Title: Winter Haven Cottages from CA $109 | Expedia.ca [Winter Haven Travel Guide](https://expedia.ca/Winter-Haven.dx7464)[Hotels in Winter Haven](https://expedia.ca/Winter-Haven-Hotels.d7464.Travel-Guide-Hotels)[Vacation Rentals in Winter Haven](https://expedia.ca/Winter-Haven-Vacation-Rentals.d7464.Travel-Guide-VacationRentals)[Flights to Winter Haven](https://expedia.ca/Cheap-Flights-To-Winter-Haven.d7464.Travel-Guide-Flights)[Things to do in Winter Haven](https://expedia.ca/Things-To-Do-In-Winter-Haven.d7464.Travel-Guide-Activities)[Winter Haven Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Haven.d7464.Car-Rental-Guide)[Winter Haven Vacation Packages](https://expedia.ca/Winter-Haven.d7464.Destination-Travel-Guides) ![Legoland Florida showing signage and rides](https://images.trvl-media.com/place/6153639/fda15cc5-b61f-4932-b081-d6d5e0df3165.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6153639/fda15cc5-b61f-4932-b081-d6d5e0df3165.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winter Haven cottages ![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) ![Interior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/1d7e29a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/3f53f763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.Hotel-Information) 10/10 Exceptional (2 reviews) "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 $160 CA $388 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/13dc8494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/75562742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/37041c63.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/acae569e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Lovely-Lakefront-Home-W-Grill-7-Mi-To-Legoland.h93532553.Hotel-Information) 10/10 Exceptional (3 reviews) "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 $237 CA $608 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Winter-Haven-Hotels-Lovely-Lakefront-Home-W-Grill-7-Mi-To-Legoland.h93532553.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) ![Lake](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/bf31d8de.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) ![Quadruple Room, Non Smoking, Lake View | Living area](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/3f904c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information) 7.2/10 Good (188 reviews) "We have stayed here several times. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martha CA $97 CA $109 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.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/90000000/89640000/89635100/89635062/01cc4a42.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) ![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) ### Cottage in Lake Hamilton [](https://www.expedia.ca/Lake-Hamilton-Hotels-Luxury-Cottage-Near-Legoland-Chain-Of-Lakes.h89635062.Hotel-Information) 10/10 Exceptional (6 reviews) "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 $139 CA $284 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Lake-Hamilton-Hotels-Luxury-Cottage-Near-Legoland-Chain-Of-Lakes.h89635062.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/b7c683bb.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) ![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) ![Interior](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/4b563550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Polk City [](https://www.expedia.ca/Polk-City-Hotels-Charming-Historic-Cottage-With-Cozy-Porch-And-Garden-Retreat.h117619898.Hotel-Information) 10/10 Exceptional (1 review) "The communication with the property owner was excellent. The cottage is attached to the owners home but is quite private and comfortable. I’ve already recommended it to family members who wish to visit that area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina O. CA $106 CA $279 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Polk-City-Hotels-Charming-Historic-Cottage-With-Cozy-Porch-And-Garden-Retreat.h117619898.Hotel-Information) ![Microwave, stovetop](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/5a99d51c.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) ![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) ![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) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.Hotel-Information) 8.6/10 Excellent (4 reviews) "Just needed a place to stay close to Disney for the night and the place was clean and easy to check in and out. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jena B. CA $111 CA $258 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/b5aeb802.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) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/04d5c0c3.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) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.Hotel-Information) 10/10 Exceptional (1 review) "Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joyce R. CA $125 CA $284 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94349800/94349752/f35435d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94349800/94349752/7032768a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94349800/94349752/7ec11444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94349800/94349752/2de4b41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Indian Ridge [](https://www.expedia.ca/Orlando-Hotels-Sunny-Kissimmee-Gem-W-Game-Room-Hot-Tub.h94349752.Hotel-Information) CA $161 CA $654 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Orlando-Hotels-Sunny-Kissimmee-Gem-W-Game-Room-Hot-Tub.h94349752.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/108000000/107620000/107619900/107619849/2eed9a03.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/108000000/107620000/107619900/107619849/6cf42041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Cottage-Your-Home-Away-From-Home-4-Miles-From-Disney.h107619849.Hotel-Information) 10/10 Exceptional (2 reviews) "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 $137 CA $388 total includes taxes & fees Feb 10 - Feb 11 [](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/100000000/99480000/99472500/99472427/1344906b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/b3fcb277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/w1170h775x0y10-04e3660f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/w1170h775x0y0-46037233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Casa-Kiwi-Margaritaville-Cottage-5-Minutes-To-Disney.h99472427.Hotel-Information) 9.8/10 Exceptional (7 reviews) "Wonderful place to stay overnight. Nice furnishings. Good room layout for family. Convenience of washer and dryer. Host was quick and responsive. Thank you for a terrific stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George L. CA $149 CA $404 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Orlando-Hotels-Casa-Kiwi-Margaritaville-Cottage-5-Minutes-To-Disney.h99472427.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/124000000/123530000/123529400/123529301/efa0f2e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123530000/123529400/123529301/c3ade632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123530000/123529400/123529301/739c3336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123530000/123529400/123529301/2acdfd0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Serenity-Family-Pet-Friendly.h123529301.Hotel-Information) [](https://www.expedia.ca/Orlando-Hotels-Serenity-Family-Pet-Friendly.h123529301.