Title: 10 Best Hotels in Oakland, Winter Garden for 2026 | Expedia.ca [Vacation Rentals in Winter Garden](https://expedia.ca/Winter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals)[Flights to Winter Garden](https://expedia.ca/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.ca/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d6360404.Car-Rental-Guide)[Oakland Vacations](https://expedia.ca/Oakland.d6360404.Destination-Travel-Guides) ![Panoramic view of Lake Apopka and nature Florida.](https://images.trvl-media.com/place/6360403/5cbd79a8-2e61-4cef-8769-e792f96b305a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6360403/5cbd79a8-2e61-4cef-8769-e792f96b305a.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 Tonight [Mar 22 - Mar 23](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-03-22&endDate=2026-03-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 23 - Mar 24](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-03-23&endDate=2026-03-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2026-04-03&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Our top choices for Oakland hotels ![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/81e6b4c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/6e9ade0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/119a4279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/e1b28117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kompose Boutique Resort at Theme Parks [](https://www.expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) 24.9 km from Oakland 9.4/10 Exceptional (3,210 reviews) "Breakfast was great clean and delish I will stay here again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $46 CA $112 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/41313b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/3681ea81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/8d005bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/8c8c0f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel [](https://www.expedia.ca/Orlando-Hotels-Quality-Suites-Orlando-Convention-Center-Area.h18667.Hotel-Information) 19.6 km from Oakland 8.4/10 Very good (1,034 reviews) "Beautiful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelleen CA $122 CA $138 total includes taxes & fees Apr 19 - Apr 20 [](https://www.expedia.ca/Orlando-Hotels-Quality-Suites-Orlando-Convention-Center-Area.h18667.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/05cb2d91.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/32000000/31950000/31941500/31941472/fab2d3be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom (2 Queenbed & 1 Sofabed)](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/5cf2d29a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/ac9ae7dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Orlando International Drive [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) 20.6 km from Oakland 9.4/10 Exceptional (1,631 reviews) "Clean room great staff bed with excellent slept so good great breakfast overall stay loved it!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colin CA $163 CA $184 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/fdd50135.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/c3a09134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Parlor) | Living area](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/e39de17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/d59ae214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton at the Entrance to Universal Orlando [](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) 19.2 km from Oakland 8.4/10 Very good (6,850 reviews) "Amazing hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $149 CA $168 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6900/6856/94c09ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/6900/6856/9a4b78a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 9 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/6900/6856/22d963fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 9 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/6900/6856/8ab1ecf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orlando Palms Hotel [](https://www.expedia.ca/Orlando-Hotels-The-London-Orlando-At-The-Florida-Mall.h6856.Hotel-Information) 25.8 km from Oakland 7.8/10 Good (2,509 reviews) "Great place to stay at" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Glennrick CA $105 CA $135 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Orlando-Hotels-The-London-Orlando-At-The-Florida-Mall.h6856.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/61000000/60520000/60517400/60517339/a3e034f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible, Non Smoking](https://images.trvl-media.com/lodging/61000000/60520000/60517400/60517339/56cb6aec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/61000000/60520000/60517400/60517339/bcc37d1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/61000000/60520000/60517400/60517339/08bfdc37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cambria Hotel Orlando Airport [](https://www.expedia.ca/Orlando-Hotels-Cambria-Hotel-Orlando-Airport.h60517339.Hotel-Information) 31.4 km from Oakland 8.8/10 Excellent (1,901 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mario CA $156 CA $176 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Orlando-Hotels-Cambria-Hotel-Orlando-Airport.h60517339.Hotel-Information) ![Outdoor banquet area](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/abbcc72a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/6214f96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![11 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/edfdae69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/e9850ee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Shingle Creek [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) 24.2 km from Oakland 9.4/10 Exceptional (4,651 reviews) "Great family place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alberto CA $146 CA $165 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) ![Fitness facility](https://images.trvl-media.com/lodging/69000000/68500000/68496700/68496636/31d8938f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68500000/68496700/68496636/b2d5e945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/69000000/68500000/68496700/68496636/2d4300f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Accessible, Non Smoking (Mobility,tub w grab bars) | Fitness facility](https://images.trvl-media.com/lodging/69000000/68500000/68496700/68496636/544f6f30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Garden Orlando Airport [](https://www.expedia.ca/Orlando-Hotels-Wyndham-Garden-Orlando-Airport.h68496636.Hotel-Information) 29.9 km from Oakland 9.0/10 Wonderful (4,048 reviews) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $149 CA $168 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Orlando-Hotels-Wyndham-Garden-Orlando-Airport.h68496636.Hotel-Information) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/c8859517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/b33a5f59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/742ee36a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/d80c5432.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Universal's Endless Summer Resort - Dockside Inn and Suites [](https://www.expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information) 19.8 km from Oakland 9.0/10 Wonderful (5,118 reviews) "Amazing stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katherine CA $156 CA $176 total includes taxes & fees Apr 19 - Apr 20 [](https://www.expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/9600/9577/588f352f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/10000/9600/9577/ae4e7caa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/9600/9577/729ccb50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/9600/9577/106b9547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Orlando/Altamonte Springs [](https://www.expedia.ca/Orlando-Hotels-Hilton-OrlandoAltamonte-Springs.h9577.Hotel-Information) 26.5 km from Oakland 9.0/10 Wonderful (1,315 reviews) "The Hilton never disappoints, always a great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Travis CA $162 CA $187 total includes taxes & fees Apr 2 - Apr 3 [](https://www.expedia.ca/Orlando-Hotels-Hilton-OrlandoAltamonte-Springs.h9577.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/03926ba2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/b063e7a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/dffbfa04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/fee6a1f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Orlando International Airport by IHG [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Express-Orlando-International-Airport.h327322.Hotel-Information) 31.3 km from Oakland 9.0/10 Wonderful (1,960 reviews) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiffney CA $159 CA $179 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Express-Orlando-International-Airport.h327322.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/ffaf091a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/8172cfbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/7849376b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cafe](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/0da7d63b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westgate Lakes Resort & Spa Universal Studios Area [](https://www.expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) 20.9 km from Oakland 8.4/10 Very good (5,974 reviews) "Great place to stay and very close to all Disney attractions. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas F CA $155 CA $220 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151100/151072/c79dd6b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/160000/151100/151072/ed596aff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/160000/151100/151072/77c0521a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/160000/151100/151072/3c3b8518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Orlando Downtown [](https://www.expedia.ca/Orlando-Hotels-Courtyard-By-Marriott-Orlando-Downtown.h151072.Hotel-Information) 25 km from Oakland 9.6/10 Exceptional (1,008 reviews) "Great hotel with great staff. Hotel bar and restaurants were nice as well" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan CA $198 CA $222 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Orlando-Hotels-Courtyard-By-Marriott-Orlando-Downtown.h151072.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/40000000/39070000/39065100/39065095/c574100e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/40000000/39070000/39065100/39065095/91d93c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/40000000/39070000/39065100/39065095/2a0b9ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39070000/39065100/39065095/cc14cd88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### avid hotel Orlando International Airport by IHG [](https://www.expedia.ca/Orlando-Hotels-Avid-Hotels-Orlando-International-Airport.h39065095.Hotel-Information) 31.5 km from Oakland 9.2/10 Wonderful (2,183 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $156 CA $176 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Orlando-Hotels-Avid-Hotels-Orlando-International-Airport.h39065095.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/f7ec0145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/1f245bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/7966ced0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Grove Resort & Water Park Orlando [](https://www.expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) 21.6 km from Oakland 8.0/10 Very good (9,222 reviews) "Was a wonderful stay " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Sharlene CA $232 CA $337 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26800/26703/ca31fce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/26800/26703/caff738c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One King Bed, Mobility/Hearing Handicap Room, Roll-In Shower, Non-Smoking | Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/26800/26703/b84ae920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Queen Beds, Pool View, Non Smoking | View from room](https://images.trvl-media.com/lodging/1000000/30000/26800/26703/cbcb8d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### B&B Hotel Orlando International Drive Near Universal - Newly Renovated! [](https://www.expedia.ca/Orlando-Hotels-Floridian-Express-Extended-Stay-Hotel.h26703.Hotel-Information) 19.2 km from Oakland 8.2/10 Very good (416 reviews) "it was so nice, very clean, and comfy .. definitely going to come back " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ive CA $88 CA $100 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Orlando-Hotels-Floridian-Express-Extended-Stay-Hotel.h26703.Hotel-Information) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/5cf8836a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/faa812b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/0ff8c8f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/2ba89a06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Orlando near Universal [](https://www.expedia.ca/Orlando-Hotels-Spark-By-Hilton-Orlando-Near-Universal.h15927.Hotel-Information) 18.9 km from Oakland 8.8/10 Excellent (938 reviews) "Great rooms, staff cleaned well" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noah CA $111 CA $125 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Orlando-Hotels-Spark-By-Hilton-Orlando-Near-Universal.h15927.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4410000/4408100/4408039/15cb5630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/5000000/4410000/4408100/4408039/c8099ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom](https://images.trvl-media.com/lodging/5000000/4410000/4408100/4408039/379c4dfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; sushi](https://images.trvl-media.com/lodging/5000000/4410000/4408100/4408039/f5e4827f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Grand Orlando Resort Bonnet Creek [](https://www.expedia.ca/Orlando-Hotels-Wyndham-Grand-Orlando-Resort-Bonnet-Creek.h4408039.Hotel-Information) 24 km from Oakland 9.0/10 Wonderful (2,894 reviews) "Loved the hotel and property " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $218 CA $311 total includes taxes & fees Apr 11 - Apr 12 [](https://www.expedia.ca/Orlando-Hotels-Wyndham-Grand-Orlando-Resort-Bonnet-Creek.h4408039.Hotel-Information) ![Poolside Family Suite - Exterior Entry (Includes Early Park Admission*) | View from room](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/4c48bd3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/09c3f299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Volcano Bay View 2-Bedroom Suite (Includes Early Park Admission*)](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/d9e7d6aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/e86976c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Universal's Cabana Bay Beach Resort [](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) 18.5 km from Oakland 9.0/10 Wonderful (6,456 reviews) "We loved the staff and location