Title: Osprey Vacation Home Rentals from CA $284: Search Top Private Vacation Homes for Rent | 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) # Osprey Vacation Rentals - ![](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 [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Osprey Vacation Homes ![Beach towels](https://images.trvl-media.com/lodging/121000000/120690000/120681800/120681763/68ecfea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120690000/120681800/120681763/b9ad1c9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120690000/120681800/120681763/24f433bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/121000000/120690000/120681800/120681763/9ef89cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Osprey Home Bay Acres CA $252 CA $449 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Osprey-Hotels-Charming-Osprey-Home.h120681763.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/108000000/107130000/107124400/107124315/59d65e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107130000/107124400/107124315/672e08fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107130000/107124400/107124315/a1cf43be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107130000/107124400/107124315/7bbc5d51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable 3-bedroom home with WiFi and AC in Englewood, 3.5 mil. to beache Englewood Central 9.6/10 Exceptional (4) "This property is clean, well appointed, and made it very easy to get to the family gathering we were attending. Once the beach is repaired from the hurricanes this fall, it's a short drive to the beach, it's half a mile from a grocery store and pharmacy, and feels very cozy and private. The host communicated well. I would definitely recommend this property to anyone visiting Englewood. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Library G. CA $120 CA $507 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Englewood-Hotels-Comfortable-3-Bedroom-Home-With-WiFi-And-AC-In-Englewood.h107124315.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/12c40feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/6732718a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/4388cc53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111600000/111594000/111593945/44d01fef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nestled in North Port. Updated 2 Bed / 1 Bath. North Port 10/10 Exceptional (11) "Very cute and cozy home in North Port FL close to shops and not a far drive to the beach. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James Y. CA $101 CA $287 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/North-Port-Hotels-Nestled-In-North-Port-Updated-2-Bed-1-Bath.h111593945.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/87000000/86150000/86141600/86141519/0e99ebb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/87000000/86150000/86141600/86141519/e4384efb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/87000000/86150000/86141600/86141519/e62d3bc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86150000/86141600/86141519/35770cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coastal duplex with private beach access & deck - dog-friendly Manasota Key 8.4/10 Very good (12) "Like the golf cart pickup to take you to restaurants" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheri S. CA $124 CA $519 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Englewood-Hotels-Coastal-Duplex-With-Easement-Access-To-Private-Beach-Deck-Dog-Friendly.h86141519.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/101000000/100470000/100460700/100460636/986859b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100470000/100460700/100460636/389e910c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/101000000/100470000/100460700/100460636/b34722ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100470000/100460700/100460636/a6c905a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PLACE TO BE. we have everything you need Warm Mineral Springs 9.6/10 Exceptional (8) "We thoroughly enjoyed our stay! The property was impeccably clean, boasted a prime location, and featured a well-equipped kitchen. It had everything we needed for a wonderful stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex M. CA $124 CA $377 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/North-Port-Hotels-PLACE-TO-BE-We-Have-Everything-You-Need.h100460636.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/93000000/92390000/92387100/92387071/cdeff57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, printers](https://images.trvl-media.com/lodging/93000000/92390000/92387100/92387071/3070f17e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92390000/92387100/92387071/1ca7b18b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92390000/92387100/92387071/8c82ae31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Getaway with the pool North Port 10/10 Exceptional (26) "Nice house." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joanne f. CA $138 CA $485 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/North-Port-Hotels-Perfect-Getaway-With-The-Pool.h92387071.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/6fb611a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/c128477b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/822b1606.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/3520b4e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Floridian cottage in Historic Gulf Village Olde Englewood Village 9.8/10 Exceptional (60) "Had a nice stay. Clean and well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debi D. CA $138 CA $347 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/108000000/107080000/107080000/107079950/30aed0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107080000/107080000/107079950/eeca4027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107080000/107080000/107079950/a7dd08c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107080000/107080000/107079950/e41f7ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxation Awaits: Luxurious Vacation Home with Heated Pool near Mineral Springs North Port 10/10 Exceptional (6) "This house is big and beautiful with all the amenities! Would definitely recommend to anyone!