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

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Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 Dec

Our top choices for Siesta Key guest houses

A lifeguard tower with a blue umbrella and a yellow flag on a sandy beach.

1. Close to Siesta Key beach with a hot tub and a large garden

Close to Siesta Key beach with a hot tub and a large garden
Sarasota
9.8 out of 10, Exceptional, (142 reviews)
"place was spotless when we arrived.. and had excellent communication with the host from start to finish. the location was perfect for our family vacation and we had an amazing time!"
United States
Robert R.
The price is SAR 422
SAR 952 total
includes taxes & fees
25 Oct - 26 Oct
Close to Siesta Key beach with a hot tub and a large garden
A covered outdoor deck with a ceiling fan, wooden railing, and a seating area with cushions.

2. Siesta key Guest House 5 star on the water Private

Siesta key Guest House 5 star on the water Private
South Sarasota
8.8 out of 10, Excellent, (21 reviews)
"Great location, right on the Phillipi Creek. Host was super friendly and welcoming. "
United States
Scott E.
The price is SAR 375
SAR 1,103 total
includes taxes & fees
26 Oct - 27 Oct
Siesta key Guest House 5 star on the water Private
A beach with gentle waves and a sunset.

3. Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball

Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
Central Sarasota
9.8 out of 10, Exceptional, (140 reviews)
"Cute place in a great location! Accurate listing, clean, and easy place to relax."
United States
Kathleen R.
The price is SAR 420
SAR 715 total
includes taxes & fees
26 Oct - 27 Oct
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
A marina with boats docked, a wooden dock, and a clear sky.

4. ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym

ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
Whitfield Estates
7.4 out of 10, Good, (6 reviews)
"Looking for a couple nights close to Anna Maria Island without being ON the island. Turns out we were here once before and didnt realize it was the same place. Love the "Back Yard" surprises"
United States
Susan B.
The price is SAR 427
SAR 806 total
includes taxes & fees
23 Oct - 24 Oct
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
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

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"I loved how close to the private beach this property was. We walked to the beach in under 5 min. It's a lovely beach. It was also nice to have a kitchen to cook our own food."
Sonja 2-night trip
Posted 4 hours ago
Tropical Beach Resorts