Title: Osprey Guest Houses from CA $290 | Expedia.ca [Hotels in Osprey](https://expedia.ca/Osprey-Hotels.d55888.Travel-Guide-Hotels)[Vacation Rentals in Osprey](https://expedia.ca/Osprey-Vacation-Rentals.d55888.Travel-Guide-VacationRentals)[Flights to Osprey](https://expedia.ca/Cheap-Flights-To-Osprey.d55888.Travel-Guide-Flights)[Osprey Car Rentals](https://expedia.ca/Car-Rentals-In-Osprey.d55888.Car-Rental-Guide)[Osprey Vacation Packages](https://expedia.ca/Osprey.d55888.Destination-Travel-Guides) ![Great Heron](https://images.trvl-media.com/place/55888/92c919ca-2448-4c40-b1eb-f9207c3d50df.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Guest Houses in Osprey from CA $290 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Osprey Guest Houses ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/4ffe13e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/w3998h2258x0y0-57eeb69f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/7f7b2ea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/w4000h2196x0y0-722bffee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Close to Siesta Key beach with a hot tub and a large garden Sarasota 9.8/10 Exceptional (111) "This place is a must stay we could not fault the place they have thought of everything. Highly recommend this place." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Danny P. CA $158 CA $346 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Sarasota-Hotels-5-Minutes-To-Siesta-And-Cresent-Beaches-In-Sarasota.h65549419.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/2550bef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/c634db4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/193334ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/3d9028d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quick and Easy Walk Downtown - Tons of Amenities Central Sarasota 9.8/10 Exceptional (120) "Outstanding gem in downtown Sarasota. Everything you could possibly need in a terrific location. Definitely would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert P. CA $175 CA $290 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Sarasota-Hotels-Quick-And-Easy-Walk-Downtown-Tons-Of-Amenities.h90345607.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/3267e6a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/4a7b0053.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/e3a8d43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/852b9ee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magical Guesthouse 1 mi from SRQ airport Whitfield Estates 10/10 Exceptional (3) "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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa D. CA $203 CA $375 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Sarasota-Hotels-Magical-1-Bedroom-Guesthouse-1-Mi-From-SRQ-Airport.h92071840.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/f52cf6cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/c4961f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/9b40207f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/85eef7c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta key Guest House 5 star on the water Private South Sarasota 9.0/10 Wonderful (18) "House was really comfortable, everything worked fine and was cozy. About 15 mins away from Siesta Key Beach..Would def come back. Highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giancarlo CA $210 CA $494 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Key-Guest-House-5-Star-On-The-Water-Private.h71059253.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2025-12-15&endDate=2025-12-16®ionId=55888&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_55888) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOsprey-Guest-Houses.d55888-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOsprey-Guest-Houses.d55888-aaGuestHouses.Travel-Guide-Accommodation) ## Top Osprey Hotel Reviews ![Golden Host Resort - Sarasota](https://images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg) ### Golden Host Resort - Sarasota 10/10 Excellent "My favorite staycation sanctuary on the suncoast... the staff is great... the hut is great... the north trail is great (if you're a local)!!!" [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information) ![Lido Beach Resort](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg) ### Lido Beach Resort 10/10 Excellent "Great experience " [](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![Carlisle Inn](https://images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/9a1b0e30_y.jpg) ### Carlisle Inn 10/10 Excellent "Great rooms… Great staff… Very nice location close to everything" [](https://expedia.ca/Sarasota-Hotels-Carlisle-Inn.h19761082.Hotel-Information) ![Hyatt Place Sarasota/Bradenton Airport](https://images.trvl-media.com/lodging/3000000/2280000/2277500/2277489/6e9ac4ec_y.jpg) ### Hyatt Place Sarasota/Bradenton Airport 10/10 Excellent "😍" [](https://expedia.ca/Sarasota-Hotels-Hyatt-Place-SarasotaBradenton-Airport.h2277489.Hotel-Information) ![Casey Key Resorts - Mainland](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/164f19b9_y.jpg) ### Casey Key Resorts - Mainland 10/10 Excellent "Nice pool solid clean rooms quiet atmosphere" [](https://expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![Art Ovation Hotel, Autograph Collection](https://images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/w4000h2662x0y0-652c5c90_y.jpg) ### Art Ovation Hotel, Autograph Collection 10/10 Excellent "Great location and nice hotel. Staff was friendly and accommodating " [](https://expedia.ca/Sarasota-Hotels-Art-Ovation-Hotel.h19900973.Hotel-Information) ![Hibiscus Suites - Gateway to Siesta Key](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/6ff58e07_y.jpg) ### Hibiscus Suites - Gateway to Siesta Key 10/10 Excellent "The room was perfect. It was a last minute trip just for a night, will definitely return. Staff was great!!" [](https://expedia.ca/Sarasota-Hotels-Hibiscus-Suites-Gateway-To-Siesta-Key.h1212924.Hotel-Information) ![Captiva Beach Resort](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3fe58375_y.jpg) ### Captiva Beach Resort 10/10 Excellent "This is great place to stay. Clean, amenities are great. The staff is super friendly. We borrow from them the beach bench to enjoy the sunset at their private beach. We love it!" [](https://expedia.ca/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.Hotel-Information) ![DoubleTree by Hilton Sarasota Bradenton Airport](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7_y.jpg) ### DoubleTree by Hilton Sarasota Bradenton Airport 10/10 Excellent "Clean room and friendly prompt check in" [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ## Find out more about Osprey ## Osprey Guest Houses information | Number of reviews | 240 | | --- | --- | | Accommodation | 17 Guest Houses | | Lowest Price | CA $290 | | Highest Price | CA $494 | ## Explore a world of travel with Expedia - Lodging - Packages - Vacation Rental - Other - More ways to book - [Beach Hotel Hotels in Bay Acres](https://www.expedia.ca/Bay-Acres-Osprey-Hotels-Beach-Hotel.0-n553248635976472153-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Bay Acres Hotels](https://www.expedia.ca/Bay-Acres-Osprey-Hotels.0-n553248635976472153-0.Travel-Guide-Filter-Hotels) - 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[Rivendell Hotels](https://www.expedia.ca/Rivendell-Osprey-Hotels.0-n553248635976481518-0.Travel-Guide-Filter-Hotels) - [Hotels near Sarasota Square](https://www.expedia.ca/Sarasota-Square-Hotels.0-l553248621563219817-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Sorrento Shores](https://www.expedia.ca/Sorrento-Shores-Osprey-Hotels-Historic-Hotel.0-n553248635976480913-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Sorrento Shores](https://www.expedia.ca/Sorrento-Shores-Osprey-Hotels-Waterpark-Hotels.0-n553248635976480913-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Hotels near Stoneybrook Golf & Country Club](https://www.expedia.ca/Stoneybrook-Golf-Country-Club-Hotels.0-l6068717-0.Travel-Guide-Filter-Hotels) - [Hotels near The Oaks Club](https://www.expedia.ca/The-Oaks-Club-Hotels.0-l553248635976489805-0.Travel-Guide-Filter-Hotels) - [Hotels near Turtle Beach](https://www.expedia.ca/Turtle-Beach-Hotels.0-l6296228-0.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Vamo](https://www.expedia.ca/Vamo-Sarasota-Hotels-Beach-Hotel.0-n553248623282278448-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Vamo](https://www.expedia.ca/Vamo-Sarasota-Hotels-Boutique-Hotel.0-n553248623282278448-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Vamo](https://www.expedia.ca/Vamo-Sarasota-Hotels-Oceanfront-Hotels.0-n553248623282278448-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Vamo Hotels](https://www.expedia.ca/Vamo-Sarasota-Hotels.0-n553248623282278448-0.Travel-Guide-Filter-Hotels) - [Visit Casey Key](https://www.expedia.ca/Casey-Key.dx6167273) - [Jim Neville Marine Preserve](https://www.expedia.ca/Jim-Neville-Marine-Preserve-Siesta-Key.d6295999.Vacation-Attraction) - [Oscar Scherer State Park](https://www.expedia.ca/Oscar-Scherer-State-Park-Osprey.d6296013.Vacation-Attraction) - [Visit Rivendell](https://www.expedia.ca/Osprey-Rivendell.dx553248635976481518) - [Visit Osprey Village](https://www.expedia.ca/Osprey-Village.dx553248635976482375) - [Visit Vamo](https://www.expedia.ca/Sarasota-Vamo.dx553248623282278448) - [Stoneybrook Golf & Country Club](https://www.expedia.ca/Stoneybrook-Golf-Country-Club-Palmer-Ranch.d6068717.Vacation-Attraction) - [Casey Key Vacation Rentals](https://www.expedia.ca/Casey-Key-Vacation-Rentals.d6167273.Travel-Guide-VacationRentals) - [Things to do in Casey Key](https://www.expedia.ca/Things-To-Do-In-Casey-Key.d6167273.Travel-Guide-Activities) - [Book Guest Houses in Osprey on Expedia.com](https://www.expedia.com/Osprey-Guest-Houses.d55888-aaGuestHouses.Travel-Guide-Accommodation)