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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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 HK$777
HK$2,275 total
includes taxes & fees
29 Sept - 30 Sept
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.
The price is HK$784
HK$2,373 total
includes taxes & fees
30 Sept - 1 Oct
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A hammock tied between two palm trees, a pink building with a red roof, and a bush with red flowers.

3. 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 HK$763
HK$4,243 total
includes taxes & fees
30 Sept - 1 Oct
Pink Mango Cottage steps from the beach
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.
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.

5. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is HK$3,098
HK$5,571 total
includes taxes & fees
4 Oct - 5 Oct
Siesta Heron 6 / Sunset
A small, single-story building with a blue roof and yellow walls, surrounded by a white picket fence and palm trees.

6. Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
Blue Dolphin Cottage steps from the beach
A two-story building with a blue and white exterior, a balcony, and a sign that reads "Gidget's Coastal Preserve."

7. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is HK$5,397
HK$7,412 total
includes taxes & fees
2 Oct - 3 Oct
Beach Road
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

8. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
The price is HK$690
HK$2,488 total
includes taxes & fees
5 Oct - 6 Oct
Lido Key Casita w Pool Steps to the Beach
A patio with a table set for two, a blue umbrella, and a white fence.

9. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
The price is HK$733
HK$2,537 total
includes taxes & fees
1 Oct - 2 Oct
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.

10. 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 HK$1,875
HK$3,423 total
includes taxes & fees
8 Oct - 9 Oct
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.

11. 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 HK$706
HK$1,841 total
includes taxes & fees
12 Oct - 13 Oct
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.

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 HK$424
HK$1,770 total
includes taxes & fees
29 Sept - 30 Sept
Cozy Private Cottage, Minutes to Anna Maria Island
A small house with a porch, surrounded by a grassy yard and dense foliage.

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is HK$628
HK$1,975 total
includes taxes & fees
29 Sept - 30 Sept
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
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 HK$777
HK$1,655 total
includes taxes & fees
29 Sept - 30 Sept
The "Grouper"
A beachfront property with a house, palm trees, and a view of the ocean.

15. 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.
The price is HK$2,338
HK$4,480 total
includes taxes & fees
9 Oct - 10 Oct
Casey Key Beachfront Escape: Charming 1BR Cottage
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 HK$1,373
HK$2,635 total
includes taxes & fees
29 Sept - 30 Sept
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
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.
The price is HK$1,451
HK$2,905 total
includes taxes & fees
5 Oct - 6 Oct
Bridge Street Beach House | Wi-Fi | Center of All
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

18. 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 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, (29 reviews)
"We were enjoying our stay."
United States
Inna K.
The price is HK$353
HK$1,088 total
includes taxes & fees
1 Oct - 2 Oct
Charming cottage for 2 across warm mineral springs park
A balcony with wicker furniture, a grill, and a view of a marina with boats and greenery.

20. 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)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
The price is HK$1,953
HK$4,364 total
includes taxes & fees
29 Sept - 30 Sept
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
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

Tropical Breeze Resort

Tropical Breeze Resort

8/10 Good
"They upgraded my reservation, with a full kitchen and extra room. Location was right behind the village, for easy walking. Was able to bring my dog. Staff friendly and helpful."
Susan 2-night trip
Posted 4 hours ago
Tropical Breeze Resort

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
554
Accommodation
59 Cottages
Lowest Price
HK$1,088
Highest Price
HK$7,412

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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