Title: Lakeland - Winter Haven Vacation Rentals from CA $120: Short-Term Rentals for 2025 | 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)[Flights to Lakeland - Winter Haven](https://expedia.ca/Cheap-Flights-To-Lakeland-Winter-Haven.d6048230.Travel-Guide-Flights)[Things to do in Lakeland - Winter Haven](https://expedia.ca/Things-To-Do-In-Lakeland-Winter-Haven.d6048230.Travel-Guide-Activities)[Lakeland - Winter Haven Car Rentals](https://expedia.ca/Car-Rentals-In-Lakeland-Winter-Haven.d6048230.Car-Rental-Guide)[Lakeland - Winter Haven Vacation Packages](https://expedia.ca/Lakeland-Winter-Haven.d6048230.Destination-Travel-Guides) ![Lakeland - Winter Haven showing a sporting event as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63660-Lakeland-Winter-Haven.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Lakeland - Winter Haven Vacation Rentals ![](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 Tonight [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-19&endDate=2025-10-20&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-20&endDate=2025-10-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6048230&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Lakeland - Winter Haven ![Interior](https://images.trvl-media.com/lodging/28000000/27550000/27548600/27548551/23050871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/28000000/27550000/27548600/27548551/26d508b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Elite Cottage, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/28000000/27550000/27548600/27548551/09444671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/28000000/27550000/27548600/27548551/f3c73455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Margaritaville Cottages Orlando by Rentyl Kissimmee 8.8/10 Excellent (1662) "It was a great stay !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dianelly [](https://www.expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando-Cottages-By-Rentyl.h27548551.Hotel-Information) ![5 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/110000/104100/104060/9a5b9775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom, Accessible | Private kitchen](https://images.trvl-media.com/lodging/1000000/110000/104100/104060/a1a41214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House, 3 Bedrooms, Non Smoking, Resort View | Private kitchen](https://images.trvl-media.com/lodging/1000000/110000/104100/104060/73a602a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/110000/104100/104060/23ae93e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Summer Bay Orlando by Exploria Resorts Clermont 8.4/10 Very good (5653) "We loved our stay here. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Andrew CA $107 CA $165 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Orlando-Hotels-Summer-Bay-Orlando-By-Exploria-Resorts.h104060.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/c7c5e131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/4a4db2cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/93c8e502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/cb9347c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Berkley, Orlando Kissimmee 9.6/10 Exceptional (1952) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $154 CA $189 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Orlando-Hotels-The-Berkley.h1695932.Hotel-Information) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/5000000/4660000/4651300/4651255/2fcd2016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Townhome, 4 Bedrooms, Private Pool | Living area](https://images.trvl-media.com/lodging/5000000/4660000/4651300/4651255/e651e5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/5000000/4660000/4651300/4651255/8a7bab70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/5000000/4660000/4651300/4651255/b0f8f739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Encantada Resort Vacation Townhomes by IDILIQ Kissimmee 8.6/10 Excellent (1390) "2nd time staying here safe to say this is our second home " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie CA $113 CA $405 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-CLC-Encantada-Resort-Vacation-Townhomes.h4651255.Hotel-Information) ![2 outdoor pools, open 8 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/600000/597200/597113/027f136a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 3 Bedrooms (Lodge)](https://images.trvl-media.com/lodging/1000000/600000/597200/597113/085be557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 3 Bedrooms (Lodge) | Private kitchen](https://images.trvl-media.com/lodging/1000000/600000/597200/597113/b4b69417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/600000/597200/597113/2909eab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Orlando Breeze Resort by IHG Davenport 9.2/10 Wonderful (491) "Quiet environment " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alice CA $139 CA $177 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-Orlando-Breeze-Resort.h597113.Hotel-Information) ![Dock](https://images.trvl-media.com/lodging/38000000/37620000/37613200/37613141/6af08a1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/38000000/37620000/37613200/37613141/15a7f110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/38000000/37620000/37613200/37613141/8b42a824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/38000000/37620000/37613200/37613141/d6c448ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Lake