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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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) ## 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/94000000/93540000/93532600/93532553/56573fe6.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 CA $217 CA $526 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Winter-Haven-Hotels-Lovely-Lakefront-Home-W-Grill-7-Mi-To-Legoland.h93532553.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350012/c8a0798f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350012/w1197h795x3y4-cd5339aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350012/77b93516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350012/w1200h795x0y4-d3973fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5180 Spectacular 5bd4ba- Private Pool&spa Solterra Resort CA $138 CA $552 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Orlando-Hotels-5180-Spectacular-5bd4ba-Private-Poolspa.h119350012.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) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/c242c8bd.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) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/419df642.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 $204 total includes taxes & fees Oct 21 - Oct 22 [](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) ![Porch](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/50a06dbd.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 view](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/a2866d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Ida Beach Resort Winter Haven 7.4/10 Good (181) "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 $118 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information) ![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) ![Microwave, stovetop](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/4a623c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/82c0666a.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) ### Tiny house close to Disney KISSIMMEE Kissimmee CA $79 CA $221 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.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) ![TV](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/21005d2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/bf0d1cc9.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 $312 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Orlando-Hotels-Hidden-Lake-View-Cottage-5-Miles-From-Disney.h72359158.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) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107730000/107721700/107721689/fde69571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107730000/107721700/107721689/3e4c71af.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 $153 CA $362 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Orlando-Hotels-Charming-2-Bedroom-Cottage-In-Kissimmee.h107721689.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) ![TV](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/6887a27b.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) ### 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 $391 total includes taxes & fees Oct 21 - Oct 22 [](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/108000000/107620000/107619900/107619849/b73e0a20.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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/7b1c1f66.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 $125 CA $336 total includes taxes & fees Oct 21 - Oct 22 [](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/64000000/63750000/63741700/63741626/f8838170.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) ![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) ![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) ### 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 $304 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-Jedi-Cottage-4-Miles-From-Disney-Mins-From-Universal.h63741626.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/a40dabb3.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) ![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) ### Southern Dunes Family Retreat: Hot Tub & Game Room Haines City CA $161 CA $510 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) ![House (6 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350018/f782462d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350018/685ab0a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350018/7e1ca6e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350018/bacf9da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 411 Wanderlust Heaven 5bed/pool Kissimmee CA $178 CA $765 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-411-Wanderlust-Heaven-5bedpool.h119350018.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) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/fe821527.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) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/994d0a0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Place for a Perfect Vacation Kissimmee 10/10 Exceptional (1) CA $130 CA $287 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Orlando-Hotels-Perfect-Place-For-A-Perfect-Vacation.h70286316.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) ![A heated pool](https://images.trvl-media.com/lodging/46000000/45690000/45682800/45682757/w750h561x0y0-8dd68549.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) ![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) ### 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 $304 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-Vrbo-Property.h45682757.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) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89640000/89635100/89635062/5bc04f02.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 $289 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Lake-Hamilton-Hotels-Luxury-Cottage-Near-Legoland-Chain-Of-Lakes.h89635062.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) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/ce115948.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) ### Charming Historic Cottage with Cozy Porch and Garden Retreat Polk City CA $177 CA $373 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Polk-City-Hotels-Charming-Historic-Cottage-With-Cozy-Porch-And-Garden-Retreat.h117619898.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) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/d9043965.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) ![Pool](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/35cf1402.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 $114 CA $287 total includes taxes & fees Nov 3 - Nov 4 [](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) ![Exterior](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/8f893913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/717f73dd.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) ### Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more! Kissimmee CA $125 CA $305 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/3ed7040c.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/948252d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Cottage Near Orlando’s Top Attractions Kissimmee CA $126 CA $287 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.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/d241c4e1.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 | Living room](https://images.trvl-media.com/lodging/72000000/71430000/71428800/71428707/0b49dc0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wellerden at Reunion Resort!by Shine Villas Reunion CA $261 CA $907 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Orlando-Hotels-Wellerden-At-Reunion-Resort-By-Shine-Villas.h71428707.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=2025-11-03&endDate=2025-11-04®ionId=6048230&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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 "Good view and haven't tried the food yet. " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.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 "Clean Room and great Staff" [](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 "Spacious 2 bedroom cottage with full kitchen, washer/dryer, and pool in the backyard. We will definitely cone back." [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando-Cottages-By-Rentyl.h27548551.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 "Nice place" [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.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 "Friendly staff. Big , clean roooms" [](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 "Everything. " [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.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 "No comment, great stay overall" [](https://expedia.ca/Orlando-Hotels-Voco-Kissimmee-Orlando-By-IHG.h41083.Hotel-Information) ![Destiny Palms Hotel Maingate West](//images.trvl-media.com/lodging/1000000/430000/427400/427337/d056f561_y.jpg) ### Destiny Palms Hotel Maingate West 10/10 Excellent "The hotel have plenty room to offer breakfast, that will be great to rated it as a 4 starts." [](https://expedia.ca/Orlando-Hotels-Destiny-Palms-Hotel-Maingate-West.h427337.Hotel-Information) ![Summer Bay Orlando by Exploria Resorts](//images.trvl-media.com/lodging/1000000/110000/104100/104060/9a5b9775_y.jpg) ### Summer Bay Orlando by Exploria Resorts 10/10 Excellent "Great location. Good amenities for families and quick response for assistance. Would definitely return. " [](https://expedia.ca/Orlando-Hotels-Summer-Bay-Orlando-By-Exploria-Resorts.h104060.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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