was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline CA $185 CA $208 total includes taxes & fees Apr 19 - Apr 20 [](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/9a7827e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/dcdec8a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/13ee8fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/93a5e496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Resort Orlando Suites - Waterpark by IHG [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Suites-Waterpark.h281608.Hotel-Information) 25.3 km from Oakland 7.2/10 Good (5,076 reviews) "Overall great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shary CA $99 CA $171 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Suites-Waterpark.h281608.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=2026-04-05&endDate=2026-04-06®ionId=6360404&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Where to stay in Oakland Find the best Oakland areas and neighborhoods for the activities you enjoy most. - Horizon West - Vista del Lago - Downtown Winter Garden - Killarney [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=977491569791938560) ![Horizon West map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:gtrlDr%7ChqNis%40oFg_%40%7B_%40iY%7CXoc%40xC%7B%5CwEosEn%40a%40o%7EEdW_SiLqPTojApiAf%40%7CVoXnjAmBgAqt%40%60z%40spAlpAlShy%40kYhy%40szCnOaJbk%40mBMxdK%5CvkApDdkDwp%40pIqaA%60h%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=n3TSCtO6nPipKEzIk53t6RYKq48=) ### Horizon West While visiting Horizon West, you might make a stop by sights like Walt Disney World® Resort and Orange County National Golf Club. [See properties](https://www.expedia.ca/Hotel-Search?regionId=977491569791938560) ![Orange sunset over distant hills on Lake Apopka near Orlando, Florida.](https://images.trvl-media.com/place/553248635976471720/1fc7b96c-c215-4476-8213-e925a1aa892e.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976471720) ![Vista del Lago map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:qsalDbkhqNuTMSum%40bMBb%40%7BIaFkIAmHnSCG%7CB_AjAb%40fBtMlGnGw%40pBpGdNIDsCzMDKd%5Ew%7C%40RA%7CX&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=playiTafgON9EE4xbK3rnHR1y1U=) ### Vista del Lago While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976471720) ![Love this tiny town, just 20 minutes from Walt Disney World. Inside #PlantStreetMarket you’ll find multiple vendors including local food, honey, coffee and desserts, and #crookedcanbrewing #wintergarden #lifeatexpedia ](https://images.trvl-media.com/place/7898/3b52e4d7-c036-43a0-acdb-0ec758a9700c.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by Shannon Maya ![March 25, 2023, Winter Garden, FL: The West Orange bicycle trail through Winter Garden, Florida](https://images.trvl-media.com/place/944538218785796096/91cceb08-bb0f-4c59-80cf-9c6369c42839.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Great coffee shop alert! Axum Coffee in historic Winter Garden not only serves up delicious coffee roasts, flavored lattes, loose leaf teas, but also donates all of its profits to an orphanage in Axum, Ethiopia! A coffee experience that is socially conscious in word and deed.](https://images.trvl-media.com/place/7898/009b6bc5-b7ec-48a0-a990-35b53cd918b0.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by JoyFilledWander ![A great collection of organic & local products for your kitchen, bath & home. The cafe in the back is delightful, with smoothies, juices, wraps & salads all prepared fresh with as many local & organic ingredients as possible. Stop in and try the La Fiesta wrap, and grab some locally roasted coffee beans on your way out! ](https://images.trvl-media.com/place/7898/cb95c63e-1643-4fd5-9c7d-53d86c64c4a4.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by JoyFilledWander ![The Crooked Can at the Plant St market in Winter Garden, Fl](https://images.trvl-media.com/place/7898/101b44bd-bc20-4438-abce-90a5ff458dae.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by Nancy [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=944538218785796096) ![Downtown Winter Garden map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:eximDn%7C%7EpNsMUGcP%7DIIGme%40fBOhV%5DArn%40MjI&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=1VUib_Z3T3Au8u27r8QEdv-WKNs=) ### Downtown Winter Garden While visiting Downtown Winter Garden, you might make a stop by sights like West Orange Trail and Central Florida Railroad Museum. [See properties](https://www.expedia.ca/Hotel-Search?regionId=944538218785796096) ![Panoramic view of Lake Apopka and nature Florida.](https://images.trvl-media.com/place/6360403/5cbd79a8-2e61-4cef-8769-e792f96b305a.