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

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Our top choices for Siesta Key cottages

1. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (203 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 ¥35,635
¥49,084 total
includes taxes & fees
Aug 13 - Aug 14
The Inn On Siesta Key

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, (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 ¥15,766
¥48,423 total
includes taxes & fees
Aug 17 - Aug 18
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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, (189 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is ¥34,163
¥66,938 total
includes taxes & fees
Sep 2 - Sep 3
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

4. Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (4 reviews)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
United States
Derek N.
The price is ¥39,800
¥108,765 total
includes taxes & fees
Aug 13 - Aug 14
Nook Cottage Across street from beach and Heated Pool

5. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is ¥60,674
¥110,580 total
includes taxes & fees
Aug 23 - Aug 24
Siesta Heron 6 / Sunset

6. 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 ¥52,433
¥174,014 total
includes taxes & fees
Aug 13 - Aug 14
Cabana Cottage Across street from Beach and Heated Pool

7. Lookout Cottage Across street from Beach and Heated Pool

Lookout Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (1 review)
"The place was beautiful, tastefully furnished and decorated, and so clean! Plenty of towels and nice sheets. Loved the amenities like the pool and the beach chairs. The best part is the location - right across the street from a fantastic beach, close enough to walk to the main business district but not so close that you have to deal with all the people of you don’t want to. Perfect place for a couple looking for some R&R!"
United States
Keeley L.
Lookout Cottage Across street from Beach and Heated Pool

8. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is ¥92,763
¥131,251 total
includes taxes & fees
Sep 2 - Sep 3
Beach Road

9. Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is ¥95,489
¥166,045 total
includes taxes & fees
Aug 19 - Aug 20
Siesta Heron 7

10. Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
The price is ¥13,883
¥52,880 total
includes taxes & fees
Aug 12 - Aug 13
Cozy Lido Key Bungalow by Pool & Beach

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

Lido Bungalow Walk to Beach & St. Armand's Circle
Lido Key
The price is ¥13,883
¥52,880 total
includes taxes & fees
Aug 18 - Aug 19
Lido Bungalow Walk to Beach & St. Armand's Circle

12. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
The price is ¥15,618
¥54,998 total
includes taxes & fees
Aug 17 - Aug 18
Sunny Lido Studio - Modern Touches

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 ¥15,618
¥33,440 total
includes taxes & fees
Aug 12 - Aug 13
The "Grouper"

14. Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (11 reviews)
"Very nice location. "
United States
Daniel o.
The price is ¥12,740
¥42,208 total
includes taxes & fees
Aug 30 - Aug 31
Coastal Luxury 7mi to Anna Maria Private Cottage

15. 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 ¥39,124
¥85,922 total
includes taxes & fees
Aug 16 - Aug 17
Casey Key Beachfront Escape: Charming 1BR Cottage

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 ¥27,608
¥53,004 total
includes taxes & fees
Aug 13 - Aug 14
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

17. 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, (27 reviews)
"We were enjoying our stay."
United States
Inna K.
The price is ¥6,310
¥20,982 total
includes taxes & fees
Aug 24 - Aug 25
Charming cottage for 2 across warm mineral springs park

18. 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 ¥47,170
¥103,146 total
includes taxes & fees
Aug 12 - Aug 13
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

19. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is ¥372,314
¥486,786 total
includes taxes & fees
Aug 13 - Aug 14
3716 7th Ave W

20. Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
The price is ¥17,874
¥57,863 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Lido Key Studio Steps to Beach & Kayaking
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

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
662
Accommodation
54 Cottages
Lowest Price
¥20,982
Highest Price
¥486,786

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.