Title: Best Cottages in Winter Haven in 2026 | Expedia.co.uk [Winter Haven Travel Guide](https://expedia.co.uk/Winter-Haven.dx7464)[Hotels in Winter Haven](https://expedia.co.uk/Winter-Haven-Hotels.d7464.Travel-Guide-Hotels)[Holiday Rentals in Winter Haven](https://expedia.co.uk/Winter-Haven-Holiday-Rentals.d7464.Travel-Guide-HolidayRentals)[Flights to Winter Haven](https://expedia.co.uk/Cheap-Flights-To-Winter-Haven.d7464.Travel-Guide-Flights)[Things to do in Winter Haven](https://expedia.co.uk/Things-To-Do-In-Winter-Haven.d7464.Travel-Guide-Activities)[Winter Haven Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winter-Haven.d7464.Car-Hire-Guide)[Winter Haven Holidays](https://expedia.co.uk/Winter-Haven.d7464.Holidays-City-Breaks) ![Winter Haven which includes rides](https://images.trvl-media.com/place/7464/a00f555f-1771-4135-ad57-834cb1a10a56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/7464/a00f555f-1771-4135-ad57-834cb1a10a56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=7464&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=7464&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) In three months [8 May - 10 May](https://www.expedia.co.uk/Hotel-Search?regionId=7464&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [5 Jun - 7 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=7464&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winter Haven cottages ![Exterior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/ad468c68.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) ![TV](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/6887a27b.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.co.uk/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. £203 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.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 | TV](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 | TV](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, pool loungers](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/a66b5fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Ida Beach Resort [](https://www.expedia.co.uk/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 £61 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/13dc8494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/acae569e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/39ee6e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/37041c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn [](https://www.expedia.co.uk/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 £320 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/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.co.uk/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. £138 includes taxes & fees 13 Feb - 14 Feb [](https://www.expedia.co.uk/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125124000/125123956/03ec00c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125124000/125123956/4395e92a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125124000/125123956/aa817c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125124000/125123956/86484b8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 201-4-hb-beautiful Home at Terraverde [](https://www.expedia.co.uk/Orlando-Hotels-201-4-Hb-Beautiful-Home-At-Terraverde.h125123956.Hotel-Information) Kissimmee £2,125 includes taxes & fees 14 Mar - 15 Mar [](https://www.expedia.co.uk/Orlando-Hotels-201-4-Hb-Beautiful-Home-At-Terraverde.h125123956.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/108000000/107620000/107619900/107619849/945e14a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/0eda7c58_edited_1bbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/6cf42041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee [](https://www.expedia.co.uk/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. £204 includes taxes & fees 26 Feb - 27 Feb [](https://www.expedia.co.uk/Orlando-Hotels-Beautiful-Cottage-Your-Home-Away-From-Home-4-Miles-From-Disney.h107619849.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89640000/89635100/89635062/d94a6bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Interior](https://images.trvl-media.com/lodging/90000000/89640000/89635100/89635062/3f617b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Cottage Near Legoland & Chain of Lakes [](https://www.expedia.co.uk/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. £153 includes taxes & fees 26 Feb - 27 Feb [](https://www.expedia.co.uk/Lake-Hamilton-Hotels-Luxury-Cottage-Near-Legoland-Chain-Of-Lakes.h89635062.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/120000000/119360000/119350100/119350018/1dad3a2f.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.co.uk/Orlando-Hotels-411-Wanderlust-Heaven-5bedpool.h119350018.Hotel-Information) Kissimmee £365 includes taxes & fees 13 Feb - 14 Feb [](https://www.expedia.co.uk/Orlando-Hotels-411-Wanderlust-Heaven-5bedpool.h119350018.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/95000000/94350000/94349800/94349752/7032768a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94349800/94349752/ae645d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94350000/94349800/94349752/2de4b41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool [](https://www.expedia.co.uk/Orlando-Hotels-Sunny-Kissimmee-Gem-W-Game-Room-Hot-Tub.h94349752.Hotel-Information) Indian Ridge £345 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Orlando-Hotels-Sunny-Kissimmee-Gem-W-Game-Room-Hot-Tub.h94349752.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/dae30245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/4fc571b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC [](https://www.expedia.co.uk/Orlando-Hotels-Mickeys-Hideaway-Cottage-4-Miles-From-Disney-In-Kissimmee-With-WiFi-And-AC.h117841053.Hotel-Information) Kissimmee £162 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Orlando-Hotels-Mickeys-Hideaway-Cottage-4-Miles-From-Disney-In-Kissimmee-With-WiFi-And-AC.h117841053.