Siesta Key, FL Cottage Rentals from $312

Q: 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.

Q: 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!

Q: 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.

A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

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Our top choices for Siesta Key cottages

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

1. The Inn On Siesta Key

Siesta Key

Stephen

$276 nightly

Oct 18 - Oct 19

Total with taxes and fees

A room with a dining table, chairs, a television, a sofa, and a lamp.

2. BlueDolphin Cottage Walk To Siesta Beach

Siesta Key Village

$351 nightly

Oct 19 - Oct 20

Total with taxes and fees

A yellow house with a porch, a mailbox, and a number 5306 on the door.

3. Yellow Palm Cottage, Heart of Siesta Key

Siesta Key Village

$341 nightly

Oct 18 - Oct 19

Total with taxes and fees

A patio area with a grill, potted plants, and a building with a teal door.

4. Beach Tree Cottage,Walk To Beach& Siesta

Siesta Key Village

$325 nightly

Oct 18 - Oct 19

Total with taxes and fees

A wooden deck with a glass door leading to a lake view, surrounded by greenery.

5. Siesta Heron 6 / Sunset

Siesta Key

$622 nightly

Oct 26 - Oct 27

Total with taxes and fees

A patio with two blue lounge chairs, a potted plant, and a gravel area.

6. Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Bradenton

Rob

$297 nightly

Oct 17 - Oct 18

Total with taxes and fees

A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

7. 3716 7th Ave W

Bradenton

$2,731 nightly

Oct 19 - Oct 20

Total with taxes and fees

A residential house with a garage, a front door, and a small front yard.

8. Home < 1-mi Walk to Warm Mineral Springs Park!

North Port

$395 nightly

Oct 20 - Oct 21

Total with taxes and fees

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Top Siesta Key Hotel Reviews

Siesta Key Inn

10/10 Excellent

"Great place to stay close to the beach. The apartment is fully equipped, very clean, new appliances. Excellent communication! I definitely recommend this place, you won’t be disappointed."

Cottages at Siesta Key Inn

10/10 Excellent

"The Cottages were sold to Azul Resorts which has another similar location around the corner. The entire complex went through a renovation in December of 2025. Expedia still shows it under the old name, and that was a little confusing when I arrived. It looked very clean and new for the most part. I booked the Studio unit with a King size bed. The bed was comfortable and the pillows were great. There is a 65" TV on the wall. It was exactly the same as the one I have at home which was great because I didn't have to learn how to work it. :-) The location is about 250 ft. from the beach access entrance (#13), which is another 200 foot walking path to the sand. The path leaves you about 150 feet from the water (low tide), and about 100 feet from the water (high tide). So if walking is difficult for you, know that you will walk approximately 550 feet before you can wet your toes in the Gulf of America. Regarding the location, it is about 4 miles South of the Sarasota Village downtown, 3 miles South of the main Sarasota Beach public parking area, but there are plenty of restaurant and tiki bars within 1 or 2 miles of the Azul Resort. The only cons I found were that the pool wasn't heated, and someone operates a chair and umbrella rental service that blocks a huge part of the beach area. There is room to the left of the path, or you can go to the right of the blocked off area. They also leave a small strip in front of the blocked area. We didn't have a problem finding room on d'sand."

Siesta Key Beach Resort and Suites

8/10 Good

"I had a three night stay at this hotel on Siesta Key. Great location, and I walked every where safely alone. Very friendly staff! My comments on the room. - the mattress needs to be replaced in room 102 - a threshold at the door would be nice to keep any critters from crawling into the room. - the dehumidifier in the room makes some very loud sounds, frequently, which woke me often."

Tropical Breeze Resort

8/10 Good

"Place was great. It was clean. Amenities was nice prime location, walking distance to the beach walking distance to all the shops and restaurants. Only problem is once the front office is closed. You can’t get anything, unfortunately I didn’t realize we didn’t have bath towels so 10 o’clock calling them no response nothing. So make sure you check everything before the front office closes."

The Ringling Beach House

10/10 Excellent

"We had a wonderful stay at The Ringling Beach House! The location was perfect, within walking distance of the beach and so many great shops and restaurants. The place was beautiful, very clean, and comfortable. Our host was amazing, friendly, and always quick to communicate, making our stay even more enjoyable. We truly enjoyed our time here and would definitely recommend it to anyone looking for a relaxing beach getaway. We would love to stay again!"

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews	214
Accommodation	66 Cottages
Lowest Price	$312
Highest Price	$3,086

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.

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