Title: Lakeland - Winter Haven Vacation Home Rentals from CA $145: Search Top Private Vacation Homes for Rent | 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](https://images.trvl-media.com/place/6048230/8f47b8b8-82cb-478d-aa45-11932c63dbb0.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Lakeland - Winter Haven Vacation Rentals - ![](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 prices for these dates In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Lakeland - Winter Haven vacation homes ![Lobby](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/c7c5e131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/4a4db2cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 4 Bedrooms (2 King, 1 Queen, & 2 Trundle Bed) | Balcony view](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/c3a6b674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/cb9347c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Berkley, Orlando [](https://www.expedia.ca/Orlando-Hotels-The-Berkley.h1695932.Hotel-Information) Kissimmee 9.6/10 Exceptional (2003) "Recommended amazing stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elf CA $176 CA $213 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Orlando-Hotels-The-Berkley.h1695932.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/65000000/64410000/64407800/64407773/fa5d831a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/65000000/64410000/64407800/64407773/66d0b065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/65000000/64410000/64407800/64407773/68bff206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/65000000/64410000/64407800/64407773/76a8485d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Great quiet and comfortable, South Central Lakeland location. [](https://www.expedia.ca/Lakeland-Hotels-Great-Quiet-And-Comfortable.h64407773.Hotel-Information) Lake Hollingsworth 9.8/10 Exceptional (169) "The property is awesome, great location and very quiet. Will stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fred CA $105 CA $145 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Lakeland-Hotels-Great-Quiet-And-Comfortable.h64407773.Hotel-Information) ![Villa, Patio | Terrace/patio](https://images.trvl-media.com/lodging/122000000/121150000/121146200/121146198/9a371b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121150000/121146200/121146198/d731dfd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/122000000/121150000/121146200/121146198/84fc3adb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/122000000/121150000/121146200/121146198/bdad171c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Villa [](https://www.expedia.ca/Haines-City-Hotels-Modern-Villa.h121146198.Hotel-Information) Haines City CA $234 CA $331 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Haines-City-Hotels-Modern-Villa.h121146198.Hotel-Information) ![Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/57600/57584/708057f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/60000/57600/57584/37572760.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/57600/57584/54516d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/60000/57600/57584/5839679e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marriott's Sabal Palms [](https://www.expedia.ca/Orlando-Hotels-Marriotts-Sabal-Palms.h57584.Hotel-Information) Orlando 9.6/10 Exceptional (204) "Room was great, staff friendly and grounds are clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DENNIS CA $351 CA $395 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Orlando-Hotels-Marriotts-Sabal-Palms.h57584.Hotel-Information) ![Townhome, 6 Bedrooms | Living area](https://images.trvl-media.com/lodging/116000000/115330000/115325100/115325024/0e4f6f5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 6 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/116000000/115330000/115325100/115325024/fbc82f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 6 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/116000000/115330000/115325100/115325024/61d91734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 6 Bedrooms | Interior](https://images.trvl-media.com/lodging/116000000/115330000/115325100/115325024/12909784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse [](https://www.expedia.ca/Orlando-Hotels-Harmony-Haven-Boutique-Townhome-At-Azzure-Resort-Near-Disney-By-Shine-Villas-6-Bedroom-Townhouse.h115325024.Hotel-Information) Loughman CA $138 CA $1,014 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Orlando-Hotels-Harmony-Haven-Boutique-Townhome-At-Azzure-Resort-Near-Disney-By-Shine-Villas-6-Bedroom-Townhouse.h115325024.Hotel-Information) ![House](https://images.trvl-media.com/lodging/122000000/121730000/121723700/121723665/ee3ad759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121730000/121723700/121723665/c4091eb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121730000/121723700/121723665/40d39018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121730000/121723700/121723665/9d20d33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Lakeland Landing Cute Bungalow by Downtown [](https://www.expedia.ca/Lakeland-Hotels-NEW-Lakeland-Landing-Cute-Bungalow-By-Downtown.h121723665.Hotel-Information) Dixieland CA $324 CA $663 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Lakeland-Hotels-NEW-Lakeland-Landing-Cute-Bungalow-By-Downtown.h121723665.Hotel-Information) ![Luxury House, 3 Bedrooms, Garden View | Living area](https://images.trvl-media.com/lodging/117000000/116480000/116470200/116470105/018b394c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury House, 3 Bedrooms, Garden View | Living area](https://images.trvl-media.com/lodging/117000000/116480000/116470200/116470105/3e620084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/117000000/116480000/116470200/116470105/9650f692.