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99480000/99472500/99472427/1344906b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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.co.uk/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. £225 includes taxes & fees 10 Mar - 11 Mar [](https://www.expedia.co.uk/Orlando-Hotels-Casa-Kiwi-Margaritaville-Cottage-5-Minutes-To-Disney.h99472427.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105957200/105957115/dc3bbc70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105960000/105957200/105957115/504f5bcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105960000/105957200/105957115/w1079h710x0y4-025e1c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105960000/105957200/105957115/b985ffa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD [](https://www.expedia.co.uk/Davenport-Hotels-MID-CENTURY-TINY-FOREST-HOME-CLOSE-TO-DISNEY-WORLD.h105957115.Hotel-Information) Davenport 5.0/10 (2 reviews) "Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca F. £109 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Davenport-Hotels-MID-CENTURY-TINY-FOREST-HOME-CLOSE-TO-DISNEY-WORLD.h105957115.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) ![Interior](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/70c3f621.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) ### Charming Historic Cottage with Cozy Porch and Garden Retreat [](https://www.expedia.co.uk/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. [](https://www.expedia.co.uk/Polk-City-Hotels-Charming-Historic-Cottage-With-Cozy-Porch-And-Garden-Retreat.h117619898.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/126000000/125130000/125124000/125123952/427afce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125124000/125123952/de0eab7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125124000/125123952/dc76d97d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125130000/125124000/125123952/79e63265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 161-4-cb-cozy Villa at Terra Verde [](https://www.expedia.co.uk/Orlando-Hotels-161-4-Cb-Cozy-Villa-At-Terra-Verde.h125123952.Hotel-Information) Kissimmee £2,060 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Orlando-Hotels-161-4-Cb-Cozy-Villa-At-Terra-Verde.h125123952.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38840000/38837100/38837004/ad7a21f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/39000000/38840000/38837100/38837004/b0795fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38840000/38837100/38837004/b5c300ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38840000/38837100/38837004/bd427dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Life Cottage near Disney with Margaritaville Resort & Island H2O Access. [](https://www.expedia.co.uk/Orlando-Hotels-Island-Life-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8026SU.h38837004.Hotel-Information) Kissimmee 10/10 Exceptional (1 review) "Great location for all things Disney." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris B. £370 includes taxes & fees 10 Mar - 11 Mar [](https://www.expedia.co.uk/Orlando-Hotels-Island-Life-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8026SU.h38837004.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) ![TV](https://images.trvl-media.com/lodging/39000000/38840000/38835700/38835612/4f9aa2e0.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.co.uk/Orlando-Hotels-Playa-Verde-Cottage-With-Private-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Access-8028DR.h38835612.Hotel-Information) Kissimmee £350 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/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/39000000/38830000/38825400/38825324/c6fbd9ba.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) ![Pool](https://images.trvl-media.com/lodging/39000000/38830000/38825400/38825324/3cbc7102.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) ### Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island. [](https://www.expedia.co.uk/Orlando-Hotels-Sun-Baked-Cottage-With-Hot-Tub-Near-Disney-With-Margaritaville-Resort-Orlando-8089DR.h38825324.Hotel-Information) Kissimmee £350 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/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/39000000/38840000/38836600/38836519/70554e33.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/39000000/38840000/38836600/38836519/af4362e5.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.co.uk/Orlando-Hotels-Lovely-Cottage-3-Miles-From-Disney-W-Hot-Tub-And-Margaritaville-Resort-Access-8092DR.h38836519.Hotel-Information) Kissimmee £350 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Orlando-Hotels-Lovely-Cottage-3-Miles-From-Disney-W-Hot-Tub-And-Margaritaville-Resort-Access-8092DR.h38836519.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/125000000/124460000/124457000/124456948/6533a7d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124460000/124457000/124456948/d1fc8964.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.co.uk/Davenport-Hotels-Orlando-Theme-Park-Basecamp-Family-Home-W-Patio.h124456948.Hotel-Information) Davenport £266 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Davenport-Hotels-Orlando-Theme-Park-Basecamp-Family-Home-W-Patio.h124456948.