Title: The Best Hotels in Oakland, Winter Garden - 2025 Updated Prices | Expedia.co.uk [Holiday Rentals in Winter Garden](https://expedia.co.uk/Winter-Garden-Holiday-Rentals.d7898.Travel-Guide-HolidayRentals)[Flights to Winter Garden](https://expedia.co.uk/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.co.uk/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Oakland Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Oakland.d6360404.Car-Hire-Guide)[Oakland Holidays](https://expedia.co.uk/Oakland.d6360404.Holidays-City-Breaks) ![At the Oakland Preserve. Nice Boardwalk plus an animal sanctuary ](https://images.trvl-media.com/place/6360404/d013c781-9bde-4c95-8530-be7e0380ccba.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Gregg Yutko # Search Hotels in Oakland, Winter Garden ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Oakland Spa [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&amenities=SPA_ON_SITE) Pool [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&amenities=POOL) Apart hotel [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&lodging=APART_HOTEL) Hot tub [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&amenities=HOT_TUB) Resort [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&lodging=HOTEL_RESORT) Apart­ment [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&lodging=APARTMENT) Cottage [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&lodging=COTTAGE) Pet friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&amenities=PETS) Family friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&travelerType=family_friendly) Condo [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&lodging=CONDO) Villa [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&lodging=VILLA) Waterpark [](https://www.expedia.co.uk/Hotel-Search?destination=Oakland%2C+Winter+Garden%2C+Florida%2C+United+States+of+America®ionId=6360404&latLong=28.555%2C-81.633133&adults=2&startDate=2025-10-04&d1=2025-10-04&endDate=2025-10-06&d2=2025-10-06&amenities=WATER_PARK) ## Check prices for these dates Tonight [20 Sept - 21 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6360404&startDate=2025-09-20&endDate=2025-09-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [21 Sept - 22 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6360404&startDate=2025-09-21&endDate=2025-09-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [26 Sept - 28 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6360404&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [3 Oct - 5 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6360404&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Property class ## Top Trending Hotels Near Oakland, Winter Garden ## Our top choices for Oakland hotels ![Hypo-allergenic bedding, minibar, in-room safe, individually decorated](https://images.trvl-media.com/lodging/90000000/89970000/89963100/89963011/1db79ca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89970000/89963100/89963011/74ee1a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, minibar, in-room safe, individually decorated](https://images.trvl-media.com/lodging/90000000/89970000/89963100/89963011/a76a1c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/90000000/89970000/89963100/89963011/8d29552d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pestana Orlando Suites - Lake Buena Vista 13.9 mi from Oakland 9.4/10 Exceptional (1785) "Very easy to get to the parks from this hotel! Nice area with nearby places to eat and stuff, very clean; would stay here again! " £69 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Pestana-Orlando-Suites-Lake-Buena-Vista.h89963011.Hotel-Information) ![4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/cca9a672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/2ac14176.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/a5c2174b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1470000/1460500/1460425/89cab51d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Shingle Creek 15 mi from Oakland 9.4/10 Exceptional (4008) "Great resort vibes while being close to the parks and other tourist places. " £78 includes taxes & fees 10 Oct - 11 Oct [](https://www.expedia.co.uk/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/880000/874700/874635/43673d50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/880000/874700/874635/05a6203e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/1000000/880000/874700/874635/81076fce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/1000000/880000/874700/874635/35a13e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Vacation Club Polynesian Isles Kissimmee 17.1 mi from Oakland 9.8/10 Exceptional (1930) "Everything about our stay was excellent. Large, clean room, friendly staff, nice grounds and reasonable price. " £81 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Polynesian-Isles-Resort.h874635.Hotel-Information) ![Suite, 1 King Bed with Sofa bed, Balcony | 1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/d84c06b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/24b848d6.