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=6360403) ![Killarney map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:keimDj%60mqNij%40saB%7EHu%7B%40rcBkG%7EFat%40hb%40kDhz%40z%60BuCv%7B%40sSfZuu%40zE%7DxAj%60%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=QMWxfWyixWBofYiTIYo5XkD4OX8=) ### Killarney If you're looking for some top things to see and do in Killarney and surrounding area, you can visit Bella Collina Golf Club and West Orange Trail. [See properties](https://www.expedia.ca/Hotel-Search?regionId=6360403) ## Top Oakland Hotel Reviews ![Holiday Inn Resort Orlando Suites - Waterpark by IHG](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/9a7827e4_y.jpg) ### Holiday Inn Resort Orlando Suites - Waterpark by IHG 8/10 Good "The room didn't have much lighting but it was clean. Overall affordable." [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Suites-Waterpark.h281608.Hotel-Information) ![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg) ### Rosen Inn at Pointe Orlando 10/10 Excellent "Great stay !! Here for Megacon. Clean, convenient distance from convention center. Very friendly staff !! " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/4c48bd3d_y.jpg) ### Universal's Cabana Bay Beach Resort 8/10 Good "I enjoyed the establishment in it's entirety, except the intensive prices." [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Drury Plaza Hotel Orlando - Disney Springs Area](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/6af5b762_y.jpg) ### Drury Plaza Hotel Orlando - Disney Springs Area 10/10 Excellent "The staff was awesome. The location is just minutes from Disney Springs for shopping and several food options. It was not far from the Disney attractions and Universal. I recommend this hotel." [](https://expedia.ca/Orlando-Hotels-Drury-Plaza-Hotel-Orlando-Lake-Buena-Vista.h24103.Hotel-Information) ![Coco Key Hotel & Water Park Resort](https://images.trvl-media.com/lodging/1000000/10000/300/228/84c2249c_y.jpg) ### Coco Key Hotel & Water Park Resort 10/10 Excellent "Friendly " [](https://expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information) ![B&B Hotel Orlando International Drive Near Universal - Newly Renovated!](https://images.trvl-media.com/lodging/1000000/30000/26800/26703/ca31fce1_y.jpg) ### B&B Hotel Orlando International Drive Near Universal - Newly Renovated! 8/10 Good "Stayed here for Megacon for three nights.Very clean hotel and newly renovated as advertised.There’s a few things that could be improved on.The television which had no channels and unable to connect it to the internet to watch Netflix or YouTube. It’s a nice TV, shame it couldn’t be put to use during our stay.The internet connection itself wasn’t that great.You guys should really put a password on it so people who aren’t staying can’t connect to it and make it slower. The door to the back side adjacent to the check in area needs to be fixed.It was unlocked during the day but at night the badge access wasn’t working so you had to walk all the way back to the entrance to the hotel and then all the way back to my room located in the backside of the hotel.I would go to the front and buy a Coke Zero every once in awhile and different employees charged different prices.One charged me $4.00 for a can and another charged me $3.00,so you may want to speak to the employees (which were very friendly by the way) to get a consistent price going.The shower door doesn’t stay closed when you’re using it so you have to wedge a wash cloth in between the door to keep it secured.Everything else was very clean and new. The AC was great and kept the room very cool and comfortable.Price was great. I really hope they add a gym someday.I would recommend and stay here again myself.The location it’s in is great with a Dairy Queen less then 50 ft away from the hotel and an Applebees across the street. " [](https://expedia.ca/Orlando-Hotels-Floridian-Express-Extended-Stay-Hotel.h26703.Hotel-Information) ![Rosen Inn Lake Buena Vista](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg) ### Rosen Inn Lake Buena Vista 6/10 Okay "The breakfast is only a milk, a fruit and a lemonade. Disappointing. Does not have a gym or fitness center. They charge the parking. You can hear to everything that is happening outside your room. Not recommended for resting or business. I would only use it again of going to parks given the location" [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/91c45539_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Lovely property, very comfortable with lots of options for pool, tennis, restaurants and bars. Would highly recommend!" [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/ffaf091a_y.jpg) ### Westgate Lakes Resort & Spa Universal Studios Area 6/10 Okay "The off site car rental and shuttle was not convenient Get a car at the airport and save loads of time both ways " [](https://expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ## Find out more about Oakland ### Top reasons to visit Oakland - **Family-Friendly Activities:** Oakland offers a variety of engaging activities perfect for families, ensuring fun for all ages. - **Beautiful Outdoor Spaces:** Explore scenic locations like Oak Island, Oak Groves, and Oak Lake Beach, ideal for relaxation and recreation. - **Water Sports & Wellness:** Enjoy a mix of thrilling water sports and calming wellness centres, catering to both adventure and relaxation seekers. - **Diverse Accommodations:** Choose from family-friendly resorts and pet-friendly hotels that