Title: Central Florida's Historic Gem & wedding venue- The Oakland Manor House - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Central Florida's Historic Gem & wedding venue- The Oakland Manor House Lakefront vacation home in Winter Garden with a fitness center ## Photo gallery for Central Florida's Historic Gem & wedding venue- The Oakland Manor House ![Interior - Central Florida's Historic Gem & wedding venue- The Oakland Manor House (Oakland)](https://images.trvl-media.com/lodging/111000000/110940000/110939000/110938960/636458bf.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Terrace/patio - Central Florida's Historic Gem & wedding venue- The Oakland Manor House (Oakland)](https://images.trvl-media.com/lodging/111000000/110940000/110939000/110938960/w1200h796x0y0-b410242f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining - Central Florida's Historic Gem & wedding venue- The Oakland Manor House (Oakland)](https://images.trvl-media.com/lodging/111000000/110940000/110939000/110938960/28dc0c37.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Living area - Central Florida's Historic Gem & wedding venue- The Oakland Manor House (Oakland)](https://images.trvl-media.com/lodging/111000000/110940000/110939000/110938960/w1200h770x0y0-d00778a1.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Central Florida's Historic Gem & wedding venue- The Oakland Manor House (Oakland)](https://images.trvl-media.com/lodging/111000000/110940000/110939000/110938960/dbb468be.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Central Florida's Historic Gem & wedding venue- The Oakland Manor House provides amenities like laundry facilities and a gym. Guests can connect to in-room WiFi. ## Reviews 10 Exceptional ### Entire home 5 bedrooms7 bathrooms ## Popular amenities - Washer - Dryer - Pet friendly - Air conditioning - Gym ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Central Florida's Historic Gem & wedding venue- The Oakland Manor House Originally built in the early 1900’s, this gracious manor was carefully renovated, preserving its historic craftsman-style. As you pass through the gates & moss-draped oaks, you will feel like you have stepped back in time. For a relaxing getaway, OMHouse has five overnight bedrooms with private baths, each with its own theme, crafted by local artists, and representing an area attraction and its history. There is a separate yet attached bungalow that can be added to the entire home rental or rented on its own for smaller parties. The 700 sq. ft. lakeside porch has been the site of many social gatherings, retreats and weddings. Enjoy the proximity to the Magic Kingdom and all the attractions Orlando has to offer, as we are located in Oakland, Florida, within just 30 minutes of most central Florida highlights and the convenience of the Florida turnpike nearby. The West Orange Trail runs through the neighborhood to nearby Winter Garden to the east, with its Farmer’s Market, restaurants, brewery, and music venues and to the west, the Oakland Nature Preserve and Clermont. ## Property amenities ### Internet - Available in the house: WiFi ### Bedrooms - 5 bedrooms - Bedsheets provided ### Bathroom - 6.5 bathrooms - Bathtub or shower - Hair dryer ### Outdoor areas - Porch/lanai ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - Pet friendly - Welcoming dogs only - One pet total (up to 50 lbs per pet) ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - On a lake ### Things to do - Gym - Golfing nearby - Theme park nearby ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) ## Similar properties ![Interior](https://images.trvl-media.com/lodging/112000000/111160000/111151500/111151452/8d885b54.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Enchanted 2 Bedroom Home near Downtown Winter Garden Winter Garden - Kitchen - Washer - Dryer - Pet friendly 9.6 Exceptional 4 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-11&endDate=2026-02-12&selected=111151452&PinnedHotelID=111151452&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101160000/101158800/101158768/ad62a4ee.