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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Featured Cottages in Siesta Key

Our top choices for Siesta Key cottages

The Inn On Siesta Key
Balcony view

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The Inn On Siesta Key
Remodeled Siesta Key Escape Walk to the Beach!
Interior

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!
Interior

Siesta Key Village Home < Half Mi to Beach!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great location and home. Easy communication with owner. We had a wonderful time! "
Siesta Key Village Home < Half Mi to Beach!
Sarasota Vacation Rental w/ Pool & Game Room!
Interior

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!
Exterior

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!
Front of property

Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!

3.0 star property
Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!
Flip Flop Cottages
Exterior

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!
Outdoor pool

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!
Interior

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
Interior

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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Top Siesta Key Hotel Reviews

Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"Beach was close as well as bars and restaurants "
Mike 5-night trip
Posted 2 days ago
Siesta Key Beach Resort and Suites

Find out more about Siesta Key

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
185
Accommodation
10 Cottages
Lowest Price
Highest Price

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 holidaying 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-fuelled day for travellers 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 holiday 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia