Title: Lakeland - Winter Haven Vacation Home Rentals from CA $148: 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 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 # 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 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select 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) ![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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/4a4db2cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Kissimmee 9.6/10 Exceptional (1986) "Recommended amazing stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elf CA $167 CA $204 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Orlando-Hotels-The-Berkley.h1695932.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/121000000/120110000/120101900/120101847/665c82cc.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) ### Vacation Home in Kissimmee CA $113 CA $526 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Orlando-Hotels-Super-Cool-Sleeps-17-Newly-Built-Near-Parks.h120101847.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 | Living area](https://images.trvl-media.com/lodging/116000000/115470000/115464800/115464733/7da91279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Kissimmee CA $155 CA $515 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Orlando-Hotels-FL-1844-GOBI-DR.h115464733.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 | Interior](https://images.trvl-media.com/lodging/116000000/115330000/115325100/115325024/12909784.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) ### Vacation Home in Loughman CA $148 CA $1,048 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Orlando-Hotels-Harmony-Haven-Boutique-Townhome-At-Azzure-Resort-Near-Disney-By-Shine-Villas-6-Bedroom-Townhouse.h115325024.Hotel-Information) ![TV, foosball, table tennis](https://images.trvl-media.com/lodging/41000000/40910000/40903200/40903120/2c3b2dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi](https://images.trvl-media.com/lodging/41000000/40910000/40903200/40903120/48a4871d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/41000000/40910000/40903200/40903120/6cfeeee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/41000000/40910000/40903200/40903120/ce2f2e14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Kissimmee 9.2/10 Wonderful (43) "This property was close to everything and was so convenient and felt safe...we definitely loved our stay there" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vithra CA $92 CA $263 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Orlando-Hotels-Enchanting-Newly-Renovated-15miles-To-Disney-And-Near-Tons-Of-Restaurants-760.h40903120.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) ### Vacation Home in 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 $62 CA $239 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Lakeland-Hotels-Lovely-One-Bedroom-Home.h72288502.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/113000000/112440000/112437900/112437852/c449842a.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) ### Vacation Home in 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 $162 CA $210 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Lake-Wales-Hotels-Charming-2-Bedroom-House-In-Downtown-Lake-Wales.h112437852.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) ![Exterior](https://images.trvl-media.com/lodging/117000000/116480000/116470200/116470105/45f9c2f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116480000/116470200/116470105/0fd93fb7.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) ### Vacation Home in Winter Haven CA $96 CA $365 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Winter-Haven-Hotels-BlockHaven-Near-Legoland-Disney.h116470105.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) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/37000000/36870000/36863800/36863729/86323ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36870000/36863800/36863729/89eaec5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Winter Haven 9.4/10 Exceptional (64) "A pleasant stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andeelynn D. CA $176 CA $401 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Winter-Haven-Hotels-32GorgeousNEWLakeHome2AceLoc4miLEGOLAND1724.h36863729.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) ![Smart TV](https://images.trvl-media.com/lodging/65000000/64410000/64407800/64407773/76a8485d.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/65000000/64410000/64407800/64407773/53e227a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in 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 $107 CA $148 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Lakeland-Hotels-Great-Quiet-And-Comfortable.h64407773.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/119000000/118980000/118975900/118975859/c49ecb83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118980000/118975900/118975859/b93648ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/119000000/118980000/118975900/118975859/d39c9c0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Private kitchen](https://images.trvl-media.com/lodging/119000000/118980000/118975900/118975859/6a98343c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Crescent Lakes [](https://www.expedia.ca/Kissimmee-Hotels-South-Facing-W-Private-Pool-Spa.h118975859.Hotel-Information) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120101900/120101835/08622a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120101900/120101835/0d30a66a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120101900/120101835/3573eec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/121000000/120110000/120101900/120101835/1b89eb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Cumbrian Lakes CA $151 CA $586 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Kissimmee-Hotels-Super-Lush-Foam-Beds-W-Pool-Games.h120101835.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) ![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) ![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) ### Vacation Home in 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 $100 CA $235 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Lakeland-Hotels-Hidden-Emerald-Apartment-With-Kitchen-And-Laundry.h97109338.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/100000000/99830000/99825100/99825047/378d0c33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's play area - outdoor](https://images.trvl-media.com/lodging/100000000/99830000/99825100/99825047/2a402a66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury House | Living area](https://images.trvl-media.com/lodging/100000000/99830000/99825100/99825047/7c3b2700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury House | Private kitchen](https://images.trvl-media.com/lodging/100000000/99830000/99825100/99825047/97092c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Crescent Lakes [](https://www.expedia.ca/Kissimmee-Hotels-Aster-Cove.h99825047.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) ![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/1000000/60000/57600/57584/37572760.