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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Featured Cottages in Siesta Key

The Inn On Siesta Key
Balcony view

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (170)
"We were happy with everything!"
The price is S$937
includes taxes & fees
16 Mar - 17 Mar
The Inn On Siesta Key
Siesta Key Couple's Escape - Walk to Beaches!
Interior

Siesta Key Couple's Escape - Walk to Beaches!

3.0 star property
Siesta Key Couple's Escape - Walk to Beaches!
Siesta Key Village Home < Half Mi to Beach!
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!
Outdoor dining

Sarasota Vacation Rental w/ Pool & Game Room!

3.0 star property
Sarasota Vacation Rental w/ Pool & Game Room!
Scenic Siesta Key Home ~ 1 Mi to Village & Beach!
Private kitchen

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

2.5 star property
Scenic Siesta Key Home ~ 1 Mi to Village & Beach!
Flip Flop Cottages
Outdoor pool

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!
Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!
Interior

Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!

3.0 star property
Siesta Key Oasis w/ Outdoor Pool + Screened 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!
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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Other property types in Siesta Key

Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4579)
"Excellent accommodations. Staff was very helpful. Room was very good. Overall great value."
The price is S$454
includes taxes & fees
17 Mar - 18 Mar
Tropical Beach Resorts
The Ringling Beach House
Aerial view

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (293)
"Great location. Updated unit which was very clean and comfortable. I did not realize I had to bring my own toilet paper, so we had to make a trip to the store after settling in. There is not 1 hook or rack to hang a wet towel or bathing suit. 3 bath towels given for 3 people so they needed to be hung to be re-used for a few days. There was no bath mat or extra towel to put down on the floor for getting out of the shower. There was no place to put luggage on other than the floor. Wifi barely...
The price is S$518
includes taxes & fees
13 Mar - 14 Mar
The Ringling Beach House
Captiva Beach Resort
Private kitchen

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1074)
"Really enjoyed our stay at Captiva Beach Resort. Easy check in/out, communicative staff, and perfect location. We would absolutely book again. "
The price is S$491
includes taxes & fees
13 Mar - 14 Mar
Captiva Beach Resort
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.

Frequently asked questions

Are there any family-friendly cottages in Siesta Key?
Many visitors searching for 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 a picnic area, you’ll feel right at home here. Another top pick for families seeking a break close to nature is Flip Flop Cottages. WiFi and a barbecue grill help make this 3-star cottage a comfy base for your Siesta Key getaway. Once you’ve checked in and unpacked, there’s no shortage of family-friendly attractions to visit in and around Siesta Key. St. Boniface Episcopal Church Labyrinth and Point of Rocks are two popular options.
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.