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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Siesta Key cottages

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

1. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (204 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 CA $276
CA $389 total
includes taxes & fees
Aug 31 - Sep 1
The Inn On Siesta Key
A residential house with a white fence, a palm tree, and a parked car.

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 CA $137
CA $418 total
includes taxes & fees
Sep 2 - Sep 3
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A two-story building with a blue exterior and white railings.

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, (190 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is CA $303
CA $596 total
includes taxes & fees
Sep 2 - Sep 3
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A balcony with a white railing, a blue chair, and a view of palm trees and a house.

4. 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.
The price is CA $325
CA $759 total
includes taxes & fees
Sep 1 - Sep 2
Haven cottage Across street from beach and Heated Pool
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

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 CA $356
CA $1,365 total
includes taxes & fees
Sep 1 - Sep 2
Cabana Cottage Across street from Beach and Heated Pool
A wooden deck with a glass door leading to a lake view, surrounded by greenery.

6. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is CA $549
CA $988 total
includes taxes & fees
Sep 8 - Sep 9
Siesta Heron 6 / Sunset
A balcony with a white railing, a blue woven table, and chairs, overlooking a house and palm trees.

7. Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
United States
Marti C.
The price is CA $320
CA $756 total
includes taxes & fees
Aug 31 - Sep 1
Nest Cottage Across street from beach and Heated Pool
A covered outdoor seating area with a sofa, a chair, and a coffee table.

8. 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 CA $320
CA $921 total
includes taxes & fees
Aug 31 - Sep 1
Nook Cottage Across street from beach and Heated Pool
A kitchen with white cabinets, a coffee bar, a wooden shelf with decorative items, and a view of the outside.

9. 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.
The price is CA $320
CA $756 total
includes taxes & fees
Aug 31 - Sep 1
Lookout Cottage Across street from Beach and Heated Pool
A two-story building with a blue and white exterior, a balcony, and a sign that reads "Gidget's Coastal Preserve."

10. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is CA $797
CA $1,134 total
includes taxes & fees
Sep 2 - Sep 3
Beach Road
A wooden deck with outdoor furniture, a table, and chairs, overlooking a body of water.

11. Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is CA $636
CA $1,231 total
includes taxes & fees
Aug 31 - Sep 1
Siesta Heron 7
A bedroom with a bed, a bedside table, a mirror, a ceiling fan, and a view of a kitchen area.

12. Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
The price is CA $122
CA $463 total
includes taxes & fees
Sep 3 - Sep 4
Cozy Lido Key Bungalow by Pool & Beach
A bedroom with a bed, a desk, a wardrobe, and a ceiling fan.

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

Lido Bungalow Walk to Beach & St. Armand's Circle
Lido Key
The price is CA $122
CA $460 total
includes taxes & fees
Sep 1 - Sep 2
Lido Bungalow Walk to Beach & St. Armand's Circle
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

14. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
The price is CA $152
CA $501 total
includes taxes & fees
Sep 3 - Sep 4
Sunny Lido Studio - Modern Touches
A patio with a table set for two, a blue umbrella, and a white fence with plants.

15. Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
The price is CA $130
CA $469 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Lido Key Studio Steps to Beach & Kayaking
A two-story house with a green exterior, a blue door, and orange trim.

16. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (74 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is CA $137
CA $294 total
includes taxes & fees
Sep 3 - Sep 4
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, (130 reviews)
"A beautiful location and super comfortable!"
United States
K B.
The price is CA $247
CA $630 total
includes taxes & fees
Sep 3 - Sep 4
Casey Key Beachfront Escape: Charming 1BR Cottage
A keyless entry system with a red pathway leading to a gated entrance.

18. 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 CA $100
CA $350 total
includes taxes & fees
Sep 3 - Sep 4
Coastal Luxury 7mi to Anna Maria Private Cottage

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is CA $111
CA $360 total
includes taxes & fees
Sep 2 - Sep 3
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A patio with two blue lounge chairs, a potted plant, and a gravel area.

20. 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 CA $242
CA $465 total
includes taxes & fees
Sep 3 - Sep 4
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

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"Super clean and spacious. Amazing location, with the private beach right behind it. Pool was brand new and peaceful. Great property!"
Deborah 2-night trip
Posted 7 hours ago
Tropical Beach Resorts

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
591
Accommodation
58 Cottages
Lowest Price
CA $294
Highest Price
CA $1,365

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-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 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.

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