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

Search Guest Houses in Siesta Key

  • 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
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6

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, (141 reviews)
"Wonderful place to stay! Spacious, near Siesta Key beaches, and great pizza walking distance "
United States
Kari H.
The price is ￥18,751
￥40,936 total
includes taxes & fees
Oct 17 - Oct 18
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 ￥23,685
￥56,765 total
includes taxes & fees
Oct 12 - Oct 13
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, (139 reviews)
"Stephanie is a great host. The coach house is very clean and comfortable and all of the extras available to us made the trip so good - like beach chairs, umbrellas, e-bikes. It’s a great location with Main Street walkable and fantastic beaches by car."
United Kingdom
Liz
The price is ￥16,580
￥28,852 total
includes taxes & fees
Oct 13 - Oct 14
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 ￥17,977
￥33,915 total
includes taxes & fees
Oct 10 - Oct 11
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.
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

SeaSpray Resort

SeaSpray Resort

10/10 Excellent
"The only problem was a 2 floor walk up ! We are 83 years old with disable stickers . They did help us with luggage. In the future will only repeat it we get ground floor"
BARRY 2-night trip
Posted less than an hour ago
SeaSpray Resort

Find out more about Siesta Key

Siesta Key Guest Houses information

Number of reviews
307
Accommodation
2 Guest Houses
Lowest Price
￥28,852
Highest Price
￥56,765