Title: Book the Best HISTORIC Hotels in Lakeland - Winter Haven in 2025 | Expedia.ca [Lakeland - Winter Haven Travel Guide](https://expedia.ca/Lakeland-Winter-Haven.dx6048230)[Hotels in Lakeland - Winter Haven](https://expedia.ca/Lakeland-Winter-Haven-Hotels.d6048230.Travel-Guide-Hotels)[Vacation Rentals in Lakeland - Winter Haven](https://expedia.ca/Lakeland-Winter-Haven-Vacation-Rentals.d6048230.Travel-Guide-VacationRentals)[Flights to Lakeland - Winter Haven](https://expedia.ca/Cheap-Flights-To-Lakeland-Winter-Haven.d6048230.Travel-Guide-Flights)[Things to do in Lakeland - Winter Haven](https://expedia.ca/Things-To-Do-In-Lakeland-Winter-Haven.d6048230.Travel-Guide-Activities)[Lakeland - Winter Haven Car Rentals](https://expedia.ca/Car-Rentals-In-Lakeland-Winter-Haven.d6048230.Car-Rental-Guide)[Lakeland - Winter Haven Vacation Packages](https://expedia.ca/Lakeland-Winter-Haven.d6048230.Destination-Travel-Guides) ![Lakeland - Winter Haven featuring rides and signage as well as an individual child](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63378-Lakeland-Winter-Haven.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Lakeland - Winter Haven, FL - ![](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 Lakeland - Winter Haven Historic Hotels Tonight [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Lakeland - Winter Haven Historic Hotels ![Meeting facility](https://images.trvl-media.com/lodging/1000000/210000/209700/209651/d3314a29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/210000/209700/209651/3c5a406e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/209700/209651/7c4454a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/210000/209700/209651/79fa5cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Terrace Hotel Lakeland, Tapestry Collection by Hilton Downtown Lakeland 9.2/10 Wonderful (336) "Very clean and centrally located. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander CA $183 CA $205 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Lakeland-Hotels-The-Terrace-Hotel-Lakeland.h209651.Hotel-Information) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/10000/800/702/74ea6ef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 9 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/800/702/e1a4eff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch LED TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/10000/800/702/43789e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Accessible, Kitchenette | Private kitchenette](https://images.trvl-media.com/lodging/1000000/10000/800/702/38c9c0f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home 1 Suites Extended Stay - Kissimmee Kissimmee 6.6/10 (1015) "Ive stayed at this hotel years ago " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George CA $77 CA $87 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Orlando-Hotels-Home-1-Suites-Extended-Stay-Kissimmee.h702.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33703900/33703840/495f3e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33710000/33703900/33703840/2773a9a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33710000/33703900/33703840/f2400863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33703900/33703840/1968fb21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake View 2 Bed 2 Bath LOFT With Pool, Gym, Pickleball ---- L@@K FOR DISCOUNTS ! Brandon 9.8/10 Exceptional (199) "The property is perfect. Relaxing, tranquil and convenient! Very clean! It had all the necessities for a stay. Great area with plenty of places to eat and easy access. You might consider black out curtains for the bedroom. :)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darren W. CA $167 CA $497 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Tampa-Hotels-Lake-View-2-Bed-2-Bath-Loft-With-Pool.h33703840.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/68000000/67050000/67045900/67045843/w4089h2720x7y0-b93cf7d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/68000000/67050000/67045900/67045843/effc7e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67050000/67045900/67045843/w1021h679x3y4-2b99f806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, offices](https://images.trvl-media.com/lodging/68000000/67050000/67045900/67045843/a25e767a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 3BR Lake Morton Bungalow Walk to Downtown East Lake Morton 9.6/10 Exceptional (21) "Loved the property. Very nice kitchen for holiday cooking. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christie P. CA $132 CA $433 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Lakeland-Hotels-Luxury-3BR-Lake-Morton-Bungalow-Walk-To-Downtown.h67045843.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/30000000/29640000/29635100/29635018/1443b0f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, table tennis, stereo](https://images.trvl-media.com/lodging/30000000/29640000/29635100/29635018/e73784bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29640000/29635100/29635018/90-4dc5a9a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29640000/29635100/29635018/f073b8a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 95+/N TODAY-30, NOV 20-DEC 26 POOL LAKE FIREWORK VIEW 9:30PM LOVELY 1 BDR 2 BTHS Orlando 9.4/10 Exceptional (142) "Great location close to everything - the bedroom needed attention with the ceiling fan, lights and a few of the outlets didn’t work- the master bath sink didn’t drain well- also the other bath had the same issue- but loved the balcony (minus the 70’s music selection lol) and space in the place! We would def stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Crystal B. CA $133 CA $382 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Orlando-Hotels-DEAL-DEC-11-25-79N-1-BDR-2BTHS-SUITE-8-FLPOOL.h29635018.