Title: Osprey Condo Rentals from CA $186 | 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 Condos Rentals in Osprey from CA $186 - ![](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 In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Osprey Condo Rentals ![Property grounds](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/08b5bced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/aa27a0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Microwave](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/3375a4fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/105c6d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Manasota Key 10/10 Exceptional (14) "Great place and location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cathy CA $111 CA $756 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3fe58375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3d46ab53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Florida Family Single | Private kitchen](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/06d7bc78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Luxury Single | Private kitchenette](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/13f03971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in South Village 9.0/10 Wonderful (1165) "Very good stay, clean, safe, and steps from the beach" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon CA $143 CA $186 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/89000000/88080000/88075900/88075899/f5ad5c78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/89000000/88080000/88075900/88075899/1b9ca01a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88080000/88075900/88075899/a3f44af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/89000000/88080000/88075900/88075899/6a65d678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in South Bradenton 9.8/10 Exceptional (17) "Accommodating for family group, quick drive to the beach." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ginger B. CA $167 CA $500 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Bradenton-Hotels-New-Renovated-Coastal-22.h88075899.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/70000000/69770000/69763000/69762951/d347fd7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69770000/69763000/69762951/53ccd5c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69770000/69763000/69762951/w1024h681x0y2-4a60577e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69770000/69763000/69762951/cc9a40ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in South Bradenton 9.6/10 Exceptional (21) "Cool place. Everything just as mentioned. Kids had a blast at pool and place was super clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason G. CA $167 CA $511 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Bradenton-Hotels-Charming-2bed-2-Bath-6-Mins-From-IMG.h69762951.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71100000/71094700/71094685/8831bab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71100000/71094700/71094685/d996faac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71100000/71094700/71094685/6f355594.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/72000000/71100000/71094700/71094685/9a0ecdc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Manasota Key 9.8/10 Exceptional (39) "Perfect for 2 adults and 2 kids. The house was very clean and all the extras in the kitchen were nice. Also, beach essentials are onsite so no need to bring much. Found lots of sharks teeth too! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Koren L. CA $161 CA $481 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Steps-To-Water-Sea-Glass-Beach-To-Bay.h71094685.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/91000000/90950000/90945000/90944912/cc29e572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90950000/90945000/90944912/d8fc392d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90950000/90945000/90944912/68d9d154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90950000/90945000/90944912/w1290h958x0y0-30849da0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Manasota 9.8/10 Exceptional (6) "Nice place to stay, close to the beach, hunting for fossilized shark teeth was fun." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vance E. CA $196 CA $648 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Englewood-Hotels-Cozy-Beach-House-Just-Steps-Away-From-The-World-Class-Manasota-Beach.h90944912.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/42000000/41030000/41030000/41029916/23c23942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41030000/41030000/41029916/c4381bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/42000000/41030000/41030000/41029916/69a532f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/42000000/41030000/41030000/41029916/2c35e622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Bradenton 10/10 Exceptional (117) "We enjoyed our stay. Host is nice and respond quickly. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Sonia S. CA $155 CA $454 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Sarasota-Hotels-Newly-Listed-Lakefront-Condo-IMG-Academy-5-Mins-Near-Beachesanna-Mariasrq.h41029916.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/84000000/83060000/83058500/83058493/ad597696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83060000/83058500/83058493/5fcd2574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/84000000/83060000/83058500/83058493/be16b4bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83060000/83058500/83058493/b13049d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in South Bradenton 10/10 Exceptional (22) "Great location, attentive host, great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JUDY T. CA $167 CA $516 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Bradenton-Hotels-Upscale-22-Key-West-Style-Condo-6-Mins-From-IMG.h83058493.