Title: Lakeland - Winter Haven Cottages from CA $111 | 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 ![](https://images.trvl-media.com/place/6048230/acc91465-25e0-4c9a-8d30-5268c597e4d5.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 [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two 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 three 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) In four months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-05-29&endDate=2026-05-31&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/94000000/93540000/93532600/93532553/37041c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/39ee6e2d.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 $234 CA $599 total includes taxes & fees Feb 8 - Feb 9 [](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/122000000/121010000/121006800/121006717/5a99d51c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/fade59e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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) ### 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 reviews) "Just needed a place to stay close to Disney for the night and the place was clean and easy to check in and out. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jena B. CA $109 CA $254 total includes taxes & fees Feb 13 - Feb 14 [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.Hotel-Information) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125060000/125053900/125053855/41126582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125060000/125053900/125053855/w798h533x2y0-5d2bac8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125060000/125053900/125053855/d6795bb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125060000/125053900/125053855/386614ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 541-7-ld-dream Home - Private Pool&spa [](https://www.expedia.ca/Orlando-Hotels-541-7-Ld-Dream-Home-Private-Poolspa.h125053855.Hotel-Information) Kissimmee CA $3,082 CA $4,262 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Orlando-Hotels-541-7-Ld-Dream-Home-Private-Poolspa.h125053855.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 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 Feb 8 - Feb 9 [](https://www.expedia.ca/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/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) ![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) ![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 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 $137 CA $285 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Lake-Hamilton-Hotels-Luxury-Cottage-Near-Legoland-Chain-Of-Lakes.h89635062.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/b7c683bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/ce115948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/70c3f621.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) ### 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 review) "The communication with the property owner was excellent. The cottage is attached to the owners home but is quite private and comfortable. I’ve already recommended it to family members who wish to visit that area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina O. CA $156 CA $341 total includes taxes & fees Feb 14 - Feb 15 [](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/120000000/119360000/119350100/119350018/332ddedd.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/fff14553.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 $296 CA $888 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Orlando-Hotels-411-Wanderlust-Heaven-5bedpool.h119350018.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 reviews) "We have stayed here several times. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martha CA $99 CA $111 total includes taxes & fees Feb 13 - Feb 14 [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/d04f2cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/df48ecb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/4fc571b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/dae30245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 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 $127 CA $302 total includes taxes & fees Feb 9 - Feb 10 [](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) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/2eed9a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 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 $122 CA $374 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Cottage-Your-Home-Away-From-Home-4-Miles-From-Disney.h107619849.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/125000000/124460000/124457000/124456948/fe8d90ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124460000/124457000/124456948/3f33172d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124460000/124457000/124456948/6533a7d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124460000/124457000/124456948/a6386ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orlando Theme Park Basecamp: Family Home w/ Patio [](https://www.expedia.ca/Davenport-Hotels-Orlando-Theme-Park-Basecamp-Family-Home-W-Patio.h124456948.Hotel-Information) Davenport CA $193 CA $497 total includes taxes & fees Feb 7 - Feb 8 [](https://www.expedia.ca/Davenport-Hotels-Orlando-Theme-Park-Basecamp-Family-Home-W-Patio.h124456948.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) ![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) ![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) ### "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) "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 $134 CA $379 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Orlando-Hotels-Casa-Kiwi-Margaritaville-Cottage-5-Minutes-To-Disney.h99472427.Hotel-Information) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125060000/125054000/125053909/985b42cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125060000/125054000/125053909/665cfdb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125060000/125054000/125053909/66c450d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125060000/125054000/125053909/6cd0f401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 7613-8-bl-only 10 Minutes From Disney [](https://www.expedia.ca/Orlando-Hotels-7613-8-Bl-Only-10-Minutes-From-Disney.h125053909.Hotel-Information) Kissimmee CA $3,144 CA $4,497 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Orlando-Hotels-7613-8-Bl-Only-10-Minutes-From-Disney.h125053909.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) ![Interior](https://images.trvl-media.com/lodging/39000000/38840000/38832000/38831945/3ac34b99.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) ![TV](https://images.trvl-media.com/lodging/39000000/38840000/38832000/38831945/fcebd801.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 $294 CA $681 total includes taxes & fees Mar 4 - Mar 5 [](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/39000000/38840000/38836500/38836446/84a37bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38840000/38836500/38836446/f2639b09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/39000000/38840000/38836500/38836446/ee425c51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38840000/38836500/38836446/5683b47d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage with Hot Tub Near Disney with Margaritaville Resort & Island H2O. [](https://www.expedia.ca/Orlando-Hotels-Cozy-Cottage-With-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Access-8056DR.h38836446.Hotel-Information) Kissimmee CA $283 CA $667 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Orlando-Hotels-Cozy-Cottage-With-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Access-8056DR.h38836446.