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Featured Cottages in Siesta Key

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (181)
"The Inn on Siesta Key was awesome. Paige and Gabe were friendly and always helpful and they provided everything you would need for the beach. The property was clean and well maintained. The beach is literally across the street with a 3 minute walk. We will definitely be coming back. "
The Inn On Siesta Key

Remodeled Siesta Key Escape Walk to the Beach!

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

Siesta Key Village Home < Half Mi to Beach!

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

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!

Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!

3.0 star property
Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!

Flip Flop Cottages

3.0 star property
7.8 out of 10, Good, (6)
"Very cute. Pool was a bit small"
Flip Flop Cottages

Luxe Bayfront Sarasota Home Rental: Pool, Lanai!

3.0 star property
Luxe Bayfront Sarasota Home Rental: Pool, Lanai!

Modern Siesta Key Getaway w/ Private Pool!

3.0 star property
Modern Siesta Key Getaway w/ Private Pool!

3 Mi to Siesta Key Beach: Snowbird Haven w/ Lanai

3 Mi to Siesta Key Beach: Snowbird Haven w/ Lanai
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?
Many visitors needing a family-friendly cottage in Siesta Key choose The Inn On Siesta Key. With a 3.5-star rating and amenities including a nearby beach and laundry facilities, it'll feel like your home away from home. Another great option for vacationing families is Flip Flop Cottages. Laundry facilities and a barbecue grill help make this 3-star cottage a comfortable base for your Siesta Key trip. Siesta Key has lots of family-friendly attractions to visit that'll entertain the kids. Siesta Key Beach and Lido Beach promise a fun-fueled day for travelers both young and old.
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.