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Our top choices for Siesta Key cottages

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 NZ$581
includes taxes & fees
21 Dec - 22 Dec
The Inn On Siesta Key

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.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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.
Cabana Cottage Across street from Beach and Heated Pool

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 NZ$564
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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 NZ$856
includes taxes & fees
19 Jan - 20 Jan 2026
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
Yellow Palm 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

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.
Nook 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

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.
Lookout Cottage Across street from Beach and Heated Pool

#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 NZ$269
includes taxes & fees
21 Dec - 22 Dec
#3 Small house walking distance to Warm Mineral Spring

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 NZ$551
includes taxes & fees
1 Jan - 2 Jan 2026
7mi to Anna Maria Newly Renovated Private Cottage

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 NZ$299
includes taxes & fees
1 Jan - 2 Jan 2026
Charming cottage for 2 across warm mineral springs park

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 NZ$714
includes taxes & fees
22 Dec - 23 Dec
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

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 NZ$365
includes taxes & fees
30 Dec - 31 Dec
The "Grouper"

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 NZ$578
includes taxes & fees
6 Jan - 7 Jan 2026
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace

5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!
South Sarasota
The price is NZ$876
includes taxes & fees
21 Dec - 22 Dec
5 star Guest House heated pool on the water!

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 NZ$780
includes taxes & fees
24 Dec - 25 Dec
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

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
576
Accommodation
33 Cottages
Lowest Price
NZ$269
Highest Price
NZ$870

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