Search Cottages in Siesta Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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.
The price is AED 764
AED 1,535 total
includes taxes & fees
26 May - 27 May
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very Good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
Unwind Poolside + Walk to Beach! Sarasota Retreat

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, (182 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is AED 915
AED 1,715 total
includes taxes & fees
10 May - 11 May
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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.
The price is AED 364
AED 1,102 total
includes taxes & fees
20 May - 21 May
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, (198 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is AED 1,083
AED 1,427 total
includes taxes & fees
10 May - 11 May
The Inn On Siesta Key

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
"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.
The price is AED 953
AED 2,769 total
includes taxes & fees
12 May - 13 May
Yellow Palm Cottage steps from the beach

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is AED 905
AED 2,705 total
includes taxes & fees
12 May - 13 May
Blue Dolphin Cottage steps from the beach

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.
The price is AED 1,758
AED 2,914 total
includes taxes & fees
10 May - 11 May
Nest Cottage Across street from beach and Heated Pool

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is AED 2,132
AED 3,762 total
includes taxes & fees
13 May - 14 May
Siesta Heron 7

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.
The price is AED 1,648
AED 3,186 total
includes taxes & fees
11 May - 12 May
Nook Cottage Across street from beach and Heated Pool

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.
The price is AED 1,523
AED 2,619 total
includes taxes & fees
14 May - 15 May
Lookout Cottage Across street from Beach and Heated Pool

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.
The price is AED 911
AED 1,942 total
includes taxes & fees
12 May - 13 May
Direct Beachfront 2BR Cottage on Casey Key!

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, (24 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
The price is AED 202
AED 551 total
includes taxes & fees
14 May - 15 May
Charming cottage for 2 across warm mineral springs park

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (7 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.
The price is AED 347
AED 1,041 total
includes taxes & fees
11 May - 12 May
Coastal Luxury 7mi to Anna Maria Private Cottage

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.
The price is AED 551
AED 1,984 total
includes taxes & fees
27 May - 28 May
Romantic Island Getaway! Just Steps from the Beach

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay
cortez
10.0 out of 10, Exceptional, (104 reviews)
"Very peaceful place. Would love to come back!"
United States
Amanda G.
The price is AED 602
AED 1,063 total
includes taxes & fees
19 May - 20 May
Private historical completely renovated cottage with 60 ft dock on Sarasota Bay

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (65 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
The price is AED 364
AED 775 total
includes taxes & fees
16 May - 17 May
The "Grouper"

5 Mi to Riverwalk: Bradenton Family Home w/ Yard

5 Mi to Riverwalk: Bradenton Family Home w/ Yard
3.0 star property
Bayshore Gardens
The price is AED 511
AED 1,440 total
includes taxes & fees
9 May - 10 May
5 Mi to Riverwalk: Bradenton Family Home w/ Yard

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, (125 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is AED 1,098
AED 2,387 total
includes taxes & fees
10 May - 11 May
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

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.
The price is AED 459
AED 762 total
includes taxes & fees
26 May - 27 May
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
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

Frequently asked questions

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.