Siesta Key, FL Cottage Rentals from $139

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.

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Our top choices for Siesta Key cottages

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Sarasota

ASHISH

$498 nightly

Jun 21 - Jun 22

Total with taxes and fees

The Inn On Siesta Key

Siesta Key

Michele

$456 nightly

Jul 5 - Jul 6

Total with taxes and fees

Unwind Poolside + Walk to Beach! Sarasota Retreat

South Village

"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "

Eleuterio

$540 nightly

Jul 12 - Jul 13

Total with taxes and fees

Siesta Heron 6 / Sunset

Siesta Key

$779 nightly

Jun 21 - Jun 22

Total with taxes and fees

Beach Road

Siesta Key

$1,199 nightly

Jun 21 - Jun 22

Total with taxes and fees

Siesta Heron 7

Siesta Key

$994 nightly

Jun 30 - Jul 1

Total with taxes and fees

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

North Port

$431 nightly

Jun 20 - Jun 21

Total with taxes and fees

Charming cottage for 2 across warm mineral springs park

Warm Mineral Springs

$125 nightly

Jun 22 - Jun 23

Total with taxes and fees

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Top Siesta Key Hotel Reviews

Tropical Breeze Resort

10/10 Excellent

"Awesome resort."

3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport

10/10 Excellent

"Communicate your needs with the host/property manager. They are very responsive and helpful. Pillows are really soft. Just in case people need firmer pillows. They can probably help with that too, I was just too tired late at night to contact them."

Azul Resort Siesta Key

10/10 Excellent

"We visited in mid june 2026 very clean confortable room within walking distance to the beach, the room comes with an assign parking spot, every room comes with a small table and two chairs just outside the room which we used often and luckily it was always shaded, you can borrow beach chairs but they are first comes first served my suggestion is you better bring your own and a good beach umbrella and beach towels and a buggy to carry everything to the beach, we stay in room 115 which comes with free body wash , shampoo and conditioner, coffee maker with everything you need to make coffee and a wine cooler, pool and pool area and all surrounding areas was well maintained, all in all a very good experience and we will definitely go back"

Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!

10/10 Excellent

"This is a small, charming studio-style apartment directly across the street from the stunning Siesta Key Public Beach. The apartment has all of the appliances, creature comforts, and facilities for a wonderful stay, including beach chairs, beach umbrellas, and rolling caddy for a trip to the beach. A small well-kept and private courtyard sits just outside the door with a bench swing, chairs, and a picnic table. This ground floor space is quiet, has adjacent parking, and is located a short distance (less than 0.5 mile) forom Siesta Key Village, home to a beautiful grocery market, cafes, and shops. The internet, large screen, and appliances worked perfectly and the bathroom and shower facilities were sleek, functional, and comfortable. I would stay again both solo or with a partner."

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews	874
Accommodation	55 Cottages
Lowest Price	$139
Highest Price	$2,979

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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Our top choices for Siesta Key cottages