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Our top choices for Longboat Key cottages

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (71 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
The price is CA $274
CA $660 total
includes taxes & fees
Apr 16 - Apr 17
Direct Beachfront 2BR Cottage on Casey Key!

Family Fun: Ping Pong, Bbq, Walk to Park Nearby

Family Fun: Ping Pong, Bbq, Walk to Park Nearby
3.0 star property
Fruitville
The price is CA $184
CA $781 total
includes taxes & fees
Apr 17 - Apr 18
Family Fun: Ping Pong, Bbq, Walk to Park Nearby

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (57 reviews)
"I would recommend this place to anyone! It was extremely clean and neat, and we had a lovely time here! The host was very responsive and kind too. Overall, this place was above my expectations and a great place to stay."
United States
Lana
The price is CA $137
CA $295 total
includes taxes & fees
Apr 15 - Apr 16
The "Grouper"

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

Steps 2 Beach- Cottage w/king bd +2bikes +parking
Pass-a-Grille
9.8 out of 10, Exceptional, (47 reviews)
"Everything that was needed for a restful holiday was included. Quiet location surrounded by restaurants, a block from the beach made our vacation the perfect choice! The hustle and bustle of condos and the busy beach fronts of St Beach beach melted away in the powdery sands of Pass-a-Grille. "
United States
Sherri C.
The price is CA $334
CA $672 total
includes taxes & fees
Apr 15 - Apr 16
Steps 2 Beach- Cottage w/king bd +2bikes +parking

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is CA $356
CA $1,053 total
includes taxes & fees
Apr 20 - Apr 21
Blue Dolphin Cottage steps from the beach

7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage
Bradenton
10.0 out of 10, Exceptional, (6 reviews)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
United States
MO L.
The price is CA $131
CA $407 total
includes taxes & fees
Apr 15 - Apr 16
7mi to Anna Maria Newly Renovated Private Cottage

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, (123 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is CA $469
CA $974 total
includes taxes & fees
May 5 - May 6
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

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, (181 reviews)
"Very close to the village and we only had to cross the road to access the beach!! Loved it!!"
United States
Kim H.
The price is CA $386
CA $702 total
includes taxes & fees
May 10 - May 11
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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, (36 reviews)
"Everything was fantastic!"
United States
Kevin O.
The price is CA $372
CA $1,207 total
includes taxes & fees
May 14 - May 15
Beautiful Guest House Near the Beach with Private Pool!

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · 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 $226
CA $506 total
includes taxes & fees
Apr 21 - Apr 22
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.8 out of 10, Excellent, (3 reviews)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
The price is CA $211
CA $488 total
includes taxes & fees
Apr 27 - Apr 28
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Stylish Retro Vibes Private BBQ & Beach Access

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
Sarasota
The price is CA $117
CA $542 total
includes taxes & fees
Apr 22 - Apr 23
Stylish Retro Vibes Private BBQ & Beach Access

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
The price is CA $375
CA $1,078 total
includes taxes & fees
Apr 20 - Apr 21
Yellow Palm Cottage steps from the beach

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
The price is CA $375
CA $1,078 total
includes taxes & fees
Apr 20 - Apr 21
Pink Mango Cottage steps from the beach

Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.0 out of 10, Wonderful, (19 reviews)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
The price is CA $212
CA $464 total
includes taxes & fees
May 7 - May 8
Sunny PaG Island rental w/bikes-just steps2beach

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

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Pass-a-Grille
10.0 out of 10, Exceptional, (22 reviews)
"Super cute location and unit! Close parking and within walking distance to restaurants (dinner, lunch, breakfast) and soooo close to the beach! "
United States
Shaunte W.
The price is CA $237
CA $492 total
includes taxes & fees
May 4 - May 5
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

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, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is CA $137
CA $416 total
includes taxes & fees
Apr 28 - Apr 29
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.6 out of 10, Exceptional, (45 reviews)
"Everything was wonderful. We would love to stay there again. Great location, lots of room, and very comfy beds. "
United States
Jennifer B.
The price is CA $473
CA $1,453 total
includes taxes & fees
May 1 - May 2
Adorable Cottage with Covered Balconies and Private Pool

Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach

Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"This was our family’s first time visiting AMI and we will definitely be back. The location of the property was awesome - its steps from the beach. It’s less than a mile to walk to restaurants and shops, but we loved having a golf cart that made it easy to go out for dinners and get groceries from the Publix. I was a little nervous with what I read about the Bean Point beach because of the currents, but my 4, 6, and 8 year olds were totally fine in the water. The beach was clean and is great for...
United States
Tierney L.
The price is CA $1,092
CA $1,959 total
includes taxes & fees
Apr 30 - May 1
Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (118 reviews)
"Location, privacy, beach. "
United States
Paul K.
The price is CA $342
CA $713 total
includes taxes & fees
Apr 19 - Apr 20
Casey Key Beachfront Escape: Charming 1BR Cottage
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

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
698
Accommodation
23 Cottages
Lowest Price
CA $295
Highest Price
CA $1,959

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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