Title: Winter Haven Condo Rentals from CA $165 | Expedia.ca [Winter Haven Travel Guide](https://expedia.ca/Winter-Haven.dx7464)[Hotels in Winter Haven](https://expedia.ca/Winter-Haven-Hotels.d7464.Travel-Guide-Hotels)[Vacation Rentals in Winter Haven](https://expedia.ca/Winter-Haven-Vacation-Rentals.d7464.Travel-Guide-VacationRentals)[Flights to Winter Haven](https://expedia.ca/Cheap-Flights-To-Winter-Haven.d7464.Travel-Guide-Flights)[Things to do in Winter Haven](https://expedia.ca/Things-To-Do-In-Winter-Haven.d7464.Travel-Guide-Activities)[Winter Haven Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Haven.d7464.Car-Rental-Guide)[Winter Haven Vacation Packages](https://expedia.ca/Winter-Haven.d7464.Destination-Travel-Guides) ![Winter Haven showing 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__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 27 - Mar 1](https://www.expedia.ca/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 [Apr 10 - Apr 12](https://www.expedia.ca/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 [May 8 - May 10](https://www.expedia.ca/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 [Jun 5 - Jun 7](https://www.expedia.ca/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 condo rentals ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/1ef981b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch TV with cable channels, DVD player](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/f4bb77d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hiking](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/9e1fc450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch TV with cable channels, DVD player](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/4ec89cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village Orlando, Celebration [](https://www.expedia.ca/Orlando-Hotels-Vacation-Village-At-Parkway.h1068973.Hotel-Information) Kissimmee 8.6/10 Excellent (3,344 reviews) "Yes .. very clean rooms and hotel chef was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alicia CA $116 CA $165 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Orlando-Hotels-Vacation-Village-At-Parkway.h1068973.Hotel-Information) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120710000/120709200/120709160/1f44bd1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/121000000/120710000/120709200/120709160/361450b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/121000000/120710000/120709200/120709160/75976c65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/121000000/120710000/120709200/120709160/fc1a789f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake View•Gardens•Private Balcony Suite•Legoland [](https://www.expedia.ca/Lake-Wales-Hotels-Lake-ViewGardensPrivate-Balcony-SuiteLegoland.h120709160.Hotel-Information) Lake Wales 8.8/10 Excellent (6 reviews) CA $159 CA $205 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Lake-Wales-Hotels-Lake-ViewGardensPrivate-Balcony-SuiteLegoland.h120709160.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/125000000/124420000/124419900/124419860/77d8cd74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/125000000/124420000/124419900/124419860/26f09460.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/125000000/124420000/124419900/124419860/8da095f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124420000/124419900/124419860/e829ee79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright Ground Floor Condo Minutes to Parks [](https://www.expedia.ca/Orlando-Hotels-Bright-Ground-Floor-Condo-Minutes-To-Parks.h124419860.Hotel-Information) Kissimmee CA $113 CA $407 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Orlando-Hotels-Bright-Ground-Floor-Condo-Minutes-To-Parks.h124419860.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/92000000/91320000/91315200/91315112/3c54e46c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/92000000/91320000/91315200/91315112/4e5a01f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, table tennis](https://images.trvl-media.com/lodging/92000000/91320000/91315200/91315112/54a81065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91320000/91315200/91315112/01c953f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Scenic Resort Home Close to Disney and Universal [](https://www.expedia.ca/Orlando-Hotels-Scenic-LakeView-Condo.h91315112.Hotel-Information) Kissimmee 10/10 Exceptional (1 review) "Would 1000 times over stay here than in a hotel!! The location to everything is ideal. You are not in the middle of all the traffic and lime light of tourism but still close enough of a short drive. You have all the convenience unlike a cramped hotel room. The property felt safe. Would absolutely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa S. CA $109 CA $277 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Orlando-Hotels-Scenic-LakeView-Condo.h91315112.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111350000/111348500/111348407/a8e14a61.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/112000000/111350000/111348500/111348407/6233441b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/112000000/111350000/111348500/111348407/e075c2c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111350000/111348500/111348407/bab5f889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parkway Palms Resort 1 bedroom condo mins to Disney World. [](https://www.expedia.ca/Orlando-Hotels-Parkway-Palms-Resort-1-Bedroom-Condo-Mins-To-Disney-World.h111348407.Hotel-Information) Kissimmee 10/10 Exceptional (1 review) "The condo is ideally located for Disney World with many restaurants close by. The property manager was quick to respond to any questions and we would definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael G. CA $82 CA $484 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Orlando-Hotels-Parkway-Palms-Resort-1-Bedroom-Condo-Mins-To-Disney-World.h111348407.