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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Browse Select Longboat Key Cottages

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Terrace/patio

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (56)
"Was easy to grab this little oasis in a pristine location to grab some much needed getaway time with the family. The surrounding area is low key and relaxed, plenty to do and see or just walk out and enjoy the beach!"
The price is £646
includes taxes & fees
27 Jun - 28 Jun
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Outdoor dining

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (89)
"Beautiful sunsets and loved walking out to the back patio and onto the beach. Great place for 2 people. "
The price is £579
includes taxes & fees
26 Jun - 27 Jun
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Outdoor pool

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

9.6 out of 10, Exceptional, (75)
"We loved everything about this rental! There are so many fun restaurants and bars within walking distance! There's also the convenience of the trolley stop right across the street for trips into the Village. The pool was nice and the beach was very close. We'd definitely recommend this location and we hope to be back next year!"
The price is £225
includes taxes & fees
6 Jul - 7 Jul
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Terrace/patio

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

10.0 out of 10, Exceptional, (4)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
The price is £278
includes taxes & fees
21 Jul - 22 Jul
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Pool Beach Supplies Outdoor Shower PingPong Table
Fridge, microwave, oven, stovetop

Pool Beach Supplies Outdoor Shower PingPong Table

10.0 out of 10, Exceptional, (7)
"This was a super cute house, the property was just as great. Everything was super clean and nice. We had a wonderful stay!"
Pool Beach Supplies Outdoor Shower PingPong Table
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (30)
"Fun stay, great location"
The price is £185
includes taxes & fees
27 Jun - 28 Jun
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
The "Grouper"
Interior

The "Grouper"

9.6 out of 10, Exceptional, (29)
"My stay was absolutely wonderful! The location is great, very convenient. The place itself is extremely comfortable, cozy, and it had everything we needed. The hosts were kind and attentive. It was truly worth every minute."
The price is £158
includes taxes & fees
29 Jun - 30 Jun
The "Grouper"
Charming Anna Maria Island condo close to Bridge Street - Tradewinds #9
TV

Charming Anna Maria Island condo close to Bridge Street - Tradewinds #9

2.0 star property
8.0 out of 10, Very good, (2)
"We have stayed at this property at least 20 times before but always booked through the hotel. The property and location are terrific for what we want from Anna Maria Island. However booking through this agency was more expensive and while it worked out OK, the idea that at this price you can only have one trash bag, two roles of toilet paper, and two dishwasher pods seems a bit extreme and showed a lack of good will we thought."
The price is £386
includes taxes & fees
6 Jul - 7 Jul
Charming Anna Maria Island condo close to Bridge Street - Tradewinds #9
Steps to Beach+bikes VaCay getaway on PaG island
Smart TV, DVD player, books, music library

Steps to Beach+bikes VaCay getaway on PaG island

10.0 out of 10, Exceptional, (10)
"Clean and convenient to all of Pass A Grill beach, Dt Pete’s beach and surrounding area. Freebee picks you up and takes you back which is a great option for dinning. Host had all information needed for a great stay. Only small thing was 1 of the bikes seat was loose and kickstand doesn’t stay up so it was unbridle but all was great other then that."
The price is £244
includes taxes & fees
7 Jul - 8 Jul
Steps to Beach+bikes VaCay getaway on PaG island
Steps 2 Beach-Island Cottage w/king bd+2bike+parking
Exterior detail

Steps 2 Beach-Island Cottage w/king bd+2bike+parking

9.8 out of 10, Exceptional, (38)
"Super cute little getaway for a couple. Great location- just a few steps to the beach! "
The price is £354
includes taxes & fees
3 Jul - 4 Jul
Steps 2 Beach-Island Cottage w/king bd+2bike+parking
Sunny PaG Island rental w/bikes-just steps2beach
Dining

Sunny PaG Island rental w/bikes-just steps2beach

9.0 out of 10, Wonderful, (17)
"Cute little beach house a short walk to the beach, property shared with several other rentals but felt peaceful and quiet. Parking is on street nearby. Convenient location to explore the St. Petersburg area."
The price is £275
includes taxes & fees
29 Jun - 30 Jun
Sunny PaG Island rental w/bikes-just steps2beach
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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Frequently asked questions

Are there any family-friendly cottages in Longboat Key?
Get comfortable at Queen's Gate Resort, a 2.5-star cottage not far from downtown. Amenities here include a nearby beach and a barbecue grill. Another family-friendly pick where you can swap the concrete jungle for fresh air and nature 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. Longboat Key has no shortage of family-friendly attractions to check out that'll entertain the kids. Florida Maritime Museum at Cortez and Island Gallery West promise a fun day out for visitors of all ages.
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.