Title: Osprey Guest Houses from CA $255 | 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495790-osprey.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Guest Houses in Osprey from CA $255 ![](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-12-05&endDate=2025-12-07&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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/f28582f9.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 (108) "everything was as listed and worked perfectly for us. " CA $158 CA $346 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Sarasota-Hotels-5-Minutes-To-Siesta-And-Cresent-Beaches-In-Sarasota.h65549419.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/32862b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/c3e6b6ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/f4f00fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/9bad2281.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." CA $209 CA $502 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Key-Guest-House-5-Star-On-The-Water-Private.h71059253.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) ![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) ![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) ![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." CA $174 CA $338 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Sarasota-Hotels-Magical-1-Bedroom-Guesthouse-1-Mi-From-SRQ-Airport.h92071840.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) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/baa92889.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 (115) "Great little place to stay! " CA $145 CA $255 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Sarasota-Hotels-Quick-And-Easy-Walk-Downtown-Tons-Of-Amenities.h90345607.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=2025-10-23&endDate=2025-10-24®ionId=55888&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](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 ![Carlisle Inn](//images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/9a1b0e30_y.jpg) ### Carlisle Inn 10/10 Excellent "It was a really pleasant stay. I recommend the property, breakfast was excellent and the front desk staff were professional, welcoming and friendly. " [](https://expedia.ca/Sarasota-Hotels-Carlisle-Inn.h19761082.Hotel-Information) ![Ameniti Bay, BW Signature Collection](//images.trvl-media.com/lodging/39000000/38800000/38796200/38796114/79763f71_y.jpg) ### Ameniti Bay, BW Signature Collection 10/10 Excellent "Recently stayed here with our 6 year old and had a wonderful time. The property is incredibly well maintained. The pool area is wonderful you feel like your in your own tropical land. " [](https://expedia.ca/Sarasota-Hotels-Ameniti-Bay.h38796114.Hotel-Information) ![The Westin Sarasota](//images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3_y.jpg) ### The Westin Sarasota 10/10 Excellent "Roof top bar and pool was a good view cooler then being on street level" [](https://expedia.ca/Sarasota-Hotels-The-Westin-Sarasota.h16818933.Hotel-Information) ![Tropical Beach Resorts](//images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg) ### Tropical Beach Resorts 10/10 Excellent "My wife and I came here for our honeymoon and it was a wonderful experience! My wife didn’t want to leave. Everything was clean, housekeeping was excellent it was so much to do and so many free forms or transportation! EVERYONE was nice, and the beach clean and breath taking. I can’t wait to go back " [](https://expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![DoubleTree by Hilton Sarasota Bradenton Airport](//images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7_y.jpg) ### DoubleTree by Hilton Sarasota Bradenton Airport 10/10 Excellent "Great stay! Thank you very much " [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Lido Beach Resort](//images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg) ### Lido Beach Resort 10/10 Excellent "The property is situated right on the beach. Very well maintained hotel with all the amenities possible. Staff is friendly and helpful! " [](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![Kompose Boutique Hotel](//images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg) ### Kompose Boutique Hotel 10/10 Excellent "Great customer seevice" [](https://expedia.ca/Sarasota-Hotels-Kompose-Hotel-Sarasota.h38215316.Hotel-Information) ![Tropical Breeze Resort](//images.trvl-media.com/lodging/1000000/880000/879700/879629/9de12888_y.jpg) ### Tropical Breeze Resort 10/10 Excellent "As expected. This is our 3rd or 4th stay. " [](https://expedia.ca/Sarasota-Hotels-Tropical-Breeze-Resort.h879629.Hotel-Information) ![voco Sarasota by IHG](//images.trvl-media.com/lodging/2000000/1580000/1577400/1577382/dc3c2bf5_y.jpg) ### voco Sarasota by IHG 10/10 Excellent "Very comfortable " [](https://expedia.ca/Sarasota-Hotels-Voco-Sarasota.h1577382.Hotel-Information) ## Find out more about Osprey ## Osprey Guest Houses information | Number of reviews | 235 | | --- | --- | | Accommodation | 17 Guest Houses | | Lowest Price | CA $255 | | Highest Price | CA $502 | ## 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) - [Apartments in Cape Coral](https://www.expedia.ca/Cape-Coral-Apartments.d6521-aaApartments.Travel-Guide-Accommodation) - 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[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)