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### \*Travel Themed Property with Backyard Oasis\* Maitland - Pool - Kitchen - Washer - Dryer 9.8 Exceptional 34 reviews CA $837 CA $1,375 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-16&endDate=2026-02-17&selected=101158768&PinnedHotelID=101158768&HadPinnedHotel=true®ionId=-1&adults=2) ![Pool](https://images.trvl-media.com/lodging/103000000/102340000/102333400/102333362/b9ae09a2.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Mayfair Forrest Retreat ! Come and Enjoy our Clean and Spacious home sleeps 18! Sanford - Pool - Kitchen - Washer - Dryer 9.4 Exceptional 31 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-11&endDate=2026-02-12&selected=102333362&PinnedHotelID=102333362&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/114000000/113040000/113039700/113039630/03f5acec.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Oakland Manor House Oakland - Pet friendly - Parking included - Free WiFi - Air conditioning [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-11&endDate=2026-02-12&selected=113039630&PinnedHotelID=113039630&HadPinnedHotel=true®ionId=-1&adults=2) ![Lobby](https://images.trvl-media.com/lodging/116000000/115190000/115183100/115183013/w1348h899x1y1-81ef273a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Garden Luxe Retreat Winter Garden - Pool - Kitchen - Washer - Dryer 10 Exceptional 2 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-11&endDate=2026-02-12&selected=115183013&PinnedHotelID=115183013&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9800/9711/1913ff15.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Walt Disney World Swan Bay Lake - On private beach - Pool - Hot tub - Kids pool 9.2 Wonderful 2,014 reviews CA $360 CA $482 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-08&endDate=2026-02-09&selected=9711&PinnedHotelID=9711&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/13000000/12420000/12413200/12413148/8ee44865.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance Bay Lake - Pool - Hot tub - Breakfast included - Pet friendly 9.0 Wonderful 1,664 reviews CA $135 CA $151 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=12413148&PinnedHotelID=12413148&HadPinnedHotel=true®ionId=-1&adults=2) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/2b752fc1.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center Bay Lake - Pool - Breakfast included - Free WiFi - Restaurant 9.4 Exceptional 4,488 reviews CA $164 CA $185 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-09&endDate=2026-02-10&selected=61340843&PinnedHotelID=61340843&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-02-11&endDate=2026-02-12&selected=110938960&PinnedHotelID=110938960&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=110938960,111151452,101158768,102333362,113039630) ## Policies ### Check-in Check-in time starts at 3:00 PM Minimum check-in age: 18 ### Check-out Check-out before 11:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions Information provided by the property may be translated using automated translation tools ### Pets Pets allowed Service animals are welcome, and are exempt from fees Welcoming dogs only 1 total (up to 50 lbs per pet) ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Onsite parties or group events are strictly prohibited Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### Property is also known as 8392 ## About the area Located in Oakland, a neighborhood in Winter Garden, this vacation home is near theme parks and on a lake. Orlando International Premium Outlets is worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Magic Kingdom® Park and Walt Disney World® Resort. The Wizarding World of Harry Potter™ and Universal Studios Florida are not to be missed. Spend some time exploring the area's activities, including golfing. [Visit our Winter Garden travel guide](https://www.expedia.ca/Winter-Garden.dx7898) [View more Vacation homes in Winter