Title: The Best Hotels in Oakland, Winter Garden - 2026 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) ![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) # Search Hotels in Oakland, Winter Garden - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [24 Dec - 25 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6360404&startDate=2025-12-24&endDate=2025-12-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [25 Dec - 26 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6360404&startDate=2025-12-25&endDate=2025-12-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [26 Dec - 28 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6360404&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [2 Jan - 4 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6360404&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Property class ## Our top choices for Oakland hotels ![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) ![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) ![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) ### Rosen Shingle Creek [](https://www.expedia.co.uk/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) 15 mi from Oakland 9.4/10 Exceptional (4370) "Great resort will revisit one day " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jewel £92 includes taxes & fees 23 Jan - 24 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Rosen-Shingle-Creek.h1460425.Hotel-Information) ![2 outdoor pools, a heated pool, pool cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/fe46d0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/e0072702.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/400962c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Universal's Cabana Bay Beach Resort [](https://www.expedia.co.uk/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) 11.5 mi from Oakland 9.0/10 Wonderful (5834) "Solid place for a vacation Will be staying again in the future " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jared G £111 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/1492ecfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed | Premium bedding, desk, iron/ironing board, free cots/infant beds](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/69bc7507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/bathtub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/8c29ff94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1820000/1813900/1813900/94d5773b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seasons Florida Resort [](https://www.expedia.co.uk/Orlando-Hotels-Seasons-Florida-Resort.h1813900.Hotel-Information) 18.8 mi from Oakland 8.8/10 Excellent (3306) "Excellent location and value, very clean and friendly check in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason £42 includes taxes & fees 11 Jan - 12 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Seasons-Florida-Resort.h1813900.Hotel-Information) ![Outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/55b45a9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/d5745363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/575efd8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/1fbd324f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham I-Drive Avanti Resort & Conference Center [](https://www.expedia.co.uk/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) 11.9 mi from Oakland 7.4/10 Good (3939) "Excellent room and the beds were very comfortable, also very clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daisy £68 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, pay films](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/7f4a5e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/a43383ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/f911355a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 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) 11.9 mi from Oakland 8.4/10 Very good (6908) "Great hotel great food" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malika £75 includes taxes & fees 15 Jan - 16 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children’s play area – outdoor](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/42b17c52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children’s play area – outdoor](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/78188457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/e5914c73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Inn at Pointe Orlando [](https://www.expedia.co.uk/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) 12.9 mi from Oakland 8.6/10 Excellent (5429) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie £69 includes taxes & fees 14 Jan - 15 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/b94616ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/48efc8c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/daabd874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/c45757b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Kissimmee Gateway [](https://www.expedia.co.uk/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information) 15.6 mi from Oakland 8.0/10 Very good (3912) "Phenomenal hotel for the price point as well as the children. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Destiny £57 includes taxes & fees 7 Jan - 8 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/f8c22738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/938e82c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/57d203ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Inn Lake Buena Vista [](https://www.expedia.co.uk/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) 14.2 mi from Oakland 8.6/10 Excellent (5639) "Great property to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deepankar £60 includes taxes & fees 19 Jan - 20 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![6 outdoor pools, free pool cabanas, pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-golf](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/45c63d74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children’s play area – outdoor](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/5799425f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/b969c931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando [](https://www.expedia.co.uk/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) 15.1 mi from Oakland 9.4/10 Exceptional (4160) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shawna £93 includes taxes & fees 14 Jan - 15 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.