Title: Osprey Guest Houses from CA $345 | 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) ![Osprey showing a bay or harbor](https://images.trvl-media.com/place/55888/4df1d5b3-0ca2-4dd3-91c6-479b5ebaf671.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/55888/4df1d5b3-0ca2-4dd3-91c6-479b5ebaf671.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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) ![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) ### Close to Siesta Key beach with a hot tub and a large garden [](https://www.expedia.ca/Sarasota-Hotels-5-Minutes-To-Siesta-And-Cresent-Beaches-In-Sarasota.h65549419.Hotel-Information) Sarasota 9.8/10 Exceptional (115 reviews) "Host was very hospitable and the guesthouse is clean. It was smaller than I imagined, but clean and nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carl CA $155 CA $345 total includes taxes & fees Jan 31 - Feb 1 [](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/93000000/92080000/92071900/92071840/3267e6a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/ed70386e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/dd5f1123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/384f8979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magical Guesthouse 1 mi from SRQ airport [](https://www.expedia.ca/Sarasota-Hotels-Magical-1-Bedroom-Guesthouse-1-Mi-From-SRQ-Airport.h92071840.Hotel-Information) Whitfield Estates 10/10 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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa D. CA $211 CA $378 total includes taxes & fees Jan 28 - Jan 29 [](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/d4dbcc79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/4e18c132.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/753a219a.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) ### Siesta key Guest House 5 star on the water Private [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Key-Guest-House-5-Star-On-The-Water-Private.h71059253.Hotel-Information) South Sarasota 9.0/10 Wonderful (18 reviews) "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 $205 CA $492 total includes taxes & fees Jan 29 - Jan 30 [](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/91000000/90350000/90345700/90345607/2550bef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/8c8fe8bc.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) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/735bde6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball [](https://www.expedia.ca/Sarasota-Hotels-Quick-And-Easy-Walk-Downtown-Tons-Of-Amenities.h90345607.Hotel-Information) Central Sarasota 9.8/10 Exceptional (123 reviews) "Great stay! Convenient location, clean, comfortable, and well stocked. Would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin CA $293 CA $441 total includes taxes & fees Feb 7 - Feb 8 [](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=2026-02-09&endDate=2026-02-10®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 ![Tropical Beach Resorts](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg) ### Tropical Beach Resorts 10/10 Excellent "Amazing job" [](https://expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![Carlisle Inn](https://images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/9a1b0e30_y.jpg) ### Carlisle Inn 10/10 Excellent "Bedroom and bathroom very clean and good size. I loved that coffee tea and cookies are available at all times in the lobby. I wish there was a towel bar or hook near the shower to hold the towel or even a small table to put clothes on when coming out of the shower. Location was very convenient. " [](https://expedia.ca/Sarasota-Hotels-Carlisle-Inn.h19761082.Hotel-Information) ![The Ritz-Carlton, Sarasota](https://images.trvl-media.com/lodging/1000000/810000/806200/806101/90558b2d_y.jpg) ### The Ritz-Carlton, Sarasota 10/10 Excellent "Amenities great, beach club pool was wonderful! Good location, walkable to many restaurants and shops" [](https://expedia.ca/Sarasota-Hotels-The-Ritz-Carlton.h806101.Hotel-Information) ![Spark by Hilton Sarasota Siesta Key Gateway](https://images.trvl-media.com/lodging/1000000/30000/26400/26397/18d283d6_y.jpg) ### Spark by Hilton Sarasota Siesta Key Gateway 10/10 Excellent "All the above " [](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information) ![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg) ### Kompose Boutique Hotel 10/10 Excellent "The staff here is excellent and extremely attentive. " [](https://expedia.ca/Sarasota-Hotels-Kompose-Boutique-Hotel.h38215316.Hotel-Information) ![Zota Beach Resort](https://images.trvl-media.com/lodging/16000000/15710000/15703500/15703469/277458de_y.jpg) ### Zota Beach Resort 10/10 Excellent "We had an excellent stay at Zota Beach Resort. The location is beautiful, the staff was wonderful, and everything felt calm and well taken care of. Highly recommend!" [](https://expedia.ca/Sarasota-Hotels-Zota-Beach-Resort.h15703469.Hotel-Information) ![Golden Host Resort - Sarasota](https://images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg) ### Golden Host Resort - Sarasota 10/10 Excellent "Friendly staff. Fairly easy and quick check-in" [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.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 "Super Clean, wonderful Location " [](https://expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![Extended Stay America Premier Suites - Bradenton](https://images.trvl-media.com/lodging/112000000/112000000/111997000/111996951/92d26979_y.jpg) ### Extended Stay America Premier Suites - Bradenton 10/10 Excellent "The first room had a bad odor. The gentlemen at the front desk was quick to give us another room that was perfect. Very friendly and the room was perfect. Only downside was the breakfast wasn't worth it." [](https://expedia.ca/Bradenton-Hotels-Extended-Stay-America-Premier-Suites-Bradenton.h111996951.Hotel-Information) ## Find out more about Osprey ## Osprey Guest Houses information | Number of reviews | 248 | | ----------------- | --------------- | | Accommodation | 17 Guest Houses | | Lowest Price | CA $345 | | Highest Price | CA $492 | ## 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) - [Cabin Rentals in Cape Coral ](https://www.expedia.ca/Cape-Coral-Cabins.d6521-aaCabins.Travel-Guide-Accommodation) - [Chalets in Cape Coral ](https://www.expedia.ca/Cape-Coral-Chalets.d6521-aaChalets.Travel-Guide-Accommodation) - 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