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) ![Living area](https://images.trvl-media.com/lodging/66000000/65350000/65346000/65345942/98ab1e53.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) ### Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -. [](https://www.expedia.ca/Orlando-Hotels-Comfy-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8087KD.h65345942.Hotel-Information) Kissimmee CA $283 CA $666 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Orlando-Hotels-Comfy-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8087KD.h65345942.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38840000/38836600/38836519/70554e33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38840000/38836600/38836519/af4362e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/39000000/38840000/38836600/38836519/93773bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38840000/38836600/38836519/670e3b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely Cottage 3 miles from Disney w/ Hot Tub and Margaritaville Resort &. [](https://www.expedia.ca/Orlando-Hotels-Lovely-Cottage-3-Miles-From-Disney-W-Hot-Tub-And-Margaritaville-Resort-Access-8092DR.h38836519.Hotel-Information) Kissimmee CA $283 CA $667 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Orlando-Hotels-Lovely-Cottage-3-Miles-From-Disney-W-Hot-Tub-And-Margaritaville-Resort-Access-8092DR.h38836519.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38830000/38825400/38825324/c6fbd9ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38830000/38825400/38825324/1bbb7b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/39000000/38830000/38825400/38825324/3cbc7102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/39000000/38830000/38825400/38825324/84507576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island. [](https://www.expedia.ca/Orlando-Hotels-Sun-Baked-Cottage-With-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Orlando-8089DR.h38825324.Hotel-Information) Kissimmee CA $283 CA $667 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Orlando-Hotels-Sun-Baked-Cottage-With-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Orlando-8089DR.h38825324.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38840000/38835700/38835612/3227fed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38840000/38835700/38835612/32e94ee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/39000000/38840000/38835700/38835612/cbe70f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38840000/38835700/38835612/b5417c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Playa Verde Cottage with Private Hot Tub near Disney with Margaritaville Resort. [](https://www.expedia.ca/Orlando-Hotels-Playa-Verde-Cottage-With-Private-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Access-8028DR.h38835612.Hotel-Information) Kissimmee CA $283 CA $667 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Orlando-Hotels-Playa-Verde-Cottage-With-Private-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Access-8028DR.h38835612.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100990000/100983100/100983068/6033a3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100990000/100983100/100983068/b3a96983.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/101000000/100990000/100983100/100983068/e4429ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/101000000/100990000/100983100/100983068/6aaba27f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Peach Cottage near Disney with Margaritaville Resort & Island H2O Access -. [](https://www.expedia.ca/Orlando-Hotels-Cozy-Peach-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8029DR.h100983068.Hotel-Information) Kissimmee CA $283 CA $667 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Orlando-Hotels-Cozy-Peach-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8029DR.h100983068.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=2026-02-20&endDate=2026-02-21®ionId=6048230&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=COTTAGE) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=APART_HOTEL) Villas [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=VILLA) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=HOUSE_BOAT) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=VACATION_HOME) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CHALET) Residences [](https://www.expedia.ca/Hotel-Search?destination=Lakeland+-+Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=6048230&latLong=27.861735%2C-81.691156&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&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%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 ![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 "Clean and spacious room" [](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 "Clean. The staff was busy but nice. One elevator was not working but there was another one." [](https://expedia.ca/Lakeland-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lakeland-West.h84646.Hotel-Information) ![Margaritaville Resort Orlando](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg) ### Margaritaville Resort Orlando 10/10 Excellent "Staff was great and the rooms were a great value " [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.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 "This was a very pleasant stay room was nice and clean. Room is very descent I would stay again and recommend it to a family or friend " [](https://expedia.ca/Orlando-Hotels-Westgate-Town-Center-Resort.h426819.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 "Room was spotless, amenities were great, quiet" [](https://expedia.ca/Orlando-Hotels-Westgate-Vacation-Villas-Resort.h98920.Hotel-Information) ![Destiny Palms Hotel Maingate West](https://images.trvl-media.com/lodging/1000000/430000/427400/427337/d056f561_y.jpg) ### Destiny Palms Hotel Maingate West 10/10 Excellent "Clean room, great staff. Very close to oark and the RunDisney event start. " [](https://expedia.ca/Orlando-Hotels-Destiny-Palms-Hotel-Maingate-West.h427337.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 "Staff was great great and the room was nice " [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Holiday Inn Winter Haven by IHG](https://images.trvl-media.com/lodging/1000000/10000/7900/7835/1b5518c0_y.jpg) ### Holiday Inn Winter Haven by IHG 10/10 Excellent "Spotless spacious room, comfy beds." [](https://expedia.ca/Winter-Haven-Hotels-Holiday-Inn-Winter-Haven.h7835.Hotel-Information) ![voco Kissimmee Orlando by IHG](https://images.trvl-media.com/lodging/1000000/50000/41100/41083/b3397abc_y.jpg) ### voco Kissimmee Orlando by IHG 10/10 Excellent "very clean and comfortable " [](https://expedia.ca/Orlando-Hotels-Voco-Kissimmee-Orlando-By-IHG.h41083.Hotel-Information) ## Find out more about Lakeland - Winter Haven ## Lakeland - Winter Haven Cottages information | Number of reviews | 199 | | ----------------- | ----------- | | Accommodation | 78 Cottages | | Lowest Price | CA $111 | | Highest Price | CA $888 | ## 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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