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/75000000/74620000/74618500/74618445/e2fea912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/75000000/74620000/74618500/74618445/cb3a427e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/75000000/74620000/74618500/74618445/457c26c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/75000000/74620000/74618500/74618445/bcba98d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in South Bradenton 9.8/10 Exceptional (26) "This was the perfect place to stay for an IMG baseball tournament. Very close to the facility as described. This condo unit was modern and clean. An overall excellent place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lassier CA $167 CA $507 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Bradenton-Hotels-Farmhouse-22-Renovated-Condo-6-Mins-From-IMG.h74618445.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/36000000/35670000/35662800/35662757/37a8db83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35670000/35662800/35662757/a29cb2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35670000/35662800/35662757/f040f403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35670000/35662800/35662757/97f55d65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Manasota Key 9.6/10 Exceptional (21) "Nice location, clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Al H. CA $205 CA $569 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Englewood-Hotels-Oceanfront-Condo-Walk-To-Beaches.h35662757.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73100000/73097800/73097706/55f0c15e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73100000/73097800/73097706/243da37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/74000000/73100000/73097800/73097706/d4b2699d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73100000/73097800/73097706/1b988693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Bradenton 9.8/10 Exceptional (60) "It was clean, comfy and ideal locarion. Close to beaches AMI and the pool was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marge G. CA $188 CA $535 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Bradenton-Hotels-Fantastic-Shorewalk-Vacation-2-Bed2-Bath-CondoLake-Viewclose-To-IMG.h73097706.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/62000000/61110000/61106200/61106139/b75e5c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/62000000/61110000/61106200/61106139/3d113325.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61110000/61106200/61106139/21f9ff9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/62000000/61110000/61106200/61106139/d7fff6ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Indian Beach Sapphire Shores 9.8/10 Exceptional (55) "A cute and cozy place to stay. Located in a good spot. Close to every thing we wanted to do. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth H. CA $105 CA $210 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Sarasota-Hotels-Sapphire-Shores-Arcadia-1bed1bath.h61106139.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/58000000/57230000/57225900/57225886/0f39df90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57230000/57225900/57225886/afc540ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57230000/57225900/57225886/d47674ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57230000/57225900/57225886/w1030h718x0y1-6642b7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Bradenton 9.8/10 Exceptional (146) "Nice clean condo. Situated in a good location for multiple beach days." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) victoria c. CA $111 CA $328 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Sarasota-Hotels-Beautifully-Furnished-Condo.h57225886.Hotel-Information) ![Sun loungers](https://images.trvl-media.com/lodging/108000000/107900000/107890500/107890468/901649cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107900000/107890500/107890468/0e480656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107900000/107890500/107890468/0198d8d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107900000/107890500/107890468/07eed6f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Longboat Key 9.4/10 Exceptional (12) "Enjoyed our stay in this quiet little place with close access to restaurants and just a few minutes from Bradenton. Would come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd B. CA $188 CA $557 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Longboat-Key-Hotels-Charming-Longboat-Key-Bungalow-With-Private-Beach-5-Min-Walk-Away.h107890468.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/64000000/63920000/63918500/63918463/a2129691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63920000/63918500/63918463/4fe65013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/64000000/63920000/63918500/63918463/daedf07d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/64000000/63920000/63918500/63918463/3e4cd61a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Bayou Oaks 9.6/10 Exceptional (68) "Very comfortable and perfect location to the airport! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andreha CA $126 CA $274 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Sarasota-Hotels-Casa-Azul-2bed1bath.h63918463.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/39000000/38450000/38441200/38441108/52185304.