Title: Book the Best Siesta Key WINERY Hotels in 2025 | Expedia.ca [Siesta Key Travel Guide](https://expedia.ca/Siesta-Key.dx6881)[Hotels in Siesta Key](https://expedia.ca/Siesta-Key-Hotels.d6881.Travel-Guide-Hotels)[Vacation Rentals in Siesta Key](https://expedia.ca/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals)[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 Car Rentals](https://expedia.ca/Car-Rentals-In-Siesta-Key.d6881.Car-Rental-Guide)[Siesta Key Vacation Packages](https://expedia.ca/Siesta-Key.d6881.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/65000/65413-Siesta-Key.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Siesta Key, FL from CA $218 ![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 availability on Siesta Key Winery Hotels Tonight [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=6881&startDate=2025-09-28&endDate=2025-09-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=6881&startDate=2025-09-29&endDate=2025-09-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6881&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6881&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Siesta Key Winery Hotels ![Private beach nearby, white sand, free beach shuttle](https://images.trvl-media.com/lodging/12000000/11800000/11795500/11795409/184f21fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed, Pool View (UNIT3) | Private kitchen](https://images.trvl-media.com/lodging/12000000/11800000/11795500/11795409/61442a47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed (Unit 6) | Terrace/patio](https://images.trvl-media.com/lodging/12000000/11800000/11795500/11795409/03169117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed, Pool View (UNIT3) | Terrace/patio](https://images.trvl-media.com/lodging/12000000/11800000/11795500/11795409/433accb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Twin Palms at Siesta Siesta Key 9.6/10 Exceptional (558) "I really enjoyed my stay and will definitely return!" CA $193 CA $218 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Sarasota-Hotels-Twin-Palms-At-Siesta.h11795409.Hotel-Information) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/34000000/33940000/33937000/33936979/7389ede0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33940000/33937000/33936979/b7ad3fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33940000/33937000/33936979/0f359af8.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/34000000/33940000/33937000/33936979/a17f98a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to beach Heated POOL King bed DAILY WEEKLY Villa 1 SPECIALS Sarasota 9.6/10 Exceptional (55) "Very clean and great location”" CA $96 CA $297 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Sarasota-Hotels-Brand-New-Luxury-King-Villa-1-Pool-Walk-To-Beach-Xmas-30-OFF.h33936979.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/2550bef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/baa92889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/193334ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/c634db4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quick and Easy Walk Downtown - Tons of Amenities Central Sarasota 9.8/10 Exceptional (115) "Great little place to stay! " CA $145 CA $253 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Sarasota-Hotels-Quick-And-Easy-Walk-Downtown-Tons-Of-Amenities.h90345607.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) ![Dining](https://images.trvl-media.com/lodging/94000000/93180000/93177100/93177085/d3fd4bac.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) ### 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. " CA $181 CA $501 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Beach-Duplex-Close-To-Sarasota-BeachPet-Friendly.h93177085.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/32000000/31950000/31948600/31948573/589db89e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/32000000/31950000/31948600/31948573/1a65d36e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31950000/31948600/31948573/401be974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31950000/31948600/31948573/06c0ce32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo with Private Beach Access, Great Shared Amenities - Private Beach House Siesta Key 9.0/10 Wonderful (43) "This rental was in a great area with access to the free trolley. The beach was amazing! I would definitely stay here again." CA $293 CA $755 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Siesta-Key-Hotels-Condo-With-Private-Beach-Access.h31948573.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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/40000000/39999300/39999266/b140818e.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!" CA $448 CA $1,028 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Siesta-Key-Hotels-Vinca-Pet-Friendly-Home-Located-In-Siesta-Key-Village-W-Heated-Pool.h39999266.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/41000000/40220000/40218200/40218120/4e7cc31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games](https://images.trvl-media.com/lodging/41000000/40220000/40218200/40218120/32397d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/41000000/40220000/40218200/40218120/227db68a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/41000000/40220000/40218200/40218120/fd4e0bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stay at Summer Salt: Shared Heated Pool, Steps to Siesta Key Village and Beach Siesta Key Village 9.8/10 Exceptional (38) "The property was well kept, appeared to have been updated recently with new appliances. The location in the village and proximity to restaurants, shopes was perfect. Within walking distance to the beach. Management company was very responsive." CA $279 CA $654 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Siesta-Key-Hotels-Stay-At-Summer-Salt-Shared-Heated-Pool.h40218120.