Title: Lakeland - Winter Haven Cottages | 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 a sporting event as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63660-Lakeland-Winter-Haven.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Lakeland - Winter Haven Cottage 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 Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Lakeland - Winter Haven Cottages ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/3e94c18f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/417eb849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/ce928403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/961c6be6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn Winter Haven 10/10 Exceptional (3) "We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John [](https://www.expedia.ca/Winter-Haven-Hotels-Lovely-Lakefront-Home-W-Grill-7-Mi-To-Legoland.h93532553.Hotel-Information) ![Children's area](https://images.trvl-media.com/lodging/108000000/107730000/107721700/107721689/5a590007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/108000000/107730000/107721700/107721689/139634ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107730000/107721700/107721689/59e8ff36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107730000/107721700/107721689/fde69571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom cottage in Kissimmee Kissimmee 10/10 Exceptional (1) "Kudos to the hosts. A seamless experience. My first ever vacation rental and I was very impressed. The cottage was super clean and was equipped with everything and then some. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gail E. CA $94 CA $286 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Orlando-Hotels-Charming-2-Bedroom-Cottage-In-Kissimmee.h107721689.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/9a3ce3e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/419df642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/71e79adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/0d69889a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### This old Florida feeling getaway is 420 friendly and a great place to just relax Avon Park 10/10 Exceptional (1) "We loved our stay at Kellie’s farm, the property is big and has a big pond or little lake at the back, the scenery looks like you’re somewhere in the wild side of Montana and feels like a grizzly bear can come out of the trees at any moment! Haha but it’s very safe, nothing to worry about. The farm has chickens, pigs, a calf, dogs, etc. if you love animals you will love this place for sure! We would definitely come back and we 100% recommend this place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve M. CA $107 CA $203 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Avon-Park-Hotels-This-Old-Florida-Feeling-Getaway-Is-420-Friendly-And-A-Great-Place-To-Just-Relax.h96737713.Hotel-Information) ![Microwave, stovetop](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/4a623c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/fade59e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/f8c94a4e.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/122000000/121010000/121006800/121006717/71673f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny house close to Disney KISSIMMEE Kissimmee CA $78 CA $220 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/50a06dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking | Living area](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/9828479e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/a66b5fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking | Private kitchenette](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/4549c4d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Ida Beach Resort Winter Haven 7.4/10 Good (183) "This room served my needs well. I enjoyed the full kitchen and bathtub." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rafael CA $105 CA $117 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/8f02e263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/99d15874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/8224d871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/21005d2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Lake View Cottage 5 miles from Disney! Kissimmee 9.0/10 Wonderful (2) "Awesome" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bulmaro S. CA $112 CA $311 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Orlando-Hotels-Hidden-Lake-View-Cottage-5-Miles-From-Disney.h72359158.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/ad468c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/a7d343f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/1d7e29a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/6887a27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn Winter Haven 10/10 Exceptional (2) "Just what we needed for a weekend trip with our grandsons for the weekend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine B. CA $161 CA $390 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/64000000/63750000/63741700/63741626/f8838170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/64000000/63750000/63741700/63741626/w750h561x0y0-166794de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/64000000/63750000/63741700/63741626/9d834719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63750000/63741700/63741626/48b38fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jedi cottage 4 miles from Disney! Mins from universal! Kissimmee 9.4/10 Exceptional (23) "We loved staying here! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emma Kate y. CA $105 CA $302 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Orlando-Hotels-Jedi-Cottage-4-Miles-From-Disney-Mins-From-Universal.h63741626.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/b73e0a20.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/108000000/107620000/107619900/107619849/906240fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/0eda7c58_edited_1bbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/945e14a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee Kissimmee 10/10 Exceptional (2) "We stayed and visited universal snd drove to Jacksonville it was a cute cottage" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer b. CA $132 CA $345 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Cottage-Your-Home-Away-From-Home-4-Miles-From-Disney.h107619849.