Title: Lakeland - Winter Haven Cottages from CA $131 | 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 aircraft](https://images.trvl-media.com/place/6048230/acc91465-25e0-4c9a-8d30-5268c597e4d5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Visit Central Florida # Search Lakeland - Winter Haven Cottage Rentals from CA $131 - ![](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 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6048230&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 four months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6048230&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) ## Our top choices for Lakeland - Winter Haven cottages ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/b6402d13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/22bd9d81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/6e1ebfac.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) "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 Dec 27 - Dec 28 [](https://www.expedia.ca/Winter-Haven-Hotels-Lovely-Lakefront-Home-W-Grill-7-Mi-To-Legoland.h93532553.Hotel-Information) ![Microwave, stovetop](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/f5f31efd.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/c1a2c56f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/71673f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny house close to Disney KISSIMMEE [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.Hotel-Information) Kissimmee 9.0/10 Wonderful (2) "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 $110 CA $255 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/9a3ce3e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/419df642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/0d69889a.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) ### 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 $201 total includes taxes & fees Dec 29 - Dec 30 [](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) ![Lake view](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/a2866d00.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) ![Standard Room, 1 Queen Bed, Non Smoking | Private kitchenette](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/4549c4d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Ida Beach Resort [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information) Winter Haven 7.2/10 Good (187) "We have stayed here several times. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martha CA $117 CA $131 total includes taxes & fees Jan 15 - Jan 16, 2026 [](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/90000000/89640000/89635100/89635062/983e7aa9.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) ### 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 $284 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Lake-Hamilton-Hotels-Luxury-Cottage-Near-Legoland-Chain-Of-Lakes.h89635062.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) ![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) ### 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 $374 total includes taxes & fees Jan 1 - Jan 2, 2026 [](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/123000000/122400000/122394200/122394132/d90102b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/123000000/122400000/122394200/122394132/7ef6bcf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394200/122394132/w1919h1080x1y0-3aa8328f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394200/122394132/w1919h1080x1y0-73658746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upstay: Bright Family-friendly Retreat With Patio [](https://www.expedia.ca/Orlando-Hotels-Upstay-Bright-Family-Friendly-Retreat-With-Patio.h122394132.Hotel-Information) Chatham Park CA $130 CA $381 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Orlando-Hotels-Upstay-Bright-Family-Friendly-Retreat-With-Patio.h122394132.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/108000000/107620000/107619900/107619849/7b1c1f66.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/108000000/107620000/107619900/107619849/945e14a3.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) "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 $169 CA $435 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Cottage-Your-Home-Away-From-Home-4-Miles-From-Disney.h107619849.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/4b563550.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) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/034df557.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 CA $193 CA $391 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Polk-City-Hotels-Charming-Historic-Cottage-With-Cozy-Porch-And-Garden-Retreat.h117619898.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/3ed7040c.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 $278 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123560000/123552100/123552014/92718e88.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/f42d25a0.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) ### 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 4 - Jan 5, 2026 [](https://www.expedia.ca/Lakeland-Hotels-2BR-Dog-Friendly-W-Yard.h123552014.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) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/df48ecb3.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) ![Dining](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/d04f2cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC [](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 5 - Jan 6, 2026 [](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/108000000/107720000/107716100/107716064/b5c4778e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107720000/107716100/107716064/98e77b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107720000/107716100/107716064/d91b1f85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107720000/107716100/107716064/22b2677c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Charming-1-Bedroom-Cottage-In-Kissimmee.h107716064.Hotel-Information) Kissimmee CA $137 CA $341 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Orlando-Hotels-Charming-1-Bedroom-Cottage-In-Kissimmee.h107716064.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/97000000/96060000/96051000/96050914/5557415a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96060000/96051000/96050914/ed6faf61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96060000/96051000/96050914/be3a5ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/97000000/96060000/96051000/96050914/58774300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Lake Cottage - 4 miles to Disney [](https://www.expedia.ca/Orlando-Hotels-Cozy-Lake-Cottage-4-Miles-To-Disney.h96050914.Hotel-Information) Kissimmee CA $184 CA $391 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Orlando-Hotels-Cozy-Lake-Cottage-4-Miles-To-Disney.h96050914.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/e197c85d.