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116480000/116470200/116470105/45f9c2f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BlockHaven near Legoland & Disney [](https://www.expedia.ca/Winter-Haven-Hotels-BlockHaven-Near-Legoland-Disney.h116470105.Hotel-Information) Winter Haven CA $139 CA $407 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Winter-Haven-Hotels-BlockHaven-Near-Legoland-Disney.h116470105.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/30000000/29760000/29759000/29758985/e5adeed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/30000000/29760000/29759000/29758985/edb43b9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Private kitchen](https://images.trvl-media.com/lodging/30000000/29760000/29759000/29758985/82ec7f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/30000000/29760000/29759000/29758985/fb7ebffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Davenport Vacation Homes by Shine FM [](https://www.expedia.ca/Orlando-Hotels-Davenport-Vacation-Homes-By-Shine-FM.h29758985.Hotel-Information) Tuscan Hills 8.4/10 Very good (26) "it was a great property to stay in!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $150 CA $332 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Orlando-Hotels-Davenport-Vacation-Homes-By-Shine-FM.h29758985.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72290000/72288600/72288502/609746e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72290000/72288600/72288502/f844c6c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72290000/72288600/72288502/b80f4d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/73000000/72290000/72288600/72288502/70b34008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely One Bedroom Home [](https://www.expedia.ca/Lakeland-Hotels-Lovely-One-Bedroom-Home.h72288502.Hotel-Information) Lakeland 9.6/10 Exceptional (14) "Nice little cozy getaway. Just right for one or two people. Stayed there four nights while working in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darrell H. CA $94 CA $271 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Lakeland-Hotels-Lovely-One-Bedroom-Home.h72288502.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/73000000/72290000/72288800/72288736/3b5ae69f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72290000/72288800/72288736/3a730428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/73000000/72290000/72288800/72288736/89be8801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/73000000/72290000/72288800/72288736/3158a70f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MODERN TWO BEDROOM HOME! [](https://www.expedia.ca/Lakeland-Hotels-MODERN-TWO-BEDROOM-HOME.h72288736.Hotel-Information) Lakeland 10/10 Exceptional (11) "This place was perfect! We stayed for my son’s Weigjtlifting tournament and the area didn’t disappoint. The host was amazing and very accommodating! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kris CA $113 CA $308 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Lakeland-Hotels-MODERN-TWO-BEDROOM-HOME.h72288736.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112440000/112437900/112437852/b5c25157.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112440000/112437900/112437852/8ad2970c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112440000/112437900/112437852/43e05855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112440000/112437900/112437852/df496290.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom house in Downtown Lake Wales. [](https://www.expedia.ca/Lake-Wales-Hotels-Charming-2-Bedroom-House-In-Downtown-Lake-Wales.h112437852.Hotel-Information) Lake Wales 9.8/10 Exceptional (9) "Our stay was enjoyable and close to everything. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LaShunda M. CA $158 CA $205 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Lake-Wales-Hotels-Charming-2-Bedroom-House-In-Downtown-Lake-Wales.h112437852.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97110000/97109400/97109338/2b392310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97110000/97109400/97109338/4975b209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/98000000/97110000/97109400/97109338/2e0e25d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/98000000/97110000/97109400/97109338/386a6a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Emerald-Apartment with Kitchen and Laundry [](https://www.expedia.ca/Lakeland-Hotels-Hidden-Emerald-Apartment-With-Kitchen-And-Laundry.h97109338.Hotel-Information) Cleveland Heights 10/10 Exceptional (10) "Very clean and comfortable. Would definitely stay there again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret S. CA $77 CA $206 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Lakeland-Hotels-Hidden-Emerald-Apartment-With-Kitchen-And-Laundry.h97109338.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/37000000/36870000/36863800/36863729/3f2914a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/37000000/36870000/36863800/36863729/86323ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/37000000/36870000/36863800/36863729/557b9613.