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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Browse Select Longboat Key Cottages

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

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

2BR Gulf Front, Feel the Gulf Breezes on the Porch
2BR Cottage Bay Views Bayside
Fridge, microwave, oven, stovetop

2BR Cottage Bay Views Bayside

2BR Cottage Bay Views Bayside
Longboat Key Cottage: Extended Stays Welcome!
Beach nearby

Longboat Key Cottage: Extended Stays Welcome!

Longboat Key Cottage: Extended Stays Welcome!
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 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
Charming Bayside 1BR Cottage
On the beach

Charming Bayside 1BR Cottage

Charming Bayside 1BR Cottage
2BR Cottage Gulf Side of Property, Resort Amenities
On the beach

2BR Cottage Gulf Side of Property, Resort Amenities

2BR Cottage Gulf Side of Property, Resort Amenities
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
Gulf Side 1BR Cottage, Steps to Beach
Beach

Gulf Side 1BR Cottage, Steps to Beach

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

3BR Cottage- Footsteps to the Sand

3BR Cottage- Footsteps to the Sand
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
1BR Cottage Steps to the Soft Sands of Longboat Key
Terrace/patio

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
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!
Relax and Recharge in this 1BR Cottage
On the beach

Relax and Recharge in this 1BR Cottage

Relax and Recharge in this 1BR Cottage
1BR Cottage Gulfside Steps to the Water
On the beach

1BR Cottage Gulfside Steps to the Water

1BR Cottage Gulfside Steps to the Water
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
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (304)
"Inside the studio it was clean, comfortable, quiet and great location."
Sea Club I Beach Resort
The Beach on Longboat Key #104 Resort by RVA
On the beach

The Beach on Longboat Key #104 Resort by RVA

9.0 out of 10, Wonderful, (93)
"Very pleasant stay."
The Beach on Longboat Key #104 Resort by RVA
THE BEACH CONDO #107. DIRECLY ON GULF FULL VIEW
On the beach, sun-loungers, beach towels

THE BEACH CONDO #107. DIRECLY ON GULF FULL VIEW

9.8 out of 10, Exceptional, (64)
"Location of this place was amazing and we loved how quiet the beach was, especially during spring break week."
The price is £349
includes taxes & fees
4 May - 5 May
THE BEACH CONDO #107. DIRECLY ON GULF FULL VIEW
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.