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Our top choices for Siesta Key cottages

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · 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.
$379 nightly
The price is $379
Apr 14 - Apr 15
Total with taxes and fees
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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.
$268 nightly
The price is $299
Apr 13 - Apr 14
Total with taxes and fees
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, (181 reviews)
"Very close to the village and we only had to cross the road to access the beach!! Loved it!!"
United States
Kim H.
$441 nightly
The price is $492
May 10 - May 11
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (196 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
$372 nightly
The price is $420
Apr 14 - Apr 15
Total with taxes and fees
The Inn On Siesta Key

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.
$1,072 nightly
The price is $1,161
Apr 14 - Apr 15
Total with taxes and fees
Cabana Cottage Across street from Beach and Heated Pool

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.
$891 nightly
The price is $981
Apr 11 - Apr 12
Total with taxes and fees
Nook Cottage Across street from beach and Heated Pool

Beach Road

Beach Road
2.0 star property
Siesta Key
$921 nightly
The price is $1,041
May 10 - May 11
Total with taxes and fees
Beach Road

Stylish Retro Vibes Private BBQ & Beach Access

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
Sarasota
$332 nightly
The price is $375
Apr 14 - Apr 15
Total with taxes and fees
Stylish Retro Vibes Private BBQ & Beach Access

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (22 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
$135 nightly
The price is $150
Apr 12 - Apr 13
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (71 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
$471 nightly
The price is $527
Apr 16 - Apr 17
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!

Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
Bradenton Beach
8.8 out of 10, Excellent, (3 reviews)
"It was great! Check in was super easy and anything you would need is nearby. "
United States
Thomas N.
$515 nightly
The price is $574
Apr 12 - Apr 13
Total with taxes and fees
Romantic Island Getaway! Just Steps from the Beach

7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage
Bradenton
10.0 out of 10, Exceptional, (6 reviews)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
United States
MO L.
$253 nightly
The price is $283
Apr 15 - Apr 16
Total with taxes and fees
7mi to Anna Maria Newly Renovated Private Cottage

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (57 reviews)
"I would recommend this place to anyone! It was extremely clean and neat, and we had a lovely time here! The host was very responsive and kind too. Overall, this place was above my expectations and a great place to stay."
United States
Lana
$189 nightly
The price is $211
Apr 13 - Apr 14
Total with taxes and fees
The "Grouper"

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.8 out of 10, Excellent, (3 reviews)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
$306 nightly
The price is $342
Apr 12 - Apr 13
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

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, (4 reviews)
"The property was very well stocked, had a bowl for our dog an very clean! It was the petfect place for our visit with local family. The "Florida Room" was lovely and the view was excellent. Very peaceful location."
United States
Marie W.
$182 nightly
The price is $202
May 3 - May 4
Total with taxes and fees
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

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, (123 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
$660 nightly
The price is $736
Apr 11 - Apr 12
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (118 reviews)
"Excellent Host, Great location, Excited to return"
United States
Anonymous traveler
$451 nightly
The price is $504
Apr 19 - Apr 20
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage

Family Fun: Ping Pong, Bbq, Walk to Park Nearby

Family Fun: Ping Pong, Bbq, Walk to Park Nearby
3.0 star property
Fruitville
$432 nightly
The price is $489
Apr 13 - Apr 14
Total with taxes and fees
Family Fun: Ping Pong, Bbq, Walk to Park Nearby

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,724 nightly
The price is $3,078
Apr 15 - Apr 16
Total with taxes and fees
3716 7th Ave W
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
761
Accommodation
54 Cottages
Lowest Price
$150
Highest Price
$3,078

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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