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 $240 ![](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 Winery Hotels Tonight [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=6881&startDate=2025-10-19&endDate=2025-10-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=6881&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6881&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6881&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Siesta Key Winery Hotels ![Interior](https://images.trvl-media.com/lodging/35000000/34340000/34330800/34330706/94c7261f.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/35000000/34340000/34330800/34330706/111b0865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool, sun loungers](https://images.trvl-media.com/lodging/35000000/34340000/34330800/34330706/68b70d55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, shampoo, toilet paper](https://images.trvl-media.com/lodging/35000000/34340000/34330800/34330706/0f55e01a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### POOL VIEW V5 King Bedroom Siesta Key Walk to beach DAILY SPECIALS Sarasota 9.8/10 Exceptional (110) "Very comfortable beds and linens, extremely clean room and beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesica Aznar CA $139 CA $294 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Sarasota-Hotels-New-Everything-V5-Luxury-King-Bedroom-Siesta-Key-Pool-Walk-To-Beach-AUG-13-TH.h34330706.Hotel-Information) ![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) | Terrace/patio](https://images.trvl-media.com/lodging/12000000/11800000/11795500/11795409/433accb0.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) ![Outdoor pool, a heated pool, open open 24 hours, sun loungers](https://images.trvl-media.com/lodging/12000000/11800000/11795500/11795409/9914d09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Twin Palms at Siesta Siesta Key 9.6/10 Exceptional (562) "I really enjoyed my stay and will definitely return!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caitlin CA $212 CA $240 total includes taxes & fees Oct 21 - Oct 22 [](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) ![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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33940000/33937000/33936979/78375ea6.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”" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Attila CA $125 CA $330 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Sarasota-Hotels-Brand-New-Luxury-King-Villa-1-Pool-Walk-To-Beach-Xmas-30-OFF.h33936979.Hotel-Information) ![Beach towels](https://images.trvl-media.com/lodging/25000000/24940000/24934300/24934298/87099c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/25000000/24940000/24934300/24934298/2645a6cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/25000000/24940000/24934300/24934298/58be21f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/25000000/24940000/24934300/24934298/cdac4878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### POOL VIEW V6 2 bed 2 bath VILLA Walk to beach DAILY WEEKLY SPECIALS Sarasota 9.6/10 Exceptional (48) "Great place and location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason E. CA $209 CA $468 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Siesta-Key-Hotels-POOL-VIEW-V6-Luxury-2-Bed-2-Bath-VILLA-Walk-To-Beach-DAILY-WEEKLY-SPECIALS.h24934298.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/33000000/32070000/32062300/32062218/4fe7114f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32070000/32062300/32062218/a2dd7ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/33000000/32070000/32062300/32062218/d946e722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32070000/32062300/32062218/3a1f804d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta beach....one and only Sarasota 9.6/10 Exceptional (188) "Great property, clean, friendly, great area, and communication " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Courtney C. CA $175 CA $643 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Beachone-And-Only.h32062218.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) ![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) ![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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) N A. CA $186 CA $504 total includes taxes & fees Oct 20 - Oct 21 [](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) ![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31950000/31948600/31948573/06c0ce32.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) ![TV](https://images.trvl-media.com/lodging/32000000/31950000/31948600/31948573/1a65d36e.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 (44) "Great overall stay Looks like the place may have never been rented before and fresh out of a remodel Dishwasher not mounted I think the wash machine leaked pretty bad. We did 5 loads of laundry and 2twice there was a bunch of water coming from the closet by the laundry.The vent for the dryer does no vent to the exterior it vents in the closet and fills with hot air and moisture when running, you can already see the shelf de laminating, if not remedied mold with appear really soon. It was also... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joellen H. CA $251 CA $698 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Siesta-Key-Hotels-Condo-With-Private-Beach-Access.h31948573.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) ![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/41000000/40220000/40218100/40218100/1d321003.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) ### 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 20 - Oct 21 [](https://www.expedia.ca/Siesta-Key-Hotels-Shared-Heated-Pool.h40218100.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/19000000/19000000/18992900/18992855/2197968d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/19000000/18992900/18992855/95e9801a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/19000000/18992900/18992855/af0c372e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/19000000/18992900/18992855/95b48188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3 bedr townhouse beach retreat, only 60 steps to Siesta Key Public Beach! Siesta Key 9.6/10 Exceptional (79) "This ended up being a perfect location for our beach vacation! Close to the beach, provided plenty of beach chairs/umbrellas/boogie boards, and close to trolley stops. We had a great time in this VRBO!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary H. CA $694 CA $1,226 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Sarasota-Hotels-Safe-Clean-Royal-Palm-Suite-Only-60-Steps-To-The-Siesta-Key-Public-Beach.h18992855.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) ![Exterior](https://images.trvl-media.com/lodging/76000000/75800000/75790500/75790488/e4b6e19f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75800000/75790500/75790488/cfa37abd.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) "Near beach and town." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kim d. 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) 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=2025-11-02&endDate=2025-11-03®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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