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Cottages in Siesta Key

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (179)
"A very accommodating property. Very clean and well maintained. The staff are extremely helpful and friendly. Great location."
$255 nightly
The price is $289
Jun 25 - Jun 26
Total includes taxes and fees
The Inn On Siesta Key

ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

9.8 out of 10, Exceptional, (21)
"This home is paradise and just a short walk to the beach. The pool is lovely, clean and the Adirondack chairs are such a nice way to enjoy it. The house is well equiped for a group as well."
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

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. "
$330 nightly
The price is $330
Jun 25 - Jun 26
Total includes taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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."
$547 nightly
The price is $610
Jul 14 - Jul 15
Total includes taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

10.0 out of 10, Exceptional, (2)
"The property was very nice and clean. It's also in a great location - very close to the beach and the Village. I will definitely stay here again."
Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

Remodeled Siesta Key Escape – Walk to the Beach!

10.0 out of 10, Exceptional, (8)
"Overall the location and cottage was good. We had a few issues but the Property Manager was quick to respond and made sure we were accommodated. My husband and I would recommend."
Remodeled Siesta Key Escape – Walk to the Beach!

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (321)
"Very cute beach cottage! Great location,very clean ,no complaints,if ever in Siesta Key again would definitely stay here "
Across The Street From #1 Beach

Remodeled Siesta Key Escape Walk to the Beach!

3.0 star property
Remodeled Siesta Key Escape Walk to the Beach!

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!"
$268 nightly
The price is $299
Jul 6 - Jul 7
Total includes taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Prem 2Bed/2Bath Gate House Cottage with private beach access!

9.6 out of 10, Exceptional, (63)
"Everything was just right!"
Prem 2Bed/2Bath Gate House Cottage with private beach access!

Siesta Key Village Home < Half Mi to Beach!

3.0 star property
Siesta Key Village Home < Half Mi to Beach!

Haven cottage Across street from beach and Heated Pool

9.8 out of 10, Exceptional, (6)
"Wonderful staff, very clean and convenient to village and beach. You can't go wrong."
Haven cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool

10.0 out of 10, Exceptional, (2)
"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."
Nest Cottage Across street from beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool

10.0 out of 10, Exceptional, (5)
"The Inn at Siesta Key was perfect for our trip. It was super clean, had everything we needed and then some. The owner is very accommodating and was there for anything we needed. Will definitely be back!"
Cabana Cottage Across street from Beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool

10.0 out of 10, Exceptional, (4)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
$393 nightly
The price is $424
Jun 25 - Jun 26
Total includes taxes and fees
Nook Cottage Across street from beach and Heated Pool

Cozy Cottage with Hot Tub

10.0 out of 10, Exceptional, (2)
"We loved the home and location and would definitely stay here again!"
Cozy Cottage with Hot Tub

Close to the beach! Pool acccess and Private Backyard - Crescent Cottage

10.0 out of 10, Exceptional, (1)
"This was the perfect spot for the two of us! Parking right outside our door, king size bed, just the right size kitchen, private side yard and walking distance to the beach and shopping and restaurants! We'd choose this again! Great set-up!"
Close to the beach! Pool acccess and Private Backyard - Crescent Cottage

Sarasota Vacation Rental w/ Pool & Game Room!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The property was perfect for our family. We had enough space for everyone. We enjoyed the pool, game room and the patio to grill. the neighbors were friendly! I would put a rug in front of the pool patio door inside to catch any dirt walking in, and that area can be very slippery with wet feet walking on the tile. Great stay! "
Sarasota Vacation Rental w/ Pool & Game Room!

Scenic Siesta Key Home ~ 1 Mi to Village & Beach!

2.5 star property
Scenic Siesta Key Home ~ 1 Mi to Village & Beach!

Lookout Cottage Across street from Beach and Heated Pool

10.0 out of 10, Exceptional, (1)
"The place was beautiful, tastefully furnished and decorated, and so clean! Plenty of towels and nice sheets. Loved the amenities like the pool and the beach chairs. The best part is the location - right across the street from a fantastic beach, close enough to walk to the main business district but not so close that you have to deal with all the people of you don’t want to. Perfect place for a couple looking for some R&R!"
Lookout 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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Frequently asked questions

Are there any family-friendly cottages in Siesta Key?
Vacationing with your group in Siesta Key is a cinch at The Inn On Siesta Key. With conveniences including a nearby beach and WiFi, you're sure to feel comfortable at this 3.5-star cottage. Flip Flop Cottages is another family-friendly stay where you and your squad can escape the hectic pace of the city. This cottage has a 3-star rating and amenities including a picnic area and a barbecue grill. After checking in and kicking back together in your cozy new digs, it's time to head out and explore the sights. Siesta Key Beach and Lido Beach are popular family-friendly attractions in Siesta Key.
Why book your cottage in Siesta Key with Expedia?
Booking a cottage in Siesta Key is as easy as entering your travel dates and picking your ideal place for a vacation in the outdoors. From upscale retreats to inexpensive stays and cottages that offer perks like a pool, Expedia has something for all styles. As for terrific deals? We have them too!
How can I find cheap cottages in Siesta Key?
The simplest way to score cheap cottages in Siesta Key is with Expedia's user-friendly filter tool. Narrow down your search by star rating, budget and amenities to grab awesome rates with only a few clicks.