Title: Lakeland - Winter Haven Cottages from CA $116 | 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](https://images.trvl-media.com/place/6048230/8f47b8b8-82cb-478d-aa45-11932c63dbb0.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Lakeland - Winter Haven Cottage Rentals from CA $116 - ![](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 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Lakeland - Winter Haven cottages ![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/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) ![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) ### 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) "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 $236 CA $605 total includes taxes & fees Jan 12 - Jan 13 [](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/97000000/96740000/96737800/96737713/644a29bc.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) ![Interior](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/b9623a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/9a3ce3e0.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 [](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) Avon Park 10/10 Exceptional (2) "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 $106 CA $202 total includes taxes & fees Jan 14 - Jan 15 [](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) ![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) ![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) ![Lake](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/bf31d8de.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 (188) "We have stayed here several times. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martha CA $104 CA $116 total includes taxes & fees Jan 9 - Jan 10 [](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) ![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) ![TV](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/a051d1fb.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 [](https://www.expedia.ca/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.Hotel-Information) 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 $159 CA $385 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.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) ![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) ![Miscellaneous](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/fade59e9.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 8.6/10 Excellent (4) "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 $256 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.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) ![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) ![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 [](https://www.expedia.ca/Polk-City-Hotels-Charming-Historic-Cottage-With-Cozy-Porch-And-Garden-Retreat.h117619898.Hotel-Information) Polk City 10/10 Exceptional (1) "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 $278 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Polk-City-Hotels-Charming-Historic-Cottage-With-Cozy-Porch-And-Garden-Retreat.h117619898.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) ![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) "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 $138 CA $287 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Lake-Hamilton-Hotels-Luxury-Cottage-Near-Legoland-Chain-Of-Lakes.h89635062.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) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/dae30245.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 $122 CA $291 total includes taxes & fees Jan 25 - Jan 26 [](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/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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/6624d014.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 9.8/10 Exceptional (7) "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 $136 CA $386 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Orlando-Hotels-Casa-Kiwi-Margaritaville-Cottage-5-Minutes-To-Disney.h99472427.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/120000000/119360000/119350100/119350018/1dad3a2f.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/aefe71a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Encore Swanky [](https://www.expedia.ca/Orlando-Hotels-411-Wanderlust-Heaven-5bedpool.h119350018.Hotel-Information) Kissimmee CA $322 CA $926 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Orlando-Hotels-411-Wanderlust-Heaven-5bedpool.h119350018.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/cf629094.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) ### 2BR Dog-friendly w/ Yard, Screened Porch, & Grill [](https://www.expedia.ca/Lakeland-Hotels-2BR-Dog-Friendly-W-Yard.h123552014.Hotel-Information) Dixieland CA $135 CA $379 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Lakeland-Hotels-2BR-Dog-Friendly-W-Yard.h123552014.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/dcad85d1.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) ![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) ### Family-Friendly Cottage Near Orlando’s Top Attractions [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.Hotel-Information) Kissimmee 10/10 Exceptional (1) "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 $124 CA $279 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.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/108000000/107620000/107619900/107619849/945e14a3.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) ### 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) "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 $178 CA $447 total includes taxes & fees Jan 31 - Feb 1 [](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/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) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105960000/105957200/105957115/0065e066.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) ### 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) "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 $111 CA $229 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Davenport-Hotels-MID-CENTURY-TINY-FOREST-HOME-CLOSE-TO-DISNEY-WORLD.h105957115.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) ![Interior](https://images.trvl-media.com/lodging/47000000/46980000/46970600/46970534/72eb63e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/47000000/46980000/46970600/46970534/e156bd3b.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) ### 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 [](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/101000000/100990000/100983100/100983034/f55a7f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/101000000/100990000/100983100/100983034/323d44d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/101000000/100990000/100983100/100983034/13590584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/101000000/100990000/100983100/100983034/5fafff3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Cottage with Private Hot Tub near Disney with Margaritaville Resort &. [](https://www.expedia.ca/Orlando-Hotels-Charming-Cottage-Near-Disney-With-Private-Hot-Tub-Margaritaville-Resort-Access-3025SP.h100983034.Hotel-Information) Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Charming-Cottage-Near-Disney-With-Private-Hot-Tub-Margaritaville-Resort-Access-3025SP.h100983034.