Title: Book the Best Siesta Key Village WINERY Hotels in 2025 | Expedia.ca [Siesta Key Village Travel Guide](https://expedia.ca/Siesta-Key-Siesta-Key-Village.dx6296072)[Flights to Siesta Key](https://expedia.ca/Cheap-Flights-To-Siesta-Key.d6881.Travel-Guide-Flights)[Things to do in Siesta Key](https://expedia.ca/Things-To-Do-In-Siesta-Key.d6881.Travel-Guide-Activities)[Siesta Key Village Car Rentals](https://expedia.ca/Car-Rentals-In-Siesta-Key-Village.d6296072.Car-Rental-Guide)[Siesta Key Village Vacations](https://expedia.ca/Siesta-Key-Village.d6296072.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495850-south-florida.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Siesta Key Village, FL from CA $516 ![](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 availability on Siesta Key Village Winery Hotels Tonight [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=6296072&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 21 - Oct 22](https://www.expedia.ca/Hotel-Search?regionId=6296072&startDate=2025-10-21&endDate=2025-10-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6296072&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6296072&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Siesta Key Village Winery Hotels ![Beach](https://images.trvl-media.com/lodging/94000000/93180000/93177100/93177081/efd4995b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93180000/93177100/93177081/f327afa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93180000/93177100/93177081/04100f57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/94000000/93180000/93177100/93177081/d24aabf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Close to Sarasota Beach/Pet Friendly Siesta Key Village 9.2/10 Wonderful (5) "Great house great location will definitely come back to this property " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew Y. CA $197 CA $516 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Siesta-Key-Hotels-Close-To-Sarasota-BeachPet-Friendly.h93177081.Hotel-Information) ![Fridge, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/41000000/40220000/40218100/40218100/7d764249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games](https://images.trvl-media.com/lodging/41000000/40220000/40218100/40218100/5bb3a318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/41000000/40220000/40218100/40218100/f03700de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/41000000/40220000/40218100/40218100/91a09390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shared Heated Pool, Steps to Siesta Key Village/Beach, Large Backyard Siesta Key Village 9.6/10 Exceptional (27) "Simple and easy booking and check in!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DAVID M. CA $257 CA $619 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Siesta-Key-Hotels-Shared-Heated-Pool.h40218100.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/94000000/93180000/93177100/93177085/860369ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93180000/93177100/93177085/a34f5202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93180000/93177100/93177085/w2042h1366x0y0-d7412200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93180000/93177100/93177085/c14911c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly Siesta Key Village 9.6/10 Exceptional (16) "Great location to walk to siesta key village. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) N A. CA $184 CA $500 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Beach-Duplex-Close-To-Sarasota-BeachPet-Friendly.h93177085.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/32000000/31950000/31948500/31948461/2d3a0198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31950000/31948500/31948461/c155ee00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31950000/31948500/31948461/1c655a0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31950000/31948500/31948461/75a5048c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Remodeled Townhome with Private Pool, Spa, and Ping Pong! Island Time East Siesta Key Village 9.6/10 Exceptional (46) "Love this place! Although there are ants around this area but in general it was a great place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emma CA $393 CA $882 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Siesta-Key-Hotels-Remodeled-Townhome-With-Private-Pool.h31948461.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/40000000/40000000/39999300/39999266/a8005616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/40000000/40000000/39999300/39999266/782d75f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/40000000/39999300/39999266/e86f2d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/40000000/39999300/39999266/c9bcc452.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vinca | Great Location in Siesta Key Village w/ Heated Pool, Walk to Beach! Siesta Key Village 9.4/10 Exceptional (28) "Beautifully located and walking distance to all the hot spots. Would 100% rent again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cori G. CA $493 CA $1,088 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Siesta-Key-Hotels-Vinca-Pet-Friendly-Home-Located-In-Siesta-Key-Village-W-Heated-Pool.h39999266.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/40000000/40000000/39998900/39998849/0f5d401d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/40000000/40000000/39998900/39998849/1a2e0319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/40000000/40000000/39998900/39998849/2d338236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/40000000/40000000/39998900/39998849/f5e5feb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lantana | Located in Siesta Key Village w/ Heated Pool, Walk to Beach! Siesta Key Village 9.4/10 Exceptional (10) "Truly perfectly appointed walkable distance to EVERYTHING! And decorated very modern beach decor, nothing like the pics- WAY BETTER! Stay here, you’ll love it. Def coming back!