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/123000000/122400000/122394200/122394116/7d08ae60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394200/122394116/a88a6e7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394200/122394116/w2997h2000x0y0-aa15bb02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394200/122394116/2d0912fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Solterra Resort [](https://www.expedia.ca/Orlando-Hotels-Family-Fun-Villa-W-Pool.h122394116.Hotel-Information) CA $192 CA $655 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Orlando-Hotels-Family-Fun-Villa-W-Pool.h122394116.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105957200/105957115/dc3bbc70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105960000/105957200/105957115/w1079h710x0y4-025e1c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105960000/105957200/105957115/504f5bcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105960000/105957200/105957115/b985ffa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Davenport [](https://www.expedia.ca/Davenport-Hotels-MID-CENTURY-TINY-FOREST-HOME-CLOSE-TO-DISNEY-WORLD.h105957115.Hotel-Information) 5.0/10 (2 reviews) "Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca F. CA $106 CA $224 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Davenport-Hotels-MID-CENTURY-TINY-FOREST-HOME-CLOSE-TO-DISNEY-WORLD.h105957115.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350018/332ddedd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350018/aefe71a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (6 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350018/93e82dc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350018/1dad3a2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-411-Wanderlust-Heaven-5bedpool.h119350018.Hotel-Information) CA $304 CA $906 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Orlando-Hotels-411-Wanderlust-Heaven-5bedpool.h119350018.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/d04f2cb5.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) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/4fc571b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/dae30245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Mickeys-Hideaway-Cottage-4-Miles-From-Disney-In-Kissimmee-With-WiFi-And-AC.h117841053.Hotel-Information) CA $122 CA $295 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Orlando-Hotels-Mickeys-Hideaway-Cottage-4-Miles-From-Disney-In-Kissimmee-With-WiFi-And-AC.h117841053.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/124000000/123110000/123109500/123109446/4f39d9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123110000/123109500/123109446/3e899098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/124000000/123110000/123109500/123109446/74c7b339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123110000/123109500/123109446/2d316913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Stylish-5BR-Home-With-Themed-Bedrooms.h123109446.Hotel-Information) [](https://www.expedia.ca/Orlando-Hotels-Stylish-5BR-Home-With-Themed-Bedrooms.h123109446.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123560000/123552100/123552014/0344d41e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123560000/123552100/123552014/ba95adda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123560000/123552100/123552014/6a9b332c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123560000/123552100/123552014/f42d25a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Dixieland [](https://www.expedia.ca/Lakeland-Hotels-2BR-Dog-Friendly-W-Yard.h123552014.Hotel-Information) CA $136 CA $381 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Lakeland-Hotels-2BR-Dog-Friendly-W-Yard.h123552014.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29®ionId=7464&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=VILLA) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=COTTAGE) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=CABIN) Residences [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=RESIDENCE) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=CHALET) ![](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%2FWinter-Haven-Cottages.d7464-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Haven-Cottages.d7464-aaCottages.Travel-Guide-Accommodation) ## Top Winter Haven Hotel Reviews ![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 "A++++" [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![Margaritaville Resort Orlando](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg) ### Margaritaville Resort Orlando 10/10 Excellent "Dylan was wonderful at check in. Offered free drink coupons and complimentary cabana to celebrate my husbands birthday. Room was very clean, pool was very nice and food very good. Close to restaurants and shopping. Would recommend to the traveler who does not need to be right at the theme parks." [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information) ![Meliá Orlando Celebration](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/b440f6b4_y.jpg) ### Meliá Orlando Celebration 10/10 Excellent "The room was spotless, and comfortable and had everything we needed. The pool area was amazing. The restaurant was great. I could not complain about one thing. I would definitely go back." [](https://expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.Hotel-Information) ![Best Western Plus Winter Haven Inn & Suites ](https://images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/b48185c3_y.jpg) ### Best Western Plus Winter Haven Inn & Suites 10/10 Excellent "Clean, " [](https://expedia.ca/Winter-Haven-Hotels-Best-Western-Plus-Winter-Haven-Inn-Suites.h91029909.Hotel-Information) ![Galleria Palms Hotel](https://images.trvl-media.com/lodging/1000000/90000/84700/84682/47b4a2b7_y.jpg) ### Galleria Palms Hotel 10/10 Excellent "Everything was perfect " [](https://expedia.ca/Orlando-Hotels-Galleria-Palms-Hotel.h84682.Hotel-Information) ![Ramada by Wyndham Kissimmee Gateway](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/b94616ba_y.jpg) ### Ramada by Wyndham Kissimmee Gateway 10/10 Excellent "The staff was very accommodating." [](https://expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information) ![Holiday Inn Club Vacations at Orange Lake Resort by IHG](https://images.trvl-media.com/lodging/1000000/10000/6400/6315/ac7826b3_y.jpg) ### Holiday Inn Club Vacations at Orange Lake Resort by IHG 10/10 Excellent "Did not use pool." [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.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 "Clean room, nice staff and service, nice accommodations!! Plenty of parking and great location!!" [](https://expedia.ca/Orlando-Hotels-Destiny-Palms-Hotel-Maingate-West.h427337.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 "Great property. " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ## Find out more about Winter Haven ## Winter Haven Cottages information | Number of reviews | 199 | | ----------------- | ------------- | | Accommodation | 1732 Cottages | | Lowest Price | CA $109 | | Highest Price | CA $906 | ## Frequently asked questions ### How much do cottages in Winter Haven cost? ### How many cottages are there in Winter Haven? ### Are there any family-friendly cottages in Winter Haven? ### Why book your cottage in Winter Haven with Expedia? ### How can I find cheap cottages in Winter Haven? ### What is there to do in Winter Haven near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Guest Houses in Auburndale ](https://www.expedia.ca/Auburndale-Guest-Houses.d6048255-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Auburndale ](https://www.expedia.ca/Auburndale-Holiday-Parks.d6048255-aaHolidayParks.Travel-Guide-Accommodation) - 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