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

Search Longboat Key Cottage Rentals from CA $304

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Longboat Key cottages

A two-story house with a green exterior, a blue door, and orange trim.

1. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (76 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is CA $141
CA $304 total
includes taxes & fees
Oct 15 - Oct 16
The "Grouper"
A patio with two blue lounge chairs, a potted plant, and a gravel area.

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 CA $249
CA $478 total
includes taxes & fees
Oct 15 - Oct 16
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A pair of stacked front-loading washing machines in a commercial setting.

3. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
Beach View 100ft To Beach and SPA
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

4. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (13 reviews)
"Clean and nice place"
United States
Ismael
The price is CA $122
CA $387 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Private Cottage, Minutes to Anna Maria Island
A covered outdoor area with a wooden deck, green walls, and blue chairs.

5. Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
Bradenton Beach
8.6 out of 10, Excellent, (4 reviews)
"It was nice to be so close to the beach, and walking distance to places to eat. I enjoyed driving around the island and seeing the little villages. The cottage was comfortable and had many conveniences. "
United States
Valerie T.
The price is CA $207
CA $769 total
includes taxes & fees
Oct 19 - Oct 20
Romantic Island Getaway! Just Steps from the Beach
A yellow house with a porch, a mailbox, and a number 5306 on the door.

6. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is CA $210
CA $522 total
includes taxes & fees
Oct 15 - Oct 16
Yellow Palm Cottage, Heart of Siesta Key
A covered porch with a sign reading "BEACH HOUSE," outdoor seating, a grill, and a view of the water.

7. Bridge Street Pier Beach House + Dog-friendly

Bridge Street Pier Beach House + Dog-friendly
Bridge Street
9.6 out of 10, Exceptional, (37 reviews)
"Great place! Perfect location to the beach and shops "
United States
Michelle R.
Bridge Street Pier Beach House + Dog-friendly
A room with a dining table, chairs, a television, a sofa, and a lamp.

8. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is CA $241
CA $556 total
includes taxes & fees
Oct 19 - Oct 20
BlueDolphin Cottage Walk To Siesta Beach
A patio with a table set for two, a blue umbrella, and a white fence.

9. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
The price is CA $211
CA $585 total
includes taxes & fees
Oct 16 - Oct 17
Studio by Lido Beach w heated pool
Shared sunbathing deck by the pool, at the resort.

10. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is CA $178
CA $493 total
includes taxes & fees
Oct 20 - Oct 21
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A single-story house with a blue exterior, a front door, and a small porch area.

11. Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
The price is CA $147
CA $374 total
includes taxes & fees
Oct 15 - Oct 16
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A residential house with a white fence, a palm tree, and a parked car.

12. 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 CA $141
CA $432 total
includes taxes & fees
Oct 24 - Oct 25
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A two-story building with a blue exterior and white railings.

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, (192 reviews)
"Loved the location of this property! The property manager was easy to contact and the property was exactly as shown in the pictures. Would stay here again!"
United States
Tracie B.
The price is CA $287
CA $582 total
includes taxes & fees
Oct 19 - Oct 20
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

14. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is CA $2,919
CA $3,894 total
includes taxes & fees
Oct 17 - Oct 18
3716 7th Ave W
A coastal residential area with houses, a river, and a beach.

15. Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (53 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is CA $361
CA $1,318 total
includes taxes & fees
Oct 25 - Oct 26
Adorable Cottage with Covered Balconies and Private Pool
A balcony with wicker furniture, a grill, and a view of a marina with boats and greenery.

16. 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)
"Place is great and clean. Love how smooth everything was. Jenny is easy to communicate as well"
United States
Natalia D.
The price is CA $354
CA $839 total
includes taxes & fees
Oct 15 - Oct 16
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

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

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.4 out of 10, Exceptional, (28 reviews)
"Wonderful place to stay. Great location to the beach, restaurants and shopping. If you want a peaceful getaway highly recommend."
United States
Janise W.
The price is CA $176
CA $459 total
includes taxes & fees
Nov 1 - Nov 2
Sunny PaG Island rental w/bikes-just steps2beach
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

18. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.4 out of 10, Very good, (10 reviews)
"The house was truly lovely, and the hosts were exceptionally caring, kind, and attentive in their communication. It was wonderful to be so close to the beach, with stores conveniently nearby, making the stay feel comfortable and welcoming."
United States
Kandra R.
The price is CA $340
CA $659 total
includes taxes & fees
Oct 15 - Oct 16
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A wooden deck with a view of the ocean, a barbecue grill, and a cart.

19. Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (84 reviews)
"Great vacation!!"
United States
Dominic C.
The price is CA $282
CA $721 total
includes taxes & fees
Oct 18 - Oct 19
Direct Beachfront 2BR Cottage on Casey Key!
A yellow house with a blue door and the number 2202.

20. 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, (52 reviews)
"Clean, quiet and an easy walk to the beach."
United States
Marion W.
The price is CA $323
CA $683 total
includes taxes & fees
Oct 19 - Oct 20
Steps 2 Beach- Cottage w/king bd +2bikes +parking
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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Top Longboat Key Hotel Reviews

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

10/10 Excellent
"Nice place, very clean, and grounds are well kept. Loved that the beach was out our back door!"
Tim C. 6-night trip
Posted 21 hours ago
Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
642
Accommodation
19 Cottages
Lowest Price
CA $304
Highest Price
CA $3,894

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 favourite. 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.

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