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/92000000/91550000/91546100/91546033/182c5e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/92000000/91550000/91546100/91546033/55d5c37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91550000/91546100/91546033/8add918c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91550000/91546100/91546033/b26f8a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upstay - Pet-Friendly Condo - Sauna, Pool [](https://www.expedia.ca/Orlando-Hotels-Pet-Friendly-Condo-Hot-Tub.h91546033.Hotel-Information) Winter Garden CA $139 CA $402 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Orlando-Hotels-Pet-Friendly-Condo-Hot-Tub.h91546033.Hotel-Information) ![Golf](https://images.trvl-media.com/lodging/34000000/33600000/33590600/33590600/b998406d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33600000/33590600/33590600/ca50c74b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33600000/33590600/33590600/f32f4cb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/34000000/33600000/33590600/33590600/7d60bc72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LUXURY 2 BEDROOM SECOND FLOOR (CORNER) CONDO IN SOUTHERN DUNES [](https://www.expedia.ca/Haines-City-Hotels-LUXURY-2-BEDROOM-SECOND-FLOOR.h33590600.Hotel-Information) Haines City 9.2/10 Wonderful (63 reviews) "We extended our stay by two weeks, please read my previous review. Can not complain about anything apart from location from theme parks, at least a 45 minute drive from attractions." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Anthony M. CA $186 CA $639 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Haines-City-Hotels-LUXURY-2-BEDROOM-SECOND-FLOOR.h33590600.Hotel-Information) ![Room](https://images.trvl-media.com/lodging/123000000/122950000/122948400/122948378/86e6295a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/123000000/122950000/122948400/122948378/8cd560a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122950000/122948400/122948378/9f963f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/123000000/122950000/122948400/122948378/5fbec1ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish Retreat/86\`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake [](https://www.expedia.ca/Lake-Wales-Hotels-Stylish-Retreat86TVKing-BedSpa-ShowerShuffleboardNear-The-Lake.h122948378.Hotel-Information) Lake Wales 6.0/10 (2 reviews) "Had an amazing stay! Property was exactly how it was described- clean, comfortable, very safe. (As a solo woman traveling alone feeling safe always makes a trip easier) The bed and sheets were sooo comfortable! Micki was kind, attentive, incredibly responsive and happily accommodated me, making my entire experience was seamless. I felt right at home, would happily return. 5 Stars is not enough to describe how wonderful Micki is as host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $191 CA $242 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Lake-Wales-Hotels-Stylish-Retreat86TVKing-BedSpa-ShowerShuffleboardNear-The-Lake.h122948378.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33270000/33262400/33262341/187ca528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33270000/33262400/33262341/a59104f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33270000/33262400/33262341/bc05f2d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33270000/33262400/33262341/946a4493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bahama Bay, Davenport, Florida Oversize 2 Br condo [](https://www.expedia.ca/Orlando-Hotels-Bahama-Bay.h33262341.Hotel-Information) Bahama Bay 9.6/10 Exceptional (9 reviews) "Was good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) June C. CA $183 CA $396 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Orlando-Hotels-Bahama-Bay.h33262341.Hotel-Information) ![Printers](https://images.trvl-media.com/lodging/110000000/109990000/109989900/109989899/6ccd8924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Printers](https://images.trvl-media.com/lodging/110000000/109990000/109989900/109989899/70f3c050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109990000/109989900/109989899/dced47e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109990000/109989900/109989899/f3165c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 Min to Disney! 2BR Condo w/ King Bed, Pool, Fast WiFi & SmartTV+kitchen+washer [](https://www.expedia.ca/Orlando-Hotels-5-Min-To-Disney-2BR-Condo-W-King-Bed.h109989899.Hotel-Information) Kissimmee 10/10 Exceptional (2 reviews) "The place was perfect. Had plenty of space and everything we needed. Quiet, clean, & has a good layout. Host was great and had wonderful communication. Definitely will be back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $128 CA $389 total includes taxes & fees Mar 11 - Mar 12 [](https://www.expedia.ca/Orlando-Hotels-5-Min-To-Disney-2BR-Condo-W-King-Bed.h109989899.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/97000000/96540000/96533100/96533055/09b69ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96540000/96533100/96533055/14147fba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96540000/96533100/96533055/8b501a5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/97000000/96540000/96533100/96533055/197c89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super spacious near Disney with private pool [](https://www.expedia.ca/Orlando-Hotels-Super-Spacious-Near-Disney-With-Private-Pool.h96533055.Hotel-Information) Kissimmee 9.6/10 Exceptional (4 reviews) "Great house on a very convenient location. Communication with host was smooth and i highly recommend the house! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fernando N. CA $176 CA $676 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Orlando-Hotels-Super-Spacious-Near-Disney-With-Private-Pool.h96533055.