Title: Book the Best Winter Haven LUXURY Hotels - Upscale Hotels in Winter Haven, FL | Expedia.ca [Winter Haven Travel Guide](https://expedia.ca/Winter-Haven.dx7464)[Hotels in Winter Haven](https://expedia.ca/Winter-Haven-Hotels.d7464.Travel-Guide-Hotels)[Vacation Rentals in Winter Haven](https://expedia.ca/Winter-Haven-Vacation-Rentals.d7464.Travel-Guide-VacationRentals)[Flights to Winter Haven](https://expedia.ca/Cheap-Flights-To-Winter-Haven.d7464.Travel-Guide-Flights)[Things to do in Winter Haven](https://expedia.ca/Things-To-Do-In-Winter-Haven.d7464.Travel-Guide-Activities)[Winter Haven Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Haven.d7464.Car-Rental-Guide)[Winter Haven Vacation Packages](https://expedia.ca/Winter-Haven.d7464.Destination-Travel-Guides) ![Winter Haven showing rides](https://images.trvl-media.com/place/7464/a00f555f-1771-4135-ad57-834cb1a10a56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Winter Haven, FL - ![](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 availability on Winter Haven Luxury Hotels Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-12&endDate=2025-12-13&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-13&endDate=2025-12-14&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-12&endDate=2025-12-14&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-19&endDate=2025-12-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Winter Haven luxury hotels ![Blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/71d67783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/fda6d33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/e9fdf4e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/8800/8718/e4447b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Winter Haven FL [](https://www.expedia.ca/Winter-Haven-Hotels-Howard-Johnson-By-Wyndham-Winter-Haven-FL.h8718.Hotel-Information) Winter Haven 7.0/10 Good (1008) "Nice hotel. Clean and great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raylene CA $117 CA $131 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Winter-Haven-Hotels-Howard-Johnson-By-Wyndham-Winter-Haven-FL.h8718.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/66ef3784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/db1d10af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/91512114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/7dd4826d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Roy Beach Inn [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Roy-Beach-Inn.h1887650.Hotel-Information) Winter Haven 7.0/10 Good (987) "Great very nice comfortable room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rian CA $125 CA $141 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Roy-Beach-Inn.h1887650.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=2025-12-26&endDate=2025-12-27®ionId=7464&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Winter Haven ### Winter Havenand its attractions for luxury travelers Winter Haven, Florida, is a hidden gem that offers luxury travellers a unique blend of relaxation and adventure. Begin your exploration at Legoland Florida Resort, where both children and adults can immerse themselves in interactive rides and impressive Lego sculptures, ensuring a fun-filled family day. For a more tranquil experience, the beautiful Bok Tower Gardens features lush landscapes and stunning architecture, perfect for a leisurely stroll or a picnic amidst nature’s beauty. For those who enjoy water activities, the Chain of Lakes provides opportunities for private boat rentals, allowing you to explore the serene waterways at your own pace. If golf is your passion, the nearby Cypresswood Golf and Country Club boasts an exquisite course set in lush surroundings, where you can enjoy a round in a peaceful setting. To truly indulge in luxury, consider staying in the upscale area around Lake Eloise, where high-end hotels offer beautiful lake views, spacious suites, and top amenities, ensuring an experience that caters to your need for comfort and pampering. After a day of fun, you’ll appreciate returning to your hotel for a relaxing evening by the water, dining on gourmet cuisine, and enjoying attentive service that anticipates your every need. ### Find the best luxury hotels and resorts in Winter Haven For those seeking a luxurious getaway in Winter Haven, Florida, these recommended hotels offer exquisite amenities and exceptional service to enhance your stay. [**Best Western Plus Winter Haven Inn & Suites**](https://www.expedia.ca/Winter-Haven-Hotels-Best-Western-Plus-Winter-Haven-Inn-Suites.h91029909.Hotel-Information) - **Why it's great for a luxury retreat:** Embrace a refined stay at the Best Western Plus Winter Haven Inn & Suites, where luxury blends seamlessly with comfort, earning a remarkable guest review rating of 9.4\. Guests will appreciate the air-conditioned rooms that promise a restful retreat, alongside an inviting outdoor pool perfect for relaxation under the sun, complete with sun loungers and pool umbrellas for added comfort. - **Other amenities:** This hotel also offers a kitchenette in select rooms, ideal for those who prefer a touch of home during their travels. Other features include daily housekeeping, free breakfast options, and a fitness centre for maintaining your routine. Guests can also enjoy the convenience of electric car charging stations and self-parking options, making this hotel a practical choice for luxury travellers. - **Nearby attractions:** LEGOLAND® Florida - 