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) ![Lobby](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/b3fcb277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/w1170h764x0y0-3a2495e4.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 (6) "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 $164 CA $414 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Orlando-Hotels-Casa-Kiwi-Margaritaville-Cottage-5-Minutes-To-Disney.h99472427.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350015/c0f582a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350015/w1171h750x5y0-5fbc1675.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) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350015/c292fa95.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 CA $467 CA $1,388 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Davenport-Hotels-1209-9-B-Mansion-Themed-With-Pool-Near-Disney.h119350015.Hotel-Information) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394200/122394155/c0f9fb09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394200/122394155/w1599h1066x1y1-e5c60bc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394200/122394155/w1599h1066x1y1-81e90d9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122400000/122394200/122394155/w1599h1066x1y1-62e2ad4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upstay Lakeside Retreat w Private Pool & Game Room [](https://www.expedia.ca/Orlando-Hotels-Upstay-Lakeside-Retreat-W-Private-Pool-Game-Room.h122394155.Hotel-Information) Sandy Ridge [](https://www.expedia.ca/Orlando-Hotels-Upstay-Lakeside-Retreat-W-Private-Pool-Game-Room.h122394155.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96060000/96050800/96050707/7fd1f046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/97000000/96060000/96050800/96050707/9c50ec99.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/97000000/96060000/96050800/96050707/e90548cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/97000000/96060000/96050800/96050707/8e558232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Tropical Cottage - 4 mi to Disney [](https://www.expedia.ca/Orlando-Hotels-Cozy-Tropical-Cottage-4-Mi-To-Disney.h96050707.Hotel-Information) Kissimmee CA $184 CA $394 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Orlando-Hotels-Cozy-Tropical-Cottage-4-Mi-To-Disney.h96050707.Hotel-Information) ![House, 6 Bedrooms | Exterior](https://images.trvl-media.com/lodging/72000000/71430000/71428800/71428707/w1021h764x3y4-bccfb2df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71430000/71428800/71428707/a0237592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71430000/71428800/71428707/d241c4e1.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 [](https://www.expedia.ca/Orlando-Hotels-Wellerden-At-Reunion-Resort-By-Shine-Villas.h71428707.Hotel-Information) Reunion CA $445 CA $1,105 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Orlando-Hotels-Wellerden-At-Reunion-Resort-By-Shine-Villas.h71428707.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/122000000/121340000/121337000/121336925/46406ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/122000000/121340000/121337000/121336925/6e20576e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/122000000/121340000/121337000/121336925/0d817fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121340000/121337000/121336925/0bd141d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &. [](https://www.expedia.ca/Orlando-Hotels-Dreamy-Coral-Cottage-With-Hot-Tub-Near-Disney-With-Margaritaville-Resort.h121336925.Hotel-Information) Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Dreamy-Coral-Cottage-With-Hot-Tub-Near-Disney-With-Margaritaville-Resort.h121336925.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=2026-01-04&endDate=2026-01-05®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 ![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 "Very spacious " [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![Hilton Vacation Club Aqua Sol Orlando West](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg) ### Hilton Vacation Club Aqua Sol Orlando West 10/10 Excellent "What a wonderful stay! I cannot brag enough about this place. Comfortable beds, clean unit and linens, pools and amenities around the campus were so much fun to explore. Staff were helpful, friendly, and great to talk to. Campus felt like you were coming home. Safe and convenient location, quiet and family friendly. This was our third time visiting. .. we will be back! " [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Quality Inn & Suites By the Parks](https://images.trvl-media.com/lodging/1000000/20000/18900/18866/7474f0f7_y.jpg) ### Quality Inn & Suites By the Parks 10/10 Excellent "Breakfast was excellent, property needs maintenance attention specially walkways painting on upper floors " [](https://expedia.ca/Orlando-Hotels-Quality-Inn-Suites-By-The-Parks.h18866.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 "HUGE GATED RESORT! Shuttles run around complex from 8AM to 11PM. Pools are heated, lazy river is relaxing! Access to great pools, hot tubs, dining, golf, pickleball & so much more! Marketplace serves Starbucks coffee & has its own grocery & souvenir sections. Family friendly resort, activities for kids & adults. Staff is helpful, friendly & very accommodating. Will be back in the future. " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.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 "It was a very nice place to stay " [](https://expedia.ca/Lakeland-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lakeland-West.h84646.Hotel-Information) ![Ramada by Wyndham Davenport Orlando South](https://images.trvl-media.com/lodging/1000000/50000/41600/41556/7399552c_y.jpg) ### Ramada by Wyndham Davenport Orlando South 10/10 Excellent "Love love this property, beautiful, clean , safe and the staff excellent service " [](https://expedia.ca/Davenport-Hotels-Ramada-By-Wyndham-Davenport-Orlando-South.h41556.Hotel-Information) ![Margaritaville Resort Orlando](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg) ### Margaritaville Resort Orlando 10/10 Excellent "We love staying at this hotel. " [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.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 "Loved this resort. I do wish the restaurant stayed open later, but overall 10/10\. " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Omni Orlando Resort at ChampionsGate](https://images.trvl-media.com/lodging/2000000/1030000/1030000/1029950/a4fe8de4_y.jpg) ### Omni Orlando Resort at ChampionsGate 10/10 Excellent "Excellent resort, a1 services" [](https://expedia.ca/Orlando-Hotels-Omni-Orlando-Resort-At-ChampionsGate.h1029950.Hotel-Information) ## Find out more about Lakeland - Winter Haven ## Lakeland - Winter Haven Cottages information | Number of reviews | 197 | | ----------------- | ----------- | | Accommodation | 78 Cottages | | Lowest Price | CA $131 | | Highest Price | CA $1,388 | ## 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 - 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