Title: Winter Haven Cottages from CA $121 | 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) ![Winter Haven showing rides](https://images.trvl-media.com/place/7464/a00f555f-1771-4135-ad57-834cb1a10a56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/7464/a00f555f-1771-4135-ad57-834cb1a10a56.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 [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 two months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2026-06-19&endDate=2026-06-21&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 ![Porch](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/50a06dbd.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) ![Lake](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/bf31d8de.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) ### Lake Ida Beach Resort [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information) Winter Haven 7.2/10 Good (189 reviews) "We have stayed here several times. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martha CA $108 CA $121 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.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/a051d1fb.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) ![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) ### Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn [](https://www.expedia.ca/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.Hotel-Information) Winter Haven 8.8/10 Excellent (3 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 $157 CA $384 total includes taxes & fees Mar 2 - Mar 3 [](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/94000000/93540000/93532600/93532553/37041c63.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) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/39ee6e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn [](https://www.expedia.ca/Winter-Haven-Hotels-Lovely-Lakefront-Home-W-Grill-7-Mi-To-Legoland.h93532553.Hotel-Information) Winter Haven 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 $233 CA $598 total includes taxes & fees Mar 28 - Mar 29 [](https://www.expedia.ca/Winter-Haven-Hotels-Lovely-Lakefront-Home-W-Grill-7-Mi-To-Legoland.h93532553.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122392/1535ac91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122392/w1349h899x0y1-8cf18278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122392/72dab00e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125122400/125122392/w1349h899x0y1-8d6a7992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW King Bed Glow In The Dark Kid Cave [](https://www.expedia.ca/Kissimmee-Hotels-NEW-King-Bed-Glow-In-The-Dark-Kid-Cave.h125122392.Hotel-Information) Cumbrian Lakes CA $352 CA $831 total includes taxes & fees Mar 18 - Mar 19 [](https://www.expedia.ca/Kissimmee-Hotels-NEW-King-Bed-Glow-In-The-Dark-Kid-Cave.h125122392.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532589/85946612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532589/39332604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532589/79058bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532589/18e91c65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront Babson Park Escape: Pet Friendly! [](https://www.expedia.ca/Babson-Park-Hotels-Lakefront-Babson-Park-Escape-Pet-Friendly.h93532589.Hotel-Information) Babson Park CA $267 CA $645 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Babson-Park-Hotels-Lakefront-Babson-Park-Escape-Pet-Friendly.h93532589.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) ![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) ![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) ### Tiny house close to Disney KISSIMMEE [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.Hotel-Information) Kissimmee 8.4/10 Very good (6 reviews) "The location was great. We really just needed somewhere to sleep because we spent the day at the Disney Parks. The place had enough beds and was a great price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine M. CA $123 CA $269 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.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) ![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) ![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) ### Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC [](https://www.expedia.ca/Orlando-Hotels-Mickeys-Hideaway-Cottage-4-Miles-From-Disney-In-Kissimmee-With-WiFi-And-AC.h117841053.Hotel-Information) Kissimmee CA $126 CA $301 total includes taxes & fees Mar 2 - Mar 3 [](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/108000000/107620000/107619900/107619849/b73e0a20.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) ![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 [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Cottage-Your-Home-Away-From-Home-4-Miles-From-Disney.h107619849.Hotel-Information) Kissimmee 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 $167 CA $432 total includes taxes & fees Mar 4 - Mar 5 [](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/90000000/89640000/89635100/89635062/d94a6bf0.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) ![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) ### Luxury Cottage Near Legoland & Chain of Lakes [](https://www.expedia.ca/Lake-Hamilton-Hotels-Luxury-Cottage-Near-Legoland-Chain-Of-Lakes.h89635062.Hotel-Information) Lake Hamilton 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 $136 CA $285 total includes taxes & fees Mar 3 - Mar 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/100000000/99480000/99472500/99472427/1344906b.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) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/6624d014.