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

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is £262
includes taxes & fees
12 Jul - 13 Jul
The Inn On Siesta Key

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 £226
includes taxes & fees
2 Aug - 3 Aug
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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, (186 reviews)
The price is £349
includes taxes & fees
12 Jul - 13 Jul
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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.
Nook Cottage Across street from beach and Heated Pool

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
The price is £456
includes taxes & fees
12 Jul - 13 Jul
Unwind Poolside + Walk to Beach! Sarasota Retreat

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is £680
includes taxes & fees
4 Aug - 5 Aug
Siesta Heron 6 / Sunset

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 £462
includes taxes & fees
12 Jul - 13 Jul
Haven cottage Across street from beach and Heated Pool

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

Beach Road

Beach Road
2.0 star property
Siesta Key
The price is £933
includes taxes & fees
19 Jul - 20 Jul
Beach Road

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, (25 reviews)
"Easy check in, clean and cozy."
United States
Robert J.
The price is £106
includes taxes & fees
12 Jul - 13 Jul
Charming cottage for 2 across warm mineral springs park

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 £333
includes taxes & fees
12 Jul - 13 Jul
Home < 1-mi Walk to Warm Mineral Springs Park!

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 £163
includes taxes & fees
15 Jul - 16 Jul
The "Grouper"

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (78 reviews)
"It was perfect. We had a great time."
United States
Karen M.
The price is £425
includes taxes & fees
12 Jul - 13 Jul
Direct Beachfront 2BR Cottage on Casey Key!

Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
The price is £263
includes taxes & fees
12 Jul - 13 Jul
Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
The price is £263
includes taxes & fees
15 Jul - 16 Jul
Cozy Lido Key Studio Steps to Beach & Kayaking

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 £193
includes taxes & fees
13 Jul - 14 Jul
Coastal Luxury 7mi to Anna Maria Private Cottage

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, (126 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is £509
includes taxes & fees
12 Jul - 13 Jul
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth
Englewood
9.8 out of 10, Exceptional, (42 reviews)
"Wow....this is one of the best VRBOs we've stayed in. Evan was a great host, very welcoming, helpful and quick to respond to questions. Location is so convenient to either Lemon Bay or the beach."
United States
Marla W.
Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (126 reviews)
"Fantastic property and exactly as described. Can’t beat being right on the beach!"
United States
Alina K.
The price is £406
includes taxes & fees
16 Jul - 17 Jul
Casey Key Beachfront Escape: Charming 1BR Cottage

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

Lido Bungalow Walk to Beach & St. Armand's Circle
Lido Key
Lido Bungalow Walk to Beach & St. Armand's Circle
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
203
Accommodation
55 Cottages
Lowest Price
£251
Highest Price
£2,301

Frequently asked questions

Are there any family-friendly cottages in Siesta Key?
Put your feet up at The Inn On Siesta Key, a 3.5-star cottage only a quick drive from downtown. Conveniences here include a nearby beach and a picnic area. Another family-friendly option where you can swap the concrete jungle for wide open spaces is Flip Flop Cottages. WiFi and laundry facilities help make this 3-star cottage a hit with guests. Siesta Key has plenty of family-friendly attractions to visit when the kids are getting restless. Ed Smith Stadium and Sarasota BayWalk promise a fun-filled day for travellers 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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