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

Search Siesta Key Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
The price is ￥24,557
￥59,477 total
includes taxes & fees
Oct 16 - Oct 17
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 ￥24,226
￥59,044 total
includes taxes & fees
Oct 18 - Oct 19
Yellow Palm Cottage, Heart of Siesta Key
A room with a dining table, chairs, a television, a sofa, and a lamp.

3. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is ￥27,219
￥62,425 total
includes taxes & fees
Oct 19 - Oct 20
BlueDolphin Cottage Walk To Siesta Beach
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.
The price is ￥19,830
￥55,326 total
includes taxes & fees
Oct 20 - Oct 21
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A residential house with a white fence, a palm tree, and a parked car.

5. 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.
The price is ￥15,705
￥48,079 total
includes taxes & fees
Oct 24 - Oct 25
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A two-story building with a blue exterior and white railings.

6. 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 ￥34,353
￥67,152 total
includes taxes & fees
Oct 18 - Oct 19
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.

7. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is ￥61,436
￥111,202 total
includes taxes & fees
Oct 26 - Oct 27
Siesta Heron 6 / Sunset
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
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.
The price is ￥37,843
￥70,828 total
includes taxes & fees
Nov 14 - Nov 15
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.

10. 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 ￥16,419
￥41,763 total
includes taxes & fees
Oct 15 - Oct 16
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
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
Cozy Lido Studio by Beach & St Armand's
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

12. 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
The price is ￥13,538
￥42,635 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Private Cottage, Minutes to Anna Maria Island
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.
The price is ￥15,676
￥33,722 total
includes taxes & fees
Oct 19 - Oct 20
The "Grouper"
A small house with a porch, surrounded by a grassy yard and dense foliage.

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is ￥12,683
￥40,024 total
includes taxes & fees
Oct 25 - Oct 26
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A riverfront restaurant with outdoor seating and a view of the water.

15. 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.
The price is ￥23,593
￥49,083 total
includes taxes & fees
Nov 12 - Nov 13
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
A patio with two blue lounge chairs, a potted plant, and a gravel area.

16. 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
The price is ￥27,710
￥53,200 total
includes taxes & fees
Oct 16 - Oct 17
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A wooden deck with a view of the ocean, a barbecue grill, and a cart.

17. 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.
The price is ￥31,411
￥79,438 total
includes taxes & fees
Oct 18 - Oct 19
Direct Beachfront 2BR Cottage on Casey Key!
A small, single-story building with a gray exterior, a white door, and a window with shutters.

18. 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)
"Host responded quicklyWould stay again"
United States
VIKTOR M.
The price is ￥6,334
￥21,060 total
includes taxes & fees
Oct 17 - Oct 18
Charming cottage for 2 across warm mineral springs park
A covered outdoor area with a wooden deck, green walls, and blue chairs.

19. 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.
The price is ￥23,130
￥84,692 total
includes taxes & fees
Oct 19 - Oct 20
Romantic Island Getaway! Just Steps from the Beach
A covered porch with a sign reading "BEACH HOUSE," outdoor seating, a grill, and a view of the water.

20. Bridge Street Pier Beach House + Dog-friendly

Bridge Street Pier Beach House + Dog-friendly
Bridge Street
9.6 out of 10, Exceptional, (36 reviews)
"Great place! Perfect location to the beach and shops "
United States
Michelle R.
Bridge Street Pier Beach House + Dog-friendly
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
"Clean , nice , close to everything"
Shane 4-night trip
Posted 14 hours ago
SeaSpray Resort

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
458
Accommodation
58 Cottages
Lowest Price
￥21,060
Highest Price
￥111,202

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.