Title: Lakeland - Winter Haven Cottages from CA $117 | 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 featuring rides and signage as well as an individual child](https://images.trvl-media.com/place/6048230/fd516f05-78fc-4dc9-94cd-10e2896d4318.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Visit Central Florida ![](https://images.trvl-media.com/place/6048230/fd516f05-78fc-4dc9-94cd-10e2896d4318.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 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2026-05-15&endDate=2026-05-17&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 (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/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/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/f42d25a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Dixieland [](https://www.expedia.ca/Lakeland-Hotels-2BR-Dog-Friendly-W-Yard.h123552014.Hotel-Information) CA $136 CA $381 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Lakeland-Hotels-2BR-Dog-Friendly-W-Yard.h123552014.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) ![Smart TV](https://images.trvl-media.com/lodging/97000000/96740000/96737800/96737713/0d69889a.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) ### Cottage in Avon Park [](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) 10/10 Exceptional (2 reviews) "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 31 - Feb 1 [](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) ![Exterior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/ad468c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/a051d1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/110000000/109310000/109302000/109301943/6887a27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.Hotel-Information) 10/10 Exceptional (2 reviews) "Just what we needed for a weekend trip with our grandsons for the weekend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine B. CA $160 CA $390 total includes taxes & fees Jan 21 - Jan 22 [](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) ![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) ![Miscellaneous](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/fade59e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.Hotel-Information) 8.6/10 Excellent (4 reviews) "Just needed a place to stay close to Disney for the night and the place was clean and easy to check in and out. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jena B. CA $111 CA $257 total includes taxes & fees Feb 13 - Feb 14 [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/126000000/125060000/125053900/125053854/5267ea55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125060000/125053900/125053854/8a1b702c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125060000/125053900/125053854/1bbec667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125060000/125053900/125053854/f3d032b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Calabay Parc [](https://www.expedia.ca/Orlando-Hotels-439-4-Od-Perfect-Vacation-Rental.h125053854.Hotel-Information) CA $3,191 CA $4,264 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Orlando-Hotels-439-4-Od-Perfect-Vacation-Rental.h125053854.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/4b563550.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) ### Cottage in Polk City [](https://www.expedia.ca/Polk-City-Hotels-Charming-Historic-Cottage-With-Cozy-Porch-And-Garden-Retreat.h117619898.Hotel-Information) 10/10 Exceptional (1 review) "The communication with the property owner was excellent. The cottage is attached to the owners home but is quite private and comfortable. I’ve already recommended it to family members who wish to visit that area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina O. CA $106 CA $283 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Polk-City-Hotels-Charming-Historic-Cottage-With-Cozy-Porch-And-Garden-Retreat.h117619898.Hotel-Information) ![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) ![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) ![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) ### Cottage in Winter Haven [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information) 7.2/10 Good (188 reviews) "We have stayed here several times. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martha CA $104 CA $117 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350018/6922fbca.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/ee7c7efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350018/2141b038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (6 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350018/1b4db48f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-411-Wanderlust-Heaven-5bedpool.h119350018.Hotel-Information) CA $285 CA $884 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Orlando-Hotels-411-Wanderlust-Heaven-5bedpool.h119350018.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) ![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) ![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) ### Cottage in Lake Hamilton [](https://www.expedia.ca/Lake-Hamilton-Hotels-Luxury-Cottage-Near-Legoland-Chain-Of-Lakes.h89635062.Hotel-Information) 10/10 Exceptional (6 reviews) "This place is tiny but everything you need for a comfortable stay! Would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dallas C. CA $139 CA $287 total includes taxes & fees Jan 22 - Jan 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/108000000/107620000/107619900/107619849/b73e0a20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/2eed9a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/6cf42041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/945e14a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Cottage-Your-Home-Away-From-Home-4-Miles-From-Disney.h107619849.Hotel-Information) 10/10 Exceptional (2 reviews) "We stayed and visited universal snd drove to Jacksonville it was a cute cottage" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer b. CA $137 CA $397 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Cottage-Your-Home-Away-From-Home-4-Miles-From-Disney.h107619849.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94349800/94349752/f35435d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94349800/94349752/ae645d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94349800/94349752/7032768a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/95000000/94350000/94349800/94349752/f4670bc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Indian Ridge [](https://www.expedia.ca/Orlando-Hotels-Sunny-Kissimmee-Gem-W-Game-Room-Hot-Tub.h94349752.Hotel-Information) CA $161 CA $654 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Orlando-Hotels-Sunny-Kissimmee-Gem-W-Game-Room-Hot-Tub.h94349752.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/1344906b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/b3fcb277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/6624d014.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) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Casa-Kiwi-Margaritaville-Cottage-5-Minutes-To-Disney.h99472427.Hotel-Information) 9.8/10 Exceptional (7 reviews) "Wonderful place to stay overnight. Nice furnishings. Good room layout for family. Convenience of washer and dryer. Host was quick and responsive. Thank you for a terrific stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George L. CA $149 CA $399 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Orlando-Hotels-Casa-Kiwi-Margaritaville-Cottage-5-Minutes-To-Disney.h99472427.