Resort Kissimmee 9.2/10 Wonderful (145) "Amber was great we had a ball definitely coming back resort was beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) TAIYLAR [](https://www.expedia.ca/Orlando-Hotels-The-Grand-Lake-Resort.h37613141.Hotel-Information) ![Private pool](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/9a3d3e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Townhome, 5 Bedrooms, Private Pool | Living area](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/85d76152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Townhome, 4 Bedrooms, Private Pool | Living area](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/f89a4e36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Townhome, 5 Bedrooms, Private Pool](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/74efd052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Formosa Valley Resort by UNE Homes Kissimmee 9.4/10 Exceptional (177) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Johnny CA $211 CA $687 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-Formosa-Valley-Resort-By-UNE-Homes.h75962058.Hotel-Information) ![Lake view](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068972/cacc5dfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068972/1f6424a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068972/a57e1571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068972/7e68d8eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lifetime of Vacations Resort Kissimmee 9.4/10 Exceptional (147) "Quiet place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Iliana [](https://www.expedia.ca/Orlando-Hotels-Lifetime-Of-Vacations-Resort.h1068972.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119870000/119860500/119860410/w1596h1063x4y3-b97aec9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/120000000/119870000/119860500/119860410/w1599h1066x1y1-5cfa44d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119870000/119860500/119860410/w1599h1066x1y1-eb05bef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, 1 King Bed | Living area](https://images.trvl-media.com/lodging/120000000/119870000/119860500/119860410/w1599h1066x1y1-ab5809ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VedaHive Luxury Villa Solterra Resort 4.0/10 (3) "If you enjoy your vacation with a older lady with a daughter telling you what to do and how to act in the house, then this place is for you. The hot tub at the house does not work. There's limited toilet paper so bring your own toiletries. And the bedroom I stayed in did not have sheets on the bed. Must read all the rules before staying at this house. The clubhouse water park is not included in your stay. That is an additional fee$" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $50 CA $120 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Orlando-Hotels-VedaHive-Luxury-Villa.h119860410.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/42000000/41900000/41898100/41898043/59585f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/42000000/41900000/41898100/41898043/2de67906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/42000000/41900000/41898100/41898043/e26eb297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41900000/41898100/41898043/4655c996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool Kissimmee 9.6/10 Exceptional (48) "The home was perfect for our family trip to Disney! Its conveniently located near all of the FUN!! Great place to stay! I would definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela S. [](https://www.expedia.ca/Orlando-Hotels-Glam-Villa-Near-The-Parks-W-Gamer-Princess-BRs.h41898043.Hotel-Information) ![2 outdoor pools](https://images.trvl-media.com/lodging/112000000/111360000/111358100/111358085/f4f51507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Apartment, Balcony | Living area](https://images.trvl-media.com/lodging/112000000/111360000/111358100/111358085/w1479h998x0y0-fe77f980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Apartment, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/112000000/111360000/111358100/111358085/d70dd7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Apartment, Balcony | Private kitchen](https://images.trvl-media.com/lodging/112000000/111360000/111358100/111358085/6bd8d102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Champions Gate condos by UNE Champions Gate 9.0/10 Wonderful (41) "The Condo where we stayed was perfect for us, great view of the golf course, had everything we needed for our stay and more. Would definitely recommend and hopefully will return in the future" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Neil CA $151 CA $426 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-Champions-Gate-Condos-By-UNE.h111358085.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/2000000/1690000/1688400/1688356/d4d1d522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms, Hot Tub (Basic Caribe Cove Aruba Villa 2 Bedro) | Dining](https://images.trvl-media.com/lodging/2000000/1690000/1688400/1688356/b1fc5216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/2000000/1690000/1688400/1688356/153c379c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1690000/1688400/1688356/14ed7ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Caribe Cove Resort Kissimmee 8.8/10 Excellent (2258) "We had a great family vacation " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica [](https://www.expedia.ca/Orlando-Hotels-Caribe-Cove-Resort.h1688356.