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victoria V. CA $737 CA $1,515 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Siesta-Key-Hotels-Lantana-Pet-Friendly-Home-Located-In-Siesta-Key-Village-W-Heated-Pool.h39998849.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22121900/22121870/71154fe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22130000/22121900/22121870/524a3b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/23000000/22130000/22121900/22121870/0b3ae689.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/23000000/22130000/22121900/22121870/587f9ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog Friendly, Private Heated Pool, Steps to the Beach and Shops! -Aruba Siesta Key Village 9.6/10 Exceptional (53) "Great location for a family with 3 sons in their 20's. Walk to everything. Both bunks are singles, a little tight for guys 6', but they got over it. Very easy check in & check out process. Never had any issues with noise from the bars that are close by. The hot water was a little wanky at times, but to be expected at the beach. Would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John P. CA $491 CA $966 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Siesta-Key-Hotels-Dog-Friendly.h22121870.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75800000/75790500/75790488/3c26ecf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75800000/75790500/75790488/eca98c8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75800000/75790500/75790488/e4b6e19f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75800000/75790500/75790488/45bb7376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach! Siesta Key Village 10/10 Exceptional (21) "Great location, cleaned @ cozy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ELIZABETH C. CA $627 CA $1,246 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Siesta-Key-Hotels-Sea-Foam-Pet-Friendly.h75790488.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/23000000/22130000/22121100/22121091/52ea1fe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22121100/22121091/fed2a931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22121100/22121091/9a48480b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels](https://images.trvl-media.com/lodging/23000000/22130000/22121100/22121091/b593dad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly Siesta Key Village 9.8/10 Exceptional (74) "We had the best time. Excellent location. Perfect cottage for entertaining. Loved that it was private and fenced around the pool. We were very comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandy M. CA $515 CA $971 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Siesta-Key-Hotels-Private-Heated-Pool.h22121091.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111510000/111508300/111508293/15048a57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111510000/111508300/111508293/140f8104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/112000000/111510000/111508300/111508293/e2fa7ec7_edited_42cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111510000/111508300/111508293/3f20a5ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village Siesta Key Village 9.6/10 Exceptional (15) "Great location! Cute little house with lots of potential. Needs some updating. Easy walk to everything. If you book bring a little speaker for the beach and a deck of cards. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Myria K. CA $940 CA $1,825 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Siesta-Key-Hotels-Pelicans-Place-Walk-To-Siesta-Key-Beach-Village.h111508293.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=2025-11-03&endDate=2025-11-04®ionId=6296072&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Siesta Key Village Hotel Reviews ## Explore a world of travel with Expedia - Lodging - More ways to book - [Hotels with Childcare in Clearwater Beach](https://www.expedia.ca/Clearwater-Beach-Hotels-Hotels-With-Childcare.0-0-d10759-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Golf Hotels in Clearwater](https://www.expedia.ca/Clearwater-Hotels-Golf-Hotel.0-0-d6033-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Clearwater](https://www.expedia.ca/Clearwater-Hotels-Hotel-With-Early-Check-In.0-0-d6033-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Clearwater](https://www.expedia.ca/Clearwater-Hotels-Hotels-With-Childcare.0-0-d6033-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Clearwater](https://www.expedia.ca/Clearwater-Hotels-Hotels-With-Smoking-Rooms.0-0-d6033-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - 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[Cheap Hotels in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Cheap-Hotels.0-0-d6881-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Couples-Resorts-Hotels.0-0-d6881-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Family-Hotel.0-0-d6881-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Golf-Hotel.0-0-d6881-tGolfHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Historic-Hotel.0-0-d6881-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Honeymoon-Hotels.0-0-d6881-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Hotels-With-A-Lazy-River.0-0-d6881-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Hotels-With-Balconies.0-0-d6881-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d6881-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Hotels-With-Free-Breakfast.0-0-d6881-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Hotels-With-Hot-Tubs.0-0-d6881-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Hotels-With-Indoor-Pool.0-0-d6881-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Siesta Key](https://www.expedia.ca/Siesta-Key-Hotels-Hotels-With-Kitchenettes.0-0-d6881-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - 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[Book Hotels in Siesta Key Village on Expedia.com](https://www.expedia.com/Siesta-Key-Village-Siesta-Key-Hotels-Winery-Hotel.0-n6296072-0-tWineryHotel.Travel-Guide-Filter-Hotels)