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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Siesta Key cottages

Balcony view

1. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (202 reviews)
"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...
United States
Lisa
The price is €254
includes taxes & fees
9 Aug - 10 Aug
The Inn On Siesta Key
Exterior

2. 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, (89 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 €266
includes taxes & fees
13 Aug - 14 Aug
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Exterior

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, (188 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is €361
includes taxes & fees
2 Sept - 3 Sept
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Interior

4. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is €621
includes taxes & fees
1 Sept - 2 Sept
Siesta Heron 6 / Sunset
Pool

5. Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
The price is €988
includes taxes & fees
13 Aug - 14 Aug
Cabana Cottage Across street from Beach and Heated Pool
Interior

6. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is €713
includes taxes & fees
2 Sept - 3 Sept
Beach Road
Outdoor dining

7. Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is €932
includes taxes & fees
12 Aug - 13 Aug
Siesta Heron 7
1 bedroom, iron/ironing board, WiFi, bed sheets

8. Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
The price is €293
includes taxes & fees
9 Aug - 10 Aug
Cozy Lido Key Bungalow by Pool & Beach
1 bedroom, iron/ironing board, WiFi, bed sheets

9. Lido Bungalow Walk to Beach & St. Armand's Circle

Lido Bungalow Walk to Beach & St. Armand's Circle
Lido Key
The price is €293
includes taxes & fees
24 Aug - 25 Aug
Lido Bungalow Walk to Beach & St. Armand's Circle
Hair dryer, towels, soap, shampoo

10. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
The price is €306
includes taxes & fees
13 Aug - 14 Aug
Sunny Lido Studio - Modern Touches
Exterior

11. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (129 reviews)
"A beautiful location and super comfortable!"
United States
K B.
The price is €473
includes taxes & fees
14 Aug - 15 Aug
Casey Key Beachfront Escape: Charming 1BR Cottage
House (3 Bedrooms) | Interior

12. 'ocean Breeze Oasis' w/ Boat Dock & Slip on Canal!

'ocean Breeze Oasis' w/ Boat Dock & Slip on Canal!
3.0 star property
Bayshore Gardens
10.0 out of 10, Exceptional, (1 review)
'ocean Breeze Oasis' w/ Boat Dock & Slip on Canal!
Exterior

13. The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (73 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is €187
includes taxes & fees
16 Aug - 17 Aug
The "Grouper"
Property grounds

14. Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (10 reviews)
"Very nice location. "
United States
Daniel o.
The price is €227
includes taxes & fees
30 Aug - 31 Aug
Coastal Luxury 7mi to Anna Maria Private Cottage
Exterior

15. Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (26 reviews)
"We were enjoying our stay."
United States
Inna K.
The price is €119
includes taxes & fees
16 Aug - 17 Aug
Charming cottage for 2 across warm mineral springs park
Property grounds

16. 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, (128 reviews)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
The price is €574
includes taxes & fees
9 Aug - 10 Aug
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Property grounds

17. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is €2,670
includes taxes & fees
15 Aug - 16 Aug
3716 7th Ave W
Terrace/patio

18. Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (80 reviews)
"Great vacation!!"
United States
Dominic C.
The price is €435
includes taxes & fees
9 Aug - 10 Aug
Direct Beachfront 2BR Cottage on Casey Key!
House (2 Bedrooms) | Interior

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 €291
includes taxes & fees
8 Aug - 9 Aug
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
House (4 Bedrooms) | Interior

20. Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
The price is €386
includes taxes & fees
8 Aug - 9 Aug
Home < 1-mi Walk to Warm Mineral Springs Park!
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

The Capri at Siesta

The Capri at Siesta

10/10 Excellent
"Absolutely recommend! Great place just minutes away from the crescent beach. It is on the trolley route which passes very frequently. if you’d like to go to the Siesta Key beach it is a five minute trolley ride. Offers beach toys and beach chairs to borrow daily. The kitchen is fully equipped including an oven a dishwasher. The owner is very friendly and the place is very clean."
Nihan 7-night trip
Posted 5 hours ago
The Capri at Siesta

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
450
Accommodation
54 Cottages
Lowest Price
€119
Highest Price
€2,670

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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