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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Siesta Key cottages

A pair of stacked front-loading washing machines in a commercial setting.

1. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
$313 nightly
The price is $354
Oct 4 - Oct 5
Total with taxes and fees
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
$341 nightly
The price is $385
Oct 4 - Oct 5
Total with taxes and fees
Yellow Palm Cottage, Heart of Siesta Key
A residential house with a white fence, a palm tree, and a parked car.

3. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (90 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
$270 nightly
The price is $301
Oct 4 - Oct 5
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Shared sunbathing deck by the pool, at the resort.

4. 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.
$310 nightly
The price is $346
Oct 4 - Oct 5
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A wooden deck with a glass door leading to a lake view, surrounded by greenery.

5. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$626 nightly
The price is $707
Oct 6 - Oct 7
Total with taxes and fees
Siesta Heron 6 / Sunset
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

6. Coastal Studio, Walk to St Armand's or Lido Beach

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
10.0 out of 10, Exceptional, (1 review)
"5 Stars: This cozy studio was exactly what we were looking for. Alexander was pleasant and friendly, the check in/check out process was easy. The location was fabulous- perhaps slightly too far to walk to St.Armand’s , but a quick ride on the rentable VEO bikes/scooters. The accommodations were clean, and beachy. We did not have an opportunity to use the pool, so I do have any objective comments for the pool. If we are in the area again, we would definitely stay here again!"
United States
lisa o.
$308 nightly
The price is $342
Oct 4 - Oct 5
Total with taxes and fees
Coastal Studio, Walk to St Armand's or Lido Beach
A patio with a table set for two, a blue umbrella, and a white fence.

7. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
$320 nightly
The price is $358
Oct 31 - Nov 1
Total with taxes and fees
Studio by Lido Beach w heated pool
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

8. 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)
"The house was truly lovely, and the hosts were exceptionally caring, kind, and attentive in their communication. It was wonderful to be so close to the beach, with stores conveniently nearby, making the stay feel comfortable and welcoming."
United States
Kandra R.
$414 nightly
The price is $461
Oct 8 - Oct 9
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A single-story house with a blue exterior, a front door, and a small porch area.

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
$236 nightly
The price is $263
Oct 12 - Oct 13
Total with taxes and fees
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.

10. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (13 reviews)
"Clean and nice place"
United States
Ismael
$206 nightly
The price is $230
Oct 4 - Oct 5
Total with taxes and fees
Cozy Private Cottage, Minutes to Anna Maria Island
A two-story house with a green exterior, a blue door, and orange trim.

11. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (75 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
$191 nightly
The price is $213
Oct 8 - Oct 9
Total with taxes and fees
The "Grouper"
A small house with a porch, surrounded by a grassy yard and dense foliage.

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
$226 nightly
The price is $253
Oct 3 - Oct 4
Total with taxes and fees
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

13. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
$291 nightly
The price is $324
Oct 5 - Oct 6
Total with taxes and fees
Lido Key Casita w Pool Steps to the Beach
A patio with two blue lounge chairs, a potted plant, and a gravel area.

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

Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place to stay. Clean and a lot of amenities. We enjoyed all the little touches that went into decorating the house, giving it a beach house feel. We would definitely stay here again. "
United States
Rob
$297 nightly
The price is $336
Oct 3 - Oct 4
Total with taxes and fees
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A small, single-story building with a gray exterior, a white door, and a window with shutters.

15. 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, (29 reviews)
"We were enjoying our stay."
United States
Inna K.
$120 nightly
The price is $133
Oct 3 - Oct 4
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
A beachfront property with a house, palm trees, and a view of the ocean.

16. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (132 reviews)
"Beautiful gulf view."
United States
Audrey B.
$543 nightly
The price is $605
Oct 17 - Oct 18
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
A small, single-story mobile home with a front porch, a small attached garage, and a clock tower.

17. Bridge Street Beach House | Wi-Fi | Center of All

Bridge Street Beach House | Wi-Fi | Center of All
Bridge Street
10.0 out of 10, Exceptional, (5 reviews)
"Great location, clean accommodations, good communication with host. ..."
United States
leslie m.
$371 nightly
The price is $414
Oct 26 - Oct 27
Total with taxes and fees
Bridge Street Beach House | Wi-Fi | Center of All
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

18. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,565 nightly
The price is $2,899
Oct 5 - Oct 6
Total with taxes and fees
3716 7th Ave W
A balcony with wicker furniture, a grill, and a view of a marina with boats and greenery.

19. Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (129 reviews)
"Place is great and clean. Love how smooth everything was. Jenny is easy to communicate as well"
United States
Natalia D.
$523 nightly
The price is $583
Oct 3 - Oct 4
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A wooden deck with a view of the ocean, a barbecue grill, and a cart.

20. Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (84 reviews)
"Great vacation!!"
United States
Dominic C.
$565 nightly
The price is $630
Oct 12 - Oct 13
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!
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

Siesta Key Inn

Siesta Key Inn

10/10 Excellent
"Lugar súper especial para relajarse en familia todo súper"
Alexander 2-night trip
Posted 1 hour ago
Siesta Key Inn

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
363
Accommodation
58 Cottages
Lowest Price
$133
Highest Price
$2,899

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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