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/b5aeb802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/25aafbc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/dcad85d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/3ed7040c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.Hotel-Information) 10/10 Exceptional (1 review) "Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joyce R. CA $125 CA $281 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/126000000/125060000/125050100/125050063/87c9df46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125060000/125050100/125050063/fb55dcb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125060000/125050100/125050063/fe138a8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125060000/125050100/125050063/598c61f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Solterra Resort [](https://www.expedia.ca/Orlando-Hotels-6079-7-Bo-Enchanted-Villa-By-Disney.h125050063.Hotel-Information) CA $3,191 CA $4,319 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Orlando-Hotels-6079-7-Bo-Enchanted-Villa-By-Disney.h125050063.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) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/4fc571b2.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) ![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) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Mickeys-Hideaway-Cottage-4-Miles-From-Disney-In-Kissimmee-With-WiFi-And-AC.h117841053.Hotel-Information) CA $129 CA $304 total includes taxes & fees Jan 21 - Jan 22 [](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/66000000/65350000/65346000/65345942/475df83e.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) ![Lobby](https://images.trvl-media.com/lodging/66000000/65350000/65346000/65345942/5c643c06.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) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Comfy-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8087KD.h65345942.Hotel-Information) [](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) ![Interior](https://images.trvl-media.com/lodging/39000000/38840000/38836600/38836519/670e3b8d.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) ![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/39000000/38840000/38836600/38836519/4b8a99d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Lovely-Cottage-3-Miles-From-Disney-W-Hot-Tub-And-Margaritaville-Resort-Access-8092DR.h38836519.Hotel-Information) [](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) ![Interior](https://images.trvl-media.com/lodging/39000000/38830000/38825400/38825324/fb932b07.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) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Sun-Baked-Cottage-With-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Orlando-8089DR.h38825324.Hotel-Information) [](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/101000000/100990000/100983000/100982952/e477655b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/101000000/100990000/100983000/100982952/cf9582b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/101000000/100990000/100983000/100982952/cc69e1a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/101000000/100990000/100983000/100982952/58f8da38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Inviting-Cottage-With-Private-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Access-8072DR.h100982952.Hotel-Information) [](https://www.expedia.ca/Orlando-Hotels-Inviting-Cottage-With-Private-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Access-8072DR.h100982952.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/122000000/121340000/121337000/121336925/6e20576e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Kissimmee [](https://www.expedia.ca/Orlando-Hotels-Dreamy-Coral-Cottage-With-Hot-Tub-Near-Disney-With-Margaritaville-Resort.h121336925.Hotel-Information) [](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=2026-02-03&endDate=2026-02-04®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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=CABIN) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=APART_HOTEL) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=COTTAGE) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=VILLA) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=VACATION_HOME) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=APARTMENT) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&lodging=HOUSE_BOAT) 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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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=2026-04-20&d1=2026-04-20&endDate=2026-04-23&d2=2026-04-23&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 ![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 "Great " [](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 was fantastic " [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![Margaritaville Resort Orlando](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg) ### Margaritaville Resort Orlando 10/10 Excellent "the rooms are spotless." [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information) ![Holiday Inn Express Lake Wales N-Winter Haven by IHG](https://images.trvl-media.com/lodging/3000000/2850000/2840600/2840563/ec483d12_y.jpg) ### Holiday Inn Express Lake Wales N-Winter Haven by IHG 10/10 Excellent "Plenty clean shops and stores around that you could walk to if you wanted in a nice area." [](https://expedia.ca/Lake-Wales-Hotels-Holiday-Inn-Express-Lake-Wales-N-Winter-Haven.h2840563.Hotel-Information) ![Meliá Orlando Celebration](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/b440f6b4_y.jpg) ### Meliá Orlando Celebration 10/10 Excellent "We got put in the melia due to an error at the hotel we were supposed to stay at cancelling our booking when we were supposed to arrive. What an absolute blessing in disguise. The wonderful front desk agent was so pleasant to deal with, could tell we were having a bad night due to the other hotels error and even upgraded our room for us! The rooms were clean, every staff member we spoke to were cheerful and the Wilson’s food was great. Our five year old had his birthday while we were there and the waitress overheard us and got the waitstaff to sign a card and bring a cake for him at breakfast. 10/10 would stay here again any chance we get. " [](https://expedia.ca/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.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 "good place. we will come again" [](https://expedia.ca/Lakeland-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lakeland-West.h84646.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 "Yes, it was cool." [](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 "Yes to the staff. My only complaint is that I wish I had asked for a queen bed . We had a King and only one nightstand. We stayed with you last Month. Dec 3-10 . in Building 1100\. We are planning a return visit in February around the middle of the month. I prefer the first floor. " [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.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 "The place was great and convenient to everything " [](https://expedia.ca/Orlando-Hotels-Westgate-Vacation-Villas-Resort.h98920.Hotel-Information) ## Find out more about Lakeland - Winter Haven ## Lakeland - Winter Haven Cottages information | Number of reviews | 195 | | ----------------- | ----------- | | Accommodation | 78 Cottages | | Lowest Price | CA $117 | | Highest Price | CA $884 | ## 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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