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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Siesta Key cottages

Balcony view

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
$554 nightly
The price is $626
Jun 19 - Jun 20
Total with taxes and fees
The Inn On Siesta Key
Outdoor dining

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
Exterior

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.
$589 nightly
The price is $635
Jun 17 - Jun 18
Total with taxes and fees
Yellow Palm Cottage steps from the beach
Exterior

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
$460 nightly
The price is $513
Jun 17 - Jun 18
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
$604 nightly
The price is $652
Jun 16 - Jun 17
Total with taxes and fees
Pink Mango Cottage steps from the beach
House (3 Bedrooms) | Interior

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
$540 nightly
The price is $606
Jul 12 - Jul 13
Total with taxes and fees
Unwind Poolside + Walk to Beach! Sarasota Retreat
Outdoor dining

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
$1,001 nightly
The price is $1,132
Jun 17 - Jun 18
Total with taxes and fees
Siesta Heron 7
Interior

Beach Road

Beach Road
2.0 star property
Siesta Key
$968 nightly
The price is $1,094
Jun 17 - Jun 18
Total with taxes and fees
Beach Road
Interior

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$922 nightly
The price is $1,042
Jul 7 - Jul 8
Total with taxes and fees
Siesta Heron 6 / Sunset
House (4 Bedrooms) | Interior

Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
$431 nightly
The price is $484
Jun 20 - Jun 21
Total with taxes and fees
Home < 1-mi Walk to Warm Mineral Springs Park!
Exterior

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.
$125 nightly
The price is $139
Jun 22 - Jun 23
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
Exterior

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (70 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
$190 nightly
The price is $212
Jun 26 - Jun 27
Total with taxes and fees
The "Grouper"
Terrace/patio

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (75 reviews)
"It was perfect. We had a great time."
United States
Karen M.
$520 nightly
The price is $582
Jun 22 - Jun 23
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!
Property grounds

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.
$244 nightly
The price is $272
Jun 17 - Jun 18
Total with taxes and fees
Coastal Luxury 7mi to Anna Maria Private Cottage
Outdoor dining

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Nokomis
9.6 out of 10, Exceptional, (5 reviews)
"Lowkey, quiet, clean, amenities to cook, great host and great view. Happy to go back again."
United States
Bryan S.
$164 nightly
The price is $182
Jun 28 - Jun 29
Total with taxes and fees
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Marina

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!
1 bedroom, iron/ironing board, free WiFi, bed sheets

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (40 reviews)
"Fun stay, great location"
United States
Theresa H.
$211 nightly
The price is $235
Jun 20 - Jun 21
Total with taxes and fees
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Property grounds

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.
$614 nightly
The price is $685
Jun 16 - Jun 17
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Property grounds

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,679 nightly
The price is $3,027
Jun 19 - Jun 20
Total with taxes and fees
3716 7th Ave W
House (2 Bedrooms) | Interior

Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach

Pet-friendly Bradenton Home ~ 3 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 $332
Jun 16 - Jun 17
Total with taxes and fees
Pet-friendly Bradenton Home ~ 3 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

The Capri at Siesta

The Capri at Siesta

10/10 Excellent
"Excellent place, family oriented, very clean, amenities are great, room big staff was super. We are definitely coming back, highly recommend"
Riceldys 2-night trip
Posted 5 hours ago
The Capri at Siesta

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
759
Accommodation
55 Cottages
Lowest Price
$139
Highest Price
$3,027

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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