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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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.
The price is €270
includes taxes & fees
23 Sept - 24 Sept
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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.
The price is €282
includes taxes & fees
28 Sept - 29 Sept
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A yellow house with a white door and number 5306.

3. Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (2 reviews)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
Yellow Palm Cottage steps from the beach
A hammock tied between two palm trees, a pink building with a red roof, and a bush with red flowers.

4. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is €484
includes taxes & fees
30 Sept - 1 Oct
Pink Mango Cottage steps from the beach
A small, single-story building with a blue roof and yellow walls, surrounded by a white picket fence and palm trees.

5. Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is €494
includes taxes & fees
24 Sept - 25 Sept
Blue Dolphin Cottage steps from the beach
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)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is €358
includes taxes & fees
22 Sept - 23 Sept
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 €605
includes taxes & fees
30 Sept - 1 Oct
Siesta Heron 6 / Sunset
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 €826
includes taxes & fees
2 Oct - 3 Oct
Beach Road
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

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

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
The price is €370
includes taxes & fees
16 Oct - 17 Oct
Coastal Studio, Walk to St Armand's or Lido Beach
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is €304
includes taxes & fees
23 Sept - 24 Sept
Cozy Lido Studio by Beach & St Armand's
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

11. 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 €412
includes taxes & fees
22 Sept - 23 Sept
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.

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
The price is €215
includes taxes & fees
25 Sept - 26 Sept
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
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
The price is €304
includes taxes & fees
24 Sept - 25 Sept
Lido Key Casita w Pool Steps to the Beach
A two-story house with a green exterior, a blue door, and orange trim.

14. 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.
The price is €192
includes taxes & fees
26 Sept - 27 Sept
The "Grouper"
A patio with a table set for two, a blue umbrella, and a white fence.

15. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
Studio by Lido Beach w heated pool
A keyless entry system with a red pathway leading to a gated entrance.

16. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (12 reviews)
"Very nice location. "
United States
Daniel o.
The price is €259
includes taxes & fees
20 Oct - 21 Oct
Cozy Private Cottage, Minutes to Anna Maria Island
A small house with a porch, surrounded by a grassy yard and dense foliage.

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is €233
includes taxes & fees
25 Sept - 26 Sept
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A wooden pier leading to a beach with a clear blue sky.

18. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (132 reviews)
"A beautiful location and super comfortable!"
United States
K B.
The price is €476
includes taxes & fees
26 Sept - 27 Sept
Casey Key Beachfront Escape: Charming 1BR Cottage
A patio with two blue lounge chairs, a potted plant, and a gravel area.

19. 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 €293
includes taxes & fees
3 Oct - 4 Oct
Pet-friendly Bradenton Home 1.5 Mi to Cortez 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

Siesta Key Beachside Villas

Siesta Key Beachside Villas

10/10 Excellent
"Great staff and great service. They provided all the amenities for a good trip to the nearby beach… cooler, towels, and wagon!"
Cynthia 3-night trip
Posted 4 hours ago
Siesta Key Beachside Villas

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
317
Accommodation
59 Cottages
Lowest Price
€233
Highest Price
€826

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 holidaying 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-fuelled day for travellers 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 holiday 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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