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

Book a Longboat Key Cottage

  • 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 NZ$357
includes taxes & fees
28 Aug - 29 Aug
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 NZ$562
includes taxes & fees
23 Sept - 24 Sept
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 NZ$485
includes taxes & fees
1 Sept - 2 Sept
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 NZ$424
includes taxes & fees
30 Aug - 31 Aug
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 NZ$547
includes taxes & fees
28 Aug - 29 Aug
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 NZ$1,079
includes taxes & fees
28 Aug - 29 Aug
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
Pink Mango Cottage steps from the beach

8. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
The price is NZ$599
includes taxes & fees
1 Sept - 2 Sept
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 NZ$1,514
includes taxes & fees
17 Sept - 18 Sept
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 NZ$1,426
includes taxes & fees
11 Sept - 12 Sept
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 NZ$1,390
includes taxes & fees
7 Sept - 8 Sept
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 NZ$910
includes taxes & fees
1 Sept - 2 Sept
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
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 NZ$5,078
includes taxes & fees
10 Sept - 11 Sept
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 NZ$500
includes taxes & fees
9 Sept - 10 Sept
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 NZ$471
includes taxes & fees
31 Aug - 1 Sept
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 NZ$406
includes taxes & fees
8 Sept - 9 Sept
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 NZ$613
includes taxes & fees
14 Sept - 15 Sept
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 NZ$477
includes taxes & fees
30 Aug - 31 Aug
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

20. Beach Road

Beach Road
2.0 star property
Siesta Key
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
NZ$357
Highest Price
NZ$5,078