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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Longboat Key cottages

Terrace/patio

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (73 reviews)
"It was perfect. We had a great time."
United States
Karen M.
The price is HK$3,119
HK$5,699 total
includes taxes & fees
8 Jun - 9 Jun
Direct Beachfront 2BR Cottage on Casey Key!
Property grounds

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Palmetto
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were very comfortable and clean. Quiet neighborhood. Host was extremely helpful and pleasant. The screened porch off of the kitchen was a great place to relax with the dogs. We didn't get an opportunity to enjoy the pool and hot tub because of our other obligations but definitely will plan on staying again the next time I need to visit the area. It was like a home away from home."
United States
Douglas T.
The price is HK$784
HK$1,936 total
includes taxes & fees
1 Jul - 2 Jul
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Exterior

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (68 reviews)
"Place was great, the bed was very comfortable and we loved the new screened in porch."
United States
ken h.
The price is HK$776
HK$1,653 total
includes taxes & fees
26 Jun - 27 Jun
The "Grouper"
Outdoor dining

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$1,285
HK$2,892 total
includes taxes & fees
9 Jun - 10 Jun
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior

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, (184 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is HK$2,923
HK$4,914 total
includes taxes & fees
12 Jun - 13 Jun
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

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, (21 reviews)
"Great location! "
United States
Quinton W.
The price is HK$1,254
HK$2,840 total
includes taxes & fees
7 Jun - 8 Jun
Sunny PaG Island rental w/bikes-just steps2beach
Property grounds

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is HK$18,495
HK$24,181 total
includes taxes & fees
12 Jun - 13 Jun
3716 7th Ave W
Property grounds

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, (126 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is HK$2,782
HK$5,620 total
includes taxes & fees
6 Jun - 7 Jun
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Exterior

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, (26 reviews)
"All as promised…clean, bright…small but perfect for a couple at the beach. "
United States
reva g.
The price is HK$1,545
HK$3,200 total
includes taxes & fees
16 Jun - 17 Jun
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Marina

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Southgate
9.6 out of 10, Exceptional, (15 reviews)
"Place had everything needed. Host was very communicative and helpful. "
United States
Chris R.
The price is HK$705
HK$3,301 total
includes taxes & fees
30 Jun - 1 Jul
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Property grounds

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (7 reviews)
"Place was clean, cozy and cute! Host communication was friendly, clear and concise. Would absolutely recommend!"
United States
Tracee Candace L.
The price is HK$862
HK$2,351 total
includes taxes & fees
15 Jun - 16 Jun
Coastal Luxury 7mi to Anna Maria Private Cottage
Fridge, microwave, stovetop, dishwasher

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
The price is HK$760
HK$3,181 total
includes taxes & fees
21 Jun - 22 Jun
Lido Key Getaway - Bikes & Beach Gear
Exterior

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

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (47 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is HK$4,161
HK$10,289 total
includes taxes & fees
6 Jun - 7 Jun
Adorable Cottage with Covered Balconies and Private Pool
Property grounds

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$3,981
HK$9,249 total
includes taxes & fees
27 Jun - 28 Jun
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Outdoor dining

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Nokomis
9.6 out of 10, Exceptional, (5 reviews)
"Lowkey, quiet, clean, amenities to cook, great host and great view. Happy to go back again."
United States
Bryan S.
The price is HK$901
HK$1,529 total
includes taxes & fees
28 Jun - 29 Jun
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
1 bedroom, iron/ironing board, free WiFi, bed sheets

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (39 reviews)
"Fun stay, great location"
United States
Theresa H.
The price is HK$1,136
HK$1,907 total
includes taxes & fees
5 Jun - 6 Jun
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Interior

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
The price is HK$1,434
HK$4,220 total
includes taxes & fees
11 Jun - 12 Jun
Unwind Poolside + Walk to Beach! Sarasota Retreat
Exterior

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 HK$776
HK$2,375 total
includes taxes & fees
10 Jun - 11 Jun
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Outdoor dining

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is HK$6,951
HK$10,743 total
includes taxes & fees
15 Jun - 16 Jun
Siesta Heron 7
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

Sea Club I Beach Resort

Sea Club I Beach Resort

10/10 Excellent
"A big thank you to Lisa and her team. What started out a little rocky, a room that wasn't up to their standards, finished super well. I spoke to Lisa, the property manager, and she moved us to a fantastic room. We will go back and recommend this place to our friends and family."
Steven 3-night trip
Posted 19 hours ago
Sea Club I Beach Resort

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
772
Accommodation
23 Cottages
Lowest Price
HK$1,529
Highest Price
HK$24,181

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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