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) ![Reception](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/81e6b4c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kompose Boutique Resort at Theme Parks 15.5 mi from Oakland 9.4/10 Exceptional (1340) "Great place to stay" £58 includes taxes & fees 29 Sept - 30 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/7400/7372/1c333323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/7400/7372/b28f041c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds | Bathroom | Combined shower/bathtub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/10000/7400/7372/cdca0762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/10000/7400/7372/abf568d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Plaza on International Drive 13.1 mi from Oakland 9.2/10 Wonderful (1621) "Excellent location, great staff, good food." £71 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Rosen-Plaza-On-International-Drive.h7372.Hotel-Information) ![2 outdoor pools, pool cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite | Premium bedding, pillow-top beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/925df5bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite | Premium bedding, pillow-top beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/w3836h2561x4y0-0f34b0cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/d087c6a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Orlando 13.3 mi from Oakland 9.2/10 Wonderful (1744) "Great place to stay " £134 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/3e7928e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/b126e956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/20db8430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Orlando International Drive 12.8 mi from Oakland 9.2/10 Wonderful (1015) "Had a great stay" £92 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12300/12272/bb83f9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tapas bar](https://images.trvl-media.com/lodging/1000000/20000/12300/12272/e2cc5459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/1000000/20000/12300/12272/9f451c1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/20000/12300/12272/a048980e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotel by Marriott Orlando Lake Buena Vista 14.4 mi from Oakland 9.2/10 Wonderful (1474) "Enjoyed staying here" £71 includes taxes & fees 1 Oct - 2 Oct [](https://www.expedia.co.uk/Orlando-Hotels-AC-Hotel-Orlando-Lake-Buena-Vista.h12272.Hotel-Information) ![Outdoor pool, open 6:00 AM to midnight, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/20000/11500/11432/016c4706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/11500/11432/bf2d7277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/1000000/20000/11500/11432/b50b15b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/11500/11432/51a5e50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Centre Hotel 13.7 mi from Oakland 9.0/10 Wonderful (3957) "Perfect stay close to the parks." £68 includes taxes & fees 11 Oct - 12 Oct [](https://www.expedia.co.uk/Orlando-Hotels-Rosen-Centre-Hotel.h11432.Hotel-Information) ![4 outdoor pools, pool cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/900000/891000/890951/0b826e24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/891000/890951/3de8e1d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/891000/890951/89cc4422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/900000/891000/890951/6bd9ae14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Vacation Club Mystic Dunes Orlando 16.7 mi from Oakland 9.0/10 Wonderful (4340) "Very good place, felt like home with my parents, husband, 3 years old and 10 months baby." £105 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/41854f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Mexican cuisine ](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/31e90d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Mexican cuisine ](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/e7c9feef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Mexican cuisine ](https://images.trvl-media.com/lodging/1000000/10000/7700/7622/20b0635e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Lion Hotel Orlando Lake Buena Vista South 17.7 mi from Oakland 8.8/10 Excellent (4083) "Excellent hotel and staff." £56 includes taxes & fees 25 Sept - 26 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Red-Lion-Hotel-Orlando-Lake-Buena-Vista-South.h7622.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/a264c3e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/e7188448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/w3838h2560x0y0-b722e83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/753a80d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru By Hilton Orlando Convention Center Area, FL 13.7 mi from Oakland 9.0/10 Wonderful (3317) "It was a great stay!" £70 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Tru-By-Hilton-Orlando-Convention-Center-Area.h47041344.Hotel-Information) ![Outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/20000/16400/16367/5d24052d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillow-top beds, in-room safe, individually furnished](https://images.trvl-media.com/lodging/1000000/20000/16400/16367/1bd6beeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/16400/16367/8ccf919d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/16400/16367/e7581d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Orlando - Disney Springs® Area by IHG 14.5 mi from Oakland 9.0/10 Wonderful (1382) "We have stayed here numerous times over the years and it has always been one of our favorite places to stay. I highly recommend this hotel!" £103 includes taxes & fees 29 Sept - 30 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Holiday-Inn-Orlando-Disney-Springs-Area.h16367.