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

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Siesta Key cottages

A patio with a sun lounger, a table with chairs, and an umbrella.

1. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is ￥26,443
￥65,752 total
includes taxes & fees
Nov 15 - Nov 16
Beach View 100ft To Beach and SPA
A yellow house with a porch, a mailbox, and a number 5306 on the door.

2. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is ￥37,140
￥84,116 total
includes taxes & fees
Nov 12 - Nov 13
Yellow Palm Cottage, Heart of Siesta Key
A small pink house with a white door, a blue car parked in front, and a white picket fence.

3. PinkMango Cottage Steps to Beach&Village

PinkMango Cottage Steps to Beach&Village
2.0 star property
Siesta Key Village
The price is ￥34,855
￥81,535 total
includes taxes & fees
Nov 16 - Nov 17
PinkMango Cottage Steps to Beach&Village
A two-story building with a blue exterior and white railings.

4. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (192 reviews)
"Loved the location of this property! The property manager was easy to contact and the property was exactly as shown in the pictures. Would stay here again!"
United States
Tracie B.
The price is ￥29,998
￥61,769 total
includes taxes & fees
Nov 13 - Nov 14
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A small, single-story building with a porch, surrounded by tropical vegetation.

5. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is ￥31,427
￥75,867 total
includes taxes & fees
Nov 15 - Nov 16
BlueDolphin Cottage Walk To Siesta Beach
Shared sunbathing deck by the pool, at the resort.

6. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is ￥19,840
￥50,909 total
includes taxes & fees
Nov 15 - Nov 16
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A single-story house with a front porch, a small deck, and a garage.

7. Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very good, (1 review)
"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. "
United States
Eleuterio
The price is ￥42,979
￥96,620 total
includes taxes & fees
Nov 23 - Nov 24
Unwind Poolside + Walk to Beach! Sarasota Retreat
A two-story building with a blue and white exterior, a balcony, and a sign that reads "Gidget's Coastal Preserve."

8. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is ￥98,406
￥137,790 total
includes taxes & fees
Dec 8 - Dec 9
Beach Road
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

9. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (213 reviews)
"Thank you Paige & Gabe! My husband & I had a wonderful stay last week in The Nook at your beautiful Inn. Absolutely loved the old Florida charm and perfect location. Your Inn is immaculately kept as well as comfortable. We especially loved our private patio with the fire pit at The Nook. The location of The Inn could not be more perfect being less than a 5 minute walk across the street to Siesta Key beach as well as a short 10 minute walk to town with all the restaurants & shops. Thanks again...
United States
Karen Jean
The Inn On Siesta Key
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

10. Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
Cabana Cottage Across street from Beach and Heated Pool
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

11. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
10.0 out of 10, Exceptional, (2 reviews)
"Alex was very quick to reply to my questions. Room was exactly as pictured!"
United States
Felecia P.
The price is ￥24,856
￥64,079 total
includes taxes & fees
Nov 18 - Nov 19
Lido Key Casita w Pool Steps to the Beach
A patio with a table set for two, a blue umbrella, and a white fence.

12. Lido Beach Studio with Heated Pool

Lido Beach Studio with Heated Pool
Lido Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful place!!"
United States
Lorraine B.
The price is ￥24,856
￥63,603 total
includes taxes & fees
Nov 12 - Nov 13
Lido Beach Studio with Heated Pool
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

13. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.4 out of 10, Very good, (10 reviews)
"Very close drive to the beach! Nice place to stay!"
United States
Rocio S.
The price is ￥26,862
￥57,853 total
includes taxes & fees
Nov 12 - Nov 13
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A backyard with a tree, a wooden fence, a blue shed, and a house with a door.

14. Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
The price is ￥14,856
￥38,423 total
includes taxes & fees
Dec 2 - Dec 3
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

15. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
9.8 out of 10, Exceptional, (14 reviews)
"Clean and nice place"
United States
Ismael
The price is ￥12,390
￥37,311 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Private Cottage, Minutes to Anna Maria Island
A two-story house with a green exterior, a blue door, and orange trim.

16. The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (79 reviews)
"Perfect spot"
United States
Canyon L.
The price is ￥15,713
￥32,374 total
includes taxes & fees
Nov 15 - Nov 16
The "Grouper"
A deck with a table and chairs, a blue umbrella, and a white fence.

17. Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is ￥12,713
￥38,056 total
includes taxes & fees
Nov 14 - Nov 15
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A beachfront property with a single-story house, a paved driveway, and a palm tree in the foreground.

18. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (136 reviews)
"Cute little cottage right on the beach. Doesn’t get any better than that."
United States
kelly h.
The price is ￥31,427
￥75,415 total
includes taxes & fees
Nov 12 - Nov 13
Casey Key Beachfront Escape: Charming 1BR Cottage
A small, single-story building with a gray exterior, a white door, and a window with shutters.

19. Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (30 reviews)
"Host responded quicklyWould stay again"
United States
VIKTOR M.
The price is ￥7,901
￥20,273 total
includes taxes & fees
Nov 13 - Nov 14
Charming cottage for 2 across warm mineral springs park
A riverfront restaurant with outdoor seating and a view of the water.

20. NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach

NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
Nokomis
9.2 out of 10, Wonderful, (34 reviews)
"Great location"
United States
Susan C.
The price is ￥21,963
￥44,982 total
includes taxes & fees
Nov 15 - Nov 16
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
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

Captiva Beach Resort

Captiva Beach Resort

8/10 Good
"This was really a 5 star experience in general. The reason for my 4 star rating is the room is opened with a code, which is fine, but there was no way to lock it for privacy once inside. Anyone with a code had access to our room all night. I was uncomfortable with that. Would I stay there again, probably. But there were a number of adjacent properties with the same price and amenities. I would check to see if I could privately lock my door at night so I wouldn’t have to worry about someone coming in while I was sleeping or showering and stay there instead. It isn’t something I had ever really thought about before because it’s never been an issue. Nice people, decent property for the price , clean pool, walking distance to the beach and bars. Just a minor security glitch that could easily be resolved with a door flip thing on the inside to offer privacy."
Deb 1-night trip
Posted 1 hour ago
Captiva Beach Resort

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
711
Accommodation
63 Cottages
Lowest Price
￥20,273
Highest Price
￥137,790

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.