provide excellent amenities for a comfortable stay. - **Rich Local Culture:** Experience the inviting vibe of friendly communities and cultural excursions that highlight Oakland's natural beauty. ### Find great hotels near Oakland Experience a delightful stay in Oakland, Winter Garden, Florida, where a variety of accommodations await you. Whether you're seeking a family-friendly resort, a pet-friendly hotel, or a business-themed getaway, you'll find ideal options like the Oakland Resort, Oakwood Resort, and Oak Island Resort. Enjoy the serene atmosphere and excellent amenities that cater to every traveller's needs for an unforgettable vacation. - **[Universal's Cabana Bay Beach Resort: ](https://www.expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information)** Embrace a nostalgic family vacation at Universal's Cabana Bay Beach Resort, where the vibrant retro theme sets the tone for a fun-filled getaway. Located 19.3km from Oakland, this 3.5-star hotel is perfect for families seeking adventure and entertainment. The property boasts a plethora of amenities designed for children, including a free arcade game room and complimentary cribs, ensuring a memorable stay for your little ones. Guests appreciate the family-oriented atmosphere and the resort's close proximity to Universal Studios, making it an ideal choice for thrill-seekers. - **[The Grove Resort & Water Park Orlando: ](https://www.expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information)** Experience an exhilarating nature-themed vacation at The Grove Resort & Water Park Orlando, situated 20.9km from Oakland. This 4-star resort offers a splendid array of adventure sports and recreational activities, including onsite surfing, fishing, and swimming, allowing guests to immerse themselves in Florida's natural beauty. With a complimentary water park, children's games, and a dedicated kids' pool, this resort is perfect for families seeking both relaxation and excitement. Guests rave about the diversity of activities available, ensuring that every member of the family has a fantastic time. - **[DoubleTree by Hilton at the Entrance to Universal Orlando: ](https://www.expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information)** Combining comfort and business facilities, the DoubleTree by Hilton at the Entrance to Universal Orlando is a welcoming 4-star hotel located 19.3km from Oakland. This hotel is perfect for families and business travellers alike, offering accessible meeting rooms and a fully-equipped business centre. Known for its LGBTQIA-friendly environment, the property also caters to children with amenities such as a pool for kids and an arcade game room. Guests appreciate the convenient location and exceptional service, making it a top choice for both leisure and work-related stays. ### Where to stay near Oakland Oakland, Florida, is a delightful destination perfect for family-friendly adventures and outdoor escapades. Nestled near beautiful lakes, it offers stunning views and a relaxing atmosphere ideal for weekend getaways. Explore the friendly local communities and indulge in excursions that highlight the area's natural beauty. With its inviting vibe and a variety of entertainment options, Oakland promises an unforgettable experience for travellers seeking both adventure and tranquility. - **[Killarney: ](https://www.expedia.ca/Killarney-Winter-Garden-Hotels.0-n6360403-0.Travel-Guide-Filter-Hotels)** Located a short 1.3km from Oakland, Killarney is a peaceful neighborhood that attracts visitors seeking outdoor activities and family-friendly experiences. With a peak in traveler arrivals during March, July, and December, the area offers numerous recreational opportunities including golf courses and resorts. The proximity to local landmarks such as a theme park and a picturesque lake adds to its charm, making it an ideal spot for those who enjoy a blend of sports and nature. - **[Winter Garden: ](https://www.expedia.ca/Winter-Garden-Hotels.d7898.Travel-Guide-Hotels)** As a city that encompasses Oakland, Winter Garden boasts a vibrant atmosphere perfect for families and those looking for themed entertainment. Peak visitor seasons occur in January to February and September, with a variety of shopping areas and malls available for exploration. Notable attractions include a nearby theme park and film studio, providing an exciting backdrop for your vacation. Whether you're in the mood for business or leisure, Winter Garden has something to offer everyone. - **[Reavills Corner: ](https://www.expedia.ca/Reavills-Corner-Hotels.d6188540.Travel-Guide-Hotels)** Situated 4.8km from Oakland, Reavills Corner is a quaint village that offers a unique blend of outdoor activities and entertainment options for families. With traveler numbers peaking in March, July, and December, visitors can enjoy local resorts, shopping areas, and educational activities. The village is conveniently located near stunning beaches and theme parks, making it a perfect destination for a fun-filled day with loved ones. The welcoming community atmosphere adds to the charm of this hidden