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33560000/33560000/33559971/09305881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33560000/33560000/33559971/a72d9e11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33560000/33560000/33559971/10ab1dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33560000/33560000/33559971/2407dbf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney [](https://www.expedia.ca/Orlando-Hotels-Modern-Award-Winning-Newly-Renovated.h33559971.Hotel-Information) Kissimmee 9.2/10 Wonderful (153 reviews) "Excellent accommodations." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raychelle CA $148 CA $363 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Orlando-Hotels-Modern-Award-Winning-Newly-Renovated.h33559971.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/112000000/111230000/111226500/111226497/b57102cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111230000/111226500/111226497/3078b8b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111230000/111226500/111226497/c0b6a129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111230000/111226500/111226497/c75a5dde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Golf‑View 3BR Condo, Pet‑Friendly Near Disney [](https://www.expedia.ca/Orlando-Hotels-Resort-Condo-WPool-Golf-Views.h111226497.Hotel-Information) Reunion CA $101 CA $541 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Orlando-Hotels-Resort-Condo-WPool-Golf-Views.h111226497.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78360000/78353700/78353620/w1024h669x0y7-41bf7e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78360000/78353700/78353620/a4ebd72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/79000000/78360000/78353700/78353620/w1020h683x2y0-1aad76ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78360000/78353700/78353620/7e76bd9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Near Disney/Resort Pool, Bar & Gym [](https://www.expedia.ca/Orlando-Hotels-Cozy-Tropical-Resort-15-Min-From-Theme-Parks.h78353620.Hotel-Information) Champions Gate 9.4/10 Exceptional (6 reviews) "The property was great.. very clean and relaxing" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Dawn D. CA $114 CA $388 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/Orlando-Hotels-Cozy-Tropical-Resort-15-Min-From-Theme-Parks.h78353620.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/91000000/90860000/90850400/90850368/6dd644b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90860000/90850400/90850368/72627423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/91000000/90860000/90850400/90850368/ad1a1a5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/91000000/90860000/90850400/90850368/866042c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand New 2bd/2 bth condo 300 [](https://www.expedia.ca/Orlando-Hotels-Brand-New-2bd2-Bth-Condo-300.h90850368.Hotel-Information) davenport 9.8/10 Exceptional (6 reviews) "We have stayed here before. Good location for all your needs, excellent accommodations, gated community. Would rent again if available on our next trip. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martin T. CA $146 CA $644 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Orlando-Hotels-Brand-New-2bd2-Bth-Condo-300.h90850368.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/703f29a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/7750d2a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/d1fdeb13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/114000000/113870000/113867900/113867841/dab5e8b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upstay - Large Condo Near Disney w Pool and Gym [](https://www.expedia.ca/Orlando-Hotels-Upstay-Large-Condo-Near-Disney-W-Pool-And-Gym.h113867841.Hotel-Information) Winter Garden CA $117 CA $410 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Orlando-Hotels-Upstay-Large-Condo-Near-Disney-W-Pool-And-Gym.h113867841.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/98000000/97590000/97586400/97586387/f084073d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97590000/97586400/97586387/8086acb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97590000/97586400/97586387/fa2bace5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/98000000/97590000/97586400/97586387/b79aa35f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upstay: Modern Solara Retreat w/ Pool & Games Room [](https://www.expedia.ca/Orlando-Hotels-4BR-Home-W-Full-Resort-Access-Near-Disney.h97586387.Hotel-Information) Kissimmee 9.6/10 Exceptional (7 reviews) "This was our second stay at this property. We enjoyed it just as much as our first stay! It is clean, spacious and has everything we need. The communication with the host has always been great. Close to all theme parks, restaurants, and groceries. We will stay here again on our next trip!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsey S. CA $158 CA $531 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Orlando-Hotels-4BR-Home-W-Full-Resort-Access-Near-Disney.h97586387.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/90000000/89230000/89225500/89225408/96840543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/90000000/89230000/89225500/89225408/e29aab1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/90000000/89230000/89225500/89225408/97695cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/90000000/89230000/89225500/89225408/63f5e14f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy and Brand New 2BD condo at Championsgate 291 [](https://www.expedia.ca/Orlando-Hotels-Cozy-And-Brand-New-2BD-Condo-At-Championsgate-291.h89225408.Hotel-Information) Davenport 9.8/10 Exceptional (6 reviews) "Correspondence was good, Listed accurate, clean and comfy! Thank you! Enjoyed our time there...the Oasis pools were amazing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas K. CA $142 CA $640 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Orlando-Hotels-Cozy-And-Brand-New-2BD-Condo-At-Championsgate-291.h89225408.