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashlee M. CA $193 CA $736 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/North-Port-Hotels-Relaxation-Awaits-Luxurious-Vacation-Home-With-Heated-Pool-Near-Mineral-Springs.h107079950.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109040000/109033500/109033458/8fe95d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109040000/109033500/109033458/99091efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower](https://images.trvl-media.com/lodging/110000000/109040000/109033500/109033458/4116835f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109040000/109033500/109033458/4282a8ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mermaid at Tiny House Siesta Sarasota 10/10 Exceptional (2) "It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jackeline R. CA $157 CA $284 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Sarasota-Hotels-The-Mermaid-At-Tiny-House-Siesta.h109033458.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107611800/107611754/w1290h1721x0y538-61c2ec39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107611800/107611754/3b8a52ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/108000000/107620000/107611800/107611754/71091855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/108000000/107620000/107611800/107611754/0449e44b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches! Sabal Harbour 10/10 Exceptional (19) "Everything was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa and Colin M. CA $170 CA $484 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Bradenton-Hotels-Enjoy-Coastal-Townhome-W-Sunset-Views-Near-The-Gulfs-Most-Popular-Beaches.h107611754.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97720000/97719700/97719679/78502473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/98000000/97720000/97719700/97719679/ceb06f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97720000/97719700/97719679/8f06bb27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97720000/97719700/97719679/07ee3211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Everything you need! Beach– 2 Kings - Dog Friendly Englewood Central 10/10 Exceptional (9) "We loved this place- well stocked, clean and nice location. Has a lot of amenities that made the stay nice- beach supplies, 2 size coolers, games, beach towels, bikes, good assortment of dishes and cookware. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $183 CA $442 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Englewood-Hotels-4-Min-To-The-Beach-Couples-Retreat-W-Hot-Tub-Pet-Friendly.h97719679.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/115000000/114560000/114550600/114550589/w1280h963x0y0-b07a1fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114560000/114550600/114550589/bf22ed61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114560000/114550600/114550589/a90080d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114560000/114550600/114550589/86c7dc48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom house in Englewood with WiFi and AC Englewood South CA $168 CA $419 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Englewood-Hotels-Charming-2-Bedroom-House-In-Englewood-With-WiFi-And-AC.h114550589.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/4404083b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/5db57a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/bbfe2841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75990000/75989300/75989217/8d2b7f06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Myakka River Venice 9.8/10 Exceptional (18) "What a wonderful home off the beaten path totally redone Lori has done a great job" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff L. l. CA $259 CA $642 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Venice-Hotels-Myakka-River.h75989217.Hotel-Information) ![Condo, Pool View | Private kitchen](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/0ea98630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Lake View | Private kitchen](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/74e8ca6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![39-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/044717f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/93c41295.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Heron Suites & Villas Siesta Key 8.4/10 Very good (37) "It was perfect for my family of 4 for our beach vacation!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesse [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Heron-Suites-Villas.h59661429.Hotel-Information) ![Smart TV, stereo](https://images.trvl-media.com/lodging/109000000/108590000/108585600/108585518/7e83ed7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108590000/108585600/108585518/e081ceb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108590000/108585600/108585518/7148e781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108590000/108585600/108585518/8c491d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming home near Anna Maria Island with Jacuzzi Bradenton 10/10 Exceptional (14) "Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle S. CA $170 CA $395 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Bradenton-Hotels-Charming-Home-Near-Anna-Maria-Island-With-Jacuzzi.h108585518.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84060000/84052300/84052263/5ea61254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/85000000/84060000/84052300/84052263/147a94ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/85000000/84060000/84052300/84052263/5b48aa47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/85000000/84060000/84052300/84052263/a2cb8a8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish house minutes from the beach South Venice 9.6/10 Exceptional (25) "Great location and safe neighborhood. Definitely will stay again if available." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luis M. CA $150 CA $482 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Venice-Hotels-Stylish-House-Minutes-From-The-Beach.h84052263.Hotel-Information) ![322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/aa15caa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/08963d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![711 Beach Rd, Siesta Key, FL No Pool](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/5d33a805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/9ff42f58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Key Island Rentals Siesta Key 9.6/10 Exceptional (48) "This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julianna CA $165 CA $393 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Island-Rentals.h89714291.