Search Cottages in Longboat Key

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 24 Cottages in Longboat Key with updated reviews, rates, and availability.

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
On the beach

2BR Cottage Bayside of Property, Full Resort Amenities

2BR Cottage Bayside of Property, Full Resort Amenities
Gulf Side 1BR Cottage, Steps to Beach
On the beach

Gulf Side 1BR Cottage, Steps to Beach

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

3BR Cottage- Footsteps to the Sand

3BR Cottage- Footsteps to the Sand
Little Gull 2BR Cottage with Ultimate Views of the Famous Sunsets
On the 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
On the 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.
Don't see what you're looking for?
See all available properties in Longboat Key
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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, (302)
"I love that this property is right on the beach. We were there over Christmas. The property was not fully booked, so it was fairly quiet. The Gulf was too cold for us, but we enjoyed using the the provided lounge chairs to relax on the beach. Lots of shelling to do. Not a lot of people at this time. Pool was not a bad temperature and was clean. The property looks like an old motor lodge, but they have kept it nice. Our room did not have a lot of updates, but it was sufficient. A roll of paper...
Sea Club I Beach Resort
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
On the beach

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

8.8 out of 10, Excellent, (5)
"Older building and units, but the location is great. Grocery store only a mile away. Right on the beach, so can just grab the room key and get on the beach. Kitchen had the basics. Balcony on the beach was the best part, we were out there a lot. "
The price is SAR 901
SAR 1,711 total
includes taxes & fees
23 Apr - 24 Apr
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach
On the beach

Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

9.6 out of 10, Exceptional, (5)
"We liked everything! "
The price is SAR 863
SAR 1,619 total
includes taxes & fees
18 Apr - 19 Apr
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach
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

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.