A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Siesta Key cottages

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

1. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (208 reviews)
"The property was perfect. Walk to down town and the beach. Loved the provisions for the beach which made it so convenient. Room was super clean and overall the property was well maintained."
United States
Stephen
The Inn On Siesta Key
A residential house with a white fence, a palm tree, and a parked car.

2. 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, (90 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
$259 nightly
The price is $290
Sep 23 - Sep 24
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

3. 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.
$310 nightly
The price is $346
Oct 1 - Oct 2
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A yellow house with a white door and number 5306.

4. Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (2 reviews)
"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.
$536 nightly
The price is $575
Sep 20 - Sep 21
Total with taxes and fees
Yellow Palm Cottage steps from the beach
A small, single-story building with a blue roof and yellow walls, surrounded by a white picket fence and palm trees.

5. Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
$529 nightly
The price is $568
Sep 20 - Sep 21
Total with taxes and fees
Blue Dolphin Cottage steps from the beach
A hammock tied between two palm trees, a pink building with a red roof, and a bush with red flowers.

6. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
$540 nightly
The price is $580
Sep 30 - Oct 1
Total with taxes and fees
Pink Mango Cottage steps from the beach
A kitchen with white cabinets, a coffee bar, a wooden shelf with decorative items, and a view of the outside.

7. 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.
Lookout Cottage Across street from Beach and Heated Pool
A wooden deck with a glass door leading to a lake view, surrounded by greenery.

8. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$615 nightly
The price is $694
Sep 30 - Oct 1
Total with taxes and fees
Siesta Heron 6 / Sunset
A covered outdoor seating area with a sofa, a chair, and a coffee table.

9. 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.
Nook Cottage Across street from beach and Heated Pool
A two-story building with a blue and white exterior, a balcony, and a sign that reads "Gidget's Coastal Preserve."

10. Beach Road

Beach Road
2.0 star property
Siesta Key
$764 nightly
The price is $864
Sep 21 - Sep 22
Total with taxes and fees
Beach Road
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

11. Cozy Lido Studio by Beach & St Armand's

Cozy Lido Studio by Beach & St Armand's
Lido Key
$292 nightly
The price is $326
Sep 23 - Sep 24
Total with taxes and fees
Cozy Lido Studio by Beach & St Armand's
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

12. Coastal Studio, Walk to St Armand's or Lido Beach

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
$313 nightly
The price is $349
Sep 20 - Sep 21
Total with taxes and fees
Coastal Studio, Walk to St Armand's or Lido Beach
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

13. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
$304 nightly
The price is $338
Sep 24 - Sep 25
Total with taxes and fees
Lido Key Casita w Pool Steps to the Beach
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

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

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.4 out of 10, Very good, (10 reviews)
"The house was truly lovely, and the hosts were exceptionally caring, kind, and attentive in their communication. It was wonderful to be so close to the beach, with stores conveniently nearby, making the stay feel comfortable and welcoming."
United States
Kandra R.
$416 nightly
The price is $463
Sep 18 - Sep 19
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A single-story house with a blue exterior, a front door, and a small porch area.

15. Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
$216 nightly
The price is $241
Sep 19 - Sep 20
Total with taxes and fees
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A keyless entry system with a red pathway leading to a gated entrance.

16. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (12 reviews)
"Very nice location. "
United States
Daniel o.
$220 nightly
The price is $246
Sep 21 - Sep 22
Total with taxes and fees
Cozy Private Cottage, Minutes to Anna Maria Island

17. Real Florida Up Close! Family-friendly, Pet-friendly with private pool

Real Florida Up Close! Family-friendly, Pet-friendly with private pool
Sarasota
$276 nightly
The price is $308
Sep 18 - Sep 19
Total with taxes and fees
Real Florida Up Close! Family-friendly, Pet-friendly with private pool
A small house with a porch, surrounded by a grassy yard and dense foliage.

18. Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
$232 nightly
The price is $259
Sep 18 - Sep 19
Total with taxes and fees
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A two-story house with a green exterior, a blue door, and orange trim.

19. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (75 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
$183 nightly
The price is $205
Sep 26 - Sep 27
Total with taxes and fees
The "Grouper"
A wooden pier leading to a beach with a clear blue sky.

20. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (132 reviews)
"A beautiful location and super comfortable!"
United States
K B.
$464 nightly
The price is $520
Sep 26 - Sep 27
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR 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

Tropical Breeze Resort

Tropical Breeze Resort

8/10 Good
"The room was clean and staff were pleasant but there was no microwave in the room and I was told I had to request it, which I did and it never showed up. We went to check in at the 4pm check-in time and was told they just started cleaning our room. That is unacceptable you should have the rooms cleaned by 4 PM for check-in, especially in the off season. They did move us to a room that was already cleaned, which should have been done before I asked. The 10am check out time is a bit extreme,"
Sherry 2-night trip
Posted 9 hours ago
Tropical Breeze Resort

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
335
Accommodation
58 Cottages
Lowest Price
$246
Highest Price
$864

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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