gem. ### Things to do near Oakland Oakland, Florida, offers a delightful mix of family-friendly activities and outdoor adventures. Visitors can explore nearby resorts, enjoy shopping at local malls, and partake in various recreational programs. For those seeking relaxation with a hint of excitement, water sports and wellness centres provide the perfect balance. Whether you’re looking to unwind or engage in fun activities, Oakland has something for everyone. **Shopping** [Flamingo Crossings Town Center](https://www.expedia.ca/Flamingo-Crossings-Town-Center-Hotels.0-l863361053793378304-0.Travel-Guide-Filter-Hotels), 19.3km from Oakland, offers a lively atmosphere with diverse shopping options. [Clermont Regal Shopping Center](https://www.expedia.ca/Clermont-Regal-Shopping-Center-Hotels.0-l553248621563219994-0.Travel-Guide-Filter-Hotels), 9.7km away, is perfect for family outings. [Westgate Square Shopping Center](https://www.expedia.ca/Westgate-Square-Shopping-Center-Hotels.0-l553248621563220175-0.Travel-Guide-Filter-Hotels), located 17.7km from Oakland, combines entertainment and shopping for a fun day out. **Recreation** At [Camping World Stadium](https://www.expedia.ca/Camping-World-Stadium-Hotels.0-l502139-0.Travel-Guide-Filter-Hotels), immerse yourself in the vibrant sports atmosphere and enjoy exciting events. [Disney's Palm Golf Course](https://www.expedia.ca/Disneys-Palm-Golf-Course-Hotels.0-l6069339-0.Travel-Guide-Filter-Hotels) offers a scenic outdoor experience for golf enthusiasts, while [Windermere Country Club](https://www.expedia.ca/Windermere-Country-Club-Hotels.0-l6189616-0.Travel-Guide-Filter-Hotels) provides a luxurious retreat with upscale amenities for relaxation and leisure. **Adventure** [Universal’s Volcano Bay](https://www.expedia.ca/Universals-Volcano-Bay-Hotels.0-l553248633507645899-0.Travel-Guide-Filter-Hotels), 19.3km from Oakland, offers thrilling water rides and fun for the whole family amidst a tropical setting. For a scenic hike, explore the [West Orange Trail](https://www.expedia.ca/West-Orange-Trail-Hotels.0-l553248621532653939-0.Travel-Guide-Filter-Hotels), located 4.8km away, where you can enjoy picturesque views and outdoor adventures. Experience water sports at [Watertoyz of Clermont](https://www.expedia.ca/Watertoyz-Of-Clermont-Hotels.0-l553248621532653925-0.Travel-Guide-Filter-Hotels), 12.9km from Oakland, perfect for those seeking excitement on the water. **Nightlife** In Oakland, [The Orlando Eye at ICON Park](https://www.expedia.ca/The-Orlando-Eye-At-ICON-Park-Hotels.0-l553248621565183042-0.Travel-Guide-Filter-Hotels) offers stunning views on a ferris wheel, perfect for an adventurous night. For arcade fun, head to [Carter Family Bowl](https://www.expedia.ca/Carter-Family-Bowl-Hotels.0-l553248621532653935-0.Travel-Guide-Filter-Hotels), while the [Garden Theatre](https://www.expedia.ca/Garden-Theatre-Hotels.0-l553248621532653937-0.Travel-Guide-Filter-Hotels) provides a cultural experience with its romantic and family-friendly shows, all within a short distance. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Oakland For a budget-friendly trip to Oakland, consider visiting during the cheaper months of August, September, or November. Book your hotel about a month in advance to snag the best deals, especially on Tuesdays, the least expensive day to stay. Use Expedia’s search tool to filter options by budget and sort by price for special offers. Don't forget to explore free activities and combine your hotel, flights, and activities for additional savings. Lastly, keep an eye out for last-minute deals to maximize your budget while enjoying your stay in Oakland. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay around Oakland are August to September and November, where the prices are slightly lower. This is in comparison to March to April and December, where prices are slightly higher. - **The best time to book a hotel:** The cheapest time to book a hotel around Oakland is usually 1 month out from when you are planning to stay, though if you're late to the party, have a look at Expedia's last minute deals - the green banner below the hotel's price indicates a discounted rate. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay around Oakland is Tuesday. The most expensive day to stay around Oakland is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred type of accommodation. To discover the most affordable prices and special offers, sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay in Oakland with your flights and activities through an Expedia package. ### Find the best attractions near Oakland Oakland, Winter Garden, Florida, offers a delightful vacation for families and outdoor enthusiasts. With attractions like theme parks, golf courses, and arts centres, there's something for everyone. Explore scenic spots such as Oak Island, Oak Groves, and Oak Lake Beach, along with historic seaside resorts. Whether seeking entertainment or cultural experiences, Oakland is the perfect destination for a memorable getaway. - **[Walt Disney World® Resort: ](https://www.expedia.ca/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels)** Experience the magic of this iconic theme park, located 16.1km from Oakland. With enchanting rides, beloved characters, and spectacular shows, it’s a family-friendly destination that promises fun for all ages. - **[Orange County Convention Center: ](https://www.expedia.ca/Orange-County-Convention-Center-Hotels.0-l6034972-0.Travel-Guide-Filter-Hotels)** Situated 20.9km away, this arts centre is a hub of culture and creativity. Enjoy a variety of art exhibitions, performances, and events that showcase local and international talent in a vibrant atmosphere. - **[Universal CityWalk: ](https://www.expedia.ca/Universal-CityWalk-Hotels.0-l6154318-0.Travel-Guide-Filter-Hotels)** Just 19.3km from Oakland, this bustling tourist precinct offers outdoor entertainment, dining, and shopping. Enjoy lively nightlife and family-friendly activities, making it a perfect spot to unwind after a day of exploration. ### Best time to go to Oakland The best time to visit Oakland can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Oakland falls in August, when visitor numbers are slightly low and weather is mostly sunny with moderate rain. The coolest average temperature around Oakland falls in January, visitor numbers are slightly high and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 59.9°F (15.5°C) | Light Rain | Mostly Sunny | Slightly High | Average | | February | 63.9°F (17.7°C) | Light Rain | Mostly Sunny | Slightly High | Average | | March | 67.3°F (19.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | April | 72.5°F (22.5°C) | Light Rain | Mostly Sunny | Average | Slightly High | | May | 77.2°F (25.1°C) | Light Rain | Mostly Sunny | Average | Average | | June | 81.0°F (27.2°C) | Moderate Rain | Mostly Sunny | Average | Average | | July | 82.4°F (28.0°C) | Moderate Rain | Mostly Sunny | Average | Average | | August | 82.6°F (28.1°C) | Moderate Rain | Mostly Sunny | Slightly Low | Slightly Low | | September | 80.2°F (26.8°C) | Moderate Rain | Mostly Sunny | Average | Slightly Low | | October | 74.8°F (23.8°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | November | 67.8°F (19.9°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | December | 63.7°F (17.6°C) | Light Rain | Mostly Sunny | Average | Slightly High | ### The nearest major airports for your trip to Oakland When visiting Oakland, Winter Garden, Florida, the major airports to consider are Orlando International Airport ([MCO](https://www.expedia.ca/Orlando-Intl-Airport-Hotels.0-aMCO-0.Travel-Guide-Filter-Hotels)) and Kissimmee Gateway Airport ([ISM](https://www.expedia.ca/Kissimmee-Gateway-Airport-Hotels.0-aISM-0.Travel-Guide-Filter-Hotels)). MCO is situated 35.4km from Oakland, with nearby hotels like [The Ritz-Carlton Orlando](https://www.expedia.ca/Orlando-Hotels-The-Ritz-Carlton-Orlando.h914146.Hotel-Information), Grande Lakes and [Hyatt Regency Orlando](https://www.expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) offering shuttle services. Alternatively, ISM is also 35.4km away, featuring luxury hotels such as Waldorf Astoria Orlando and [Conrad Orlando at Evermore](https://www.expedia.ca/Orlando-Hotels-Conrad-Orlando.h90603710.Hotel-Information), which provide convenient transportation options to the airport. For those travelling from Daytona Beach, Daytona Beach International Airport ([DAB](https://www.expedia.ca/Daytona-Beach-Intl-Airport-Hotels.0-aDAB-0.Travel-Guide-Filter-Hotels)) is located 90.1km from Oakland, with several hotels close by, including the [Hilton Daytona Beach Oceanfront Resort](https://www.expedia.ca/Daytona-Beach-Hotels-Hilton-Daytona-Beach-Oceanfront-Resort.h5244.Hotel-Information). ## Frequently asked questions ### When is the best time to go to Oakland? > During these months, you'll experience comfortable temperatures, typically ranging from the low 20s to high 20s Celsius (70s to 80s Fahrenheit), and lower humidity. This makes it ideal for enjoying outdoor activities, exploring the local trails, or visiting nearby attractions without the intense heat and frequent afternoon thunderstorms of the summer. It's a great time for couples seeking a relaxing getaway or families looking for comfortable conditions for day trips. > > > The summer months, from June to October, are considerably hotter and more humid, with daily chances of rain. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Oakland hotel booking with Expedia? ### How much is the nightly rate at a Oakland hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Bay Hill Hotels ](https://www.expedia.ca/Bay-Hill-Orlando-Hotels.0-n553248635975849893-0.Travel-Guide-Filter-Hotels) - [Hotels near Bella Collina Golf Club ](https://www.expedia.ca/Bella-Collina-Golf-Club-Hotels.0-l6238991-0.Travel-Guide-Filter-Hotels) - [Hotels near Central Florida Railroad Museum ](https://www.expedia.ca/Central-Florida-Railroad-Museum-Hotels.0-l553248621561885339-0.Travel-Guide-Filter-Hotels) - [Clarcona Hotels ](https://www.expedia.ca/Clarcona-Apopka-Hotels.0-n89774-0.Travel-Guide-Filter-Hotels) - 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