175 Winter Haven Vacation Rentals & Short Term Rentals

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Compare Winter Haven vacation rentals from 8 rental sites including TripAdvisor, HomeAway, Booking.com and more, ranging from $29 to $1000 a night.

Information about Winter Haven

About Winter Haven

Sitting between Tampa and Orlando, it’s home to numerous beautiful lakes and majestic towers, several world-class collections of vintage aircrafts, and the largest land of LEGOs in the entire world. There sure are plenty of places to play, to explore, and to reflect at in this Polk County area, where every day is the perfect day to bask in the glory of warm sunshine, refreshing waters, soft sands, rolling hills, and a diverse population of historic neighborhoods.

Everything you need for a perfect vacation is in and around this glorious city-- whether you are looking for a quick bite, some wild adventure, or just to spend a little down time with the entire family. Eat, drink, play, and be merry at this literal Sunshine State haven.

Things to Do in Winter Haven

Just an hour away from the theme parks of Orlando, Florida are fifty or so lakes that continue to lure bass fishing and waterskiing enthusiasts to slip on those skis, or to get out those fishing rods for some fun on the water. There’s tons to do for those hoping to have themselves a lakeside adventure, as Winter Haven’s famous Chain of Lakes has offered pulsating water-oriented activities since the 1930s. You should also be prepared to reel in the catch of a lifetime, as the area’s often been deemed as the “Bass Fishing Capital of the World!”

Go wild by trying out barefoot skiing, or head on out to the Water Ski Hall of Fame for a quick tour—it was established in 1982 to honor the pioneering skiers who put the extreme sport onto the map. You can also do some fly boarding at spaces such as Absolute Aqua Sports, or some paddle boarding starting at Lake Summit before making time to visit tourist faves such as LEGOLAND Florida, which spans 145 acres and is home to more than fifty rides, a waterpark, as well as a botanical garden. Kiddies will also love the Safari Trek, where Jeep ride-alongs offer the perfect African safari experience in the form of life-like LEGO animals! Be sure to take a stroll to the Bok Tower Gardens, a spacious 250-acre botanical haven offering lily pads, koi ponds, and great photo ops, or to enjoy a walk around the Fantasy of Flight Air Museum. What’s more is that Winter Haven is also just an all-around excellent location to raise a family, to retire at, or to enjoy a mild climate-filled Floridian getaway no matter what time of the year it is.

Winter Haven Day Trips

With Disney World, Busch Gardens, SeaWorld, and Universal Studios all within an hour's drive, Winter Haven is the perfect "home base" for vacations. You and the fam bam can also explore wildlife ops to your hearts content just outside of the city at the Circle B Bar Reserve in nearby Lakeland, Florida, which was named by USA TODAY as one of the top places in the nation to see wildlife. Gawk over snakes, bobcats, and alligators galore within almost 1,300 acres of vast natural space. For something even more exciting, why not take an Airboat Nature Tour in nearby Lake Wales, Florida by hopping aboard a six-person wonder to explore Central Florida’s best swamps and marshlands (which are home to rare birds such as egrets and hawks, as well as some super large gators!)?

Other fun outings include Camp Mack's River Resort, a recreation event venue also in Lake Wales, Florida with water access on the Kissimmee River that leads into both Lake Kissimmee and Lake Hatchineha. It’s located on a super quiet stretch and serves as a superb launching pad for fishing excursions. Shell crackers, bluegills, crappies, and good old Florida largemouth bass are just some some of the many prized catches you’ll be taking home with you after an afternoon out on the water. What are you waiting for?

Winter Haven Accommodations

Let’s just say that Winter Haven boasts a wide variety of accommodations-- from up-scale hotspots to affordable family-friendly options—you’ll no doubt be able to find somewhere nice to rest off at within an extensive listing of inns, hotels, motels, resorts, and vacation rentals. There’s certainly something for every taste and budget such as the luxurious Shergill Grand Hotel or the comfy Lake Roy Beach Inn, to the more wallet-friendly Rodeo Inn & Suites, Hampton Inn Winter Haven, or Rose Motel. Vacation rentals and camping options also come aplenty as well. So no matter what kind of plans you have in mind, there’s a fantastic spot to relax and unwind in.

Winter Haven Transportation

Major routes in and around Winter Haven include US 17, State Road 540, State Road 542, and State Road 544—making the area perfect for those looking to travel on four wheels. What’s more is that the streets of downtown are neatly arranged in a grid plan, allowing them to be super easy to navigate for all roadsters, as two sets of lettered avenues and streets run conveniently parallel in both directions.

For those looking to hop on a train, there’s also Amtrak service at the local station, as well as commuter bus services that are offered courtesy of Winter Haven Area Transit and the Citrus Connection. Jet-setters looking to fly should come and go via Winter Haven's Gilbert Airport and the adjacent Jack Browns Seaplane Base, both of which are located just three miles northwest of the central business district.

Vacation Rentals in Winter Haven

Find the best Winter Haven vacation rentals with Tripping.com. Choose from 177 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $29 a night to $1000 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 142 of homes in Winter Haven offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 136 rentals with pool or jacuzzi, or relax with the family in one of the 67 homes with cable TV.

For all those dog lovers and cat lovers, Winter Haven offers 123 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 8 rental sites in Winter Haven where the top providers in that area are TripAdvisor, HomeAway, and Booking.com. There are 91 TripAdvisor rentals, 46 HomeAway short term rentals and 23 Booking.com vacation rentals.