1 km, Peppa Pig Theme Park Florida - 1.1 km, Chain Of Wakes - 1.7 km ## Top Winter Haven 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 "Beautiful hotel with great amenities. Clean. The pools were great. Wonderful place to stay for families " [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Comfort Inn & Suites Kissimmee by the Parks](https://images.trvl-media.com/lodging/1000000/440000/430500/430452/578ae569_y.jpg) ### Comfort Inn & Suites Kissimmee by the Parks 10/10 Excellent "Front desk staff was amazing!!!" [](https://expedia.ca/Orlando-Hotels-Comfort-Inn-Maingate.h430452.Hotel-Information) ![Holiday Inn Resort Kissimmee by the Parks by IHG](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b_y.jpg) ### Holiday Inn Resort Kissimmee by the Parks by IHG 10/10 Excellent "Yes " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![Holiday Inn & Suites Orlando SW - Celebration Area by IHG](https://images.trvl-media.com/lodging/1000000/10000/7900/7855/e4318c5d_y.jpg) ### Holiday Inn & Suites Orlando SW - Celebration Area by IHG 10/10 Excellent "Food was fresh and staff is always pleasant " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Orlando-SW-Celebration-Area.h7855.Hotel-Information) ![Hilton Vacation Club Mystic Dunes Orlando](https://images.trvl-media.com/lodging/1000000/900000/891000/890951/0b826e24_y.jpg) ### Hilton Vacation Club Mystic Dunes Orlando 10/10 Excellent "Isabella at the check in counter was awesome.Thanks for " [](https://expedia.ca/Orlando-Hotels-Mystic-Dunes-Resort-Golf-Club-By-Diamond-Resorts.h890951.Hotel-Information) ![Hilton Vacation Club Aqua Sol Orlando West](https://images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg) ### Hilton Vacation Club Aqua Sol Orlando West 10/10 Excellent "Excellent " [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Delta Hotels by Marriott Orlando Celebration](https://images.trvl-media.com/lodging/1000000/10000/300/256/w4000h2663x0y0-bece67c9_y.jpg) ### Delta Hotels by Marriott Orlando Celebration 10/10 Excellent "Staff was excellent!! Very nice and friendly!!" [](https://expedia.ca/Orlando-Hotels-The-Grand-Orlando-Resort-At-Celebration.h256.Hotel-Information) ![Parkway International Resort](https://images.trvl-media.com/lodging/1000000/700000/692700/692651/fd297cb8_y.jpg) ### Parkway International Resort 10/10 Excellent "Zuri at the front desk was super serviceable and nice" [](https://expedia.ca/Orlando-Hotels-Parkway-International-Resort.h692651.Hotel-Information) ![Ramada by Wyndham Kissimmee Gateway](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/b94616ba_y.jpg) ### Ramada by Wyndham Kissimmee Gateway 10/10 Excellent "Clean room, location, facilities " [](https://expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information) ## Frequently asked questions ### Which area of Winter Haven is best to stay in for luxury hotels? > This area offers prime waterfront access and a more secluded, upscale setting compared to the busier parts of town. You'll find properties with private docks, expansive grounds, and often stunning views of the lakes, which are connected by navigable canals. It's a quieter part of Winter Haven, ideal for those seeking relaxation and natural beauty. > > > Couples looking for a romantic escape will find this area particularly appealing. The opportunity for leisurely boat trips, waterfront dining, and peaceful evenings by the lake creates a serene and memorable experience. ### How much does a luxury hotel in Winter Haven cost? ### What luxury activities and experiences are there in Winter Haven? > For those who enjoy spending time on the water, consider hiring a private boat charter. This allows for a personalised tour of the Chain of Lakes, great for a relaxed afternoon exploring the interconnected waterways, perhaps with a gourmet picnic prepared to your specifications. Many of these services can arrange for a captain, so you can simply enjoy the scenery. This is a lovely option for couples looking for a private and scenic experience. > > > Golf enthusiasts will find several well-maintained courses in and around Winter Haven, offering a premium golfing experience. Many of these courses feature challenging layouts and scenic views, with facilities that include professional instruction and well-appointed clubhouses. It's an ideal way for couples or solo travellers to enjoy a leisurely day outdoors, often followed by a high-quality meal at the course's restaurant. > > > For a unique and indulgent experience, consider a seaplane tour. Departing from one of the local lakes, these tours offer breathtaking aerial views of Winter Haven's Chain of Lakes and the surrounding Florida landscape. ### How can I save on a luxury hotel in Winter Haven with Expedia? ### Is it cheaper to book a luxury Winter Haven hotel and flights as a package? ### Can I cancel my luxury hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Beach Hotel Hotels in Auburndale ](https://www.expedia.ca/Auburndale-Hotels-Beach-Hotel.0-0-d6048255-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Auburndale ](https://www.expedia.ca/Auburndale-Hotels-Cheap-Hotels.0-0-d6048255-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Auburndale ](https://www.expedia.ca/Auburndale-Hotels-Hotel-With-Pool.0-0-d6048255-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Ski Hotels in Auburndale ](https://www.expedia.ca/Auburndale-Hotels-Ski-Hotel.0-0-d6048255-tSkiHotel.Travel-Guide-Filter-Hotels) - 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