Title: Hotels by Diamond Resorts in Windermere from CA $204 | Expedia.ca [Windermere Travel Guide](https://expedia.ca/Windermere.dx6085091)[Hotels in Windermere](https://expedia.ca/Windermere-Hotels.d6085091.Travel-Guide-Hotels)[Vacation Rentals in Windermere](https://expedia.ca/Windermere-Vacation-Rentals.d6085091.Travel-Guide-VacationRentals)[Flights to Windermere](https://expedia.ca/Cheap-Flights-To-Windermere.d6085091.Travel-Guide-Flights)[Things to do in Windermere](https://expedia.ca/Things-To-Do-In-Windermere.d6085091.Travel-Guide-Activities)[Windermere Car Rentals](https://expedia.ca/Car-Rentals-In-Windermere.d6085091.Car-Rental-Guide)[Windermere Vacation Packages](https://expedia.ca/Windermere.d6085091.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/533000/533443-tibet-butler-preserve.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels by Diamond Resorts in Windermere from CA $204 ![](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 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6085091&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=6085091&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windermere 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) ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/692700/692651/b97f34d1.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/d658e6bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parkway International Resort Kissimmee 9.6/10 Exceptional (2008) "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!" CA $160 CA $206 total includes taxes & fees Oct 16 - Oct 17 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7300/7233/854eae41.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." CA $144 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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3000/2937/c34c3dae.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) ### Bryan’s Spanish Cove Orlando 9.4/10 Exceptional (1003) "Great place for a vacation " CA $170 CA $215 total includes taxes & fees Oct 28 - Oct 29 [](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=2025-10-29&endDate=2025-10-30®ionId=6085091&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%2FWindermere-Hotels-Diamond-Resorts.0-0-d6085091--bDiamondResorts.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindermere-Hotels-Diamond-Resorts.0-0-d6085091--bDiamondResorts.Travel-Guide-Filter-Hotels) ## Top Windermere Hotel Reviews ![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) ![Universal's Endless Summer Resort - Dockside Inn and Suites](//images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/c8859517_y.jpg) ### Universal's Endless Summer Resort - Dockside Inn and Suites 10/10 Excellent "Staff was fantastic as always, this is our 4th time staying here and I couldn’t recommend it enough. " [](https://expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information) ![Hyatt Regency Orlando](//images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg) ### Hyatt Regency Orlando 10/10 Excellent "It was an amazing hotel to stay at. The staff was great. The rooms were clean. They had a 24 hr. Store for food, snacks , and drinks which was convenient. I would recommend the hotel to anyone in the market for comfort and convenience." [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.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 "Very clean room. Accommodating staff and beautiful property with a lot of food and entertainment " [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) ![Tru By Hilton Orlando Convention Center Area, FL](//images.trvl-media.com/lodging/48000000/47050000/47041400/47041344/a264c3e2_y.jpg) ### Tru By Hilton Orlando Convention Center Area, FL 10/10 Excellent "." [](https://expedia.ca/Orlando-Hotels-Tru-By-Hilton-Orlando-Convention-Center-Area.h47041344.