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) ### "Casa Kiwi" Margaritaville Cottage 5 minutes to Disney [](https://www.expedia.ca/Orlando-Hotels-Casa-Kiwi-Margaritaville-Cottage-5-Minutes-To-Disney.h99472427.Hotel-Information) Kissimmee 9.6/10 Exceptional (8 reviews) "Everything was great… Super location, easy parking, quiet." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cory & Denise CA $171 CA $423 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Orlando-Hotels-Casa-Kiwi-Margaritaville-Cottage-5-Minutes-To-Disney.h99472427.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) ![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) ![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) ### MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD [](https://www.expedia.ca/Davenport-Hotels-MID-CENTURY-TINY-FOREST-HOME-CLOSE-TO-DISNEY-WORLD.h105957115.Hotel-Information) Davenport 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 $104 CA $221 total includes taxes & fees Mar 2 - Mar 3 [](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/124000000/123530000/123529400/123529301/f4024352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123530000/123529400/123529301/4f00cc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123530000/123529400/123529301/71e4e480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/124000000/123530000/123529400/123529301/1604dca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serenity - Family & Pet Friendly, Amazing Location [](https://www.expedia.ca/Orlando-Hotels-Serenity-Family-Pet-Friendly.h123529301.Hotel-Information) Crestwynd Bay CA $188 CA $618 total includes taxes & fees Mar 7 - Mar 8 [](https://www.expedia.ca/Orlando-Hotels-Serenity-Family-Pet-Friendly.h123529301.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/47000000/46980000/46970600/46970534/a39b47e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/47000000/46980000/46970600/46970534/eceb5e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/47000000/46980000/46970600/46970534/72eb63e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/47000000/46980000/46970600/46970534/fae994e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access. [](https://www.expedia.ca/Orlando-Hotels-Seas-The-Day-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8001FF.h46970534.Hotel-Information) Kissimmee CA $375 CA $822 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Orlando-Hotels-Seas-The-Day-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8001FF.h46970534.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72310000/72301200/72301164/2e23544d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/73000000/72310000/72301200/72301164/efbab20e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72310000/72301200/72301164/a91d01d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/73000000/72310000/72301200/72301164/9b638623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark. [](https://www.expedia.ca/Orlando-Hotels-Sunny-Cottage-Near-Disney-With-Margaritaville-Resort-Access-3004SR.h72301164.Hotel-Information) Kissimmee CA $348 CA $782 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Orlando-Hotels-Sunny-Cottage-Near-Disney-With-Margaritaville-Resort-Access-3004SR.h72301164.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/e8dd0e9b.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/95000000/94350000/94349800/94349752/2de4b41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool [](https://www.expedia.ca/Orlando-Hotels-Sunny-Kissimmee-Gem-W-Game-Room-Hot-Tub.h94349752.Hotel-Information) Indian Ridge CA $158 CA $643 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Orlando-Hotels-Sunny-Kissimmee-Gem-W-Game-Room-Hot-Tub.h94349752.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/66000000/65350000/65346000/65345942/475df83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/66000000/65350000/65346000/65345942/2f97bd01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/66000000/65350000/65346000/65345942/7a2d6268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/66000000/65350000/65346000/65345942/98ab1e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -. [](https://www.expedia.ca/Orlando-Hotels-Comfy-Cottage-Near-Disney-With-Margaritaville-Resort-Island-H2O-Access.h65345942.Hotel-Information) Kissimmee CA $282 CA $660 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Orlando-Hotels-Comfy-Cottage-Near-Disney-With-Margaritaville-Resort-Island-H2O-Access.h65345942.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105660000/105650700/105650644/b29bd03b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105660000/105650700/105650644/c38f9cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/106000000/105660000/105650700/105650644/25ce8bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/106000000/105660000/105650700/105650644/c0079a2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vivid Cottage Near Disney with Margaritaville Resort & Island H2O Access -. [](https://www.expedia.ca/Orlando-Hotels-Vivid-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8020FF.h105650644.Hotel-Information) Kissimmee CA $348 CA $782 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Orlando-Hotels-Vivid-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8020FF.h105650644.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/60000000/59840000/59831700/59831674/8386ef6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/60000000/59840000/59831700/59831674/3f175bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/60000000/59840000/59831700/59831674/d9afbff7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59840000/59831700/59831674/724afe3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -. [](https://www.expedia.ca/Orlando-Hotels-Sunny-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8032LS.h59831674.Hotel-Information) Kissimmee CA $310 CA $701 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Orlando-Hotels-Sunny-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8032LS.h59831674.