Search Guest Houses in Osprey from CA $259
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Our top choices for Osprey guest houses
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 gardenSarasota
9.8 out of 10, Exceptional, (130 reviews)
"We loved our stay here!! The place was clean and comfortable. Definitely coming back! "
Cresta Blanca
The price is CA $162
CA $357 total
includes taxes & fees
Jul 5 - Jul 6
Siesta key Guest House 5 star on the water Private
Siesta key Guest House 5 star on the water PrivateSouth Sarasota
8.6 out of 10, Excellent, (20 reviews)
"Great location, right on the Phillipi Creek. Host was super friendly and welcoming. "
Scott E.
The price is CA $213
CA $510 total
includes taxes & fees
Jul 8 - Jul 9
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, PickleballCentral Sarasota
9.8 out of 10, Exceptional, (134 reviews)
"Great communication. Walking distance too many restaurants and attractions in Downtown Sarasota. Quiet neighbor and lovely accommodations."
Louise
The price is CA $148
CA $259 total
includes taxes & fees
Jun 30 - Jul 1
Magical Guesthouse 1 mi from SRQ airport
Magical Guesthouse 1 mi from SRQ airportWhitfield Estates
10.0 out of 10, Exceptional, (3 reviews)
"This house was absolutely charming! I caught myself In complete awe of every detail - from the fun decor, to the thoughtful inclusion of all kitchen supplies to make a full meal, to the soft shower towels and the incredibly comfortable bed, bedding and pillows! Fantastic stay."
Alyssa D.
The price is CA $182
CA $353 total
includes taxes & fees
Jun 29 - Jun 30
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, GymWhitfield 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"
Susan B.
The price is CA $186
CA $337 total
includes taxes & fees
Jul 16 - Jul 17
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.
Top Osprey Hotel Reviews
The Westin Sarasota
10/10 Excellent
Find out more about Osprey
Osprey Guest Houses information
Number of reviews | 293 |
|---|---|
Accommodation | 17 Guest Houses |
Lowest Price | CA $259 |
Highest Price | CA $510 |
Explore a world of travel with Expedia
- Villas in Venice
- Farmstay in Osprey Village
- Beach Hotel Hotels in Siesta Key
- B&B in Island of Venice
- Aparthotels in Lakewood Ranch
- Cottages in Siesta Key
- Oceanfront Hotels in Siesta Key
- Motels in Venice
- 5 Star Hotels in Sarasota
- Beach Hotel Hotels in Sarasota
- Osprey Hotels
- Condo Rentals in Sarasota
- Motels in Siesta Key
- Motels in Sarasota
- Oceanfront Hotels in Sarasota
- Houseboats in Sarasota
- All Inclusive Resorts and in Siesta Key
- Holiday Inn Express Venice by IHG
- Cottages in Nokomis
- Oaks Preserve Condominium
- Oceanfront Hotels in Venice
- Hotels near Crescent Beach
- Tropical Breeze Resort
- Tropical Beach Resorts
- Condo Rentals in Siesta Key
- Apartments in Osprey Village
- Rv Parks in Venice
- Apartments in Venice
- Resorts in Siesta Key
- Casey Key Resorts
- Palmer Ranch Hotels
- Condo Resorts in Sarasota
- Vacation Homes in Siesta Key
- Cottages in Sarasota
- Siesta Key Hotels
- Sarasota Surf and Racquet Club
- Hotels near Turtle Beach
- Rv Parks in Sarasota
- Cabin Rentals in Venice
- Tampa Hotels
- Villas in Sarasota
- B&B in Sarasota
- Sarasota Hotels
- Resorts in Sarasota
- Venice Hotels
- Beach Hotel Hotels in Osprey
- Home2 Suites by Hilton Nokomis Sarasota Casey Key
- Apartments in Siesta Key
- Villas in Osprey Village
- Cruise Ships in Venice
- Casino Hotels in Casey Key
- Cottages in Osprey Village
- Resorts in Osprey
- Condo Rentals in Venice
- Flights from Vancouver (YVR) to Sarasota (SRQ)
- Flights from Detroit (DTW) to Sarasota (SRQ)
- Flights from Montreal (YUL) to Sarasota (SRQ)
- Flights to Fort Myers
- Flights to Sarasota
- Flights from Toronto (YYZ) to Tampa (TPA)
- Flights to Osprey
- Flights from Toronto (YYZ) to St. Petersburg (PIE)
- Flights from Sarasota-Bradenton Intl.
- Flights from Toronto (YYZ) to Sarasota (SRQ)
- Flights to Venice
- Flights from Buffalo (BUF) to Tampa (TPA)
- Flights to Siesta Key
- Flights from Ottawa (YOW) to Sarasota (SRQ)
- Flights from Buffalo (BUF) to Sarasota (SRQ)
- Flights to Tampa
- Stoneybrook Golf & Country Club
- Visit Palmer Ranch
- Visit Casey Key
- Siesta Key Vacations
- Crescent Beach
- Nokomis Beach
- Sarasota Vacations
- Venice Vacations
- All inclusive Vacation Packages Siesta Key
- Oscar Scherer State Park
- Jim Neville Marine Preserve
- St. Armands Circle
- Visit Osprey Village
- Siesta Key Beach
- Lido Beach
- Visit Siesta Key Village