Title: Book the Best HISTORIC Hotels in Lakeland - Winter Haven in 2026 | 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 showing aircraft](https://images.trvl-media.com/place/6048230/acc91465-25e0-4c9a-8d30-5268c597e4d5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Visit Central Florida # Find Historic Hotels in Lakeland - Winter Haven, FL from CA $88 - ![](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 [Jan 8 - Jan 9](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-01-08&endDate=2026-01-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 9 - Jan 10](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-01-09&endDate=2026-01-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Lakeland - Winter Haven historic hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/210000/209700/209651/c64bc232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/210000/209700/209651/e5dc7fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/210000/209700/209651/d7ea1d6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/210000/209700/209651/12f4d0d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Terrace Hotel Lakeland, Tapestry Collection by Hilton [](https://www.expedia.ca/Lakeland-Hotels-The-Terrace-Hotel-Lakeland.h209651.Hotel-Information) Downtown Lakeland 9.2/10 Wonderful (362) "Very nice and comfortable hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ISIS CA $196 CA $220 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Lakeland-Hotels-The-Terrace-Hotel-Lakeland.h209651.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/800/702/7b6f0287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/800/702/9d8ecfc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/800/702/de28977f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home 1 Suites Extended Stay - Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Home-1-Suites-Extended-Stay-Kissimmee.h702.Hotel-Information) Kissimmee 6.6/10 (1029) "Nice place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosa CA $77 CA $88 total includes taxes & fees Jan 9 - Jan 10 [](https://www.expedia.ca/Orlando-Hotels-Home-1-Suites-Extended-Stay-Kissimmee.h702.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33703900/33703840/1968fb21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/34000000/33710000/33703900/33703840/ffd04972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33710000/33703900/33703840/13a47fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33710000/33703900/33703840/d20e966e.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 ! [](https://www.expedia.ca/Tampa-Hotels-Lake-View-2-Bed-2-Bath-Loft-With-Pool.h33703840.Hotel-Information) Brandon 9.8/10 Exceptional (205) "Excellent location, perfect little condo with all the necessities. Had a wonderful time. Loved the added bonus of having a washer and dryer" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve H. CA $137 CA $449 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Tampa-Hotels-Lake-View-2-Bed-2-Bath-Loft-With-Pool.h33703840.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) ![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 pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/a37fcdf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/174077ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*Tinkerbells Castle 2\* Private Pool & Spa Overlooking Lake & Disney Fire Works [](https://www.expedia.ca/Orlando-Hotels-Tinkerbells-Castle-2-Private-Pool-Spa-Overlooking-Lake-Disney-Fire-Works.h33584838.Hotel-Information) 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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terrianne T. CA $207 CA $601 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Orlando-Hotels-Tinkerbells-Castle-2-Private-Pool-Spa-Overlooking-Lake-Disney-Fire-Works.h33584838.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/70000000/69680000/69671300/69671236/3682188c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69680000/69671300/69671236/51e3af88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/70000000/69680000/69671300/69671236/5a3d0e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/70000000/69680000/69671300/69671236/w1668h1110x0y4-ca7f5a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 🌴 Relax & Recharge Near Disney – Top-Floor 3BR Condo at Windsor Palms 🌴 [](https://www.expedia.ca/Orlando-Hotels-Making-Memories-Resort.h69671236.Hotel-Information) Kissimmee 9.8/10 Exceptional (19) "I really enjoyed the Disney theme at the place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $152 CA $449 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Orlando-Hotels-Making-Memories-Resort.h69671236.Hotel-Information) ![4 bedrooms, memory foam beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/35000000/34590000/34580900/34580812/abab03f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/35000000/34590000/34580900/34580812/3962225b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34590000/34580900/34580812/ed31fe65.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! [](https://www.expedia.ca/Orlando-Hotels-Only-15-Miles-TO-Disney-World.h34580812.Hotel-Information) Kissimmee 9.6/10 Exceptional (113) "Family friendly. Clean apartment. Host was very responsive and friendly. Highly recommend for family functions. Very close to WDW attractions ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria M. CA $198 CA $562 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Orlando-Hotels-Only-15-Miles-TO-Disney-World.h34580812.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/49000000/48580000/48573700/48573679/cb9f118d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/49000000/48580000/48573700/48573679/edce8239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48580000/48573700/48573679/w1280h898x0y0-41a9741d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48580000/48573700/48573679/91230f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR/2BA Getaway – 7 Miles from Orlando Parks [](https://www.expedia.ca/Orlando-Hotels-Lovely-Condo-2BR2-BA.h48573679.Hotel-Information) Kissimmee 7.0/10 Good (2) "We had a wonderful time at this condo. Very clean a bit outdated with a few things that could improve but the overall experience at this condo was very good. It is a lot bigger then seen in photos both bedrooms are fairly big and nice big walk in closet in both rooms and two full bathrooms and. Laundry in suite was an excellent addition and convenient will definitely returning in the future ! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jessica R. CA $61 CA $295 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Orlando-Hotels-Lovely-Condo-2BR2-BA.h48573679.Hotel-Information) ![Sport court](https://images.trvl-media.com/lodging/34000000/33750000/33740900/33740892/7da7d731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/34000000/33750000/33740900/33740892/d535217d.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) ![Dining](https://images.trvl-media.com/lodging/34000000/33750000/33740900/33740892/73877bf6.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! [](https://www.expedia.ca/Orlando-Hotels-Huge-7-BDRM.h33740892.Hotel-Information) Kissimmee 9.2/10 Wonderful (60) "It was great and fabulous." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eunice M. CA $264 CA $766 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Orlando-Hotels-Huge-7-BDRM.h33740892.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/22000000/21640000/21637500/21637460/d4c6e822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21640000/21637500/21637460/b7f4753d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/22000000/21640000/21637500/21637460/2bb93175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/22000000/21640000/21637500/21637460/12e2e766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 6BR, Theater, Game Rooms, Pool–Min to Disney/Universal Epic Universe! [](https://www.expedia.ca/Orlando-Hotels-Theater.h21637460.Hotel-Information) Reunion 9.2/10 Wonderful (77) "It was awesome location. Lot of space to relax. Kids absolutely loved it Best vacation spot for us with a mix of kids from 3 months to 16 yo" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca L. CA $204 CA $923 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Orlando-Hotels-Theater.h21637460.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/45000000/44380000/44377900/44377814/f827044f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/45000000/44380000/44377900/44377814/f5ebe724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/45000000/44380000/44377900/44377814/2efe0aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/45000000/44380000/44377900/44377814/01e9753a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Incredible Renovated home located near all !! [](https://www.expedia.ca/Orlando-Hotels-Incredible-Renovated-Home-Located-Near-All.h44377814.Hotel-Information) Champions Gate 6.6/10 (4) "We really enjoyed Melissa’s condo Deja Blue. Quite pretty inside and quiet surroundings. Beds are comfortable, plenty of towels available, most things you need for a stay are provided. A few things in the condo could be updated but overall we had a great month in this unit and love the Champions Gate area for walking and dining." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan K. CA $109 CA $307 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Orlando-Hotels-Incredible-Renovated-Home-Located-Near-All.h44377814.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=2026-01-22&endDate=2026-01-23®ionId=6048230&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Lakeland - Winter Haven Hotel Reviews ![Hilton Vacation Club Mystic Dunes Orlando](https://images.trvl-media.com/lodging/1000000/900000/891000/890951/0b826e24_y.jpg) ### Hilton Vacation Club Mystic Dunes Orlando 10/10 Excellent "Everything " [](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](https://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 "This location is one of the best resorts I’ve been in America. They have everything for the kids,adults, and all seniors. This property was clean and the staff was phenomenal. I would recommend this location for any family or family reunions. The rooms was spacious and did not feel like you were in a motel or a hotel individual room. The restaurants was reasonably priced and the food was great. We will definitely be going back." [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ![Hilton Vacation Club Aqua Sol Orlando West](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg) ### Hilton Vacation Club Aqua Sol Orlando West 10/10 Excellent "Nice property, very friendly staff, could have a bit more opportunities for entertainment but if not, Orlando has tons of options. " [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Destiny Palms Hotel Maingate West](https://images.trvl-media.com/lodging/1000000/430000/427400/427337/d056f561_y.jpg) ### Destiny Palms Hotel Maingate West 10/10 Excellent "Everything good " [](https://expedia.ca/Orlando-Hotels-Destiny-Palms-Hotel-Maingate-West.h427337.Hotel-Information) ![Meliá Orlando Celebration](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/b440f6b4_y.jpg) ### Meliá Orlando Celebration 10/10 Excellent "Our entire stay were excellent!!! " [](https://expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.Hotel-Information) ![Quality Inn & Suites By the Parks](https://images.trvl-media.com/lodging/1000000/20000/18900/18866/7474f0f7_y.jpg) ### Quality Inn & Suites By the Parks 10/10 Excellent "Breakfast was excellent, property needs maintenance attention specially walkways painting on upper floors " [](https://expedia.ca/Orlando-Hotels-Quality-Inn-Suites-By-The-Parks.h18866.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bartow ](https://www.expedia.ca/Bartow-Hotels-Cheap-Hotels.0-0-d6397-tCheapHotels.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Bartow ](https://www.expedia.ca/Bartow-Hotels-LGBT-Friendly-Hotel.0-0-d6397-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bartow ](https://www.expedia.ca/Bartow-Hotels-Luxury-Hotel.0-0-d6397-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Central Florida ](https://www.expedia.ca/Central-Florida-Hotels-Adults-Only-Resorts.0-0-d6048177-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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