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2860000/2858800/2858797/6338d608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2860000/2858800/2858797/82f390ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 3 Bedrooms Non ADA (2 bath) | Private kitchen](https://images.trvl-media.com/lodging/3000000/2860000/2858800/2858797/11666dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Regional cuisine](https://images.trvl-media.com/lodging/3000000/2860000/2858800/2858797/cdef8a3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villas At Regal Palms Highlands Reserve 8.4/10 Very good (579) "This was the 2nd time we’ve stayed at Regal Palms and will definitely be back again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JulieAnn [](https://www.expedia.ca/Orlando-Hotels-Villas-At-Regal-Palms.h2858797.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34280000/34271300/34271273/c77b3c8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/35000000/34280000/34271300/34271273/3ab062b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/35000000/34280000/34271300/34271273/b9372bcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34280000/34271300/34271273/7e8373fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 20 bedroom Reunion Villas @ Disney's Doorstep Kissimmee 9.2/10 Wonderful (97) "Beautiful homes, would stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nou Y. [](https://www.expedia.ca/Orlando-Hotels-Luxury-20-Bedroom-Reunion-Villas-Disneys-Doorstep.h34271273.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/23000000/22250000/22247100/22247019/792c5bae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Encore Resort 11 Bedroom Vacation Home with Pool (2117) | Living room](https://images.trvl-media.com/lodging/23000000/22250000/22247100/22247019/9a30b30e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe House](https://images.trvl-media.com/lodging/23000000/22250000/22247100/22247019/b086d4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![ACO Encore Resort 6 Bedroom Vacation Home with Pool (1913) | Private kitchen](https://images.trvl-media.com/lodging/23000000/22250000/22247100/22247019/94348808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Encore Resort Kissimmee 6.4/10 (117) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesus [](https://www.expedia.ca/Orlando-Hotels-Encore-Resort.h22247019.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119210000/119208900/119208817/cabb0dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/120000000/119210000/119208900/119208817/df2bf72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/120000000/119210000/119208900/119208817/b1c65566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119210000/119208900/119208817/c576889a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Landing Townhomes Davenport Davenport 9.4/10 Exceptional (3) "The stay was great absolutely loved it " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janei Chantel [](https://www.expedia.ca/Orlando-Hotels-Landing-Townhomes-Davenport.h119208817.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350019/w1200h797x0y3-0a9b128e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350019/f5513f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350019/w1200h896x0y3-80a64688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350019/cebf31a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 7901 Luxury Retreat 3BR Villa w/ Pool & Game! Reunion [](https://www.expedia.ca/Orlando-Hotels-7901-Luxury-Retreat-3BR-Villa-W-Pool-Game.h119350019.Hotel-Information) ![Smart TV, table tennis](https://images.trvl-media.com/lodging/110000000/109350000/109346400/109346335/cb506f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109350000/109346400/109346335/44267087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/110000000/109350000/109346400/109346335/71137ac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis](https://images.trvl-media.com/lodging/110000000/109350000/109346400/109346335/3a6e0367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lux 6BRVilla w/ Pool&ResortAmenities -10m to Parks Kissimmee 10/10 Exceptional (2) "We had a fantastic stay at Franks place. Its absolutely perfect for familys. A really spacious property with everything you need to make it a comfortable stay. Really clean and tidy with lots of towels. The beach towels ready to be used were a great addition.Perfectly located, extremely close to Disney and the 192 which has lots of restaurants, giftshops and supermarkets. We would all 100% stay here again." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Kris S. CA $203 CA $716 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Orlando-Hotels-Gated-ResortSpacious-6Bedroom-Villa-Near-Disney.h109346335.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/48f41cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Villa, Multiple Bedrooms | Living area](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/39c2ad6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Villa, Multiple Bedrooms | Terrace/patio](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/b683aa14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury House, Multiple Bedrooms | Living area](https://images.trvl-media.com/lodging/39000000/38820000/38814300/38814230/6370c7b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bear's Den Resort Orlando Reunion 8.0/10 Very good (22) "Great place , I recommend it to everyone." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline [](https://www.expedia.ca/Orlando-Hotels-The-Bears-Den-At-Reunion.h38814230.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33710000/33705400/33705317/4955c28d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33710000/33705400/33705317/7cb85c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33705400/33705317/577ec582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33710000/33705400/33705317/a7c4618b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Every Amenity! 2 Theaters, Private Gym, Pool, Baby Equip FREE, Outdoor Grill Reunion 9.4/10 Exceptional (57) "Property was as advertised, very spacious and clean. The pool area, Game rooms and movie theater were hits. The only small issue was operation of TVs throughout the property (multiple remotes for each TV but unable to get the TVs or streaming apps to work properly). The Owner was very responsive, answering any questions after arrival within minutes. Will definitely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Taneisha J. [](https://www.expedia.ca/Orlando-Hotels-Every-Amenity-2-Theaters.h33705317.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=2025-11-03&endDate=2025-11-04®ionId=6048230&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FLakeland-Winter-Haven-Vacation-Rentals.d6048230.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FLakeland-Winter-Haven-Vacation-Rentals.d6048230.Travel-Guide-VacationRentals) ## Top Lakeland - Winter Haven Hotel Reviews ![The Grove Resort & Water Park Orlando](//images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg) ### The Grove Resort & Water Park Orlando 10/10 Excellent "Good view and haven't tried the food yet. " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Hilton Vacation Club Aqua Sol Orlando West](//images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg) ### Hilton Vacation Club Aqua Sol Orlando West 10/10 Excellent "Clean Room and great Staff" [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Margaritaville Cottages Orlando with H2O Waterpark by Rentyl](//images.trvl-media.com/lodging/28000000/27550000/27548600/27548551/23050871_y.jpg) ### Margaritaville Cottages Orlando with H2O Waterpark by Rentyl 10/10 Excellent "Spacious 2 bedroom cottage with full kitchen, washer/dryer, and pool in the backyard. We will definitely cone back." [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando-Cottages-By-Rentyl.h27548551.Hotel-Information) ![Holiday Inn Club Vacations at Orange Lake Resort by IHG](//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 "Nice place" [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ![Staybridge Suites Winter Haven Auburndale by IHG](//images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/0585f081_y.jpg) ### Staybridge Suites Winter Haven Auburndale by IHG 10/10 Excellent "Friendly staff. Big , clean roooms" [](https://expedia.ca/Winter-Haven-Hotels-Staybridge-Suites-Winter-Haven-Auburndale.h94674232.Hotel-Information) ![Margaritaville Resort Orlando with H2O Waterpark](//images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg) ### Margaritaville Resort Orlando with H2O Waterpark 10/10 Excellent "Everything. " [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information) ![voco Kissimmee Orlando by IHG](//images.trvl-media.com/lodging/1000000/50000/41100/41083/b3397abc_y.jpg) ### voco Kissimmee Orlando by IHG 10/10 Excellent "No comment, great stay overall" [](https://expedia.ca/Orlando-Hotels-Voco-Kissimmee-Orlando-By-IHG.h41083.Hotel-Information) ![Destiny Palms Hotel Maingate West](//images.trvl-media.com/lodging/1000000/430000/427400/427337/d056f561_y.jpg) ### Destiny Palms Hotel Maingate West 10/10 Excellent "The hotel have plenty room to offer breakfast, that will be great to rated it as a 4 starts." [](https://expedia.ca/Orlando-Hotels-Destiny-Palms-Hotel-Maingate-West.h427337.Hotel-Information) ![Summer Bay Orlando by Exploria Resorts](//images.trvl-media.com/lodging/1000000/110000/104100/104060/9a5b9775_y.jpg) ### Summer Bay Orlando by Exploria Resorts 10/10 Excellent "Great location. Good amenities for families and quick response for assistance. Would definitely return. " [](https://expedia.ca/Orlando-Hotels-Summer-Bay-Orlando-By-Exploria-Resorts.h104060.Hotel-Information) ## Find out more about Lakeland - Winter Haven **Everything you need to know about** **Lakeland - Winter Haven** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Lakeland - Winter Haven vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lakeland - Winter Haven vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Lakeland - Winter Haven vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Lakeland - Winter Haven. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lakeland - Winter Haven vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lakeland - Winter Haven vacation rentals we have selected for you start as low as CA $120 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Lakeland - Winter Haven rentals** At Expedia, we put the best Lakeland - Winter Haven vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Lakeland - Winter Haven rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lakeland - Winter Haven vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lakeland - Winter Haven. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Lakeland - Winter Haven ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)