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/8fc8f285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, American cuisine](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/4c8ad9ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/668f020d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/13000000/12340000/12337500/12337440/70a23798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance 12.1 mi from Oakland 9.0/10 Wonderful (2210) "Great and close to Disney " £73 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Orlando-Hotels-SpringHill-Suites-Orlando-At-FLAMINGO-CROSSINGS-Town-CenterWestern-Entrance.h12337440.Hotel-Information) ![2 outdoor pools, a heated pool, pool cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/19400/19384/c19268bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/19400/19384/ec251282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Café](https://images.trvl-media.com/lodging/1000000/20000/19400/19384/460dffef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/19400/19384/caa01a82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Lake Buena Vista – Disney Springs® Area 14.5 mi from Oakland 8.8/10 Excellent (2714) "We love staying here!" £104 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Wyndham-Lake-Buena-Vista-Disney-Springs-Resort-Area.h19384.Hotel-Information) ![Sports court](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/033f2fa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/83fc3e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/w3836h2561x3y0-6cfb6f06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; Italian cuisine ](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/ed3e2ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Caribe Royale Orlando 16.1 mi from Oakland 9.2/10 Wonderful (4416) "Great place to stay" £173 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4000/3910/4e7996e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/10000/4000/3910/f712282b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4000/3910/25817b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, dinner served, pizza](https://images.trvl-media.com/lodging/1000000/10000/4000/3910/e3f65876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Buena Vista Suites Orlando 16 mi from Oakland 9.2/10 Wonderful (1890) "We had an amazing time at Buena Vista , room was very spacious, breakfast in the morning was delicious, definitely will come back for next Disney family vacation! " £118 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Buena-Vista-Suites.h3910.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26800/26711/7d99a9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/1000000/30000/26800/26711/31bfeafb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Egyptian cotton sheets, premium bedding, pillow-top beds](https://images.trvl-media.com/lodging/1000000/30000/26800/26711/c49f746a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/30000/26800/26711/ead0d859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta ES Suites Orlando - International Drive 12.6 mi from Oakland 9.0/10 Wonderful (1005) "Great place & location!" £89 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Orlando-Hotels-Sonesta-ES-Suites-Orlando-International-Drive.h26711.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/1b4214e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/eef498cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/06bb2a8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Vacation Club Aqua Sol Orlando West 14.2 mi from Oakland 8.8/10 Excellent (4071) "Great stay" £115 includes taxes & fees 5 Oct - 6 Oct [](https://www.expedia.co.uk/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/60000/59995/128b4990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/1000000/60000/60000/59995/dbe85294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/60000/59995/97485c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/60000/59995/aef45e43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Vacation Club Grand Beach Orlando 15.7 mi from Oakland 9.4/10 Exceptional (1349) "Great stay " £94 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Orlando-Hotels-Hilton-Vacation-Club-Grand-Beach-Orlando.h59995.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2025-10-05&endDate=2025-10-06®ionId=6360404&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Where to stay in Oakland Find the best Oakland areas for the activities you enjoy most. - Vista del Lago - Downtown Winter Garden - Killarney [](https://www.expedia.co.uk/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:qsalD%60khqNuTKSum%40bMBb%40%7BIaFkIAmHnSCG%7CB_AjAb%40fBtMlGnGw%40pBpGdNKDsCzMFKd%5Ew%7C%40RAzX&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=wUFX3-rb7D1RuzCXZzPXGN-IeoM=) ### 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.co.uk/Hotel-Search?regionId=553248635976471720) [](https://www.expedia.co.uk/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:cximDn%7C%7EpNuMUGcP%7DIIGme%40fBOhV%5DArn%40KjI&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=9hSHnyXq3TvSJ004qkHugKCfJWo=) ### Downtown Winter Garden If you're spending some time in Downtown Winter Garden, West Orange Trail and Central Florida Railroad Museum are top sights worth seeing. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=944538218785796096) [](https://www.expedia.co.uk/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%7EHw%7B%40rcBiG%7EFat%40hb%40kDhz%40z%60BuCv%7B%40sSfZuu%40zE%7DxAj%60%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=E0pDJfXrX0s4gVMZEBkRoXlUHWg=) ### Killarney Killarney might not have many top sights, but Bella Collina Golf Club and West Orange Trail are two attractions nearby that you can check out. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=6360403) ## Top Oakland Hotel Reviews ![Walt Disney World Swan](//images.trvl-media.com/lodging/1000000/10000/9800/9711/a789d7e5_y.jpg) ### Walt Disney World Swan 10/10 Excellent "Very convenient " [](https://expedia.co.uk/Orlando-Hotels-Walt-Disney-World-Swan.h9711.Hotel-Information) ![Hyatt Regency Orlando](//images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg) ### Hyatt Regency Orlando 10/10 Excellent "Staff was very friendly. " [](https://expedia.co.uk/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) ![Universal's Cabana Bay Beach Resort](//images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "It was good " [](https://expedia.co.uk/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Marriott's Grande Vista](//images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg) ### Marriott's Grande Vista 10/10 Excellent "family-friendly " [](https://expedia.co.uk/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) ![Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center](//images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/2b752fc1_y.jpg) ### Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center 10/10 Excellent "It was perfect" [](https://expedia.co.uk/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](//images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent " Very family friendly, welcoming, and relaxing " [](https://expedia.co.uk/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![Rosen Inn at Pointe Orlando](//images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg) ### Rosen Inn at Pointe Orlando 10/10 Excellent "Very nice staff" [](https://expedia.co.uk/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Palazzo Lakeside Hotel](//images.trvl-media.com/lodging/1000000/20000/14800/14701/de0795f9_y.jpg) ### Palazzo Lakeside Hotel 10/10 Excellent "Nice hotel for the price Great location. " [](https://expedia.co.uk/Orlando-Hotels-Palazzo-Lakeside.h14701.Hotel-Information) ![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 "Absolutely beautiful resort. My kids really enjoyed the water park. " [](https://expedia.co.uk/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ## Find out more about Oakland ### Top reasons to visit Oakland - **Family-Friendly Activities:** Oakland offers a variety of outdoor adventures and entertainment options suitable for families, ensuring fun for all ages. - **Charming Atmosphere:** The welcoming neighbourhood boasts friendly locals and a delightful ambiance, perfect for a relaxing getaway. - **Nearby Attractions:** Explore popular theme parks, golf courses, and vibrant downtown areas in the surrounding Orange County. - **Diverse Accommodation:** A range of lodging options, from family-friendly resorts to pet-friendly hotels, cater to every traveller's needs. - **Scenic Parks:** Enjoy the tranquillity of picturesque parks, ideal for leisurely strolls and outdoor picnics. ### Find great hotels near Oakland Explore an array of delightful hotel options in Oakland, Winter Garden, Florida, perfect for every type of traveller. Whether you seek family-friendly resorts, pet-friendly accommodations, or business-themed hotels, Oakland offers a variety of choices to ensure a comfortable stay. With its proximity to Orlando, you'll find the best hotels that cater to your needs and preferences, making your vacation truly memorable. - **[Universal's Cabana Bay Beach Resort:](https://www.expedia.co.uk/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information)** This vibrant 3.5-star hotel exudes a retro, family-friendly theme reminiscent of the 1950s and 60s. Located 7.5km from Oakland, it offers a delightful vacation experience for families, featuring spacious rooms and a nostalgic atmosphere. The resort boasts a variety of amenities for children, including a free crib service and an exciting arcade game room, ensuring that younger guests are entertained throughout their stay. With its lively pool area and themed dining options, families can unwind and enjoy quality time together in a whimsical setting. - **[The Grove Resort & Water Park Orlando:](https://www.expedia.co.uk/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information)** A splendid 4-star resort situated 8.1km from Oakland, The Grove Resort & Water Park is a fantastic choice for families and LGBTQIA travellers alike. This modern resort promotes inclusivity and offers a wealth of