Winter Haven vacation rentals
Find spaces that suit your style
Find properties near top attractions in Winter Haven
Map Attractions
Find the best place to stay - Winter Haven
Lovely Condo Just 1 Mile From Disney w/ Resort Pool, WiFi & More
Top rated rentals - Winter Haven
Photo gallery for Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL
Clean and quiet
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Wonderful times in Winter Haven
Let Winter Haven vacation rentals welcome you to this year-round destination. Let your imagination run wild in LEGOLAND Florida Resort or go wild in the water in one of Winter Haven’s 50 lakes. Catch the community theater bug by taking in a show at the Theatre Winter Haven. If you’re really looking for some retail therapy, step back in time and explore the many antiques stores that call Winter Haven home. However you want to spend your vacation, Winter Haven is sure to have something to satisfy everyone.
Theme park and theater thrills in Winter Haven
Adults and children alike will love LEGOLAND Florida Resort! This 150-acre theme park is dedicated to family-friendly fun and will delight children of all ages. Make a splash in the adjoining water park for an additional fee, and cool off in the Floridian sun. After a day of fun in the sun, returning to the Winter Haven vacation rentals will always be welcome; but how about an evening at the theater? Theatre Winter Haven is locally renowned for its top-quality community theater. The program will, of course, depend on when you visit, but you’re guaranteed a great evening.
Wild water and amazing antiques in Winter Haven
Winter Haven is also known as “The Chain of Lakes City” and for good reason. After getting settled in Winter Haven vacation rentals, break out your bathing suit and head for one of the city’s 50 lakes! Flyboarding is one of the area’s popular water pursuits and you can book a lesson with companies operating from different lakes. Want something a bit more sedate on the water? Charter a boat and spend an afternoon bobbing on the waves while bass fishing. On land, eagle-eyed antiques enthusiasts will love browsing for souvenirs and gifts in the many antiques stores here.
It’s not called Winter Haven for nothing!
If you’re looking for year-round sunshine and warm temperatures, Winter Haven is the perfect place for you. July through August see average highs in the low 90s but also a lot of rain owing to the humid, subtropical Floridian climate. For those looking to avoid the rain, come to Winter Haven from October through May as these are by far the driest months. Winters see average highs in the high 40s so you can expect to get your fill of this town’s average 242 days of sunshine.
Love the lakes in Winter Haven
Located between Tampa and Orlando within the Central Florida Highlands, Winter Haven is not your typical Floridian beach-side community. You’ll see flatland with rolling hills all around you, as well as the lakes this city is so famous for. The lakes are full of wildlife, and nature lovers may be able to spot bald eagles and alligators as well as the bass. To get a real sense of the natural world, sit back and relax on a guided river tour and learn all about the birds and creatures that call Winter Haven home.
Transportation to and around Winter Haven
Fly into Tampa Intl. Airport (TPA), the closest airport, located 49 mi (78.9 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Tampa, FL (TPF-Peter O. Knight), which is 44.4 mi (71.5 km) away.
If you're traveling by train, the main station serving the city is Winter Haven Station.
Frequently asked questions
Explore destinations around Winter Haven
Vacation Rental options in Winter Haven
Long-term rentals in Winter Haven and around
- Monthly rentals in Florida
- Monthly rentals in Naples
- Monthly rentals in Fort Myers
- Monthly rentals in Cape Coral
- Monthly rentals in Clearwater
- Monthly rentals in St. Petersburg
- Monthly rentals in Sarasota
- Monthly rentals in Florida Keys
- Monthly rentals in Bradenton
- Monthly rentals in Fort Lauderdale
- Monthly rentals in West Palm Beach
- Monthly rentals in Kissimmee
- Monthly rentals in Port Charlotte
- Monthly rentals in Punta Gorda
- Monthly rentals in Panama City Beach
- Monthly rentals in Daytona Beach
- Monthly rentals in Lakeland
- Monthly rentals in Winter Haven
- Monthly rentals in Cocoa Beach
- Monthly rentals in Cape Canaveral
- Monthly rentals in Miramar
- Monthly rentals in Rosemary Beach
- Monthly rentals in Key West
- Monthly rentals in Destin
- Monthly rentals in Anna Maria Island
- Monthly rentals in The Villages
- Monthly rentals in Marco Island
- Monthly rentals in Tampa
- Monthly rentals in Bonita Springs
- Monthly rentals in Fernandina Beach
- Monthly rentals in Amelia Island
- Monthly rentals in Key Largo
- Monthly rentals in New Smyrna Beach
- Monthly rentals in Pensacola Beach
- Monthly rentals in Santa Rosa Beach
- Monthly rentals in Orlando
- Monthly rentals in Boca Raton
- Monthly rentals in Miami
- Monthly rentals in Miami Beach
- Monthly rentals in Siesta Key
- Monthly rentals in South Florida