Title: Osprey Condo Rentals from CA $170 | 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 Condos Rentals in Osprey from CA $170 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-02&endDate=2026-01-04&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) ![Exterior](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/105c6d3d.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) ### Chadwick Cove Resort & Marina Englewood 10/10 Exceptional (14) "Great place and location " CA $123 CA $766 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/24000000/23980000/23973100/23973025/c8fb5056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23980000/23973100/23973025/c08d6442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23980000/23973100/23973025/3dea3e3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/24000000/23980000/23973100/23973025/8d2157cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2nd Floor Retreat Overlooking the Pool & Gulf Silver Sands #251 Resort by RVA Longboat Key 8.6/10 Excellent (41) "Beautiful place with a private beach and a really nice clean condo. Had everything we needed for a relaxing weekend. Will definitely come back! Thank you." CA $181 CA $418 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-251-1-BR-1-BA-Resort-On-Longboat-Key-By-Rva.h23973025.Hotel-Information) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/75000000/74240000/74231000/74230942/w1347h900x1y0-a0293602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/75000000/74240000/74231000/74230942/w1347h900x1y0-92d3a598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74240000/74231000/74230942/d4032190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74240000/74231000/74230942/w1347h898x1y1-7756686b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sapphire Suite 1Bed/1Bath Indian Beach Sapphire Shores 9.8/10 Exceptional (83) "We loved our stay here, it was a perfect location with lots to do within even walking distance! " CA $105 CA $201 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Sarasota-Hotels-1Bed1bath-Suite.h74230942.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90950000/90945000/90944912/a71b4bf6.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) ### Cozy beach house! Just steps away from the world-class Manasota beach Englewood 9.8/10 Exceptional (6) "Great place. " CA $151 CA $589 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Englewood-Hotels-Cozy-Beach-House-Just-Steps-Away-From-The-World-Class-Manasota-Beach.h90944912.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/0caf09fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/2a71f7f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/887af080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/63000000/62600000/62599100/62599089/2ac6af12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverside Oasis 1Bed/1Bath Bayou Oaks 9.4/10 Exceptional (37) "Perfect little place for a couple days. Clean and conveniently located just a short drive away from everything you need. Host was responsive and accommodating. We would definitely stay here again. " CA $77 CA $170 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Sarasota-Hotels-Riverside-Oasis-1bed1bath.h62599089.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/64000000/63920000/63918500/63918463/2f921cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/64000000/63920000/63918500/63918463/ca15a667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/64000000/63920000/63918500/63918463/32531e4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63920000/63918500/63918463/d9d2cc79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Azul 2Bed/1Bath Bayou Oaks 9.4/10 Exceptional (66) "The home was decorated beautiful! We enjoyed ourselves. Comfortable and kitchen were stocked nicely. Great location, 5-10 minutes from most places of interest. Nice communication and easy to check in and out. " CA $126 CA $274 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Sarasota-Hotels-Casa-Azul-2bed1bath.h63918463.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/62000000/61510000/61501000/61500921/4c1f67bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/62000000/61510000/61501000/61500921/af4e5cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/62000000/61510000/61501000/61500921/c7c3880b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/62000000/61510000/61501000/61500921/f8c1a431.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront Bliss - The Beach on Longboat Key #106 Resort by RVA Longboat Key 8.8/10 Excellent (85) "Gorgeous location, the beach was exceptional and the area was quiet and felt secluded. The condo was a bit shabby but clean and had everything we needed. " CA $181 CA $422 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Sarasota-Hotels-The-Beach-On-Longboat-Key-106-Studio-1-BA-Resort-By-Rva.h61500921.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) ![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) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/4d68eb6d.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) ### Captiva Beach Resort South Village 9.0/10 Wonderful (1141) "2nd time and excellent as always..close to the beach and great surroundings " [](https://www.expedia.ca/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.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) ![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) ![Pool](https://images.trvl-media.com/lodging/70000000/69770000/69763000/69762951/32407fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*Charming 2bed 2 bath 6 mins from IMG\* South Bradenton 9.6/10 Exceptional (21) "Great place, spacious for 6 adults, clean, comfortable, organized with all the amenities one would need. Everything was simple from check in to check out. The queen-size air mattress fits seamlessly in the living room's common area and comes equipped with all necessary bedding to ensure a comfortable and restful experience.​ I would stay again!" CA $160 CA $501 total includes taxes & fees Oct 9 - Oct 10 [](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/22000000/21660000/21654400/21654400/82030823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/22000000/21660000/21654400/21654400/14078893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21660000/21654400/21654400/9b1d39a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, music library](https://images.trvl-media.com/lodging/22000000/21660000/21654400/21654400/b1c40dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway Sarasota 9.2/10 Wonderful (131) "Loved how close it is to siesta key beach" CA $195 CA $431 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Siesta-Key-Hotels-Spacious-Renovated-1-Bedroom-Siesta-Key-Beachside-Vacation-Rental-Getaway.h21654400.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) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73100000/73097800/73097706/1b988693.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/eaf6f67e.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) ### Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches Bradenton 9.8/10 Exceptional (59) "It was clean, comfy and ideal locarion. Close to beaches AMI and the pool was great. " CA $187 CA $541 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Bradenton-Hotels-Fantastic-Shorewalk-Vacation-2-Bed2-Bath-CondoLake-Viewclose-To-IMG.h73097706.