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball](https://images.trvl-media.com/lodging/37000000/36870000/36863800/36863729/b0a32758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*3/2\*GorgeousNEWLakeHome2AceLoc\*4mi\*LEGOLAND\*1724 [](https://www.expedia.ca/Winter-Haven-Hotels-32GorgeousNEWLakeHome2AceLoc4miLEGOLAND1724.h36863729.Hotel-Information) Winter Haven 9.4/10 Exceptional (65) "The accommodation at this property was exceptional. It felt safe, and was safe Parking was great, proximity to dinning and shopping was withing 5 minutes drive, and the location was peaceful and safe." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dwight CA $172 CA $391 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Winter-Haven-Hotels-32GorgeousNEWLakeHome2AceLoc4miLEGOLAND1724.h36863729.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105170000/105164300/105164207/483df7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105170000/105164300/105164207/7ce39719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105170000/105164300/105164207/d1a5f96a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105170000/105164300/105164207/e2933b66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler [](https://www.expedia.ca/Lakeland-Hotels-Enjoy-In-This-Beautiful-And-Serene-South-Lakeland-AreaPerfect-For-4-Traveler.h105164207.Hotel-Information) Lakeland Highlands 10/10 Exceptional (17) "Nice quiet spot. Clean and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael C. CA $105 CA $223 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Lakeland-Hotels-Enjoy-In-This-Beautiful-And-Serene-South-Lakeland-AreaPerfect-For-4-Traveler.h105164207.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/119000000/118980000/118975900/118975849/345c9691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118980000/118975900/118975849/51640357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/119000000/118980000/118975900/118975849/b6fde579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Private kitchen](https://images.trvl-media.com/lodging/119000000/118980000/118975900/118975849/b82ec1dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5Br Davenport Home W/ Pool & Private Hot Tub [](https://www.expedia.ca/Orlando-Hotels-5Br-Davenport-Home-W-Pool-Private-Hot-Tub.h118975849.Hotel-Information) Solterra Resort CA $298 CA $876 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Orlando-Hotels-5Br-Davenport-Home-W-Pool-Private-Hot-Tub.h118975849.Hotel-Information) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120101900/120101847/b564cae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120101900/120101847/0736f22d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120101900/120101847/9b8d7f85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120101900/120101847/cfaac518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super Cool- Sleeps 17 Newly Built Near Parks [](https://www.expedia.ca/Orlando-Hotels-Super-Cool-Sleeps-17-Newly-Built-Near-Parks.h120101847.Hotel-Information) Kissimmee CA $238 CA $659 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Orlando-Hotels-Super-Cool-Sleeps-17-Newly-Built-Near-Parks.h120101847.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/41f09c21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/435432d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/5af1b204.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books](https://images.trvl-media.com/lodging/92000000/91230000/91221300/91221257/4d2e3d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated Pool and Hot tub-near Legoland, Disney, Theme parks [](https://www.expedia.ca/Winter-Haven-Hotels-Pool-Home-Near-Legoland.h91221257.Hotel-Information) Winter Haven 9.8/10 Exceptional (39) "We had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harper B. CA $160 CA $437 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Winter-Haven-Hotels-Pool-Home-Near-Legoland.h91221257.Hotel-Information) ![Design House, 6 Bedrooms, Private Pool | Private kitchen](https://images.trvl-media.com/lodging/116000000/115470000/115464800/115464733/1a940d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design House, 6 Bedrooms, Private Pool | Terrace/patio](https://images.trvl-media.com/lodging/116000000/115470000/115464800/115464733/70a8166d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design House, 6 Bedrooms, Private Pool](https://images.trvl-media.com/lodging/116000000/115470000/115464800/115464733/2c257e0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design House, 6 Bedrooms, Private Pool | Private kitchen](https://images.trvl-media.com/lodging/116000000/115470000/115464800/115464733/4e2c3202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FL- 1844 GOBI DR [](https://www.expedia.ca/Orlando-Hotels-FL-1844-GOBI-DR.h115464733.Hotel-Information) Kissimmee CA $203 CA $560 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Orlando-Hotels-FL-1844-GOBI-DR.h115464733.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67660000/67650700/67650601/2593b266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67660000/67650700/67650601/3d422dbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/68000000/67660000/67650700/67650601/727022a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/68000000/67660000/67650700/67650601/46b3445b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RED DOOR HOUSE! [](https://www.expedia.ca/Lakeland-Hotels-RED-DOOR-HOUSE.h67650601.Hotel-Information) South Lake Morton 9.4/10 Exceptional (45) "We found this place on VRBO and chose it for our stay. My wife graduated with her Doctorate at SEU. This place was perfect for location to SEU and downtown dining pleasures as well. We will definitely choose it again and again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larry D. CA $93 CA $278 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Lakeland-Hotels-RED-DOOR-HOUSE.h67650601.