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38840000/38832000/38831945/c188155f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38840000/38832000/38831945/e04c2ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/39000000/38840000/38832000/38831945/37032849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38840000/38832000/38831945/3ac34b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Livin' for the Weekend Cottage near Disney with Margaritaville Resort & Island. [](https://www.expedia.ca/Orlando-Hotels-Livin-For-The-Weekend-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8021FF.h38831945.Hotel-Information) Kissimmee CA $310 CA $701 total includes taxes & fees Mar 11 - Mar 12 [](https://www.expedia.ca/Orlando-Hotels-Livin-For-The-Weekend-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8021FF.h38831945.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100990000/100983100/100983011/404fc74e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/101000000/100990000/100983100/100983011/e2815b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/101000000/100990000/100983100/100983011/1a94e836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/101000000/100990000/100983100/100983011/dc087122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -. [](https://www.expedia.ca/Orlando-Hotels-Crystal-Cottage-Near-Disney-With-Margaritaville-Access-8033LS.h100983011.Hotel-Information) Kissimmee CA $321 CA $715 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Orlando-Hotels-Crystal-Cottage-Near-Disney-With-Margaritaville-Access-8033LS.h100983011.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=2026-03-15&endDate=2026-03-16®ionId=7464&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_7464) ## 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=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&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=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=APART_HOTEL) 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=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&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=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=COTTAGE) 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=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&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=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=CONDO) 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=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=CABIN) 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=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=CHALET) 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=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&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%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 ![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 "Great resort. Kids loved the pools! Close to Disney!" [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.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 "Handicap room needs the floor scrubbed. Our feet were black at the end of the day." [](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 "Repeat customer, love this place" [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information) ![Westgate Vacation Villas Resort](https://images.trvl-media.com/lodging/1000000/100000/99000/98920/b8afec09_y.jpg) ### Westgate Vacation Villas Resort 10/10 Excellent "Good staff. I love the gym. " [](https://expedia.ca/Orlando-Hotels-Westgate-Vacation-Villas-Resort.h98920.Hotel-Information) ![Holiday Inn & Suites Orlando SW - Celebration Area by IHG](https://images.trvl-media.com/lodging/1000000/10000/7900/7855/e4318c5d_y.jpg) ### Holiday Inn & Suites Orlando SW - Celebration Area by IHG 10/10 Excellent "Everything was great. Great location for our needs." [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Orlando-SW-Celebration-Area.h7855.Hotel-Information) ![Westgate Town Center Resort](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/410a3d83_y.jpg) ### Westgate Town Center Resort 10/10 Excellent "Good value for money. Very nice rooms and villas. Great place to stay" [](https://expedia.ca/Orlando-Hotels-Westgate-Town-Center-Resort.h426819.Hotel-Information) ![Kompose Boutique Resort at Theme Parks](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/3cf09a4a_y.jpg) ### Kompose Boutique Resort at Theme Parks 10/10 Excellent "Room’s where new and very nice..breakfast was good and the service was great " [](https://expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) ![Delta Hotels by Marriott Orlando Celebration](https://images.trvl-media.com/lodging/1000000/10000/300/256/w4000h2663x0y0-bece67c9_y.jpg) ### Delta Hotels by Marriott Orlando Celebration 10/10 Excellent "The rooms were very clean and the staff was courteous." [](https://expedia.ca/Orlando-Hotels-The-Grand-Orlando-Resort-At-Celebration.h256.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 "Grandkids had so much fun. Everything was clean and staff were so friendly and helpful. " [](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 | 208 | | ----------------- | ------------- | | Accommodation | 1732 Cottages | | Lowest Price | CA $121 | | Highest Price | CA $822 | ## 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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