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

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.
$270 nightly
The price is $301
Aug 2 - Aug 3
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
$590 nightly
The price is $636
Jul 21 - Jul 22
Total with taxes and fees
Blue Dolphin Cottage steps from the beach

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, (187 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
$420 nightly
The price is $468
Aug 15 - Aug 16
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$733 nightly
The price is $828
Aug 11 - Aug 12
Total with taxes and fees
Siesta Heron 6 / Sunset

Beach Road

Beach Road
2.0 star property
Siesta Key
$903 nightly
The price is $1,021
Aug 15 - Aug 16
Total with taxes and fees
Beach Road

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
$1,133 nightly
The price is $1,281
Jul 25 - Jul 26
Total with taxes and fees
Siesta Heron 7

Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
$313 nightly
The price is $349
Aug 9 - Aug 10
Total with taxes and fees
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
$301 nightly
The price is $335
Jul 21 - Jul 22
Total with taxes and fees
Cozy Lido Key Studio Steps to Beach & Kayaking

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.
$190 nightly
The price is $212
Jul 22 - Jul 23
Total with taxes and fees
The "Grouper"

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.
$221 nightly
The price is $247
Jul 21 - Jul 22
Total with taxes and fees
Coastal Luxury 7mi to Anna Maria Private Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (128 reviews)
"Fantastic property and exactly as described. Can’t beat being right on the beach!"
United States
Alina K.
$478 nightly
The price is $534
Jul 21 - Jul 22
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage

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.
$120 nightly
The price is $133
Jul 21 - Jul 22
Total with taxes and fees
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
$395 nightly
The price is $446
Jul 21 - Jul 22
Total with taxes and fees
Home < 1-mi Walk to Warm Mineral Springs Park!

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,636 nightly
The price is $2,979
Aug 17 - Aug 18
Total with taxes and fees
3716 7th Ave W

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, (127 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
$598 nightly
The price is $667
Jul 21 - Jul 22
Total with taxes and fees
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.
$902 nightly
The price is $1,005
Jul 31 - Aug 1
Total with taxes and fees
Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (80 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
$505 nightly
The price is $563
Aug 9 - Aug 10
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!

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
Jul 21 - Jul 22
Total with taxes and fees
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

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Siesta Key Cottages information

Number of reviews
205
Accommodation
55 Cottages
Lowest Price
$336
Highest Price
$2,979

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.

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