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 [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-24&endDate=2025-10-26&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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/210000/209700/209651/0053dec2.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 (330) "Great place to stay " CA $195 CA $218 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Lakeland-Hotels-The-Terrace-Hotel-Lakeland.h209651.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498652/f4709b0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498652/4dfe2454.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498652/c2afc928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33500000/33498700/33498652/881968e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Cottage Near Florida Southern College ~ Dogs Welcome~ Walk Everywhere Lakeland 9.8/10 Exceptional (50) "Spent a week for business and this was perfect! Loved the office nook and outdoor area. Location is quiet and close to everything in Lakeland. Communication was excellent! Highly recommend!" [](https://www.expedia.ca/Lakeland-Hotels-Lakelands-Charming-Luxury-Cottage-Retreat-Near-Downtown-Walk-Everywhere.h33498652.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) ![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) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/800/702/7b6f0287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home 1 Suites Extended Stay - Kissimmee Kissimmee 6.6/10 (1008) "Ive stayed at this hotel years ago " CA $83 CA $94 total includes taxes & fees Nov 16 - Nov 17 [](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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33710000/33703900/33703840/cae201ef.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) "Excellent location, perfect little condo with all the necessities. Had a wonderful time. Loved the added bonus of having a washer and dryer" CA $167 CA $494 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Tampa-Hotels-Lake-View-2-Bed-2-Bath-Loft-With-Pool.h33703840.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) ![Smart TV, Netflix, DVD player, books](https://images.trvl-media.com/lodging/27000000/26690000/26685200/26685198/df8828ca.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) ### Remodeled 3/2 condo minutes to Parks, shopping and entertainment Royal Palm Bay 9.4/10 Exceptional (44) "Property owner was very responsive to any and all questions and concerns. Location was ideal for convention center but you definitely need to leave time to deal with traffic. We stayed for volleyball tournament and had a lot of early morning games. " CA $125 CA $363 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Orlando-Hotels-Remodeled-32-Condo-Minutes-To-Parks.h26685198.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) ![Interior](https://images.trvl-media.com/lodging/30000000/29640000/29635100/29635018/f073b8a3.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) ![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) ### 95+/N OCT 20-24, 26-30 POOL LAKE DISNEY FIREWORK VIEW 9:30 PM LOVELY 1 BDR 2 BTH Orlando 9.4/10 Exceptional (142) "The room was better than expected and clean. My most memorable attribute was the jetted tub! Enjoyed every minute of it!" CA $120 CA $375 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Orlando-Hotels-DEAL-DEC-11-25-79N-1-BDR-2BTHS-SUITE-8-FLPOOL.h29635018.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34590000/34580900/34580812/ddfe41e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory foam beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/35000000/34590000/34580900/34580812/d1fae451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34590000/34580900/34580812/ca833898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/35000000/34590000/34580900/34580812/027523c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY! Kissimmee 9.6/10 Exceptional (106) "Everything was great clean space great location " CA $188 CA $554 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Orlando-Hotels-Only-15-Miles-TO-Disney-World.h34580812.Hotel-Information) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33750000/33740900/33740892/baa4e474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33750000/33740900/33740892/0d17e385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33750000/33740900/33740892/9936c543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, DVD player, foosball](https://images.trvl-media.com/lodging/34000000/33750000/33740900/33740892/a66e233a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 7 BDRM, Private Pool, Hot Tub, Games, New Decor, New Mgmt., 10 min to parks! Kissimmee 9.2/10 Wonderful (57) "Plenty of living space, a lovely pool/hot tub, and fantastic game room with pool table, foosball and pac man. The management were responsive to our needs and the clubhouse offered another pool and other amenities. The kids enjoyed basketball, golf and a tennis court. This was our second year in this house. I highly recommend it." CA $223 CA $732 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Orlando-Hotels-Huge-7-BDRM.h33740892.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) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/0f7bc4d1.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) ![Game room](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/e1b49758.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 house was absolutely great and perfect for our family. Its located close to Disney. We have finally found our Disney vacation spot!" CA $211 CA $611 total includes taxes & fees Oct 19 - Oct 20 [](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) ![Dining](https://images.trvl-media.com/lodging/34000000/33650000/33648300/33648289/4658c592.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) ![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 (131) "Our family of 5 stayed here (all 18) and it was perfect. Close to Disney which was nice. Pool and jacuzzi were utilized a lot in our short stay. " CA $202 CA $600 total includes taxes & fees Oct 26 - Oct 27 [](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=2025-10-30&endDate=2025-10-31®ionId=6048230&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Lakeland - Winter Haven Hotel Reviews ![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 "Our room was very nice and the staff was nice, helpful, and friendly. " [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Destiny Palms Hotel Maingate West](//images.trvl-media.com/lodging/1000000/430000/427400/427337/d056f561_y.jpg) ### Destiny Palms Hotel Maingate West 10/10 Excellent "Great place to stay. Close to the parks. Room was clean. Front desk staff were very nice. Easy convenient parking. I have stayed here numerous times. " [](https://expedia.ca/Orlando-Hotels-Destiny-Palms-Hotel-Maingate-West.h427337.Hotel-Information) ![Meliá Orlando Celebration](//images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/b440f6b4_y.jpg) ### Meliá Orlando Celebration 10/10 Excellent "Great place!" [](https://expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.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 "N/A" [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![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 "Stayed here for a conference and honestly, it felt more like a vacation! The resort was absolutely fabulous — beautiful pools, amazing dining options, and top-notch service. I could’ve easily stayed a few extra days just to relax. Perfect mix of business and leisure!" 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