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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Cottages in Longboat Key

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

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
Gulf-Front Charm with Old Florida Soul-2BR Cottage
Terrace/patio

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

Gulf-Front Charm with Old Florida Soul-2BR Cottage
2BR Cottage Bayside Close to the Pool
Exterior

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 Time for Relaxation
Exterior

2BR Cottage Bayside Time for Relaxation

2BR Cottage Bayside Time for Relaxation
2BR Cottage Bay Views Bayside
Terrace/patio

2BR Cottage Bay Views Bayside

2BR Cottage Bay Views Bayside
2BR Cottage Gulf Side of Property, Resort Amenities
Exterior

2BR Cottage Gulf Side of Property, Resort Amenities

2BR Cottage Gulf Side of Property, Resort Amenities
2BR Cottage Bayside of Property, Full Resort Amenities
Exterior

2BR Cottage Bayside of Property, Full Resort Amenities

2BR Cottage Bayside of Property, Full Resort Amenities
Charming Bayside 1BR Cottage
Exterior

Charming Bayside 1BR Cottage

Charming Bayside 1BR Cottage
Perfect cottage! Million dollar views
Terrace/patio

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
1BR Gulf Breezes & Old Florida Charm
Exterior

1BR Gulf Breezes & Old Florida Charm

1BR Gulf Breezes & Old Florida Charm
Little Gull 2BR Cottage with Ultimate Views of the Famous Sunsets
Terrace/patio

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
Exterior

Your Home Away from Home: Little Gull 4BR Cottage

Your Home Away from Home: Little Gull 4BR Cottage
Relax and Recharge in this 1BR Cottage
Exterior

Relax and Recharge in this 1BR Cottage

Relax and Recharge in this 1BR Cottage
3BR Cottage- Footsteps to the Sand
Property grounds

3BR Cottage- Footsteps to the Sand

3BR Cottage- Footsteps to the Sand
Longboat Key Cottage Steps to Pool and Bay Dock
Exterior

Longboat Key Cottage Steps to Pool and Bay Dock

Longboat Key Cottage Steps to Pool and Bay Dock
Salt Air, Sunlight, and Old Florida Flair
Exterior

Salt Air, Sunlight, and Old Florida Flair

Salt Air, Sunlight, and Old Florida Flair
Longboat Key Cottage: Extended Stays Welcome!
Property grounds

Longboat Key Cottage: Extended Stays Welcome!

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

Throwback Charm Meets Beach Bliss 1BR Cottage

Throwback Charm Meets Beach Bliss 1BR Cottage
1BR Gulfside Cottage Watch the Sunset from the Sandy Shores
Property grounds

1BR Gulfside Cottage Watch the Sunset from the Sandy Shores

1BR Gulfside Cottage Watch the Sunset from the Sandy Shores
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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Top Longboat Key Hotel Reviews

Zota Beach Resort

Zota Beach Resort

10/10 Excellent
"Amazing location, quiet, super clean. Area to play Chess and a fantastic pool. Totally awesome♥️"
Tina 1-night trip
Posted 6 days ago
Zota Beach Resort

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?
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