Garden](https://www.expedia.ca/Winter-Garden-Private-Vacation-Homes.d7898-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=28.558762,-81.6282&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:kwimDf_fqN%40S%3FO%3FQ%3FQ%40Q%40Q%40Q%40O%40Q%40QBQ%40OBSBOBQBQBOBODQBODODQDODQDOFODOFOFMFOFOFMFOFMHOFMHOHKFMJMHMHMHMJKHKJMHKJKJIJMJIJKJILKJILIJILGJILILGLGLILELGLGLELGNELENELELENCNELCNCLCNANENALANANANANALAN%3FN%3FN%3FN%3FN%3FL%3FN%40N%40N%40N%40L%40N%40N%40NDL%40NBNBLBNDLDNBLDNDLDLDNFLDLFLFLDLHLFLFJHLHLFJHLJJFJJLHJJJHJLJJHHJJJLHJJLHJHLHLHLHLHJHNFLHNFLFNFLFNFNFLDNFNDPFLDPDNDPBNDNBPDNBNBPBPBNBR%40NBP%40P%40P%40N%40P%40P%3FP%40P%3FP%3FN%3FR%3FP%3FN%3FPAP%3FPAPAPAPAPANCPAPCPCNCPCPCNEPCNENCPENEPENGNENGNENGNGLGNGLGNGNILGLINILILIJILILIJKLIJKLKJIJKJKJKHKJMJKHKFMJKHMHMFKHMFMFMHMFMDMFMDOFMDMDODMDODMDOBMBODO%40MBOBO%40O%40MBO%40O%3FO%40O%40M%3FO%40O%3FO%3FOAO%3FMAOAO%3FOAOCMAOAOCOCMAOEMCOCOEMEMEOEMEOEMGMEMGMEMGMIMGMGMIKGMIKIMIKIMIKKKKKIKKKKKKIKKMIKKKIMIMIMKKGMIMIOGMIMGOGOGKGQGMGOGOEOGOEOEOEQEOEQCOEOCQCOCQCQCOCQAQCQAOAQAQAQAQAQ%3FQ%3FQ%3FOAQ&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=PLrheFZ7ASbRM-0jhQhguyPTasA=) Oakland, FL ### What's nearby - ![www.alamy.com](https://images.trvl-media.com/place/6347698/06ae0091-59b6-4929-bcdd-175b32d4910c.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Universal Orlando Resort 17 min drive \- 26.6 km - ![Central Florida showing rides and signage](https://images.trvl-media.com/place/6048177/6bf4c5fb-1002-4324-b44d-335e930a4f87.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Universal Studios Florida 19 min drive \- 25.3 km - ![www.alamy.com](https://images.trvl-media.com/place/6034120/72f0831e-8a1f-4532-9296-e96104eeb131.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Walt Disney World® Resort 24 min drive \- 26.3 km - ![Magic Kingdom® Park which includes rides](https://images.trvl-media.com/place/6123797/788d1b08-ae6d-4d61-86b9-eff1e639ae6e.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Magic Kingdom® Park 25 min drive \- 26.6 km - Oakland Nature Preserve 17 min walk \- 1.4 km ### Getting around - Orlando Station 23 min drive - Leesburg, FL (LEE-Leesburg Intl.) 48 min drive ### Restaurants - Crooked Can Brewing Company 6 min drive - Bojangles 6 min drive - Dairy Queen 5 min drive - Hangry Bison 6 min drive - Rosallie 7 min drive ## Frequently asked questions ### Is Central Florida's Historic Gem & wedding venue- The Oakland Manor House pet-friendly? ### What time is check-in at Central Florida's Historic Gem & wedding venue- The Oakland Manor House? ### What time is check-out at Central Florida's Historic Gem & wedding venue- The Oakland Manor House? ### Where is Central Florida's Historic Gem & wedding venue- The Oakland Manor House located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Central Florida's Historic Gem & wedding venue- The Oakland Manor House Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 1 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 10 Location ## Reviews ### 10/10 Excellent #### Kristen R. Sep 28, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy We had a spectacular time at the Oakland Manor House. It's a gorgeous, historic home filled with both handsome antiques and comfortable sofas and beds. The kitchen is fully stocked and a joy to use to make meals if you're so inclined. The bathrooms were very clean and well appointed with bath products and hair dryers for use. They even had coffee beans and a grinder for use. Very nice gestures. It was spotless and located in a lovely, safe neighborhood. We had a celebration of our wedding with twelve of our closest friends and family, and there was ample space for everyone to park on the property and enjoy a romantic and intimate dinner party. The host and caretaker were very communicative and encouraging. I couldn't recommend this property enough. Thank you for offering your home to us. ##### Kristen R. Stayed 2 nights in Sep 2025 ## Expedia's Latest Trends ### Hotels > [CoCo Key Hotel and Water Resort ](https://www.expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information) > > [The Grayson Miami