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/46000000/45690000/45682800/45682757/7fe0c743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45690000/45682800/45682757/59e757da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45690000/45682800/45682757/9b26402a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/46000000/45690000/45682800/45682757/0928c447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney, Universal and Legoland Getaway Kissimmee 9.2/10 Wonderful (9) "I love the place ! It was beautiful! Enough room for everyone " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony M. CA $105 CA $303 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Orlando-Hotels-Vrbo-Property.h45682757.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/117000000/116840000/116838100/116838053/98f7a925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/117000000/116840000/116838100/116838053/b697b6eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/117000000/116840000/116838100/116838053/97b23f55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/117000000/116840000/116838100/116838053/ddaa8f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southern Dunes Family Retreat: Hot Tub & Game Room Haines City CA $284 CA $647 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Haines-City-Hotels-Southern-Dunes-Family-Retreat-Hot-Tub-Game-Room.h116838053.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89640000/89635100/89635062/d94a6bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89640000/89635100/89635062/983e7aa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89640000/89635100/89635062/3f617b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/90000000/89640000/89635100/89635062/84a3bb73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Cottage Near Legoland & Chain of Lakes Lake Hamilton 10/10 Exceptional (6) "This place is tiny but everything you need for a comfortable stay! Would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dallas C. CA $140 CA $291 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lake-Hamilton-Hotels-Luxury-Cottage-Near-Legoland-Chain-Of-Lakes.h89635062.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/638cd47a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/676c3433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/6cc6586b_edited_e804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/fe821527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Place for a Perfect Vacation Kissimmee 10/10 Exceptional (1) CA $113 CA $268 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Orlando-Hotels-Perfect-Place-For-A-Perfect-Vacation.h70286316.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/w1124h861x1y0-e56aebb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/35cf1402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/df48ecb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/d04f2cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC Kissimmee CA $123 CA $295 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Orlando-Hotels-Mickeys-Hideaway-Cottage-4-Miles-From-Disney-In-Kissimmee-With-WiFi-And-AC.h117841053.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/c40e14f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/e3e411c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/8f893913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/91196b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more! Kissimmee CA $125 CA $310 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Orlando-Hotels-Charming-Cottage-10-Mins-To-Disney.h109916919.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/dcad85d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/948252d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/25aafbc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/c31b3466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Cottage Near Orlando’s Top Attractions Kissimmee CA $126 CA $282 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.Hotel-Information) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/6919bd78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/034df557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/70c3f621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/4b563550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Historic Cottage with Cozy Porch and Garden Retreat Polk City CA $177 CA $372 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Polk-City-Hotels-Charming-Historic-Cottage-With-Cozy-Porch-And-Garden-Retreat.h117619898.Hotel-Information) ![House, 6 Bedrooms | Exterior](https://images.trvl-media.com/lodging/72000000/71430000/71428800/71428707/w1021h764x3y4-bccfb2df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71430000/71428800/71428707/a0237592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 6 Bedrooms | Pool](https://images.trvl-media.com/lodging/72000000/71430000/71428800/71428707/e7438f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71430000/71428800/71428707/d241c4e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wellerden at Reunion Resort!by Shine Villas Reunion CA $256 CA $899 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Orlando-Hotels-Wellerden-At-Reunion-Resort-By-Shine-Villas.h71428707.Hotel-Information) ![House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | Property grounds](https://images.trvl-media.com/lodging/104000000/103860000/103852500/103852456/75ca04d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage)](https://images.trvl-media.com/lodging/104000000/103860000/103852500/103852456/7679a08b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | Dining](https://images.trvl-media.com/lodging/104000000/103860000/103852500/103852456/9f46952a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103860000/103852500/103852456/79597f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lafitte's Landing Lakeview Cottage - Lakefront! Kissimmee 9.2/10 Wonderful (12) "We really enjoyed our stay, the home was so clean and comfortable.. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Geraldine CA $360 CA $725 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Orlando-Hotels-Laffites-Landing-At-Margaritaville.h103852456.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107720000/107716100/107716064/b5c4778e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107720000/107716100/107716064/98e77b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107720000/107716100/107716064/d91b1f85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107720000/107716100/107716064/22b2677c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom cottage in Kissimmee Kissimmee CA $88 CA $287 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Orlando-Hotels-Charming-1-Bedroom-Cottage-In-Kissimmee.h107716064.