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100990000/100982900/100982850/76687024.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100990000/100982900/100982850/69a4b240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/101000000/100990000/100982900/100982850/fafadeb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/101000000/100990000/100982900/100982850/7726d1ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark. [](https://www.expedia.ca/Orlando-Hotels-Dreamy-Cottage-Near-Disney-With-Private-Pool-Margaritaville-Resort-Access-2944SR.h100982850.Hotel-Information) Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Dreamy-Cottage-Near-Disney-With-Private-Pool-Margaritaville-Resort-Access-2944SR.h100982850.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/46000000/45090000/45090000/45089955/9d06ec0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/46000000/45090000/45090000/45089955/70a0a122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/46000000/45090000/45090000/45089955/e006365c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/46000000/45090000/45090000/45089955/ae8299a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coral Reef Cottage! near Disney with Margaritaville Resort & Island H2O Access. [](https://www.expedia.ca/Orlando-Hotels-Coral-Reef-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8052LS.h45089955.Hotel-Information) Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Coral-Reef-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8052LS.h45089955.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105660000/105650600/105650578/3592e178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105660000/105650600/105650578/53d3e37d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/106000000/105660000/105650600/105650578/88791aa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/106000000/105660000/105650600/105650578/6fb1f9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lively Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O. [](https://www.expedia.ca/Orlando-Hotels-Lively-Cottage-With-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Access-8030SU.h105650578.Hotel-Information) Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Lively-Cottage-With-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Access-8030SU.h105650578.Hotel-Information) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350015/cb973021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350015/32647ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350015/b19e8102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350015/d742e5ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Watersong Swanky [](https://www.expedia.ca/Davenport-Hotels-1209-9-B-Mansion-Themed-With-Pool-Near-Disney.h119350015.Hotel-Information) Davenport [](https://www.expedia.ca/Davenport-Hotels-1209-9-B-Mansion-Themed-With-Pool-Near-Disney.h119350015.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=2026-01-22&endDate=2026-01-23®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 ![Embassy Suites By Hilton Orlando Sunset Walk](https://images.trvl-media.com/lodging/91000000/90610000/90603800/90603708/68d1bc67_y.jpg) ### Embassy Suites By Hilton Orlando Sunset Walk 10/10 Excellent "Yes" [](https://expedia.ca/Orlando-Hotels-Embassy-Suites-By-Hilton-Orlando-Sunset-Walk.h90603708.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 "Everything " [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![Comfort Inn & Suites Lakeland North I-4](https://images.trvl-media.com/lodging/1000000/30000/20800/20754/2ebe4f87_y.jpg) ### Comfort Inn & Suites Lakeland North I-4 10/10 Excellent "The stay was excellent. It was clean, comfortable, and quiet. Right by I-4, so that's nice too. The wi-fi was a little wonky, but the front desk (Ethan, if I'm not mistaken) took care of it quickly." [](https://expedia.ca/Lakeland-Hotels-Comfort-Inn-Suites-Lakeland-North-I-4.h20754.Hotel-Information) ![Summer Bay Orlando by Exploria Resorts](https://images.trvl-media.com/lodging/1000000/110000/104100/104060/9a5b9775_y.jpg) ### Summer Bay Orlando by Exploria Resorts 10/10 Excellent "Rooms were clean and specious." [](https://expedia.ca/Orlando-Hotels-Summer-Bay-Orlando-By-Exploria-Resorts.h104060.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lakeland West](https://images.trvl-media.com/lodging/1000000/90000/84700/84646/58543b1b_y.jpg) ### La Quinta Inn & Suites by Wyndham Lakeland West 10/10 Excellent "great price. Clean hotel. Thank ypu!!" [](https://expedia.ca/Lakeland-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lakeland-West.h84646.Hotel-Information) ![Meliá Orlando Celebration](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/b440f6b4_y.jpg) ### Meliá Orlando Celebration 10/10 Excellent "Nice rooms " [](https://expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.Hotel-Information) ![Orbit One Vacation Villas](https://images.trvl-media.com/lodging/1000000/10000/7300/7233/f7cffdb3_y.jpg) ### Orbit One Vacation Villas 10/10 Excellent "excellent" [](https://expedia.ca/Orlando-Hotels-Orbit-One-Vacation-Villas.h7233.Hotel-Information) ![Margaritaville Resort Orlando](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg) ### Margaritaville Resort Orlando 10/10 Excellent "All of the above and customer service" [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.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 "This location is one of the best resorts I’ve been in America. They have everything for the kids,adults, and all seniors. This property was clean and the staff was phenomenal. I would recommend this location for any family or family reunions. The rooms was spacious and did not feel like you were in a motel or a hotel individual room. The restaurants was reasonably priced and the food was great. We will definitely be going back." [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ## Find out more about Lakeland - Winter Haven ## Lakeland - Winter Haven Cottages information | Number of reviews | 200 | | ----------------- | ----------- | | Accommodation | 78 Cottages | | Lowest Price | CA $116 | | Highest Price | CA $926 | ## Frequently asked questions ### How much do cottages in Lakeland - Winter Haven cost? ### How many cottages are there in Lakeland - Winter Haven? ### Why book your cottage in Lakeland - Winter Haven with Expedia? ### How can I find cheap cottages in Lakeland - Winter Haven? ### What is there to do in Lakeland - Winter Haven near my cottage? ## 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) - 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