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 "Everything was perfect " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Walt Disney World Dolphin](//images.trvl-media.com/lodging/1000000/20000/12800/12710/a6b6c49c_y.jpg) ### Walt Disney World Dolphin 10/10 Excellent "Great service and customer relations. " [](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Dolphin.h12710.Hotel-Information) ![Holiday Inn Resort Kissimmee by the Parks by IHG](//images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b_y.jpg) ### Holiday Inn Resort Kissimmee by the Parks by IHG 10/10 Excellent "Noisy family next door with multiple small children." [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![DoubleTree by Hilton at the Entrance to Universal Orlando](//images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df_y.jpg) ### DoubleTree by Hilton at the Entrance to Universal Orlando 10/10 Excellent "Great" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [3 Star Hotels in Metro West](https://www.expedia.ca/3Star-Metro-West-Orlando-Hotels.s30-n553248635976007228-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Doctor Phillips](https://www.expedia.ca/4Star-Doctor-Phillips-Orlando-Hotels.s40-n6361034-0.Travel-Guide-Filter-Hotels) - [Hotels near Arnold Palmer's Bay Hill Golf Club](https://www.expedia.ca/Arnold-Palmers-Bay-Hill-Golf-Club-Hotels.0-l6069329-0.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Bay Hill](https://www.expedia.ca/Bay-Hill-Orlando-Hotels-All-Inclusive-Hotel.0-n553248635975849893-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - 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[Orlando Vacations](https://www.expedia.ca/Orlando.d178294.Destination-Travel-Guides) - [The Wizarding World of Harry PotterTM](https://www.expedia.ca/The-Wizarding-World-Of-Harry-PotterTM-Florida-Center.d6277909.Vacation-Attraction) - [Universal Orlando Resort](https://www.expedia.ca/Universal-Orlando-Resort-Florida-Center.d6347698.Vacation-Attraction) - [Universal Studios Florida](https://www.expedia.ca/Universal-Studios-Florida-Florida-Center.d6049239.Vacation-Attraction) - [Universal’s Islands of Adventure](https://www.expedia.ca/Universals-Islands-Of-Adventure-Florida-Center.d6068693.Vacation-Attraction) - [Universal’s Volcano Bay](https://www.expedia.ca/Universals-Volcano-Bay-Florida-Center.d553248633507645899.Vacation-Attraction) - [Walt Disney World® Resort](https://www.expedia.ca/Walt-Disney-World-Resort-Orlando.d6034120.Vacation-Attraction) - [Rental cars Orlando Intl. airport](https://www.expedia.ca/Car-Rentals-In-Orlando-Intl.d5194573.Car-Rental-Guide) - [Car rentals near Orlando](https://www.expedia.ca/Car-Rentals-In-Orlando.d178294.Car-Rental-Guide) - [Car rentals near The Wizarding World of Harry PotterTM](https://www.expedia.ca/Car-Rentals-In-The-Wizarding-World-Of-Harry-PotterTM.d6277909.Car-Rental-Guide) - [Car rentals near Universal Orlando Resort](https://www.expedia.ca/Car-Rentals-In-Universal-Orlando-Resort.d6347698.Car-Rental-Guide) - [Car rentals near Universal Studios Florida](https://www.expedia.ca/Car-Rentals-In-Universal-Studios-Florida.d6049239.Car-Rental-Guide) - [Car rentals near Universal’s Islands of Adventure](https://www.expedia.ca/Car-Rentals-In-Universals-Islands-Of-Adventure.d6068693.Car-Rental-Guide) - [Minivan Car Rentals near Universal Orlando Resort](https://www.expedia.ca/Minivan-Car-Rentals-In-Universal-Orlando-Resort.d6347698-tMinivan.Car-Rental-Guide-Class) - [Pickup Car Rentals near Universal Orlando Resort](https://www.expedia.ca/Pickup-Car-Rentals-In-Universal-Orlando-Resort.d6347698-tPickup.Car-Rental-Guide-Class) - [Suv Car Rentals near Universal Orlando Resort](https://www.expedia.ca/SUV-Car-Rentals-In-Universal-Orlando-Resort.d6347698-tSUV.Car-Rental-Guide-Class) - [Sports Car Car Rentals near Universal’s Islands of Adventure](https://www.expedia.ca/Sportscar-Car-Rentals-In-Universals-Islands-Of-Adventure.d6068693-tSportscar.Car-Rental-Guide-Class) - [Standard Car Rentals near Universal Orlando Resort](https://www.expedia.ca/Standard-Car-Rentals-In-Universal-Orlando-Resort.d6347698-tStandard.Car-Rental-Guide-Class) - [Things to do in Orlando](https://www.expedia.ca/Things-To-Do-In-Orlando.d178294.Travel-Guide-Activities) - [Book Diamond Resorts in Windermere on Expedia.com](https://www.expedia.com/Windermere-Hotels-Diamond-Resorts.0-0-d6085091--bDiamondResorts.Travel-Guide-Filter-Hotels)