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/8aa0ab0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/7c9280ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/6b5f791e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33400000/33393800/33393742/1da0f055.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES Sarasota 9.6/10 Exceptional (35) "Looking forward to staying there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) aimen s. CA $113 CA $566 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Sarasota-Hotels-Extremely-Comfortableclean-VILLAS-Heated-Pool-And-Jacuzzi-SUMMER-SPECIAL-RATES.h33393742.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/96000000/95450000/95445800/95445737/b54b21c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95450000/95445800/95445737/w1599h1065x1y1-be896b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95450000/95445800/95445737/w1599h1066x1y1-abac8e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95450000/95445800/95445737/w1600h1067x0y1-f83ca066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ringling Retreat Central Sarasota 9.8/10 Exceptional (6) "This small home is very well designed and set up. Super clean and comfy. We really appreciated all the little details that helped make our 2 night stay very comfortable. We mostly walked to explore the city. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) natasha a. CA $153 CA $370 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Sarasota-Hotels-The-Ringling-Retreat.h95445737.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/28000000/27830000/27825300/27825246/54f38120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/28000000/27830000/27825300/27825246/w7358h4896x2y16-28169f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27830000/27825300/27825246/682b8a52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/28000000/27830000/27825300/27825246/111c90cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Florida bungalow with pool and fenced-in yard. Ringling Park 10/10 Exceptional (36) "Great Property. Clean, near everything but on a quiet street! Fabulous Communication with host! will Definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerry B. CA $147 CA $442 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Sarasota-Hotels-Charming-Florida-Bungalow-With-Pool-And-Fenced-In-Yard.h27825246.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=2025-11-15&endDate=2025-11-16®ionId=55888&adults=2&lodging=VACATION_HOME&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-Private-Vacation-Homes.d55888-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOsprey-Private-Vacation-Homes.d55888-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Osprey Hotel Reviews ![The Westin Sarasota](//images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3_y.jpg) ### The Westin Sarasota 10/10 Excellent "Amazing " [](https://expedia.ca/Sarasota-Hotels-The-Westin-Sarasota.h16818933.Hotel-Information) ![Tropical Breeze Resort](//images.trvl-media.com/lodging/1000000/880000/879700/879629/9de12888_y.jpg) ### Tropical Breeze Resort 10/10 Excellent "Spotless room, great staff, great location " [](https://expedia.ca/Sarasota-Hotels-Tropical-Breeze-Resort.h879629.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 "Reception staff was very friendly." [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information) ![Carlisle Inn](//images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/9a1b0e30_y.jpg) ### Carlisle Inn 10/10 Excellent "Beautiful property, very clean, very well kept " [](https://expedia.ca/Sarasota-Hotels-Carlisle-Inn.h19761082.Hotel-Information) ![Kompose Boutique Hotel](//images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg) ### Kompose Boutique Hotel 10/10 Excellent "This hotel was one for the books for my boyfriend and I. first saty here and we're already looking forward to our next stay. Location, staff, comfortability, safety, cleanliness and everything in-between was amazing!!" [](https://expedia.ca/Sarasota-Hotels-Kompose-Hotel-Sarasota.h38215316.Hotel-Information) ![Siesta Key Palms Resort](//images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/86bd1cda_y.jpg) ### Siesta Key Palms Resort 10/10 Excellent "Cute place near the beach. A great place for a gateway with the wife." [](https://expedia.ca/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.Hotel-Information) ![Hyatt Place Sarasota/Bradenton Airport](//images.trvl-media.com/lodging/3000000/2280000/2277500/2277489/6e9ac4ec_y.jpg) ### Hyatt Place Sarasota/Bradenton Airport 10/10 Excellent "Management Service was the best! " [](https://expedia.ca/Sarasota-Hotels-Hyatt-Place-SarasotaBradenton-Airport.h2277489.Hotel-Information) ![Casey Key Resorts - Mainland](//images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/164f19b9_y.jpg) ### Casey Key Resorts - Mainland 10/10 Excellent "Staff were very friendly & accommodating, rooms are clean. " [](https://expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![Comfort Suites Sarasota - Siesta Key](//images.trvl-media.com/lodging/6000000/5640000/5637500/5637457/a4f997ef_y.jpg) ### Comfort Suites Sarasota - Siesta Key 10/10 Excellent "The hotel was good and staff was great" [](https://expedia.ca/Sarasota-Hotels-Comfort-Suites-Sarasota-Siesta-Key.h5637457.Hotel-Information) ## Find out more about Osprey ## Osprey Vacation Homes information | Number of reviews | 298 | | --- | --- | | Accommodation | 3909 Vacation Homes | | Lowest Price | CA $284 | | Highest Price | CA $736 | ## Explore a world of travel with Expedia - Lodging - Packages - Vacation Rental - Other - More ways to book - [Beach Hotel Hotels in Bay Acres](https://www.expedia.ca/Bay-Acres-Osprey-Hotels-Beach-Hotel.0-n553248635976472153-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Bay Acres Hotels](https://www.expedia.ca/Bay-Acres-Osprey-Hotels.0-n553248635976472153-0.Travel-Guide-Filter-Hotels) - 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