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20140000/20139200/20139181/24e69366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/21000000/20140000/20139200/20139181/9caa008f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/21000000/20140000/20139200/20139181/8bb0ac0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, music library](https://images.trvl-media.com/lodging/21000000/20140000/20139200/20139181/1d8a6d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool Siesta Key 9.4/10 Exceptional (95) "A very pleasant and comfortable experience in a beautiful location." CA $229 CA $496 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Siesta-Key-Hotels-Walk-To-The-Beach-And-More-From-This-Fully-Renovated-Unit-W-Heated-Pool.h20139181.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/75000000/74630000/74621600/74621562/c2458bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74630000/74621600/74621562/d24a6a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/75000000/74630000/74621600/74621562/366d708c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, offices](https://images.trvl-media.com/lodging/75000000/74630000/74621600/74621562/3cf05452.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Coastal 2/2 condo w/pool 6 mins to IMG South Bradenton 10/10 Exceptional (25) "Had a great time and the pool are was super fun!" CA $160 CA $500 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Bradenton-Hotels-Modern-Coastal-22-Condo-Wpool-6-Mins-To-IMG.h74621562.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) ![Exterior](https://images.trvl-media.com/lodging/58000000/57230000/57225900/57225886/d47674ab.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) ![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) ### Beautifully furnished condo Bradenton 9.8/10 Exceptional (140) "Perfect for our weekend football tournament. Had everything we needed. " CA $84 CA $301 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Sarasota-Hotels-Beautifully-Furnished-Condo.h57225886.Hotel-Information) ![Beach nearby, beach umbrellas](https://images.trvl-media.com/lodging/24000000/23520000/23513800/23513789/b36a14be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/24000000/23520000/23513800/23513789/e18f0f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23520000/23513800/23513789/a0e753ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/24000000/23520000/23513800/23513789/d8c743bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resort w Private Beach Access/Pool-The Beach Club at Siesta Key #100B by RVA South Village 8.8/10 Excellent (80) "The place was tastefully decorated and clean. I loved the deck area. The location was close to the beach and walking distance to restaurants. There was a mildew smell that we didn't care for, but we after being in there we didn't notice it as much." CA $188 CA $430 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Sarasota-Hotels-The-Beach-Club-At-Siesta-Key-100b-1-BR-1-BA-Resort-On-Siesta-Key-By-Rva.h23513789.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/34cf9932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/9d6a1945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/8d98c265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/24000000/23300000/23291300/23291227/f3fd974c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Studio on Gulf! Cabana Beach Club #5B Longboat Key-Steps to Sand by RVA Longboat Key 8.2/10 Very good (71) "Wonderful spot. Highly recommend. " CA $174 CA $386 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Sarasota-Hotels-Cabana-Beach-Club-5b-Suite1-BA-Resort-On-Longboat-Key-By-Rva.h23291227.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/69000000/68160000/68153900/68153868/73b3f930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/69000000/68160000/68153900/68153868/6d5702ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/69000000/68160000/68153900/68153868/43b32c3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68160000/68153900/68153868/58f94d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Right on the beach.Renovated ground Floor unit 63. Longboat Key 9.4/10 Exceptional (54) "We thoroughly enjoyed our stay-perfect location, great accommodations, and wonderful staff!" CA $195 CA $465 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Sarasota-Hotels-Beach-Front-Condo-Paradise-Ground-Floor.h68153868.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/a6b1997c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/c848809a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/cdcfe3b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/24000000/23600000/23592700/23592665/812fc075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 2BR Condo! Pools~Free WiFi. Near IMG Academy~Beaches~AMI~Restaurants. Bradenton 9.8/10 Exceptional (143) "Great location, clean, everything we needed for a low key beach vacation!" CA $133 CA $426 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Sarasota-Hotels-Cozy-Condo-Free-Wifi.h23592665.Hotel-Information) ![Fridge, microwave](https://images.trvl-media.com/lodging/22000000/21660000/21655400/21655312/81a49782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/22000000/21660000/21655400/21655312/d87e47c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, music library](https://images.trvl-media.com/lodging/22000000/21660000/21655400/21655312/aca26486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21660000/21655400/21655312/b2a4804c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks Siesta Key 9.0/10 Wonderful (42) "The property was clean and comfortable. Having two bathrooms was very convenient. The only downside was that the pool was not well kept and could use a deep clean." CA $223 CA $579 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Siesta-Key-Hotels-Small-And-Quiet-Lakefront-Resort-On-Siesta-Key-W-Heated-Pool-And-Kayaks.h21655312.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/69000000/68020000/68014300/68014254/11d83294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/69000000/68020000/68014300/68014254/w1117h748x0y8-f33ff70b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68020000/68014300/68014254/5ac2c8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68020000/68014300/68014254/4c1077b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach Siesta Key 9.8/10 Exceptional (97) "The Oystercatcher cottage was an A+! It has great amenities. The screened porch with the fans was very comfortable. We enjoyed the games in the evenings after dinner. The beach cart was very functional and hauled all the provided beach supplies easily. Today we are going to try the kayaks! " CA $232 CA $583 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Siesta-Key-Hotels-Clean.h68014254.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=2025-10-22&endDate=2025-10-23®ionId=55888&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-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 ![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) ![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) ![Golden Host Resort - Sarasota](//images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg) ### Golden Host Resort - Sarasota 10/10 Excellent "Relaxing and beautiful place! The garden and pool areas are very nice to exercise and practice yoga or meditation. The staff is super friendly! The rooms are great and you can park by your room. I feel at home at the Golden Host Resort. Thank you! 🙏😃💙" [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information) ## Find out more about Osprey ## Osprey Condo Rentals information | Number of reviews | 2,112 | | --- | --- | | Accommodation | 3726 Condo Rentals | | Lowest Price | CA $170 | | Highest Price | CA $766 | ## Frequently asked questions ### How much do condos in Osprey cost? > Condos in Osprey range from CA $170 to CA $766 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 9.4. [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 3726 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 $170 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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