amenities, including a children’s pool, onsite mini-golf, and games specifically for younger guests. The resort’s children’s club, available for a fee, ensures that kids can engage in fun activities while parents relax. The impressive water park and serene surroundings make it an ideal destination for a memorable family vacation. - **[DoubleTree by Hilton at the Entrance to Universal Orlando:](https://www.expedia.co.uk/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information)** This elegant 4-star hotel, located 7.5km from Oakland, is perfect for families and pet owners seeking a welcoming atmosphere. The DoubleTree is LGBTQIA-friendly and offers a range of amenities suitable for children, including a pool and an arcade game room. For pet lovers, the hotel permits dogs and cats, with specific policies to ensure a comfortable stay for all. Guests appreciate the warm hospitality and signature chocolate chip cookies upon arrival, making it an inviting option for your Orlando adventure. ### Where to stay near Oakland Oakland, Florida, is a charming neighbourhood perfect for family-friendly adventures and outdoor activities. Nestled in Central Florida, it offers a welcoming atmosphere with friendly locals and a variety of excursions. Explore nearby attractions in Orange County, relax in the scenic parks, or visit the vibrant downtown of Lauderdale. Whether you're seeking entertainment or a tranquil escape, Oakland provides a delightful backdrop for an unforgettable holiday experience. - **[Winter Garden:](https://www.expedia.co.uk/Winter-Garden-Hotels.d7898.Travel-Guide-Hotels)** Located a mere 1.9km from Oakland, Winter Garden is a bustling city known for its delightful blend of family-friendly attractions and entertainment options. Visitors flock here year-round, particularly during the peak months of January to February and September. The city boasts a vibrant shopping area and a charming shopping mall, making it ideal for retail therapy. Furthermore, locals and tourists alike can enjoy nearby landmarks such as theme parks and beaches, ensuring a memorable experience filled with fun and relaxation. - **[Reavills Corner:](https://www.expedia.co.uk/Reavills-Corner-Hotels.d6188540.Travel-Guide-Hotels)** This quaint village, also situated 1.9km from Oakland, offers a unique outdoor experience for families and adventure-seekers alike. With visitor numbers peaking in March, July, and December, Reavills Corner provides a refreshing getaway at various times of the year. Its attractions include a delightful resort and shopping area, alongside educational venues. Nature enthusiasts will appreciate the proximity to beautiful lakes and beaches, which serve as perfect spots for picnics or leisurely strolls, adding to the village's charm. - **[Montverde:](https://www.expedia.co.uk/Montverde-Hotels.d6241597.Travel-Guide-Hotels)** Just 2.5km from Oakland, Montverde is a picturesque city that appeals to outdoor enthusiasts and families. Known for its sports facilities, particularly golf courses, this city attracts visitors mainly from January to March. With a rich array of activities, including access to resorts and scenic lakes, Montverde offers a relaxed yet engaging atmosphere. Close to film studios and theme parks, it provides ample opportunities for entertainment, ensuring that visitors leave with lasting memories of their stay. ### Things to do near Oakland Oakland, Florida, is an ideal destination for families seeking outdoor entertainment and relaxation. Visitors can enjoy a variety of activities, including exploring nearby resorts, shopping areas, and shopping mall centres. With its charming atmosphere and numerous attractions, Oakland promises a delightful vacation experience filled with fun and leisure for all ages. **Shopping** In Oakland, visit Clermont Regal Shopping Center, just 3.7km away, offering a vibrant selection of shops and eateries. If you're up for a drive, discover [Oak Hill Village Shopping Center](https://www.expedia.co.uk/Oak-Hill-Village-Shopping-Center-Hotels.0-l553248621563220168-0.Travel-Guide-Filter-Hotels), located 6.2km away, or Flamingo Crossings Town Center, situated 7.5km away, both featuring family-friendly vibes. **Recreation** At [Camping World Stadium](https://www.expedia.co.uk/Camping-World-Stadium-Hotels.0-l502139-0.Travel-Guide-Filter-Hotels), immerse yourself in the thrill of live sports events, just 8.7km from Oakland. Enjoy the serene greens at [Disney's Magnolia Golf Course](https://www.expedia.co.uk/Disneys-Magnolia-Golf-Course-Hotels.0-l6241695-0.Travel-Guide-Filter-Hotels), situated 6.8km away, or embark on a fun-filled day at Congo River Golf, 7.5km from Oakland, perfect for families and adventurers alike. **Adventure** [Universal’s Volcano Bay](https://www.expedia.co.uk/Universals-Volcano-Bay-Hotels.0-l553248633507645899-0.Travel-Guide-Filter-Hotels), a thrilling waterpark 7.5km from Oakland, offers exhilarating slides and relaxing lagoons for all ages. For hiking enthusiasts, the West Orange Trail, located 1.9km away, provides picturesque scenery and outdoor adventure. Alternatively, enjoy water sports at Watertoyz of Clermont, 5.0km from Oakland. **Nightlife** In Oakland, [The Orlando Eye at ICON Park](https://www.expedia.co.uk/The-Orlando-Eye-At-ICON-Park-Hotels.0-l553248621565183042-0.Travel-Guide-Filter-Hotels) offers