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 $196 - ![](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 [Dec 24 - Dec 25](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-12-24&endDate=2025-12-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-12-25&endDate=2025-12-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-01-02&endDate=2026-01-04&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) ![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) ![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 (352) "Good place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Octavio CA $175 CA $196 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lakeland-Hotels-The-Terrace-Hotel-Lakeland.h209651.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) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33710000/33703900/33703840/d20e966e.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) ![Smart TV](https://images.trvl-media.com/lodging/34000000/33710000/33703900/33703840/d5298c5b.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 (203) "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 $163 CA $481 total includes taxes & fees Dec 25 - Dec 26 [](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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33590000/33584900/33584838/174077ee.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) ### \*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 $205 CA $590 total includes taxes & fees Jan 6 - Jan 7, 2026 [](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/70000000/69680000/69671300/69671236/3a1b8baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69680000/69671300/69671236/c17739c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, table tennis, books](https://images.trvl-media.com/lodging/70000000/69680000/69671300/69671236/f5a79782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69680000/69671300/69671236/7c06199e.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 $144 CA $447 total includes taxes & fees Dec 25 - Dec 26 [](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/35000000/34590000/34580900/34580812/027523c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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) ### 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 (112) "The location can’t be beat and the condo was great. The owner was extremely helpful and attentive. Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leila P. CA $196 CA $557 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Orlando-Hotels-Only-15-Miles-TO-Disney-World.h34580812.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/34000000/33650000/33648300/33648289/22c12933.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) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33650000/33648300/33648289/f2307ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*Tinkerbells Castle 1\* Private Pool & Spa Overlooking Lake & Disney Fire Works [](https://www.expedia.ca/Orlando-Hotels-Tinkerbells-Castle-1-Private-Pool-Spa-Overlooking-Lake-Disney-Fire-Works.h33648289.Hotel-Information) Kissimmee 9.6/10 Exceptional (135) "Communication was great! We used the spa every night after the parks. Perfect way to relax after all that walking! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jude E. CA $410 CA $843 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Orlando-Hotels-Tinkerbells-Castle-1-Private-Pool-Spa-Overlooking-Lake-Disney-Fire-Works.h33648289.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/53000000/52810000/52806300/52806224/w1276h850x4y0-a4de230a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/53000000/52810000/52806300/52806224/cabdb925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/53000000/52810000/52806300/52806224/4f6897fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books, computer monitors](https://images.trvl-media.com/lodging/53000000/52810000/52806300/52806224/b56bbf31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Oasis Lakefront Penthouse Facing Disney [](https://www.expedia.ca/Orlando-Hotels-Serene-Oasis-Lakefront-Penthouse-Facing-Disney.h52806224.Hotel-Information) Orlando 10/10 Exceptional (10) "Great place to stay for WDW! Host is great! Location is great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kay R. CA $308 CA $589 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Serene-Oasis-Lakefront-Penthouse-Facing-Disney.h52806224.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) ![Dining](https://images.trvl-media.com/lodging/22000000/21640000/21637500/21637460/2bb93175.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) ![Outdoor dining](https://images.trvl-media.com/lodging/22000000/21640000/21637500/21637460/b8feaeef.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) "Beautiful house, 5 stars on the entire stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elmer G. CA $245 CA $968 total includes taxes & fees Jan 6 - Jan 7, 2026 [](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) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/45000000/44380000/44377900/44377814/aa2af0b9.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) ![Dining](https://images.trvl-media.com/lodging/45000000/44380000/44377900/44377814/f5ebe724.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 $120 CA $318 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Orlando-Hotels-Incredible-Renovated-Home-Located-Near-All.h44377814.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33090000/33085600/33085503/6293a9b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, table tennis](https://images.trvl-media.com/lodging/34000000/33090000/33085600/33085503/baf49380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33090000/33085600/33085503/44e5bbe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33090000/33085600/33085503/66b894de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "2 Miles to Disney, 2 min walk to Clubhouse, Big private pool, Free Water Park!" [](https://www.expedia.ca/Orlando-Hotels-2-Miles-2-Disney.h33085503.Hotel-Information) Windsor Hills 9.2/10 Wonderful (194) "We had a wonderful time, the house was perfect for our needs and the kids loved it especially the playroom and the pool." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caryn H. CA $235 CA $707 total includes taxes & fees Jan 17 - Jan 18, 2026 [](https://www.expedia.ca/Orlando-Hotels-2-Miles-2-Disney.h33085503.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=2026-01-07&endDate=2026-01-08®ionId=6048230&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Lakeland - Winter Haven Hotel Reviews ![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 "Yes" [](https://expedia.ca/Orlando-Hotels-Destiny-Palms-Hotel-Maingate-West.h427337.Hotel-Information) ![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 "Very spacious " [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.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 "What a wonderful stay! I cannot brag enough about this place. Comfortable beds, clean unit and linens, pools and amenities around the campus were so much fun to explore. Staff were helpful, friendly, and great to talk to. Campus felt like you were coming home. Safe and convenient location, quiet and family friendly. This was our third time visiting. .. we will be back! " [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.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) ![Meliá Orlando Celebration](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/b440f6b4_y.jpg) ### Meliá Orlando Celebration 10/10 Excellent "We had some small problems with the room, but everything was corrected immediately, Vicky a member of the staff took care of that for us, she was very helpful, we really appreciated that, so everything was great." [](https://expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.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 "HUGE GATED RESORT! Shuttles run around complex from 8AM to 11PM. Pools are heated, lazy river is relaxing! Access to great pools, hot tubs, dining, golf, pickleball & so much more! Marketplace serves Starbucks coffee & has its own grocery & souvenir sections. Family friendly resort, activities for kids & adults. Staff is helpful, friendly & very accommodating. Will be back in the future. " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.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) - [Beach Hotel Hotels in Central Florida ](https://www.expedia.ca/Central-Florida-Hotels-Beach-Hotel.0-0-d6048177-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Central Florida ](https://www.expedia.ca/Central-Florida-Hotels-Boutique-Hotel.0-0-d6048177-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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