Search Cottages in Siesta Key

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan
In one month
30 Jan - 1 Feb
In two months
27 Feb - 1 Mar

Our top choices for Siesta Key cottages

The Lookout, 1 King Bedroom 1 Bath | Terrace/patio
The Inn On Siesta Key

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (192)
"Great place to stay! "
United States
Carlos
The price is AED 1,265
AED 1,633 total
includes taxes & fees
3 Jan - 4 Jan
The Inn On Siesta Key
Exterior
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Cottage in South Village

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
9.6 out of 10, Exceptional, (81)
"Wonderful experience! It was perfect for a girls’ weekend which included me, my mother & my 12 yr old daughters. There was enough restaurants in walking distance, the beach was in walking distance and we appreciated the trolley and frog hopper to get to Turtle Beach for kayaking. "
United States
Michelle A.
The price is AED 364
AED 1,087 total
includes taxes & fees
12 Jan - 13 Jan
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Outdoor dining
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Cottage in Siesta Key

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior
Blue Dolphin Cottage steps from the beach

Cottage in Siesta Key Village

Blue Dolphin Cottage steps from the beach
The price is AED 551
AED 2,158 total
includes taxes & fees
6 Jan - 7 Jan
Blue Dolphin Cottage steps from the beach
Exterior
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Cottage in Sarasota

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
9.2 out of 10, Wonderful, (177)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
United States
Alexis
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds
Lookout Cottage Across street from Beach and Heated Pool

Cottage in Siesta Key

Lookout Cottage Across street from Beach and Heated Pool
10.0 out of 10, Exceptional, (1)
"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
Property grounds
Pink Mango Cottage steps from the beach

Cottage in Siesta Key Village

Pink Mango Cottage steps from the beach
Pink Mango Cottage steps from the beach
Exterior
Yellow Palm Cottage steps from the beach

Cottage in Siesta Key Village

Yellow Palm Cottage steps from the beach
The price is AED 580
AED 2,132 total
includes taxes & fees
6 Jan - 7 Jan
Yellow Palm Cottage steps from the beach
Property grounds
Haven cottage Across street from beach and Heated Pool

Cottage in Siesta Key

Haven cottage Across street from beach and Heated Pool
9.8 out of 10, Exceptional, (7)
"It was a beautiful place. Great staff. Awesome experience."
United States
Nicholas M.
Haven cottage Across street from beach and Heated Pool
Property grounds
Nest Cottage Across street from beach and Heated Pool

Cottage in Siesta Key

Nest Cottage Across street from beach and Heated Pool
10.0 out of 10, Exceptional, (2)
"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 1,409
AED 2,464 total
includes taxes & fees
3 Jan - 4 Jan
Nest Cottage Across street from beach and Heated Pool
Exterior
Charming cottage for 2 across warm mineral springs park

Cottage in Warm Mineral Springs

Charming cottage for 2 across warm mineral springs park
9.2 out of 10, Wonderful, (10)
"Property was perfect for the price."
United States
William M.
The price is AED 275
AED 634 total
includes taxes & fees
8 Jan - 9 Jan
Charming cottage for 2 across warm mineral springs park
Property grounds
7mi to Anna Maria Newly Renovated Private Cottage

Cottage in Bradenton

7mi to Anna Maria Newly Renovated Private Cottage
10.0 out of 10, Exceptional, (3)
"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 298
AED 1,001 total
includes taxes & fees
3 Jan - 4 Jan
7mi to Anna Maria Newly Renovated Private Cottage
Exterior
#3 Small house walking distance to Warm Mineral Spring

Cottage in Warm Mineral Springs

#3 Small house walking distance to Warm Mineral Spring
9.0 out of 10, Wonderful, (9)
"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.
The price is AED 275
AED 634 total
includes taxes & fees
15 Jan - 16 Jan
#3 Small house walking distance to Warm Mineral Spring
Exterior
Cozy 1-bedroom cottage that connects to a county park in beautiful Sarasota

Cottage in Bayou Oaks

Cozy 1-bedroom cottage that connects to a county park in beautiful Sarasota
2.0 star property
The price is AED 217
AED 394 total
includes taxes & fees
2 Feb - 3 Feb
Cozy 1-bedroom cottage that connects to a county park in beautiful Sarasota
Exterior
Direct Beachfront 2BR Cottage on Casey Key!

Cottage in Casey Key

Direct Beachfront 2BR Cottage on Casey Key!
9.2 out of 10, Wonderful, (69)
"The Cottage is simple and in need of a few updates, but it is a beach cottage and the salt air is not kind. Overall, the location is fantastic, the Cottage is clean and comfortable and our stay was great."
United States
Bob T.
The price is AED 1,095
AED 2,223 total
includes taxes & fees
4 Jan - 5 Jan
Direct Beachfront 2BR Cottage on Casey Key!
Exterior
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Cottage in Sarasota

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
2.0 star property
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Terrace/patio
5 star Guest House heated pool on the water!

Cottage in South Sarasota

5 star Guest House heated pool on the water!
The price is AED 918
AED 1,833 total
includes taxes & fees
2 Feb - 3 Feb
5 star Guest House heated pool on the water!
Outdoor dining
Casey Key Beachfront Escape: Charming 1BR Cottage

Cottage in Casey Key

Casey Key Beachfront Escape: Charming 1BR Cottage
9.4 out of 10, Exceptional, (109)
"A true hidden gem on a great stretch of beach. Loved my time there and would recommend it. "
United States
John V.
The price is AED 1,095
AED 2,022 total
includes taxes & fees
5 Jan - 6 Jan
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Siesta Key Hotel Reviews

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"Kimberly and the staff were great and the rooms were very cozy and clean"
Jeffrey 3-night trip
Posted 2 days ago
Tropical Beach Resorts

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.

Explore a world of travel with Expedia