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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sep - 14 Sep
In two months
10 Oct - 12 Oct

Browse Select Siesta Key Cottages

The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (182)
"Great place to stay! "
The price is ฿7,142
฿9,281 total
includes taxes & fees
20 Aug - 21 Aug
The Inn On Siesta Key
Remodeled Siesta Key Escape Walk to the Beach!
Cottage (1 Bedroom) | 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!
House (2 Bedrooms) | Interior

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!
House (3 Bedrooms) | 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!
House (2 Bedrooms) | Private kitchen

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!
House (4 Bedrooms) | 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
Property grounds

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!
Interior

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!
Outdoor dining

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

Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"Walkable distance to everything "
Tae 1-night trip
Posted 18 hours ago
Tropical Breeze Resort

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.