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

Search Siesta Key Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Siesta Key cottages

A residential house with a white fence, a palm tree, and a parked car.

1. 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 11 - Oct 12
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.

2. 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.
$281 nightly
The price is $313
Oct 12 - Oct 13
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A two-story building with a blue exterior and white railings.

3. 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.
$374 nightly
The price is $417
Oct 13 - Oct 14
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A wooden deck with a glass door leading to a lake view, surrounded by greenery.

4. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$665 nightly
The price is $751
Oct 14 - Oct 15
Total with taxes and fees
Siesta Heron 6 / Sunset
A pair of stacked front-loading washing machines in a commercial setting.

5. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
$357 nightly
The price is $403
Oct 16 - Oct 17
Total with taxes and fees
Beach View 100ft To Beach and SPA
A room with a dining table, chairs, a television, a sofa, and a lamp.

6. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
$383 nightly
The price is $433
Oct 19 - Oct 20
Total with taxes and fees
BlueDolphin Cottage Walk To Siesta Beach
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

7. 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.
$409 nightly
The price is $455
Oct 25 - Oct 26
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.

8. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
$383 nightly
The price is $427
Oct 16 - Oct 17
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.

9. 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 11 - Oct 12
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

10. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
$369 nightly
The price is $411
Nov 4 - Nov 5
Total with taxes and fees
Lido Key Casita w Pool Steps to the Beach
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

11. Cozy Lido Studio by Beach & St Armand's

Cozy Lido Studio by Beach & St Armand's
Lido Key
$425 nightly
The price is $473
Oct 31 - Nov 1
Total with taxes and fees
Cozy Lido Studio by Beach & St Armand's
A single-story house with a blue exterior, a front door, and a small porch area.

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
$239 nightly
The price is $266
Oct 12 - Oct 13
Total with taxes and fees
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A two-story house with a green exterior, a blue door, and orange trim.

13. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (76 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
$191 nightly
The price is $213
Oct 12 - Oct 13
Total with taxes and fees
The "Grouper"
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

14. 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
$242 nightly
The price is $269
Oct 11 - Oct 12
Total with taxes and fees
Cozy Private Cottage, Minutes to Anna Maria Island
A small house with a porch, surrounded by a grassy yard and dense foliage.

15. 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 11 - Oct 12
Total with taxes and fees
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A small, single-story building with a gray exterior, a white door, and a window with shutters.

16. 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 11 - Oct 12
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
A riverfront restaurant with outdoor seating and a view of the water.

17. 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, (33 reviews)
"Great location"
United States
Susan C.
$278 nightly
The price is $310
Oct 11 - Oct 12
Total with taxes and fees
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
A patio with two blue lounge chairs, a potted plant, and a gravel area.

18. 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 11 - Oct 12
Total with taxes and fees
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A beachfront property with a house, palm trees, and a view of the ocean.

19. 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.
$659 nightly
The price is $734
Nov 3 - Nov 4
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
A covered outdoor area with a wooden deck, green walls, and blue chairs.

20. Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
Bradenton Beach
8.6 out of 10, Excellent, (4 reviews)
"It was nice to be so close to the beach, and walking distance to places to eat. I enjoyed driving around the island and seeing the little villages. The cottage was comfortable and had many conveniences. "
United States
Valerie T.
$483 nightly
The price is $538
Oct 15 - Oct 16
Total with taxes and fees
Romantic Island Getaway! Just Steps from 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Siesta Key Hotel Reviews

SeaSpray Resort

SeaSpray Resort

10/10 Excellent
"The only problem was a 2 floor walk up ! We are 83 years old with disable stickers . They did help us with luggage. In the future will only repeat it we get ground floor"
BARRY 2-night trip
Posted 12 hours ago
SeaSpray Resort

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
459
Accommodation
66 Cottages
Lowest Price
$133
Highest Price
$751

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.

Explore a world of travel with Expedia