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Our top choices for Longboat Key cottages

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (196 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
The Inn On Siesta Key

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 HK$1,942
HK$4,219 total
includes taxes & fees
20 Apr - 21 Apr
Direct Beachfront 2BR Cottage on Casey Key!

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 HK$2,123
HK$6,100 total
includes taxes & fees
20 Apr - 21 Apr
Yellow Palm Cottage steps from the beach

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is HK$2,016
HK$5,887 total
includes taxes & fees
20 Apr - 21 Apr
Blue Dolphin Cottage steps from the beach

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay
cortez
10.0 out of 10, Exceptional, (104 reviews)
"The host was always available! The cottage is adorable and homey. Wonderful location and had everything you need for a fun experience."
United States
Janice C.
The price is HK$1,425
HK$2,451 total
includes taxes & fees
18 May - 19 May
Private historical completely renovated cottage with 60 ft dock on Sarasota Bay

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria 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 HK$599
HK$2,102 total
includes taxes & fees
21 Apr - 22 Apr
Coastal Luxury 7mi to Anna Maria Private Cottage

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, (182 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 HK$2,216
HK$3,974 total
includes taxes & fees
10 May - 11 May
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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 HK$2,090
HK$4,021 total
includes taxes & fees
19 May - 20 May
Steps 2 Beach- Cottage w/king bd +2bikes +parking

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
Pink Mango Cottage steps from the beach

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (60 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 HK$775
HK$1,652 total
includes taxes & fees
20 May - 21 May
The "Grouper"

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 HK$1,198
HK$2,765 total
includes taxes & fees
20 Apr - 21 Apr
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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 HK$1,204
HK$2,607 total
includes taxes & fees
7 May - 8 May
Sunny PaG Island rental w/bikes-just steps2beach

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is HK$18,797
HK$24,989 total
includes taxes & fees
21 Apr - 22 Apr
3716 7th Ave W

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 HK$1,416
HK$2,893 total
includes taxes & fees
4 May - 5 May
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

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, (26 reviews)
"Great location, clean, and spacious. Pool didn’t work fir a couple of days but they got it fixed the day before we left "
United States
Paris K.
The price is HK$2,874
HK$7,869 total
includes taxes & fees
16 May - 17 May
Beautiful Condo on Pine Ave, 2 Blocks to Beach

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, (124 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is HK$2,780
HK$5,616 total
includes taxes & fees
11 May - 12 May
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

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 HK$1,198
HK$2,672 total
includes taxes & fees
27 Apr - 28 Apr
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
United States
Marti C.
The price is HK$4,006
HK$6,536 total
includes taxes & fees
21 Apr - 22 Apr
Nest Cottage Across street from beach and Heated Pool

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 HK$2,216
HK$6,961 total
includes taxes & fees
14 May - 15 May
Beautiful Guest House Near the Beach with Private Pool!

Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
The price is HK$4,725
HK$10,614 total
includes taxes & fees
24 Apr - 25 Apr
Cabana Cottage Across street from Beach and Heated Pool
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
843
Accommodation
20 Cottages
Lowest Price
HK$1,652
Highest Price
HK$24,989

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 traveller 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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