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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Siesta Key cottages

Exterior

1. 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.
$273 nightly
The price is $304
Aug 17 - Aug 18
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Exterior

2. 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, (189 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
$356 nightly
The price is $397
Sep 2 - Sep 3
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

3. Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
United States
Marti C.
Nest Cottage Across street from beach and Heated Pool
Interior

4. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$605 nightly
The price is $683
Aug 31 - Sep 1
Total with taxes and fees
Siesta Heron 6 / Sunset
Interior

5. Beach Road

Beach Road
2.0 star property
Siesta Key
$704 nightly
The price is $796
Sep 2 - Sep 3
Total with taxes and fees
Beach Road
Outdoor dining

6. Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
$863 nightly
The price is $975
Aug 21 - Aug 22
Total with taxes and fees
Siesta Heron 7
1 bedroom, iron/ironing board, WiFi, bed sheets

7. Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
$301 nightly
The price is $335
Aug 21 - Aug 22
Total with taxes and fees
Cozy Lido Key Bungalow by Pool & Beach
Outdoor dining

8. Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
$333 nightly
The price is $370
Aug 31 - Sep 1
Total with taxes and fees
Cozy Lido Key Studio Steps to Beach & Kayaking
Hair dryer, towels, soap, shampoo

9. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
$313 nightly
The price is $349
Aug 17 - Aug 18
Total with taxes and fees
Sunny Lido Studio - Modern Touches
Exterior

10. The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (73 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
$190 nightly
The price is $212
Aug 17 - Aug 18
Total with taxes and fees
The "Grouper"
Property grounds

11. Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (11 reviews)
"Very nice location. "
United States
Daniel o.
$225 nightly
The price is $251
Aug 31 - Sep 1
Total with taxes and fees
Coastal Luxury 7mi to Anna Maria Private Cottage
House (2 Bedrooms) | Interior

12. Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Pet-friendly Bradenton Home 1.5 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 $336
Aug 17 - Aug 18
Total with taxes and fees
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
Exterior

13. 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, (27 reviews)
"We were enjoying our stay."
United States
Inna K.
$120 nightly
The price is $133
Aug 22 - Aug 23
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
1 bedroom, iron/ironing board, WiFi, bed sheets

14. Lido Bungalow Walk to Beach & St. Armand's Circle

Lido Bungalow Walk to Beach & St. Armand's Circle
Lido Key
$301 nightly
The price is $335
Aug 17 - Aug 18
Total with taxes and fees
Lido Bungalow Walk to Beach & St. Armand's Circle
Property grounds

15. Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
Bradenton Beach
8.6 out of 10, Excellent, (4 reviews)
"It was nice to be so close to the beach, and walking distance to places to eat. I enjoyed driving around the island and seeing the little villages. The cottage was comfortable and had many conveniences. "
United States
Valerie T.
$468 nightly
The price is $521
Aug 17 - Aug 18
Total with taxes and fees
Romantic Island Getaway! Just Steps from the Beach
Property grounds

16. 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, (129 reviews)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
$587 nightly
The price is $654
Aug 17 - Aug 18
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Property grounds

17. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,731 nightly
The price is $3,086
Aug 19 - Aug 20
Total with taxes and fees
3716 7th Ave W
Exterior

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
$221 nightly
The price is $247
Aug 17 - Aug 18
Total with taxes and fees
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
House (4 Bedrooms) | Interior

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

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
$395 nightly
The price is $446
Aug 17 - Aug 18
Total with taxes and fees
Home < 1-mi Walk to Warm Mineral Springs Park!
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

10/10 Excellent
"The environment"
Pedro 1-night trip
Posted 9 hours ago
Tropical Breeze Resort

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
455
Accommodation
58 Cottages
Lowest Price
$133
Highest Price
$3,086

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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