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38450000/38441200/38441108/c6d03e8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/39000000/38450000/38441200/38441108/4321036a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/39000000/38450000/38441200/38441108/9150a9a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in South Village 9.6/10 Exceptional (41) "Loved the pool and view!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victoria P. CA $139 CA $345 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Sarasota-Hotels-Pool-View-1-King-Bed-Walk-To-Beach-Private-Screen-Porch-Specials-30-OFF.h38441108.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33510000/33507600/33507564/0ddc5f45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/34000000/33510000/33507600/33507564/12d965f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/34000000/33510000/33507600/33507564/702ba6e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33510000/33507600/33507564/0c0d0871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Sarasota 9.6/10 Exceptional (44) "The location of the property could not have been better. A very short walk to the quietest beach on Siesta Key. The manager was very attentive when we called with a minor issue and had it resolved quickly. The property could use a pretty thorough cleaning of the baseboards and other nooks and crannies but overall it was pretty clean. We would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mel S. CA $139 CA $345 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Siesta-Key-Hotels-POOL-VIEW-Walk-To-Beach-King-Bed-Heated-Pool-DAILY-WEEKLY-SPECIALS-Villa-3.h33507564.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/114000000/113630000/113622600/113622534/b30186b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113630000/113622600/113622534/w1347h899x1y1-f5f455a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113630000/113622600/113622534/w1350h899x0y1-00bd0e40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/114000000/113630000/113622600/113622534/01f3fc5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Longboat Key 10/10 Exceptional (12) "So quiet, I loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sergio CA $211 CA $528 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Longboat-Key-Hotels-Sunset-And-Beach-View-Unit-402.h113622534.Hotel-Information) ![On the beach, white sand](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/d13a0271.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bayview 3 Bedroom | Living room](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/5c776782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beachside Efficiency | Bathroom](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/8ce15104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beachside One Bedroom Suite](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/31f9068d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Casey Key 9.2/10 Wonderful (576) "Location, very clean and comfortable. Nice efficiency." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chuck [](https://www.expedia.ca/Sarasota-Hotels-A-Beach-Retreat.h1533163.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/24000000/23280000/23279700/23279677/036ae829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23280000/23279700/23279677/221fbc2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23280000/23279700/23279677/d19b0a1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23280000/23279700/23279677/62d3fd00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Longboat Key 8.6/10 Excellent (72) "Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Condo is well appointed and spacious. Amenities galore! This unit can sleep five but we were only two so we had plenty of space. Comfortable bed and plenty of beach towels. Had some trouble working the tv’s but eventually got it sorted." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim &. CA $199 CA $486 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Sarasota-Hotels-The-Beach-On-Longboat-Key-101-1-BR-Den2-BA-Resort-On-Longboat-Key-By-RVA.h23279677.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=2025-12-12&endDate=2025-12-13®ionId=55888&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=APART_HOTEL) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-26&d1=2026-02-26&endDate=2026-03-01&d2=2026-03-01&lodging=VILLA) ![](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-Condos.d55888-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOsprey-Condos.d55888-aaCondos.Travel-Guide-Accommodation) ## Top Osprey Hotel Reviews ![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) ![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg) ### Kompose Boutique Hotel 10/10 Excellent "Excellent hotel, with a nice pool qnd jacuzzi area, big hot breakfast with a variety. Clean modern rooms with snazzy furnishings." [](https://expedia.ca/Sarasota-Hotels-Kompose-Hotel-Sarasota.h38215316.Hotel-Information) ![Carlisle Inn](https://images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/9a1b0e30_y.jpg) ### Carlisle Inn 10/10 Excellent "Best hotel at the price point bar none! Clean, comfortable, spacious room, amazing breakfast home made, friendly staff—can’t imagine how it could be better " [](https://expedia.ca/Sarasota-Hotels-Carlisle-Inn.h19761082.Hotel-Information) ![Tropical Beach Resorts](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg) ### Tropical Beach Resorts 10/10 Excellent "Not what I expected, smallish motel like. But nice and clean rooms with good ac and nice kitchenette. Small but cozy little pool. Beach very close. Is good for the price tbh." [](https://expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![The Westin Sarasota](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3_y.jpg) ### The Westin Sarasota 10/10 Excellent "Everything was amazing " [](https://expedia.ca/Sarasota-Hotels-The-Westin-Sarasota.h16818933.