Title: Hotels by Diamond Resorts in Oakland from CA $188 | Expedia.ca [Oakland Travel Guide](https://expedia.ca/Winter-Garden-Oakland.dx6360404)[Vacation Rentals in Winter Garden](https://expedia.ca/Winter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals)[Flights to Winter Garden](https://expedia.ca/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.ca/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d6360404.Car-Rental-Guide)[Oakland Vacations](https://expedia.ca/Oakland.d6360404.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/a8a5cc3452c5ce939a38ef30d23f8715.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Gregg Yutko # Find Hotels by Diamond Resorts in Oakland from CA $188 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-18&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Diamond Resorts Hotels ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/700000/692700/692651/fd297cb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/700000/692700/692651/8df59585.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/692700/692651/b97f34d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/1000000/700000/692700/692651/fa326de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parkway International Resort Kissimmee 9.6/10 Exceptional (2015) "Brilliant value for money absolutely mind blown by the quality of the rooms and resort. Staff were so friendly to this is our second stay we will be back!" ![](https://a.travel-assets.com/egds/marks/flags/uk.svg) Charlotte CA $144 CA $188 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Orlando-Hotels-Parkway-International-Resort.h692651.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/7300/7233/f7cffdb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/1000000/10000/7300/7233/26ae59e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/10000/7300/7233/85826b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/1000000/10000/7300/7233/c0d66da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orbit One Vacation Villas Kissimmee 9.4/10 Exceptional (1410) "The staff and facilities were excellent." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara CA $145 CA $204 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Orlando-Hotels-Orbit-One-Vacation-Villas.h7233.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2937/c7920e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/10000/3000/2937/6e28d805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms, Kitchen | Private kitchen](https://images.trvl-media.com/lodging/1000000/10000/3000/2937/703bc91c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms, Kitchen | In-room dining](https://images.trvl-media.com/lodging/1000000/10000/3000/2937/d00c44e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bryan’s Spanish Cove Orlando 9.4/10 Exceptional (1003) "Great place for a vacation " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Antony CA $159 CA $203 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Orlando-Hotels-Bryans-Spanish-Cove.h2937.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01®ionId=6360404&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Winter-Garden-Hotels-Diamond-Resorts.0-n6360404-0--bDiamondResorts.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Winter-Garden-Hotels-Diamond-Resorts.0-n6360404-0--bDiamondResorts.Travel-Guide-Filter-Hotels) ## Top Oakland Hotel Reviews ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](//images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "We hadn't stayed at this property in many years and decided to try it again for a quick trip to FL. The property was beautiful. Check in was quick and staff excellent. Our room was super clean and very well maintained. We loved staying here and area already planning to return." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.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 "I spent 3 nights here with my daughter. The room was clean & spacious, the breakfast was a great start to the day & the staff was amazing. The shuttle to the parks was convenient with several time options. Top notch customer service. We would definitely stay here again. " [](https://expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information) ![Rosen Inn Lake Buena Vista](//images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg) ### Rosen Inn Lake Buena Vista 10/10 Excellent "I only spent one night since.I can say that the rooms were very comfortable. The staff in the reception was very serviceable ..It has a very good location across the street of a very good mall." [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.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 "Great place " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.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 "Staff was amazing , living area was very clean !! Definitely booking when I head back over there for travels " [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) ![Home2 Suites by Hilton Orlando at Flamingo Crossings](//images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/9a8a6f4d_y.jpg) ### Home2 Suites by Hilton Orlando at Flamingo Crossings 10/10 Excellent "Our room was spacious clean and we could see the Disney fireworks at 9pm every night. That was a nice little bonus " [](https://expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information) ![Margaritaville Resort Orlando with H2O Waterpark](//images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg) ### Margaritaville Resort Orlando with H2O Waterpark 10/10 Excellent "We were blown away by this resort! You walk in to the grand lobby and immediately loved the smell of this place . We even asked about it and they sell it in their store! We bought a lot of it haha. Our room was so beautiful and enjoyed the balcony overlooking the pool so much. We loved using the pool and laying out by it. The grounds are beautiful and enjoyed our stay here so much. Staff are friendly and amazing. Can’t wait to come back!" [](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.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 "Great all around " [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.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 "Excellent " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ## Find out more about Oakland ## Oakland Hotels Guide Expedia.ca offers a selection of 39313 hotels in Oakland. You are sure to find cheap deals and discount rates among them with our Best Price Guarantee. No matter what type of hotel strikes your fancy, we will let you search for your preferred one to accommodate your travel needs. Expedia.ca will not only save you time, but also money when booking your stay at a hotel in Oakland. Making reservations so you can stay within your budget is easy with us. Expedia.ca even provides you with a map so you may find hotels in the Oakland neighborhood you prefer. Go ahead. 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