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) ![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) ![Room, 1 King Bed, Accessible (Mobility, Roll-In Shower) | In-room safe, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/9713e9df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/7a28810a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Orlando near Universal [](https://www.expedia.co.uk/Orlando-Hotels-Spark-By-Hilton-Orlando-Near-Universal.h15927.Hotel-Information) 11.7 mi from Oakland 9.0/10 Wonderful (469) "The rooms and breakfast were lovely" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MacKenzie Rose £74 includes taxes & fees 13 Jan - 14 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Spark-By-Hilton-Orlando-Near-Universal.h15927.Hotel-Information) ![In-room safe, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/de0795f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 9:00 AM to 9:00 PM, pool loungers](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/c2072d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/f253be82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/20000/14800/14701/28928af8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palazzo Lakeside Hotel [](https://www.expedia.co.uk/Orlando-Hotels-Palazzo-Lakeside.h14701.Hotel-Information) 18 mi from Oakland 8.2/10 Very good (5133) "Beautiful place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mohammad £66 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Palazzo-Lakeside.h14701.Hotel-Information) ![Outdoor pool, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/b440f6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/bfd880e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/ab5becdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1760000/1759600/1759572/2772ccec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Meliá Orlando Celebration [](https://www.expedia.co.uk/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.Hotel-Information) 16.5 mi from Oakland 8.6/10 Excellent (1573) "was a very nice stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Taylor Elaine £105 includes taxes & fees 7 Jan - 8 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Melia-Orlando-Celebration.h1759572.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/aa564e7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/c2c15966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside views, serves lunch, dinner and happy hour](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/c939bf2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/20000/19600/19535/0f12768a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Resort Orlando - Lake Buena Vista by IHG [](https://www.expedia.co.uk/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Lake-Buena-Vista.h19535.Hotel-Information) 14.9 mi from Oakland 8.4/10 Very good (3579) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathaniel £82 includes taxes & fees 14 Jan - 15 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Lake-Buena-Vista.h19535.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) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/40000000/39070000/39065100/39065095/fff09d70.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) ![Exterior](https://images.trvl-media.com/lodging/40000000/39070000/39065100/39065095/4c62351c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### avid hotel Orlando International Airport by IHG [](https://www.expedia.co.uk/Orlando-Hotels-Avid-Hotels-Orlando-International-Airport.h39065095.Hotel-Information) 19.6 mi from Oakland 9.2/10 Wonderful (2031) "Easy check in, great people service, clean room, great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiffany £89 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Avid-Hotels-Orlando-International-Airport.h39065095.Hotel-Information) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/f732f0b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds (Oversized, No Resort Fee) | Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/c7f078df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/027db371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/aa80c5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drury Plaza Hotel Orlando - Disney Springs Area [](https://www.expedia.co.uk/Orlando-Hotels-Drury-Plaza-Hotel-Orlando-Lake-Buena-Vista.h24103.Hotel-Information) 14.3 mi from Oakland 9.8/10 Exceptional (5435) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kiran £134 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Drury-Plaza-Hotel-Orlando-Lake-Buena-Vista.h24103.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) ![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) ![Desk, laptop workspace, blackout curtains, soundproofing](https://images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/d639070d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru By Hilton Orlando Convention Center Area, FL [](https://www.expedia.co.uk/Orlando-Hotels-Tru-By-Hilton-Orlando-Convention-Center-Area.h47041344.Hotel-Information) 13.7 mi from Oakland 9.0/10 Wonderful (3699) "Friendly staff, great service, clean rooms, enjoyed the stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katherine £74 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Tru-By-Hilton-Orlando-Convention-Center-Area.h47041344.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/61000000/60520000/60517400/60517339/fce7ad5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, desk, laptop workspace, soundproofing](https://images.trvl-media.com/lodging/61000000/60520000/60517400/60517339/c833ef93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/61000000/60520000/60517400/60517339/cef71edc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, pool 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.co.uk/Orlando-Hotels-Cambria-Hotel-Orlando-Airport.h60517339.Hotel-Information) 19.5 mi from Oakland 8.8/10 Excellent (1941) "Clean room and pleasant staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mariama Velinique £88 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Cambria-Hotel-Orlando-Airport.h60517339.