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 "Everything we needed with great value, the whole hotel was well maintained. Staff was friendly and helpful. The pool area is so relaxing even has a bar area to watch games and order drinks. The pool was heated and the jacuzzi was nice and hot. Just a shirt drive to the beaches and village. Beds are comfortable and the large TV was very nice." [](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information) ## Find out more about Osprey ## Osprey Condo Rentals information | Number of reviews | 2,402 | | --- | --- | | Accommodation | 3714 Condo Rentals | | Lowest Price | CA $186 | | Highest Price | CA $756 | ## Frequently asked questions ### How much do condos in Osprey cost? > Condos in Osprey range from CA $186 to CA $756 per night. These stays provide loads of space for your whole crew at a price that's friendly on the pocket. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### What are the best condos in Osprey? > Choose from multiple condos in Osprey with a total average guest review rating of 9.5. [Venice Beach Villas](https://www.expedia.ca/Sarasota-Hotels-Venice-Beach-Villas.h7806268.Hotel-Information) comes highly recommended if you're travelling with the whole crew or just want to stretch out. This 3-star condo also features therapeutic mineral springs and a barbecue grill. [Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village](https://www.expedia.ca/Siesta-Key-Hotels-Walk-To-The-Beach-From-Modern-Condo-Or-Hop-On-A-Bike-To-Siesta-Village.h42485447.Hotel-Information) is another guest fave. It has a 3-star rating and amenities such as a deck and a lanai. ### How many condos are there in Osprey? > Work out your vacation dates and then pick from 3714 condos in Osprey. For an official business trip, a couples' getaway or anything in between, Expedia will help you find the perfect place in a few quick clicks. ### What are the best cheap condos in Osprey? > With condos starting from CA $186 per night, you may be tempted to stay a little longer in Osprey! One property that's easy on the pocket is [Captiva Beach Resort](https://www.expedia.ca/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.Hotel-Information). It comes with the layout you're looking for as well as pillow top mattresses and a swimming pool. Another cost-effective pick is [Bs 1350 - #1 Siesta And Crescent Beach Are Walking Distance Away](https://www.expedia.ca/Sarasota-Hotels-1-Siesta-Crescent-Beach-Are-Walking-Distance-Away-Ready-For-Your-Family.h22122318.Hotel-Information), which offers a lake view and a sauna. If you prefer to save your hard-earned cash and still experience the best of Osprey, add a couple of fun and free attractions to your must-do list. [Siesta Key Beach](https://www.expedia.ca/Siesta-Key-Beach-Siesta-Key.d6066003.Vacation-Attraction) and [Venice Beach](https://www.expedia.ca/Venice-Beach-Venice.d6127832.Vacation-Attraction) will keep you on the go. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### Are there any family-friendly condos in Osprey? > Get comfortable at [Venice Beach Villas](https://www.expedia.ca/Sarasota-Hotels-Venice-Beach-Villas.h7806268.Hotel-Information), a 3-star option just a quick drive from downtown. Amenities here include a barbecue grill and a swimming pool. Another family-friendly condo is [Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village](https://www.expedia.ca/Siesta-Key-Hotels-Walk-To-The-Beach-From-Modern-Condo-Or-Hop-On-A-Bike-To-Siesta-Village.h42485447.Hotel-Information). A deck and a lanai help make this 3-star property a favourite among guests. Once you've checked in and unpacked, there's a host of family-friendly attractions to visit around Osprey. [Siesta Key Beach](https://www.expedia.ca/Siesta-Key-Beach-Siesta-Key.d6066003.Vacation-Attraction) and [Venice Beach](https://www.expedia.ca/Venice-Beach-Venice.d6127832.Vacation-Attraction) are two of our top suggestions. ### Are there any 5-star condos in Osprey? > Although there are no 5-star condos in Osprey, there are 4-star accommodations that have what you're looking for. Located about 11 kilometres from the downtown area, [Gulf Holiday By Beachside Management](https://www.expedia.ca/Sarasota-Hotels-Gulf-Holiday-By-Beachside-Management.h15052995.Hotel-Information) comes with concierge services and a swimming pool. Another upscale retreat is [Excelsior Beach To Bay - Bayside](https://www.expedia.ca/Sarasota-Hotels-Excelsior-Beach-To-Bay-Bayside.h45954544.Hotel-Information). It's roughly 8 kilometres from the centre of Osprey and has amenities like a swimming pool and a deck. ### Why book your condo in Osprey with Expedia? > With Expedia, it's a cinch to find your ideal condo in Osprey. After someplace luxurious? Make the most of our filters to search for properties that have a 5-star rating. If you have a set budget, select how much you're willing to spend and then browse our amazing options. We'll help you find the perfect fit whatever your escape looks like. ### How can I find cheap condos in Osprey? > With Expedia's user-friendly filter tool, comparing cheap condos in Osprey is a snap. To discover properties that'll make your wallet happy, refine your search by amenities, budget and star rating. ### What is there to do in Osprey near my condo? > If you'd like to make the most of your time in Osprey, be sure to stop by [Oscar Scherer State Park](https://www.expedia.ca/Oscar-Scherer-State-Park-Osprey.d6296013.Vacation-Attraction). 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[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) - 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