breathtaking views and family-friendly fun on its iconic Ferris wheel. For a unique experience, [Sleuth's Mystery Dinner Show](https://www.expedia.co.uk/Sleuths-Mystery-Dinner-Show-Hotels.0-l6154916-0.Travel-Guide-Filter-Hotels) combines entertainment and romance, while Carter Family Bowl provides an exciting arcade atmosphere perfect for families seeking adventure. ### Booking tips and Expedia advantages for Oakland To save money on your trip to Oakland, plan your visit during the cheaper months of August to September or November, avoiding the pricier March to April and December. Book your hotel about a month in advance, or check for last-minute deals on Expedia. Tuesdays are the most economical days to stay, while Saturdays are the priciest. Utilise Expedia’s search tools to filter for budget-friendly options, and consider package deals that combine flights and accommodation for additional savings. Exploring on foot can also help cut costs on transportation. - **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:** Take advantage of Expedia's search tool to refine your preferences, such as your budget, desired location, and the type of hotel you wish to stay in. To find the best prices and deals, simply adjust the price filter to sort from lowest to highest. - **Consider bundling your trip:** You could potentially save money by combining your hotel accommodation in Oakland with your flights and activities through an Expedia package deal. ### Find the best attractions near Oakland Oakland, Florida, is perfect for families seeking entertainment and outdoor adventures. Popular attractions include theme parks, golf courses, and arts centres, offering a delightful mix of fun and cultural experiences. Whether you're looking to enjoy thrilling activities or immerse yourself in the local culture, Oakland has something for everyone, making it an ideal destination for a memorable holiday. - **[Walt Disney World® Resort:](https://www.expedia.co.uk/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels)** Experience the magic of this iconic theme park, located 6.2km from Oakland. Enjoy thrilling rides, enchanting attractions, and family-friendly entertainment that will delight visitors of all ages. - **[Orange County Convention Center:](https://www.expedia.co.uk/Orange-County-Convention-Center-Hotels.0-l6034972-0.Travel-Guide-Filter-Hotels)** Situated 8.1km away, this arts centre boasts a vibrant cultural scene. Explore exhibitions and events that showcase the rich artistic heritage of the region, making it a great stop for art enthusiasts. - **[Universal CityWalk:](https://www.expedia.co.uk/Universal-CityWalk-Hotels.0-l6154318-0.Travel-Guide-Filter-Hotels)** Just 7.5km from Oakland, this lively tourist precinct offers a fantastic outdoor atmosphere. Enjoy dining, shopping, and entertainment in a family-friendly setting, perfect for making lasting memories. ### 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 main airports to consider are Orlando International Airport ([MCO](https://www.expedia.co.uk/Orlando-Intl-Airport-Hotels.0-aMCO-0.Travel-Guide-Filter-Hotels)) and Kissimmee Gateway ([ISM](https://www.expedia.co.uk/Kissimmee-Gateway-Airport-Hotels.0-aISM-0.Travel-Guide-Filter-Hotels)). Orlando International Airport is situated 13.7km from Oakland, with nearby accommodation options like [The Ritz-Carlton Orlando](https://www.expedia.co.uk/Orlando-Hotels-The-Ritz-Carlton-Orlando.h914146.Hotel-Information), Grande Lakes and [Rosen Shingle Creek](https://www.expedia.co.uk/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information), both 5.0km away, offering various transportation services. Kissimmee Gateway is also 13.7km from Oakland, featuring hotels such as Waldorf Astoria Orlando, located 4.3km from the airport. Both airports provide convenient access to the area, making your travel experience seamless. ## Frequently asked questions ### What are the best family hotels in Oakland? > [Oakland Manor House](https://www.expedia.co.uk/Winter-Garden-Hotels-Oakland-Manor-House.h113039630.Hotel-Information) in Winter Garden, Florida, is an excellent choice for families seeking a comfortable and convenient getaway. This charming property offers a cozy kitchen, great for preparing family meals, while the beautiful garden provides a lovely space for kids to play and explore. ### What are the most romantic hotels in Oakland for couples? > For a romantic retreat, [Oakland Manor House](https://www.expedia.co.uk/Winter-Garden-Hotels-Oakland-Manor-House.h113039630.Hotel-Information) in Winter Garden, FL, offers an enchanting experience with its charming amenities and beautiful surroundings. Couples can enjoy a partial lake view from their furnished balcony or patio, superb for sipping champagne as the sun sets. ### Can I cancel my hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Oakland hotel for you. ### How can I save on a Oakland hotel booking with Expedia? > With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Oakland hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings. ### How much is the nightly rate at a Oakland hotel? > Hotel prices in Oakland often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. 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