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/34000000/33580000/33572400/33572398/f8de6cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33580000/33572400/33572398/a3c13515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33580000/33572400/33572398/de603ef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/34000000/33580000/33572400/33572398/aa407b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stay in the Charming Historic District ~ Walk to FSC, Downtown & Lake Morton East Lake Morton 9.8/10 Exceptional (47) "Everything at this property is great. This was my second stay and the house is comfortable, well maintained, and near the things we wanted to do. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana S. CA $163 CA $470 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Lakeland-Hotels-Lake-Morton-Luxury-3BR-2BA-Get-Away-Downtown-Lakeland-Florida-Southern-College.h33572398.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156005/53878cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156005/f341bf29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156005/35b628ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156005/w1602h1200x158y0-29ad31c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lucaya, 4br, 3ba, 13’ to Disney Parks & Outlets. 3’ to Walmart, Publix and Aldi. Kissimmee 9.0/10 Wonderful (12) "All is good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angelo L. CA $196 CA $653 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Orlando-Hotels-Lucaya-Village-Close-To-Disney-Parks-Outlets.h24156005.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/27000000/26690000/26685200/26685198/62ea5ab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/27000000/26690000/26685200/26685198/c882a453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/27000000/26690000/26685200/26685198/e7278a58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/27000000/26690000/26685200/26685198/119abca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Remodeled 3/2 condo minutes to Parks, shopping and entertainment Royal Palm Bay 9.4/10 Exceptional (44) "The location was perfect for our needs and true to it's online description." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angie S. CA $125 CA $360 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Orlando-Hotels-Remodeled-32-Condo-Minutes-To-Parks.h26685198.Hotel-Information) ![Smart TV, video games, DVD player, foosball](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/fb1d15ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/e1b49758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, DVD player, foosball](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/e71c9e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/a9db2dc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*Tinkerbells Castle 2\* Private Pool & Spa Overlooking Lake & Disney Fire Works kissimmee 9.4/10 Exceptional (77) "The location was great and very clean. Would stay there again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan H. CA $210 CA $609 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Orlando-Hotels-Tinkerbells-Castle-2-Private-Pool-Spa-Overlooking-Lake-Disney-Fire-Works.h33584838.Hotel-Information) ![Smart TV, DVD player, foosball, books](https://images.trvl-media.com/lodging/34000000/33650000/33648300/33648289/1726442e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, foosball, books](https://images.trvl-media.com/lodging/34000000/33650000/33648300/33648289/cb82f442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33650000/33648300/33648289/3cdad71b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33650000/33648300/33648289/3ef6b534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*Tinkerbells Castle 1\* Private Pool & Spa Overlooking Lake & Disney Fire Works Kissimmee 9.6/10 Exceptional (134) "This was a great place to stay close to Disney in a quiet location . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vanessa B. CA $217 CA $617 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Orlando-Hotels-Tinkerbells-Castle-1-Private-Pool-Spa-Overlooking-Lake-Disney-Fire-Works.h33648289.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=2025-11-16&endDate=2025-11-17®ionId=6048230&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Lakeland - Winter Haven Hotel Reviews ![Holiday Inn Club Vacations at Orange Lake Resort by IHG](//images.trvl-media.com/lodging/1000000/10000/6400/6315/ac7826b3_y.jpg) ### Holiday Inn Club Vacations at Orange Lake Resort by IHG 10/10 Excellent "The property was more than we expected and the stay was amazing! We loved everything about the place, and the ad doesn’t do it justice. " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ![Hilton Vacation Club Aqua Sol Orlando West](//images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg) ### Hilton Vacation Club Aqua Sol Orlando West 10/10 Excellent "We didn’t have breakfast here we cooked instead. However it’s always a pleasure to stay here. My family and I have been going here since I was a child, although it was called something different up until a few years ago it’s always a pleasure. The staff is very friendly and attentive, they always make you feel like you’re at home. We go at least once a year and we will continue to go as long as the service stays the same. ❤️" [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Hilton Vacation Club Mystic Dunes Orlando](//images.trvl-media.com/lodging/1000000/900000/891000/890951/0b826e24_y.jpg) ### Hilton Vacation Club Mystic Dunes Orlando 10/10 Excellent "Clean by see" [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![Meli�á Orlando Celebration](//images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/b440f6b4_y.jpg) ### Meliá Orlando Celebration 10/10 Excellent "Property is close to everything and away from the chaos!" 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