little Gull 2BR Cottage with Ultimate Views of the Famous Sunsets

Little Gull 2BR Cottage with Ultimate Views of the Famous Sunsets
Your Home Away from Home: Little Gull 4BR Cottage
Beach

Your Home Away from Home: Little Gull 4BR Cottage

Your Home Away from Home: Little Gull 4BR Cottage
1BR Gulfside Cottage Watch the Sunset from the Sandy Shores
Terrace/patio

1BR Gulfside Cottage Watch the Sunset from the Sandy Shores

1BR Gulfside Cottage Watch the Sunset from the Sandy Shores
3BR Cottage- Footsteps to the Sand
Fridge, microwave, oven, coffee/tea maker

3BR Cottage- Footsteps to the Sand

3BR Cottage- Footsteps to the Sand
Salt Air, Sunlight, and Old Florida Flair
Beach

Salt Air, Sunlight, and Old Florida Flair

Salt Air, Sunlight, and Old Florida Flair
Longboat Key Cottage Steps to Pool and Bay Dock
Fridge, microwave, oven, coffee/tea maker

Longboat Key Cottage Steps to Pool and Bay Dock

Longboat Key Cottage Steps to Pool and Bay Dock
Longboat Key Cottage: Extended Stays Welcome!
Beach towels

Longboat Key Cottage: Extended Stays Welcome!

3.0 star property
Longboat Key Cottage: Extended Stays Welcome!
Throwback Charm Meets Beach Bliss 1BR Cottage
Beach

Throwback Charm Meets Beach Bliss 1BR Cottage

Throwback Charm Meets Beach Bliss 1BR Cottage
Relax and Recharge in this 1BR Cottage
Beach

Relax and Recharge in this 1BR Cottage

Relax and Recharge in this 1BR Cottage
1BR Gulf Breezes & Old Florida Charm
Terrace/patio

1BR Gulf Breezes & Old Florida Charm

1BR Gulf Breezes & Old Florida Charm
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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Frequently asked questions

Why book your cottage in Longboat Key with Expedia?
Booking a cottage in Longboat Key is as easy as deciding on your travel dates and selecting your ideal place for outdoor recreation and relaxation. From high-end retreats to affordable properties and cottages that come with amenities like a kitchenette, Expedia has something for all traveler tastes. As for the best deals around? We’ve got them too!
How can I find cheap cottages in Longboat Key?
Expedia is here to help you track down cheap cottages in Longboat Key. To find a fantastic stay in a couple of quick clicks, simply use our handy filter tool to tailor your search results by star rating, budget and amenities.