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

Search Siesta Key Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Siesta Key cottages

1. 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.
$270 nightly
The price is $303
Sep 30 - Oct 1
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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 30 - Oct 1
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

3. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
$436 nightly
The price is $493
Oct 4 - Oct 5
Total with taxes and fees
Yellow Palm Cottage, Heart of Siesta Key

4. 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)
$498 nightly
The price is $537
Sep 30 - Oct 1
Total with taxes and fees
Pink Mango Cottage steps from the beach

5. 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, (192 reviews)
"Loved the location of this property! The property manager was easy to contact and the property was exactly as shown in the pictures. Would stay here again!"
United States
Tracie B.
$381 nightly
The price is $427
Oct 2 - Oct 3
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

6. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$626 nightly
The price is $707
Oct 6 - Oct 7
Total with taxes and fees
Siesta Heron 6 / Sunset

7. Beach Road

Beach Road
2.0 star property
Siesta Key
$836 nightly
The price is $945
Oct 2 - Oct 3
Total with taxes and fees
Beach Road

8. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
$289 nightly
The price is $323
Oct 1 - Oct 2
Total with taxes and fees
Studio by Lido Beach w heated pool

9. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
$283 nightly
The price is $317
Oct 5 - Oct 6
Total with taxes and fees
Lido Key Casita w Pool Steps to the Beach

10. 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.
$389 nightly
The price is $436
Oct 8 - Oct 9
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
$210 nightly
The price is $235
Oct 12 - Oct 13
Total with taxes and fees
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

12. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (13 reviews)
"Clean and nice place"
United States
Ismael
$202 nightly
The price is $226
Sep 30 - Oct 1
Total with taxes and fees
Cozy Private Cottage, Minutes to Anna Maria Island

13. 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.
$189 nightly
The price is $211
Sep 30 - Oct 1
Total with taxes and fees
The "Grouper"

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
$225 nightly
The price is $252
Sep 30 - Oct 1
Total with taxes and fees
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

15. 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
Sep 30 - Oct 1
Total with taxes and fees
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

16. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (132 reviews)
"Beautiful gulf view."
United States
Audrey B.
$509 nightly
The price is $571
Oct 9 - Oct 10
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage

17. Bridge Street Beach House | Wi-Fi | Center of All

Bridge Street Beach House | Wi-Fi | Center of All
Bridge Street
10.0 out of 10, Exceptional, (5 reviews)
"Great location, clean accommodations, good communication with host. ..."
United States
leslie m.
$330 nightly
The price is $370
Oct 5 - Oct 6
Total with taxes and fees
Bridge Street Beach House | Wi-Fi | Center of All

18. 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.
$494 nightly
The price is $554
Sep 30 - Oct 1
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

19. 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, (29 reviews)
"We were enjoying our stay."
United States
Inna K.
$125 nightly
The price is $139
Oct 1 - Oct 2
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park

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

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
10.0 out of 10, Exceptional, (1 review)
"5 Stars: This cozy studio was exactly what we were looking for. Alexander was pleasant and friendly, the check in/check out process was easy. The location was fabulous- perhaps slightly too far to walk to St.Armand’s , but a quick ride on the rentable VEO bikes/scooters. The accommodations were clean, and beachy. We did not have an opportunity to use the pool, so I do have any objective comments for the pool. If we are in the area again, we would definitely stay here again!"
United States
lisa o.
$297 nightly
The price is $333
Oct 4 - Oct 5
Total with taxes and fees
Coastal Studio, Walk to St Armand's or Lido 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Siesta Key Hotel Reviews

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
555
Accommodation
58 Cottages
Lowest Price
$139
Highest Price
$945

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.

Explore a world of travel with Expedia