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) ### Vacation Home in Orlando 9.6/10 Exceptional (202) "Easy check in, pool was awesome " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $359 CA $403 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Orlando-Hotels-Marriotts-Sabal-Palms.h57584.Hotel-Information) ![Private pool](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/9a3d3e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Townhome, 5 Bedrooms, Private Pool | Living area](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/85d76152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Townhome, 5 Bedrooms, Private Pool | Private kitchen](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/6699c829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Townhome, 4 Bedrooms, Private Pool | Living area](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/f89a4e36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Kissimmee 9.4/10 Exceptional (191) "Overall a clean house, one of the best properties I’ve stayed in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cristian [](https://www.expedia.ca/Orlando-Hotels-Formosa-Valley-Resort-By-UNE-Homes.h75962058.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99450000/99444100/99444054/3c8402fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/100000000/99450000/99444100/99444054/e31488e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/100000000/99450000/99444100/99444054/c348628f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99450000/99444100/99444054/cea82714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Dixieland 9.8/10 Exceptional (28) "Loved everything about this place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason S. CA $176 CA $399 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Lakeland-Hotels-Historic-District-Cottage-Near-It-All-With-Dog-Friendly-Yard-Screened-Porch.h99444054.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) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301947/0f520256.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) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301947/dc29b8d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in 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 $176 CA $437 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Winter-Haven-Hotels-Getaway-Clubhouse-5-Mil-Legoland-5-Mil-Downtown.h109301947.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) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/106000000/105170000/105164300/105164207/51569532.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) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105170000/105164300/105164207/e2933b66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in 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 $108 CA $228 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Lakeland-Hotels-Enjoy-In-This-Beautiful-And-Serene-South-Lakeland-AreaPerfect-For-4-Traveler.h105164207.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/45000000/44320000/44316800/44316760/97e3089b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/45000000/44320000/44316800/44316760/f8cdeb57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/45000000/44320000/44316800/44316760/425671ea_edited_3722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/45000000/44320000/44316800/44316760/0038e2bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Kissimmee 9.4/10 Exceptional (21) "We were only here to sleep, property was super clean and impressive!! We would definitely stay here again. Only issue we had was with the pass for your car, you have to go thru the security gate with a guard and google maps wants to take you to the other entrance without a guard. The rooms are really nice and beds were super comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie W. CA $148 CA $645 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Orlando-Hotels-5-Bedrooms-4-Bathrooms-Champions-Gate.h44316760.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=2025-12-09&endDate=2025-12-10®ionId=6048230&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_6048230) ## 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=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=CABIN) 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=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=APART_HOTEL) 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=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=VACATION_HOME) 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=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=CONDO) 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=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=APARTMENT) 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=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=HOUSE_BOAT) 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=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&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=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=VILLA) 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=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&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=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&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 ![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 "Clean and plenty of amenities" [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ![Home2 Suites by Hilton Orlando South Davenport](https://images.trvl-media.com/lodging/95000000/94800000/94797500/94797473/efc0c0ed_y.jpg) ### Home2 Suites by Hilton Orlando South Davenport 10/10 Excellent "Super clean and comfy bed. " [](https://expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Davenport-Orlando-I-4.h94797473.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 "Great service. The rooms were amazing. Will definitely stay again in near future. " [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.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 "It’s really a wonderful stay. Pros: Room is very nice. Breakfast is really good and daily room service is excellent. Location is also excellent you will get almost everything around you. Close to all the Disney parks, Springs, Board walk Cons: There is no direct transportation available for Magic Kingdom and transportation to epcot is also not convenient for given timings." [](https://expedia.ca/Orlando-Hotels-Quality-Inn-Suites-By-The-Parks.h18866.Hotel-Information) ![Margaritaville Resort Orlando](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg) ### Margaritaville Resort Orlando 10/10 Excellent "Room was very clean and everyone was really nice. The entertainment was great as well. " [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information) ![The Inn at Celebration, Autograph Collection ](https://images.trvl-media.com/lodging/1000000/330000/329700/329635/7fa866f7_y.jpg) ### The Inn at Celebration, Autograph Collection 10/10 Excellent "Everything good" [](https://expedia.ca/Orlando-Hotels-Bohemian-Hotel-Celebration.h329635.Hotel-Information) ![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 "Amenities were great. Room was clean, though the showers need a caddy for those not using the shampoo, conditioner, and body wash hanging on the wall. Coffee maker provided, wish coffee pods were given. " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.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 "Breakfast great staff great" [](https://expedia.ca/Winter-Haven-Hotels-Holiday-Inn-Winter-Haven.h7835.Hotel-Information) ![Days Inn & Suites by Wyndham Lakeland](https://images.trvl-media.com/lodging/2000000/1640000/1635700/1635682/9412c3cb_y.jpg) ### Days Inn & Suites by Wyndham Lakeland 10/10 Excellent "Rooms were clean staff very friendly and helpful the only downside is the breakfast otherwise than that I will stay again" [](https://expedia.ca/Lakeland-Hotels-Days-Inn-Suites-By-Wyndham-Lakeland.h1635682.Hotel-Information) ## Find out more about Lakeland - Winter Haven ## Lakeland - Winter Haven Vacation Homes information | Number of reviews | 2,738 | | --- | --- | | Accommodation | 1255 Vacation Homes | | Lowest Price | CA $148 | | Highest Price | CA $1,048 | ## Explore a world of travel with Expedia - 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