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](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/22000/22882-Legoland-Florida.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 [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-10-25&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-10-26&endDate=2025-10-27&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top 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) ![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) ![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) ### Howard Johnson by Wyndham Winter Haven FL Winter Haven 6.8/10 (1023) "Great place and area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vilmary CA $119 CA $133 total includes taxes & fees Oct 27 - Oct 28 [](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) ![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) ![Outdoor banquet area](https://images.trvl-media.com/lodging/2000000/1890000/1887700/1887650/20bcb6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Roy Beach Inn Winter Haven 7.0/10 Good (980) "Love this place, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) PATRICIA CA $121 CA $136 total includes taxes & fees Oct 26 - Oct 27 [](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=2025-11-08&endDate=2025-11-09®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 ![Galleria Palms Hotel](//images.trvl-media.com/lodging/1000000/90000/84700/84682/47b4a2b7_y.jpg) ### Galleria Palms Hotel 10/10 Excellent "The staff are so kind and welcoming. We noted that on our last trip and it was the same this time. It makes a huge impression and the consistency of customer service has us as repeat guests. " [](https://expedia.ca/Orlando-Hotels-Galleria-Palms-Hotel.h84682.Hotel-Information) ![voco Kissimmee Orlando by IHG](//images.trvl-media.com/lodging/1000000/50000/41100/41083/b3397abc_y.jpg) ### voco Kissimmee Orlando by IHG 10/10 Excellent "Thank so much Jesse .. to let me in super early..!! You made my trip even.. better .!!! You should be a manager!!! All da Way 💗💗" [](https://expedia.ca/Orlando-Hotels-Voco-Kissimmee-Orlando-By-IHG.h41083.Hotel-Information) ![Comfort Inn & Suites Kissimmee by the Parks](//images.trvl-media.com/lodging/1000000/440000/430500/430452/578ae569_y.jpg) ### Comfort Inn & Suites Kissimmee by the Parks 10/10 Excellent "VIAJE CON FAMILIA Y ESTA BIEN UBICADO EL HOTEL PERSONAL AMABLE, LIMPIO EL HOTEL Y HABITACION, EL DESAYUNO MUY COMPLETO, MUY SEGURO YA QUE TENIA VARIOS ARTICULOS EN LA HABITACION Y TODO COMPLETO, EL PRECIO VS LO OFRECIDO EXCELENTE MUCHAS GRACIAS" [](https://expedia.ca/Orlando-Hotels-Comfort-Inn-Maingate.h430452.Hotel-Information) ![Ramada by Wyndham Kissimmee Gateway](//images.trvl-media.com/lodging/1000000/50000/40600/40513/b94616ba_y.jpg) ### Ramada by Wyndham Kissimmee Gateway 10/10 Excellent "Yes" [](https://expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information) ![Holiday Inn Club Vacations at Orange Lake Resort by IHG](//images.trvl-media.com/lodging/1000000/10000/6400/6315/ac7826b3_y.jpg) ### Holiday Inn Club Vacations at Orange Lake Resort by IHG 10/10 Excellent "Everyone was very friendly. Our condo was very clean and we felt safe on the grounds. The pools offered lots of fun and were super clean. " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-At-Orange-Lake-Resort.h6315.Hotel-Information) ![Parkway International Resort](//images.trvl-media.com/lodging/1000000/700000/692700/692651/fd297cb8_y.jpg) ### Parkway International Resort 10/10 Excellent "Our stay was short, so we didn't get to enjoy the pool area. I loved the garden tub and the spacious rooms. The screened balcony was a great surprise! " [](https://expedia.ca/Orlando-Hotels-Parkway-International-Resort.h692651.Hotel-Information) ![Holiday Inn & Suites Orlando SW - Celebration Area by IHG](//images.trvl-media.com/lodging/1000000/10000/7900/7855/e4318c5d_y.jpg) ### Holiday Inn & Suites Orlando SW - Celebration Area by IHG 10/10 Excellent "Nice clean room" [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Orlando-SW-Celebration-Area.h7855.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 "Nice property and clean room" [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.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 "great keep it up " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury trip to Winter Haven? > Expedia can help you arrange a flight to Lakeland Intl. Airport (LAL) airport or Kissimmee, FL (ISM-Kissimmee Gateway) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Winter Haven has to offer. Known for its entertainment and sporting events, Winter Haven also has some interesting things to see and do including LEGOLAND® Florida, so you may want to take in the local sights during your visit. ### When can I expect good weather in Winter Haven? > Planning for the weather is an important factor for making your trip to Winter Haven a success, especially when you're splurging. The hottest months are usually August and July with an average temp of 81°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Haven are August, July, September, and June, with each month seeing an average of 8 inches of rainfall. ### What's there to see and do in Winter Haven? > Take in the sights and attractions that Winter Haven offers with a visit to LEGOLAND® Florida, Indigo's Family Fun Center, and Theatre Winter Haven. If you have extra time while you're in the area, you might want to stop by Chain of Lakes Park and Peppa Pig Theme Park Florida. ### How can I get around Winter Haven? > It's easier to get around town comfortably when you know your options. 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