Downtown](https://www.expedia.ca/Miami-Hotels-The-Grayson-Miami-Downtown.h6535.Hotel-Information) > > [Homewood Suites by Hilton Orlando at Flamingo Crossings](https://www.expedia.ca/Orlando-Hotels-Homewood-Suites-By-Hilton-Flamingo-Crossings.h58998470.Hotel-Information) > > [Hyde Beach House](https://www.expedia.ca/Fort-Lauderdale-Hotels-Hyde-Beach-House-Resort.h42435925.Hotel-Information) > > [Radisson Resort Miami Beach ](https://www.expedia.ca/Miami-Hotels-Four-Palms-Hotel-Miami-Beach.h44891320.Hotel-Information) > > [Universal's Endless Summer Resort - Dockside Inn and Suites](https://www.expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information) > > [Home2 Suites by Hilton Orlando at Flamingo Crossings](https://www.expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information) > > [Villatel Orlando Resort](https://www.expedia.ca/Orlando-Hotels-Orlando-Resort.h97584899.Hotel-Information) > > [Fort Lauderdale Beach Resort Hotel & Suites](https://www.expedia.ca/Fort-Lauderdale-Hotels-Ft-Lauderdale-Beach-Resort-Hotel-Suites.h327478.Hotel-Information) > > [Hilton Cabana Miami Beach Resort](https://www.expedia.ca/Miami-Hotels-Hilton-Cabana-Miami-Beach-Resort.h18107.Hotel-Information) > > [Hotel Landy Orlando Universal Blvd., a Tribute Portfolio Hotel](https://www.expedia.ca/Orlando-Hotels-Hotel-Landy-Orlando-Universal-Blvd.h889939.Hotel-Information) > > [Tru by Hilton Fort Lauderdale Downtown](https://www.expedia.ca/Fort-Lauderdale-Hotels-Tru-By-Hilton-Fort-Lauderdale-Downtown-Flagler-Village.h56963641.Hotel-Information) > > [Opal Grand Oceanfront Resort & Spa](https://www.expedia.ca/Palm-Beach-West-Palm-Beach-Hotels-Opal-Grand-Oceanfront-Resort-Spa.h44943466.Hotel-Information) > > [Flow Fort Lauderdale Hotel](https://www.expedia.ca/Fort-Lauderdale-Hotels-Flow-Fort-Lauderdale.h70330603.Hotel-Information) > > [Hilton Marco Island Beach Resort and Spa](https://www.expedia.ca/Naples-Hotels-Hilton-Marco-Island-Beach-Resort.h17575.Hotel-Information) > > [Hilton Grand Vacations Club Tuscany Village Orlando](https://www.expedia.ca/Orlando-Hotels-Hilton-Grand-Vacations-At-Tuscany-Village.h1080602.Hotel-Information) > > [Bay Lake Tower at Disney's Contemporary Resort \*\*available 12/24-12/29/22\*\*](https://www.expedia.ca/Orlando-Hotels-Bay-Lake-Tower-At-Disneys-Contemporary-Resort.h42407106.Hotel-Information) > > [Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center](https://www.expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information) > > [Four Seasons Hotel and Residences Fort Lauderdale](https://www.expedia.ca/Fort-Lauderdale-Hotels-Four-Seasons-Fort-Lauderdale.h71656415.Hotel-Information) > > [Mayfair House Hotel & Garden](https://www.expedia.ca/Miami-Hotels-Mayfair-House-Hotel-Garden.h24311.Hotel-Information) > > [JW Marriott Marco Island Beach Resort](https://www.expedia.ca/Naples-Hotels-JW-Marriott-Marco-Island-Beach-Resort.h14344.Hotel-Information) > > [The Tony Hotel South Beach](https://www.expedia.ca/Miami-Hotels-The-Hotel-Of-South-Beach.h201213.Hotel-Information) > > [Park Central South Beach](https://www.expedia.ca/Miami-Hotels-The-Celino-South-Beach.h1168.Hotel-Information) > > [Hotel Greystone - Adults Only](https://www.expedia.ca/Miami-Hotels-Hotel-Greystone.h34892018.Hotel-Information) > > [Renaissance Fort Lauderdale Marina Hotel](https://www.expedia.ca/Fort-Lauderdale-Hotels-Renaissance-Fort-Lauderdale-Cruise-Port-Hotel.h658067.Hotel-Information) > > [Hampton Inn Ft. Lauderdale/Downtown Las Olas Area](https://www.expedia.ca/Fort-Lauderdale-Hotels-Hampton-Inn-By-Hilton-Ft-LauderdaleDowntown-Las-Olas-Area.h860327.Hotel-Information) > > [Embassy Suites by Hilton Fort Lauderdale 17th Street](https://www.expedia.ca/Fort-Lauderdale-Hotels-Embassy-Suites-Ft-Lauderdale17th-Street.h11909.Hotel-Information) > > [Sanibel Island Beach Resort](https://www.expedia.ca/Fort-Myers-Hotels-Sanibel-Island-Beach-Resort.h17298818.Hotel-Information) > > [The Tides on Hollywood](https://www.expedia.ca/Fort-Lauderdale-Hotels-The-Tides-On-Hollywood.h44524455.Hotel-Information)