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=2025-11-11&endDate=2025-11-12®ionId=6048230&adults=2&lodging=COTTAGE&sort=RECOMMENDED&openPlayBack=true) ![](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-Cottages.d6048230-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FLakeland-Winter-Haven-Cottages.d6048230-aaCottages.Travel-Guide-Accommodation) ## Top Lakeland - Winter Haven Hotel Reviews ![The Grove Resort & Water Park Orlando](//images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg) ### The Grove Resort & Water Park Orlando 10/10 Excellent "We have stayed here 4 times now, and every time is a truly relaxing vacation. The store is a little over priced but its a tourist location so thats as expected. All in all, wr will be staying again mext year." [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Holiday Inn Club Vacations at Orange Lake Resort by IHG](//images.trvl-media.com/lodging/1000000/10000/6400/6315/ac7826b3_y.jpg) ### Holiday Inn Club Vacations at Orange Lake Resort by IHG 10/10 Excellent "The property was more than we expected and the stay was amazing! We loved everything about the place, and the ad doesn’t do it justice. " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ![Hilton Vacation Club Aqua Sol Orlando West](//images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg) ### Hilton Vacation Club Aqua Sol Orlando West 10/10 Excellent "We didn’t have breakfast here we cooked instead. However it’s always a pleasure to stay here. My family and I have been going here since I was a child, although it was called something different up until a few years ago it’s always a pleasure. The staff is very friendly and attentive, they always make you feel like you’re at home. We go at least once a year and we will continue to go as long as the service stays the same. ❤️" [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Margaritaville Cottages Orlando with H2O Waterpark by Rentyl](//images.trvl-media.com/lodging/28000000/27550000/27548600/27548551/23050871_y.jpg) ### Margaritaville Cottages Orlando with H2O Waterpark by Rentyl 10/10 Excellent "Yes pool was clean" [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando-Cottages-By-Rentyl.h27548551.Hotel-Information) ![Staybridge Suites Winter Haven Auburndale by IHG](//images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/0585f081_y.jpg) ### Staybridge Suites Winter Haven Auburndale by IHG 10/10 Excellent "Everything from the room, parking, to complementary breakfast was excellent." [](https://expedia.ca/Winter-Haven-Hotels-Staybridge-Suites-Winter-Haven-Auburndale.h94674232.Hotel-Information) ![Margaritaville Resort Orlando with H2O Waterpark](//images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg) ### Margaritaville Resort Orlando with H2O Waterpark 10/10 Excellent "Very nice view" [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information) ![Holiday Inn Winter Haven by IHG](//images.trvl-media.com/lodging/1000000/10000/7900/7835/1b5518c0_y.jpg) ### Holiday Inn Winter Haven by IHG 10/10 Excellent "Room was perfect condition and kept well. Food was great. Good place to stay. " [](https://expedia.ca/Winter-Haven-Hotels-Holiday-Inn-Winter-Haven.h7835.Hotel-Information) ![Hilton Vacation Club Mystic Dunes Orlando](//images.trvl-media.com/lodging/1000000/900000/891000/890951/0b826e24_y.jpg) ### Hilton Vacation Club Mystic Dunes Orlando 10/10 Excellent "Clean by see" [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![voco Kissimmee Orlando by IHG](//images.trvl-media.com/lodging/1000000/50000/41100/41083/b3397abc_y.jpg) ### voco Kissimmee Orlando by IHG 10/10 Excellent "We loved it" [](https://expedia.ca/Orlando-Hotels-Voco-Kissimmee-Orlando-By-IHG.h41083.Hotel-Information) ## Find out more about Lakeland - Winter Haven ## Lakeland - Winter Haven Cottages information | Number of reviews | | | --- | --- | | Accommodation | Cottages | | Lowest Price | | | Highest Price | | ## Frequently asked questions ### How much do cottages in Lakeland - Winter Haven cost? > Cottages in Lakeland - Winter Haven range between and per night. These properties offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### How many cottages are there in Lakeland - Winter Haven? > Choose from cottages in Lakeland - Winter Haven. Whether you're traveling with the whole family, as a twosome or with a group of besties, Expedia can help you secure your perfect fit. ### Why book your cottage in Lakeland - Winter Haven with Expedia? > Reserving a cottage in Lakeland - Winter Haven is as simple as entering your travel dates and choosing an ideal place for outdoor relaxation and recreation. From chic retreats to inexpensive properties and cottages that offer conveniences like a kitchen, Expedia has something for all traveler styles. As for irresistible deals? We've got you covered! ### How can I find cheap cottages in Lakeland - Winter Haven? > Expedia can help you locate cheap cottages in Lakeland - Winter Haven. To reserve your perfect stay in just a few clicks, use our convenient filter tool to refine your search results by amenities, budget and star rating. ### What is there to do in Lakeland - Winter Haven near my cottage? > One of the best travel accessories for your Lakeland - Winter Haven adventure is an awesome itinerary! [Polk Museum of Art](https://www.expedia.ca/Polk-Museum-Of-Art-Lakeland.d6187137.Vacation-Attraction), [RP Funding Center](https://www.expedia.ca/RP-Funding-Center-Downtown-Lakeland.d6128449.Vacation-Attraction) and [Publix Field at Joker Marchant Stadium](https://www.expedia.ca/Publix-Field-At-Joker-Marchant-Stadium-Lakeland.d6127895.Vacation-Attraction) are among the leading sights if you're off to Lakeland. Winter Haven also lures travelers with its wonderful attractions, such as [Indigo's Family Fun Center](https://www.expedia.ca/Indigos-Family-Fun-Center-Winter-Haven.d6259153.Vacation-Attraction). Eager to add to your to-do list? Drop by [Chain of Lakes Park](https://www.expedia.ca/Chain-Of-Lakes-Park-Winter-Haven.d6127913.Vacation-Attraction) and [Theatre Winter Haven](https://www.expedia.ca/Theatre-Winter-Haven-Winter-Haven.d553248621532652812.Vacation-Attraction) too. ## 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) - [Ranches in Cape Canaveral](https://www.expedia.ca/Cape-Canaveral-Ranches.d6484-aaRanches.Travel-Guide-Accommodation) - 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