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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, (85 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
$272 nightly
The price is $303
Mar 26 - Mar 27
Total with taxes and fees
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, (194 reviews)
"Great place to stay! "
United States
Carlos
$570 nightly
The price is $645
Mar 9 - Mar 10
Total with taxes and fees
The Inn On Siesta Key

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

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.4 out of 10, Exceptional, (6 reviews)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
$801 nightly
The price is $801
Mar 29 - Mar 30
Total with taxes and fees
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
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.
$1,470 nightly
The price is $1,605
Mar 23 - Mar 24
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.
$915 nightly
The price is $1,006
Mar 9 - Mar 10
Total with taxes and fees
Nook Cottage Across street from beach and Heated Pool

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$1,305 nightly
The price is $1,474
Mar 12 - Mar 13
Total with taxes and fees
Siesta Heron 6 / Sunset

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.
$1,152 nightly
The price is $1,284
Mar 20 - Mar 21
Total with taxes and fees
Lookout Cottage Across street from Beach and Heated Pool

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
$1,240 nightly
The price is $1,401
Mar 10 - Mar 11
Total with taxes and fees
Siesta Heron 7

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, (15 reviews)
"Property was perfect for the price."
United States
William M.
$140 nightly
The price is $156
Mar 11 - Mar 12
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park

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
Mar 10 - Mar 11
Total with taxes and fees
Stylish Retro Vibes Private BBQ & Beach Access

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (112 reviews)
"Great location for a quick beach getaway!"
United States
Thomas D.
$510 nightly
The price is $570
Mar 14 - Mar 15
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage

Chic cottage, Vamo area, close to beaches, pet friendly, kayaks

Chic cottage, Vamo area, close to beaches, pet friendly, kayaks
Vamo
9.8 out of 10, Exceptional, (22 reviews)
"Nice place "
United States
Viktoriia
$554 nightly
The price is $617
Mar 22 - Mar 23
Total with taxes and fees
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks

#3 Small house walking distance to Warm Mineral Spring

#3 Small house walking distance to Warm Mineral Spring
Warm Mineral Springs
9.2 out of 10, Wonderful, (13 reviews)
"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."
United States
Jake R.
$140 nightly
The price is $156
Mar 16 - Mar 17
Total with taxes and fees
#3 Small house walking distance to Warm Mineral Spring

Steps to Riverwalk! Dtwn Bradenton Snowbird Haven

Steps to Riverwalk! Dtwn Bradenton Snowbird Haven
3.0 star property
Bradenton
$506 nightly
The price is $568
Mar 30 - Mar 31
Total with taxes and fees
Steps to Riverwalk! Dtwn Bradenton Snowbird Haven

7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage
Bradenton
10.0 out of 10, Exceptional, (4 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.
$288 nightly
The price is $323
Mar 31 - Apr 1
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, (50 reviews)
"We really enjoyed our stay here. So close to AMI "
United States
Taylor B.
$189 nightly
The price is $211
Mar 11 - Mar 12
Total with taxes and fees
The "Grouper"

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.
$597 nightly
The price is $665
Mar 13 - Mar 14
Total with taxes and fees
Romantic Island Getaway! Just Steps from the Beach

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

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
9.0 out of 10, Wonderful, (2 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 1 - Apr 2
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

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)
"Great place and great location........"
United States
chris w.
$739 nightly
The price is $824
Mar 7 - Mar 8
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
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
445
Accommodation
33 Cottages
Lowest Price
$156
Highest Price
$1,605

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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