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/32000000/31950000/31948500/31948461/75a5048c.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/c155ee00.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 (45) "Perfect location, quiet, and accommodations were clean and updated. Nice little, pool and hit tub." [](https://www.expedia.ca/Siesta-Key-Hotels-Remodeled-Townhome-With-Private-Pool.h31948461.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/23000000/22130000/22121500/22121423/45b4411e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/23000000/22130000/22121500/22121423/29a9cb62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/23000000/22130000/22121500/22121423/0fc71008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/23000000/22130000/22121500/22121423/f59a4d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect for Families, Steps to Siesta Key Beach and Village! Siesta Key Village 9.8/10 Exceptional (62) "Loved the convenience of this property to the beach and the center of town. Will definitely look to stay here again when we return to Siesta Key. " CA $355 CA $776 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Siesta-Key-Hotels-Perfect-For-Families.h22121423.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/40000000/39970000/39965600/39965502/afa8bab8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39970000/39965600/39965502/e6f81680.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/40000000/39970000/39965600/39965502/fcd555ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39970000/39965600/39965502/ae1b0bef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Plumbago | Prime Location in Siesta Key Village w/ Heated Pool, Walk to Beach! Siesta Key Village 10/10 Exceptional (12) "Great property, close to town and the beach!" CA $632 CA $1,373 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Siesta-Key-Hotels-Plumbago-Pet-Friendly-Home-Located-In-Siesta-Key-Village-W-Heated-Pool.h39965502.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=2025-10-12&endDate=2025-10-13®ionId=6881&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Siesta Key Hotel Reviews ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Aloha Kai](https://www.expedia.ca/Aloha-Kai-Siesta-Key-Hotels-Adults-Only-Resorts.0-n553248635976469168-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Aloha Kai](https://www.expedia.ca/Aloha-Kai-Siesta-Key-Hotels-All-Inclusive-Hotel.0-n553248635976469168-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Aloha Kai](https://www.expedia.ca/Aloha-Kai-Siesta-Key-Hotels-Beach-Hotel.0-n553248635976469168-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Aloha Kai](https://www.expedia.ca/Aloha-Kai-Siesta-Key-Hotels-Casino-Hotel.0-n553248635976469168-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Aloha Kai](https://www.expedia.ca/Aloha-Kai-Siesta-Key-Hotels-Hotels-With-Kitchenettes.0-n553248635976469168-0-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - 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[Lgbt Friendly Hotels in Siesta Key Village](https://www.expedia.ca/Siesta-Key-Village-Siesta-Key-Hotels-LGBT-Friendly-Hotel.0-n6296072-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Siesta Key Village](https://www.expedia.ca/Siesta-Key-Village-Siesta-Key-Hotels-Luxury-Hotel.0-n6296072-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Siesta Key Village](https://www.expedia.ca/Siesta-Key-Village-Siesta-Key-Hotels-Mountain-Hotels.0-n6296072-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Siesta Key Village](https://www.expedia.ca/Siesta-Key-Village-Siesta-Key-Hotels-Oceanfront-Hotels.0-n6296072-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Siesta Key Village](https://www.expedia.ca/Siesta-Key-Village-Siesta-Key-Hotels-Pet-Friendly-Hotel.0-n6296072-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Siesta Key Village](https://www.expedia.ca/Siesta-Key-Village-Siesta-Key-Hotels-Romantic-Hotel.0-n6296072-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Siesta Key Village](https://www.expedia.ca/Siesta-Key-Village-Siesta-Key-Hotels-Spa-Hotel.0-n6296072-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in St. Pete Beach](https://www.expedia.ca/St-Pete-Beach-Hotels-Casino-Hotel.0-0-d9802-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in St. Pete Beach](https://www.expedia.ca/St-Pete-Beach-Hotels-Honeymoon-Hotels.0-0-d9802-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in St. Pete Beach](https://www.expedia.ca/St-Pete-Beach-Hotels-Shopping-Hotel.0-0-d9802-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Tampa](https://www.expedia.ca/Tampa-Hotels-Business-Hotel.0-0-d602996-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Tampa](https://www.expedia.ca/Tampa-Hotels-Couples-Resorts-Hotels.0-0-d602996-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Green Hotels in Tampa](https://www.expedia.ca/Tampa-Hotels-Green-Sustainable.0-0-d602996-tGreenSustainable.Travel-Guide-Filter-Hotels) - 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