A marina with docked boats, a wooden bridge, and a building with a red roof.

Search Guest Houses in Osprey from CA $265

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Check prices for these dates

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27

Our top choices for Osprey guest houses

An outdoor patio with a table, chairs, and a barbecue grill.

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, (143 reviews)
"The hosts and the property were a joy to be involved with. We really enjoyed our stay."
United States
Dennis B.
The price is CA $158
CA $356 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $210
CA $503 total
includes taxes & fees
Nov 11 - Nov 12
Siesta key Guest House 5 star on the water Private
A patio with outdoor furniture, a staircase, and potted plants.

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 CA $179
CA $296 total
includes taxes & fees
Nov 17 - Nov 18
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
Exterior of little getaway cottage

4. Cozy studio "glamping" shack 2 miles from Englewood Beach!

Cozy studio "glamping" shack 2 miles from Englewood Beach!
Englewood Central
8.8 out of 10, Excellent, (6 reviews)
"Wonderful place hosted by a very nice family"
United States
Stephen T.
The price is CA $105
CA $265 total
includes taxes & fees
Nov 5 - Nov 6
Cozy studio "glamping" shack 2 miles from Englewood Beach!
A hotel room with two beds, a nightstand with a lamp, and a large mirror.

5. 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 CA $159
CA $305 total
includes taxes & fees
Nov 2 - Nov 3
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 Osprey Hotel Reviews

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"Nice location. Tiki bar was ok, decent convo with visitors. Training new staff was an issue but she persevered and all was good. Ice machine broken, only 1 on property. We would stay there again."
Bryan 1-night trip
Posted 3 hours ago
Golden Host Resort - Sarasota

Find out more about Osprey

Osprey Guest Houses information

Number of reviews
316
Accommodation
16 Guest Houses
Lowest Price
CA $265
Highest Price
CA $503

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