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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, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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
$351 nightly
The price is $397
Jun 15 - Jun 16
Total with taxes and fees
The Inn On Siesta Key

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
$480 nightly
The price is $538
Jun 11 - Jun 12
Total with taxes and fees
Unwind Poolside + Walk to Beach! Sarasota Retreat

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.
$733 nightly
The price is $795
Jun 17 - Jun 18
Total with taxes and fees
Yellow Palm 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, (184 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
$449 nightly
The price is $449
Jun 15 - Jun 16
Total with taxes and fees
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.
$666 nightly
The price is $686
Jun 14 - Jun 15
Total with taxes and fees
Nook Cottage Across street from beach and Heated Pool

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
$375 nightly
The price is $394
Jun 16 - Jun 17
Total with taxes and fees
Pink Mango Cottage steps from the beach

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.
$1,099 nightly
The price is $1,131
Jun 15 - Jun 16
Total with taxes and fees
Cabana Cottage Across street from Beach and Heated Pool

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$772 nightly
The price is $872
Jun 15 - Jun 16
Total with taxes and fees
Siesta Heron 6 / Sunset

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
$471 nightly
The price is $496
Jun 12 - Jun 13
Total with taxes and fees
Blue Dolphin Cottage steps from the beach

Beach Road

Beach Road
2.0 star property
Siesta Key
$1,035 nightly
The price is $1,170
Jun 14 - Jun 15
Total with taxes and fees
Beach Road

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
$1,101 nightly
The price is $1,245
Jun 15 - Jun 16
Total with taxes and fees
Siesta Heron 7

3 Mi to Beach! Englewood Family Gem + Private Pool

3 Mi to Beach! Englewood Family Gem + Private Pool
3.0 star property
Englewood
$461 nightly
The price is $517
Jun 11 - Jun 12
Total with taxes and fees
3 Mi to Beach! Englewood Family Gem + Private Pool

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, (24 reviews)
"Easy check in, clean and cozy."
United States
Robert J.
$130 nightly
The price is $136
Jun 11 - Jun 12
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (69 reviews)
"Place was great, the bed was very comfortable and we loved the new screened in porch."
United States
ken h.
$193 nightly
The price is $203
Jun 26 - Jun 27
Total with taxes and fees
The "Grouper"

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (74 reviews)
"It was perfect. We had a great time."
United States
Karen M.
$426 nightly
The price is $449
Jun 11 - Jun 12
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
$363 nightly
The price is $366
Jun 18 - Jun 19
Total with taxes and fees
Lido Key Getaway - Bikes & Beach Gear

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Southgate
9.6 out of 10, Exceptional, (15 reviews)
"Place had everything needed. Host was very communicative and helpful. "
United States
Chris R.
$384 nightly
The price is $428
Jun 30 - Jul 1
Total with taxes and fees
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (8 reviews)
"Place was clean, cozy and cute! Host communication was friendly, clear and concise. Would absolutely recommend!"
United States
Tracee Candace L.
$254 nightly
The price is $266
Jun 18 - Jun 19
Total with taxes and fees
Coastal Luxury 7mi to Anna Maria Private Cottage
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
671
Accommodation
55 Cottages
Lowest Price
$136
Highest Price
$1,245

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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