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301947/46d831be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301947/887502c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301947/cc04f93a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301947/0f520256.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Getaway Clubhouse 5 mil Legoland & .5 mil Downtown [](https://www.expedia.ca/Winter-Haven-Hotels-Getaway-Clubhouse-5-Mil-Legoland-5-Mil-Downtown.h109301947.Hotel-Information) Winter Haven 9.8/10 Exceptional (7) "Great location, clean and great communication with hosts " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angie Y. CA $172 CA $419 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Winter-Haven-Hotels-Getaway-Clubhouse-5-Mil-Legoland-5-Mil-Downtown.h109301947.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=2025-12-26&endDate=2025-12-27®ionId=6048230&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=APART_HOTEL) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=VILLA) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=CONDO) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=HOUSE_BOAT) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=CHALET) Residences [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=RESIDENCE) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FLakeland-Winter-Haven-Private-Vacation-Homes.d6048230-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FLakeland-Winter-Haven-Private-Vacation-Homes.d6048230-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Lakeland - Winter Haven Hotel Reviews ![The Grove Resort & Water Park Orlando](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg) ### The Grove Resort & Water Park Orlando 10/10 Excellent "Beautiful hotel with great amenities. Clean. The pools were great. Wonderful place to stay for families " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.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 "Very Clean the staff was excellent very polite. feel Safe Parking very safe to park to car :)" [](https://expedia.ca/Orlando-Hotels-Destiny-Palms-Hotel-Maingate-West.h427337.Hotel-Information) ![Holiday Inn Winter Haven by IHG](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/1b5518c0_y.jpg) ### Holiday Inn Winter Haven by IHG 10/10 Excellent "Staff very nice and efficient. " [](https://expedia.ca/Winter-Haven-Hotels-Holiday-Inn-Winter-Haven.h7835.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 "Isabella at the check in counter was awesome.Thanks for " [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![voco Kissimmee Orlando by IHG](https://images.trvl-media.com/lodging/1000000/50000/41100/41083/b3397abc_y.jpg) ### voco Kissimmee Orlando by IHG 10/10 Excellent "Didn't have breakfast " [](https://expedia.ca/Orlando-Hotels-Voco-Kissimmee-Orlando-By-IHG.h41083.Hotel-Information) ![Summer Bay Orlando by Exploria Resorts](https://images.trvl-media.com/lodging/1000000/110000/104100/104060/9a5b9775_y.jpg) ### Summer Bay Orlando by Exploria Resorts 10/10 Excellent "Excellent stay" [](https://expedia.ca/Orlando-Hotels-Summer-Bay-Orlando-By-Exploria-Resorts.h104060.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 "Excellent " [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Comfort Inn & Suites Lakeland North I-4](https://images.trvl-media.com/lodging/1000000/30000/20800/20754/2ebe4f87_y.jpg) ### Comfort Inn & Suites Lakeland North I-4 10/10 Excellent "Clean comfortable. The only suggestion is ground floor acustics are very loud from the lobby. " [](https://expedia.ca/Lakeland-Hotels-Comfort-Inn-Suites-Lakeland-North-I-4.h20754.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lakeland West](https://images.trvl-media.com/lodging/1000000/90000/84700/84646/58543b1b_y.jpg) ### La Quinta Inn & Suites by Wyndham Lakeland West 10/10 Excellent "My room was spotless, the hotel is beautiful and the staff are amazing!" [](https://expedia.ca/Lakeland-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lakeland-West.h84646.Hotel-Information) ## Find out more about Lakeland - Winter Haven ## Lakeland - Winter Haven Vacation Homes information | Number of reviews | 2,613 | | ----------------- | ------------------- | | Accommodation | 1255 Vacation Homes | | Lowest Price | CA $145 | | Highest Price | CA $1,014 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [5 Star Hotels in Alturas ](https://www.expedia.ca/5Star-Alturas-Hotels.s50-0-d6352565.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Alturas ](https://www.expedia.ca/Alturas-Hotels-Hilton-Hotels.0-0-d6352565--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Alturas Hotels ](https://www.expedia.ca/Alturas-Hotels.d6352565.Travel-Guide-Hotels) - [Inns in Cape Canaveral ](https://www.expedia.ca/Cape-Canaveral-Inns.d6484-aaInns.Travel-Guide-Accommodation) - [Lodges in Cape Canaveral ](https://www.expedia.ca/Cape-Canaveral-Lodges.d6484-aaLodges.Travel-Guide-Accommodation) - 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