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/dcc2b70c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/91f01ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, blackout curtains](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/331ac963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/330000/327400/327322/7db7a856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Orlando International Airport by IHG [](https://www.expedia.co.uk/Orlando-Hotels-Holiday-Inn-Express-Orlando-International-Airport.h327322.Hotel-Information) 19.5 mi from Oakland 9.0/10 Wonderful (1881) " Nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shalanda £92 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Holiday-Inn-Express-Orlando-International-Airport.h327322.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/ee39e243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/044c9db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 16.95 per person)](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/e8180b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Resort Kissimmee by the Parks by IHG [](https://www.expedia.co.uk/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) 15.3 mi from Oakland 8.4/10 Very good (1086) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven £74 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.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) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/46d55b67.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) ![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 [](https://www.expedia.co.uk/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) 12.8 mi from Oakland 9.4/10 Exceptional (1386) "Good location, good breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea £98 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-01-07&endDate=2026-01-08®ionId=6360404&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Where to stay in Oakland Find the best Oakland areas for the activities you enjoy most. - Horizon West - Vista del Lago - Downtown Winter Garden - Killarney ![](https://mediaim.expedia.com/destination/1/37b5977531ce6620ae360dd863ce8f7c.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.co.uk/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.co.uk/Hotel-Search?regionId=977491569791938560) [](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: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 Flamingo Crossings Town Center 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:eximDn%7C%7EpNsMUGcP%7DIIGme%40fBOhV%5DArn%40MjI&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=1VUib_Z3T3Au8u27r8QEdv-WKNs=) ### 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%7EHu%7B%40rcBkG%7EFat%40hb%40kDhz%40z%60BuCv%7B%40sSfZuu%40zE%7DxAj%60%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=QMWxfWyixWBofYiTIYo5XkD4OX8=) ### 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 ![The Grove Resort & Water Park Orlando](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg) ### The Grove Resort & Water Park Orlando 10/10 Excellent "Great room. Perfect for our group of 4 adults. Easy access to Disney Parks. Enjoyed the pool and green spaces. Very satisfied. " [](https://expedia.co.uk/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Wyndham I-Drive Avanti Resort & Conference Center](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/55b45a9e_y.jpg) ### Wyndham I-Drive Avanti Resort & Conference Center 10/10 Excellent "Room was clean staff was friendly check in and check out time was quick no hassle. Property area was clean good for families" [](https://expedia.co.uk/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Room was huge! Loved the experience check in was smooth only thing they don’t tell you is theirs a parking pass fee we stayed 4 days 3 nights and paid $79\. Besides that it was great! Easy smooth check in and check out everyone was nice and friendly!! " [](https://expedia.co.uk/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Waldorf Astoria Orlando - An Official Walt Disney World® Hotel](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/0589fd64_y.jpg) ### Waldorf Astoria Orlando - An Official Walt Disney World® Hotel 10/10 Excellent "Excellent " [](https://expedia.co.uk/Orlando-Hotels-Waldorf-Astoria-Orlando.h2432727.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 "We have stayed here multiple times for the AKC National Championship and will be back next year. Staff is excellent and we live the facilities. " [](https://expedia.co.uk/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Embassy Suites by Hilton Orlando International Dr Conv Ctr](https://images.trvl-media.com/lodging/1000000/10000/7000/6905/c015e5a9_y.jpg) ### Embassy Suites by Hilton Orlando International Dr Conv Ctr 10/10 Excellent "Everything in the hotel itself was amazing." [](https://expedia.co.uk/Orlando-Hotels-Embassy-Suites-By-Hilton-Orlando-International-Dr-Conv-Ctr.h6905.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent "Great place but no breakfast included" [](https://expedia.co.uk/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "Clean rooms, great staff, food court was a bit pricey but to be expected at a resort- plus food was great! 10/10 for affordable family vacation. " [](https://expedia.co.uk/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![DoubleTree by Hilton Hotel Orlando at SeaWorld](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg) ### DoubleTree by Hilton Hotel Orlando at SeaWorld 10/10 Excellent "Friendly people " [](https://expedia.co.uk/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.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? ### What are the most romantic hotels in Oakland for couples? ### 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 - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [3 Star Hotels in Clermont ](https://www.expedia.co.uk/3Star-Clermont-Hotels.s30-0-d7484.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Windermere ](https://www.expedia.co.uk/5Star-Windermere-Hotels.s50-0-d6085091.Travel-Guide-Filter-Hotels) - [Hotels near Arnold Palmer's Bay Hill Golf Club ](https://www.expedia.co.uk/Arnold-Palmers-Bay-Hill-Golf-Club-Hotels.0-l6069329-0.Travel-Guide-Filter-Hotels) - [Hotels near Bella Collina Golf Club ](https://www.expedia.co.uk/Bella-Collina-Golf-Club-Hotels.0-l6238991-0.Travel-Guide-Filter-Hotels) - 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