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Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Siesta Key cottages

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

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is ￥38,600
￥52,229 total
includes taxes & fees
Dec 21 - Dec 22
The Inn On Siesta Key
Exterior
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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, (81)
"We loved our stay at the Drift Inn. Very clean, just the right amount of room for 4, easy access to the beach and pool. The beds were very comfortable. The owner was very quick to respond to questions from beginning to end. We would stay here again."
United States
Kimberly P.
The price is ￥15,404
￥47,157 total
includes taxes & fees
Dec 20 - Dec 21
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Terrace/patio
Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
The price is ￥49,226
￥156,532 total
includes taxes & fees
Dec 21 - Dec 22
Cabana Cottage Across street from Beach and Heated Pool
Outdoor dining
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
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.
The price is ￥23,184
￥50,725 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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, (177)
"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "
United States
Kim C.
The price is ￥43,257
￥76,982 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds
Nest Cottage Across street from beach and Heated Pool

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)
"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
Exterior
Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
The price is ￥26,864
￥93,375 total
includes taxes & fees
Dec 20 - Dec 21
Yellow Palm Cottage steps from the beach
Property grounds
Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
Pink Mango Cottage steps from the beach
Terrace/patio
Nook Cottage Across street from beach and Heated Pool

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)
"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 ￥48,208
￥107,722 total
includes taxes & fees
Dec 22 - Dec 23
Nook Cottage Across street from beach and Heated Pool
Terrace/patio
Haven cottage Across street from beach and Heated Pool

Haven cottage Across street from beach and Heated Pool

Haven cottage Across street from beach and Heated Pool
Siesta Key
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
Lookout 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)
"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 ￥78,951
￥128,659 total
includes taxes & fees
Dec 29 - Dec 30
Lookout Cottage Across street from Beach and Heated Pool
Exterior
#3 Small house walking distance to Warm Mineral Spring

#3 Small house walking distance to Warm Mineral Spring

#3 Small house walking distance to Warm Mineral Spring
Warm Mineral Springs
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 ￥9,331
￥24,198 total
includes taxes & fees
Dec 20 - Dec 21
#3 Small house walking distance to Warm Mineral Spring
Property grounds
7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage
Bradenton
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 ￥18,516
￥49,544 total
includes taxes & fees
Jan 1 - Jan 2, 2026
7mi to Anna Maria Newly Renovated Private Cottage
Exterior
Charming cottage for 2 across warm mineral springs park

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, (10)
"Property was perfect for the price."
United States
William M.
The price is ￥10,108
￥25,076 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Charming cottage for 2 across warm mineral springs park
Exterior
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
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 ￥26,141
￥68,190 total
includes taxes & fees
Dec 29 - Dec 30
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Exterior
The "Grouper"

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (43)
"A beautiful little place to stay only minutes away from the beach! Very cozy and clean! "
United States
savana w.
The price is ￥15,395
￥32,807 total
includes taxes & fees
Dec 20 - Dec 21
The "Grouper"
Exterior
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace

Escape near Siesta Key with Hot Tub, BBQ, and Fireplace

Escape near Siesta Key with Hot Tub, BBQ, and Fireplace
2.0 star property
Sarasota
The price is ￥22,033
￥52,012 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace
Terrace/patio
5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!
South Sarasota
The price is ￥38,900
￥77,800 total
includes taxes & fees
Dec 20 - Dec 21
5 star Guest House heated pool on the water!
Outdoor dining
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Casey Key
9.4 out of 10, Exceptional, (108)
"Great stay, right on a beautiful private beach. Casey key is a great place, highly recommend this place!"
United States
Kathleen P.
The price is ￥30,791
￥70,063 total
includes taxes & fees
Dec 24 - Dec 25
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
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

The Capri at Siesta

The Capri at Siesta

10/10 Excellent
"Very nice place to say"
Jennifer 1-night trip
Posted 2 days ago
The Capri at Siesta

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
576
Accommodation
33 Cottages
Lowest Price
￥24,198
Highest Price
￥156,532

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.