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

Search Siesta Key Cottages

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (201 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
$443 nightly
The price is $500
Aug 7 - Aug 8
Total with taxes and fees
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, (89 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
$273 nightly
The price is $304
Aug 10 - Aug 11
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

3. Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
"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.
$598 nightly
The price is $645
Aug 5 - Aug 6
Total with taxes and fees
Yellow Palm Cottage steps from the beach

4. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
$779 nightly
The price is $847
Aug 7 - Aug 8
Total with taxes and fees
Pink Mango Cottage steps from the beach

5. 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
$377 nightly
The price is $421
Sep 2 - Sep 3
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

6. Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very Good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
$602 nightly
The price is $680
Aug 5 - Aug 6
Total with taxes and fees
Unwind Poolside + Walk to Beach! Sarasota Retreat

7. Haven cottage Across street from beach and Heated Pool

Haven cottage Across street from beach and Heated Pool
Siesta Key
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed the property, a very nice little unit, very clean and enjoyable"
United States
Michael M.
Haven cottage Across street from beach and Heated Pool

8. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$633 nightly
The price is $715
Aug 31 - Sep 1
Total with taxes and fees
Siesta Heron 6 / Sunset

9. 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.
$1,106 nightly
The price is $1,200
Aug 7 - Aug 8
Total with taxes and fees
Cabana Cottage Across street from Beach and Heated Pool

10. Beach Road

Beach Road
2.0 star property
Siesta Key
$725 nightly
The price is $820
Sep 2 - Sep 3
Total with taxes and fees
Beach Road

11. Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
$894 nightly
The price is $1,010
Aug 12 - Aug 13
Total with taxes and fees
Siesta Heron 7

12. Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
$301 nightly
The price is $335
Aug 6 - Aug 7
Total with taxes and fees
Cozy Lido Key Bungalow by Pool & Beach

13. Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
$301 nightly
The price is $335
Aug 5 - Aug 6
Total with taxes and fees
Cozy Lido Key Studio Steps to Beach & Kayaking

14. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
$313 nightly
The price is $349
Aug 6 - Aug 7
Total with taxes and fees
Sunny Lido Studio - Modern Touches

15. 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.
$223 nightly
The price is $249
Aug 30 - Aug 31
Total with taxes and fees
Coastal Luxury 7mi to Anna Maria Private Cottage

16. 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.
$191 nightly
The price is $213
Aug 12 - Aug 13
Total with taxes and fees
The "Grouper"

17. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (129 reviews)
"We loved the cottage on the beach. The view was wonderful. Very peaceful location. The cottage was clean and had everything we needed. Highly recommend!"
United States
Virginia W.
$487 nightly
The price is $543
Aug 14 - Aug 15
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage

18. 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
$297 nightly
The price is $336
Aug 5 - Aug 6
Total with taxes and fees
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

19. 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.
$120 nightly
The price is $133
Aug 16 - Aug 17
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park

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, (128 reviews)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
$583 nightly
The price is $650
Aug 5 - Aug 6
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Siesta Key Hotel Reviews

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
660
Accommodation
55 Cottages
Lowest Price
$133
Highest Price
$1,200

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.

Explore a world of travel with Expedia