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Compare 21 Cottages in Longboat Key with updated reviews, rates, and availability.

Longboat Key Cottage: Extended Stays Welcome!
Longboat Key Vacation Rental | 2BR | 2BA | Stairs Required | 2,012 Sq Ft

Longboat Key Cottage: Extended Stays Welcome!

Longboat Key Cottage: Extended Stays Welcome!
Barefoot Bungalow just steps away from the crystal sands & tourquoise water of the gulf, paradise!!

Barefoot Bungalow just steps away from the crystal sands & tourquoise water of the gulf, paradise!!

10.0 out of 10, Exceptional, (4)
"I was here on business and I’ve stayed here at the bungalow Before , Nice to come back and just relax and get away from the stress from work and walk over to the beach. I’ll stay here again if I’m in the area."
Barefoot Bungalow just steps away from the crystal sands & tourquoise water of the gulf, paradise!!
Charming Bayside 1BR Cottage

Charming Bayside 1BR Cottage

Charming Bayside 1BR Cottage
FANTASTIC COTTAGE ON LONG BOAT KEY FLORIDA...WEEK OF March 30- April 6 2024
Property grounds

FANTASTIC COTTAGE ON LONG BOAT KEY FLORIDA...WEEK OF March 30- April 6 2024

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 ON LONG BOAT KEY FLORIDA...WEEK OF March 30- April 6 2024
2BR Gulf Front, Feel the Gulf Breezes on the Porch
View from Unit

2BR Gulf Front, Feel the Gulf Breezes on the Porch

2BR Gulf Front, Feel the Gulf Breezes on the Porch
2BR Cottage Bayside Time for Relaxation

2BR Cottage Bayside Time for Relaxation

2BR Cottage Bayside Time for Relaxation
2BR Cottage Bayside of Property, Full Resort Amenities

2BR Cottage Bayside of Property, Full Resort Amenities

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

2BR Cottage Gulf Side of Property, Resort Amenities

2BR Cottage Gulf Side of Property, Resort Amenities
2BR Cottage Bay Views Bayside
View from Porch

2BR Cottage Bay Views Bayside

2BR Cottage Bay Views Bayside
2BR Cottage Bayside Close to the Pool

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
1BR Cottage Steps to the Soft Sands of Longboat Key
Porch

1BR Cottage Steps to the Soft Sands of Longboat Key

1BR Cottage Steps to the Soft Sands of Longboat Key
Longboat Key Cottage Steps to Pool and Bay Dock

Longboat Key Cottage Steps to Pool and Bay Dock

Longboat Key Cottage Steps to Pool and Bay Dock
1BR Cottage Gulfside Steps to the Water
Porch

1BR Cottage Gulfside Steps to the Water

1BR Cottage Gulfside Steps to the Water
3BR Cottage- Footsteps to the Sand
Cottage

3BR Cottage- Footsteps to the Sand

3BR Cottage- Footsteps to the Sand
Gulf Side 1BR Cottage, Steps to Beach
Porch

Gulf Side 1BR Cottage, Steps to Beach

Gulf Side 1BR Cottage, Steps to Beach
Little Gull 2BR Cottage with Ultimate Views of the Famous Sunsets
View

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

Little Gull 2BR Cottage with Ultimate Views of the Famous Sunsets
Perfect cottage! Million dollar views
The view right out side your door!

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 Gulfside Cottage Watch the Sunset from the Sandy Shores

1BR Gulfside Cottage Watch the Sunset from the Sandy Shores

1BR Gulfside Cottage Watch the Sunset from the Sandy Shores
Your Home Away from Home: Little Gull 4BR Cottage
View from Balcony

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

Relax and Recharge in this 1BR Cottage

Relax and Recharge in this 1BR Cottage
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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Other property types in Longboat Key

Sea Club I Beach Resort
Beach

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (300)
"It was a family trip. This our third time in this place. Very peaceful. Great customer service"
Sea Club I Beach Resort
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
Community heated pool

Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

9.8 out of 10, Exceptional, (137)
"Cute little cottage with 2br, 1ba. Very clean, close to the beach. Lots of supplies for the beach. Could use softer towels in bathroom and perhaps some instructions on the shower as it was quite hot on any setting. Prior communication was slow but once there was pretty attentive. "
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
Breathtaking Beach Front Property Ground Floor Condo
Gulf of Mexico on Longboat Key

Breathtaking Beach Front Property Ground Floor Condo

9.6 out of 10, Exceptional, (129)
"Thank You, Matt for the perfect condo to enjoy our vacation. The condo was clean and had everything we needed to make our stay perfect. The grounds,beach and pool were perfect also. We would definitely rent again 😀🌴☀️ Also enjoyed our daily visits from George 🕊"
Breathtaking Beach Front Property Ground Floor Condo
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.

Frequently asked questions

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