A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Search Longboat Key Cottage Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Longboat Key cottages

1. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (74 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is ¥15,768
¥34,239 total
includes taxes & fees
Sep 8 - Sep 9
The "Grouper"

2. Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place to stay. Clean and a lot of amenities. We enjoyed all the little touches that went into decorating the house, giving it a beach house feel. We would definitely stay here again. "
United States
Rob
The price is ¥27,872
¥53,511 total
includes taxes & fees
Aug 31 - Sep 1
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

3. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (204 reviews)
"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...
United States
Lisa
The price is ¥31,690
¥44,635 total
includes taxes & fees
Aug 31 - Sep 1
The Inn On Siesta Key

4. Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (11 reviews)
"Very nice location. "
United States
Daniel o.
The price is ¥11,474
¥40,637 total
includes taxes & fees
Aug 30 - Aug 31
Coastal Luxury 7mi to Anna Maria Private Cottage

5. Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
The price is ¥14,024
¥53,257 total
includes taxes & fees
Sep 3 - Sep 4
Cozy Lido Key Bungalow by Pool & Beach

6. Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (129 reviews)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
The price is ¥47,622
¥104,134 total
includes taxes & fees
Aug 30 - Aug 31
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

7. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
The price is ¥18,427
¥96,045 total
includes taxes & fees
Sep 7 - Sep 8
Pink Mango Cottage steps from the beach

8. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
The price is ¥17,530
¥57,537 total
includes taxes & fees
Sep 1 - Sep 2
Sunny Lido Studio - Modern Touches

9. Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (51 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is ¥40,446
¥146,267 total
includes taxes & fees
Sep 17 - Sep 18
Adorable Cottage with Covered Balconies and Private Pool

10. Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
8.8 out of 10, Excellent, (37 reviews)
"House was in great condition and very comfortable. Ideal location! "
United States
Scott B.
The price is ¥39,413
¥135,399 total
includes taxes & fees
Sep 11 - Sep 12
Beautiful Guest House Near the Beach with Private Pool!

11. Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beautiful Condo on Pine Ave, 2 Blocks to Beach
Anna Maria
8.8 out of 10, Excellent, (29 reviews)
"Nice place, a little noisy in the morning but a good convenient location for a girls trip. It was clean and beds were decent. The water pressure was not great but that being said, I would stay here again!"
United States
Amy H.
The price is ¥40,446
¥136,836 total
includes taxes & fees
Sep 7 - Sep 8
Beautiful Condo on Pine Ave, 2 Blocks to Beach

12. Haven cottage Across street from beach and Heated Pool

Haven cottage Across street from beach and Heated Pool
Siesta Key
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed the property, a very nice little unit, very clean and enjoyable"
United States
Michael M.
The price is ¥37,440
¥87,546 total
includes taxes & fees
Sep 1 - Sep 2
Haven cottage Across street from beach and Heated Pool

13. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (190 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is ¥34,339
¥68,061 total
includes taxes & fees
Sep 2 - Sep 3
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

14. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is ¥375,877
¥491,445 total
includes taxes & fees
Sep 10 - Sep 11
3716 7th Ave W

15. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (90 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is ¥15,768
¥48,429 total
includes taxes & fees
Sep 8 - Sep 9
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

16. Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.2 out of 10, Wonderful, (26 reviews)
"Great location! "
United States
Quinton W.
The price is ¥16,255
¥45,077 total
includes taxes & fees
Aug 31 - Sep 1
Sunny PaG Island rental w/bikes-just steps2beach

17. Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is ¥12,758
¥41,693 total
includes taxes & fees
Sep 8 - Sep 9
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

18. Steps 2 Beach- Cottage w/king bd +2bikes +parking

Steps 2 Beach- Cottage w/king bd +2bikes +parking
Pass-a-Grille
9.6 out of 10, Exceptional, (50 reviews)
"Clean, quiet and an easy walk to the beach."
United States
Marion W.
The price is ¥24,478
¥59,204 total
includes taxes & fees
Sep 14 - Sep 15
Steps 2 Beach- Cottage w/king bd +2bikes +parking

19. Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Pass-a-Grille
9.8 out of 10, Exceptional, (31 reviews)
"Such a great place to stay at a beautiful location! Will be back for sure!"
United States
Erin W.
The price is ¥15,299
¥43,837 total
includes taxes & fees
Aug 30 - Aug 31
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

20. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is ¥93,704
¥132,582 total
includes taxes & fees
Sep 2 - Sep 3
Beach Road
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Longboat Key Hotel Reviews

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
875
Accommodation
19 Cottages
Lowest Price
¥34,239
Highest Price
¥491,445

Frequently asked questions

Are there any family-friendly cottages in Longboat Key?
Put your feet up at Queen's Gate Resort, a 2.5-star cottage just a short drive from downtown. Conveniences here include a nearby beach and WiFi. Another family-friendly option where you can swap the concrete jungle for wide open spaces is 105b 12th Street South Front 2 Bedroom Apts By Redawning. A barbecue grill and WiFi help make this 3-star cottage a guest favorite. After checking in and chilling in your comfortable new digs, it's time to head out and start exploring. Coquina Beach and Cortez Beach are among the best family-friendly attractions in Longboat Key.
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.