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33507200/33507197/73f412f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33510000/33507200/33507197/52854ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33510000/33507200/33507197/3def2840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33507200/33507197/a58f9c82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bahama Bay Resort - Platinum Deluxe Condo Great for Families or Couples [](https://www.expedia.ca/Orlando-Hotels-Bahama-Bay-Resort-Platinum-Deluxe-Condo-Great-For-Families-Or-Couples.h33507197.Hotel-Information) Bahama Bay 9.6/10 Exceptional (137 reviews) "My family loved the space and ease of this property. Lots of room and the pools were fantastic! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle K. CA $153 CA $427 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Orlando-Hotels-Bahama-Bay-Resort-Platinum-Deluxe-Condo-Great-For-Families-Or-Couples.h33507197.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/84000000/83410000/83403600/83403510/w1290h968x0y911-aebf8e6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/84000000/83410000/83403600/83403510/w508h683x258y0-808fe7a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83410000/83403600/83403510/w907h683x59y0-7df03684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83410000/83403600/83403510/w506h683x259y0-b9004539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Valentina’s Condo-Resort Style! [](https://www.expedia.ca/Orlando-Hotels-Valentinas-Condo-Resort-Style.h83403510.Hotel-Information) Kissimmee 10/10 Exceptional (6 reviews) "Nice neighborhood, local pool and condo. Would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason M. CA $134 CA $353 total includes taxes & fees Feb 24 - Feb 25 [](https://www.expedia.ca/Orlando-Hotels-Valentinas-Condo-Resort-Style.h83403510.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=2026-03-01&endDate=2026-03-02®ionId=7464&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_7464) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VILLA) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APART_HOTEL) Condos [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CABIN) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=HOUSE_BOAT) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CHALET) Residences [](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America®ionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&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%2FWinter-Haven-Condos.d7464-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Haven-Condos.d7464-aaCondos.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 "Awesome place " [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.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 "The room was clean and the staff was friendly, thank you guys!" [](https://expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.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 "My room was spotless and comfortable. I only stayed about ten hours so unfortunately I didn't get to use any of the resort amenities. Although I checked in online it still took over 20 minutes on property to get my key (this is actual time with a representative, not a line). I think I would stay here again if the opportunity was to present itself. " [](https://expedia.ca/Orlando-Hotels-Vacation-Village-At-Parkway.h1068973.Hotel-Information) ![Howard Johnson by Wyndham Winter Haven FL](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/71d67783_y.jpg) ### Howard Johnson by Wyndham Winter Haven FL 10/10 Excellent "This hotel was clean and the customer service was friendly upon checking in and during the stay. However, checking out the young lady wasn't so pleasant & friendly. Very cold it could be it was too early in the morning, which is totally understandable. The rooms were beautiful with the updated decor. I will definitely stay here again. " [](https://expedia.ca/Winter-Haven-Hotels-Howard-Johnson-By-Wyndham-Winter-Haven-FL.h8718.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 "This hotel " [](https://expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.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 "Everything ws perfect " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Margaritaville Resort Orlando](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg) ### Margaritaville Resort Orlando 10/10 Excellent "Yes everything was wonderful,friendly and very very clean. " [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information) ![Holiday Inn Club Vacations at Orange Lake Resort by IHG](https://images.trvl-media.com/lodging/1000000/10000/6400/6315/ac7826b3_y.jpg) ### Holiday Inn Club Vacations at Orange Lake Resort by IHG 10/10 Excellent "Everything was great" [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ![Westgate Towers Resort](https://images.trvl-media.com/lodging/1000000/180000/170900/170878/bd08ea58_y.jpg) ### Westgate Towers Resort 10/10 Excellent "Very clean, everyone was friendly " [](https://expedia.ca/Orlando-Hotels-Westgate-Towers-Resort.h170878.Hotel-Information) ## Find out more about Winter Haven ## Winter Haven Condo Rentals information | Number of reviews | 3,610 | | ----------------- | ------------------ | | Accommodation | 3446 Condo Rentals | | Lowest Price | CA $165 | | Highest Price | CA $676 | ## Frequently asked questions ### How much do condos in Winter Haven cost? ### How many condos are there in Winter Haven? ### Are there any family-friendly condos in Winter Haven? ### Why book your condo in Winter Haven with Expedia? ### How can I find cheap condos in Winter Haven? ### What is there to do in Winter Haven near my condo? ## Explore a world of travel with Expedia - 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