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106250000/106245400/106245314/3ce0092d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/107000000/106250000/106245400/106245314/7c9e00b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/107000000/106250000/106245400/106245314/876b01e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106250000/106245400/106245314/6d6492e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access. [](https://www.expedia.co.uk/Orlando-Hotels-Caraway-Cove-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8024SU.h106245314.Hotel-Information) Kissimmee £350 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Orlando-Hotels-Caraway-Cove-Cottage-Near-Disney-With-Margaritaville-Resort-Access-8024SU.h106245314.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.co.uk/Hotel-Search?startDate=2026-02-25&endDate=2026-02-26®ionId=7464&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APART_HOTEL) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=VACATION_HOME) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=VILLA) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APARTMENT) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CONDO) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=COTTAGE) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CABIN) Houseboats [](https://www.expedia.co.uk/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=HOUSE_BOAT) Residences [](https://www.expedia.co.uk/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=RESIDENCE) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CHALET) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Haven-Cottages.d7464-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Haven-Cottages.d7464-aaCottages.Travel-Guide-Accommodation) ## Top 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 "Clean room, great staff." [](https://expedia.co.uk/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![Kompose Boutique Resort at Theme Parks](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/3cf09a4a_y.jpg) ### Kompose Boutique Resort at Theme Parks 10/10 Excellent "The hotel is very clean" [](https://expedia.co.uk/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) ![Vacation Village Orlando, Celebration](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/fb6985f5_y.jpg) ### Vacation Village Orlando, Celebration 10/10 Excellent "Todo impecable " [](https://expedia.co.uk/Orlando-Hotels-Vacation-Village-At-Parkway.h1068973.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 "It was good" [](https://expedia.co.uk/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.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 "Such an amazing resort, and HUGE! Our room was spacious and very clean. Front desk was very helpful, fast with our check-in and very informative. We would definitely stay here again..we just hope the cold doesn’t follow us down next time haha " [](https://expedia.co.uk/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ![Legoland Florida Hotel](https://images.trvl-media.com/lodging/114000000/113250000/113243700/113243677/cfc6de7c_y.jpg) ### Legoland Florida Hotel 10/10 Excellent "We had the absolute best time at the Legoland Pirate Island Hotel with my two little boys (5 and 7). The lobby is so much fun (they loved playing in the castle with other kids and building lego), we enjoyed the PJ Dance Party at night and a little show before that. The decor is perfect for any kid - especially for those that love pirates. Our boys were blown away and so excited for their bunk beds and little mini room “on their own”. The hotel doesn’t get enough credit — of course it’s not a 5-star, the food isn’t the best in the world but it’s absolutely perfect for families. The staff are incredible and attentive. If you go into it from a kids perspective, you know they’ll remember it forever! Bathrooms have kid-height sinks/dryers and our room even had a built in potty seat for anyone who wanted to use it! The kids loved the treasure hunt as soon as we got in the room and the interactive elevators. The breakfast in the morning was perfect too! It was served family style and everyone got exactly what they needed! Loved this experience! It’s one we’ll never forget" [](https://expedia.co.uk/Winter-Haven-Hotels-Legoland-Florida-Hotel.h113243677.Hotel-Information) ![Ramada by Wyndham Kissimmee Gateway](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/b94616ba_y.jpg) ### Ramada by Wyndham Kissimmee Gateway 10/10 Excellent "N/a" [](https://expedia.co.uk/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information) ![Westgate Towers Resort](https://images.trvl-media.com/lodging/1000000/180000/170900/170878/bd08ea58_y.jpg) ### Westgate Towers Resort 10/10 Excellent "Clean and comfortable room" [](https://expedia.co.uk/Orlando-Hotels-Westgate-Towers-Resort.h170878.Hotel-Information) ![Silver Lake Resort](https://images.trvl-media.com/lodging/1000000/20000/14600/14518/f53cedc1_y.jpg) ### Silver Lake Resort 10/10 Excellent "Great stay! My kid had a great time. Entry and exit was smooth everyday and we were left alone. The timeshare company took no for an answer at check in. If I had a bad thing to say, it would be that the toilet paper could use an upgrade." [](https://expedia.co.uk/Orlando-Hotels-Silver-Lake-Resort.h14518.Hotel-Information) ## Find out more about Winter Haven ## Winter Haven Cottages information | Number of reviews | 201 | | ----------------- | ------------- | | Accommodation | 1732 Cottages | | Lowest Price | £61 | | Highest Price | £370 | ## Frequently asked questions ### How much do cottages in Winter Haven cost? ### How many cottages are there in Winter Haven? ### Are there any family-friendly cottages in Winter Haven? ### Why book your cottage in Winter Haven with Expedia? ### How can I find cheap cottages in Winter Haven? ### What is there to do in Winter Haven near my cottage? ## Explore a world of travel with Expedia - More ways to book - [Book Cottages in Winter Haven on Expedia.com ](https://www.expedia.com/Winter-Haven-Cottages.d7464-aaCottages.Travel-Guide-Accommodation)