Good to know: Visit and neighborhood recommendations in Winter Haven Winter Haven’s 50 lakes provide a unique setting for outdoor activities like boating, fishing, and paddleboarding. The city maintains a welcoming atmosphere with a small-town feel and easy access to nature and entertainment. From waterfront dining to live music in the park, Winter Haven delivers year-round enjoyment. Families, couples, and solo travelers all find something to love in this Florida gem. Where to look for an Airbnb in Winter Haven Downtown Winter Haven Downtown Winter Haven is the cultural and culinary heart of the city, offering walkable access to shops, restaurants, and live entertainment. Vacation rentals in Winter Haven include stylish lofts, restored historic apartments, and modern Airbnbs above local boutiques. Guests can enjoy craft breweries, farmers markets, and concerts at Central Park. Lake Howard Area Located near the center of the Chain of Lakes, the Lake Howard Area is ideal for those wanting waterfront access and beautiful views. Airbnbs nea the Lake Howard often feature private docks, screened porches, and easy access to water activities. Visitors can boat through canals connecting to other lakes or relax with a picnic by the shore. This area is great for couples and families seeking a tranquil, nature-oriented stay. Cypress Gardens Area Once home to Florida’s first theme park, the Cypress Gardens Area is now the location of Legoland Florida and its surrounding accommodations. Vacation rentals range from family houses to modern apartments with quick park access. Visitors staying here benefit from proximity to theme park excitement, botanical gardens, and waterfront paths. Lake Elbert Neighborhood Lake Elbert Neighborhood is a peaceful, residential area known for its wide lake views and serene environment. Travelers will find charming bungalows, lakefront homes, and traditional Florida rentals ideal for extended stays. The neighborhood offers a relaxing ambiance while still being a short drive from downtown. Nature lovers and long-term guests will appreciate the quiet and beauty here. Auburndale Border Area Located on the northern edge of Winter Haven, the Auburndale Border Area provides access to both cities and a more suburban vibe. Vacation rentals in Auburndale Border area include single-family homes with yards and comfortable interiors suited for families or groups. Guests can explore nearby trails, parks, and local eateries in both Winter Haven and Auburndale. What to do if you spend a vacation in Winter Haven Legoland Florida Resort One of the main attractions in town, Legoland Florida Resort is a must for families with children. It features roller coasters, water rides, themed zones, and interactive exhibits for all ages. The park also includes a hotel and water park, making it a full-day or weekend destination. Legoland blends fun, creativity, and colorful adventures in the heart of Winter Haven. Chain of Lakes The Chain of Lakes is a network of over 20 interconnected lakes that offer endless water recreation. Boating, fishing, kayaking, and jet skiing are popular ways to enjoy the water. Several city parks and public boat ramps provide access to the lakes throughout town. The scenic canals and lush surroundings make this a highlight for nature enthusiasts. Downtown Winter Haven Downtown Winter Haven is a lively destination filled with culture, food, and local events. Visitors can explore boutiques, dine at award-winning restaurants, or catch a performance at Theatre Winter Haven. The area frequently hosts art walks, parades, and community gatherings in Central Park. Polk Museum of Art (in nearby Lakeland) A short drive away in Lakeland, the Polk Museum of Art offers a diverse collection of classical and contemporary works. Visitors can enjoy rotating exhibitions, educational programs, and art classes in a modern facility. The museum enriches the cultural experience of the region and is affiliated with Florida Southern College. Theatre Winter Haven Recognized as one of the best community theaters in Florida, Theatre Winter Haven offers high-quality live productions year-round. From Broadway-style musicals to comedies and dramas, the theater provides entertainment for all ages. The venue is intimate and engaging, often featuring local talent. Bok Tower Gardens Located about 30 minutes away, Bok Tower Gardens is a National Historic Landmark featuring stunning gardens and a 205-foot singing tower. Guests can stroll through acres of landscaped trails, picnic under shady trees, or attend seasonal concerts. The tower’s carillon concerts create a peaceful and magical atmosphere. Peppa Pig Theme Park Adjacent to Legoland, the Peppa Pig Theme Park is designed especially for preschoolers and young children. It features gentle rides, character meet-and-greets, splash areas, and themed play zones. The park’s compact size makes it easy to enjoy without overwhelming younger guests. Lake Eva Community Park Located nearby in Haines City, Lake Eva Community Park offers sports facilities, walking trails, and a family-friendly aquatic center. It’s a popular spot for local events and picnics with great views of Lake Eva. The park also includes a playground and community center hosting seasonal festivities. Where to find a vacation rental near Winter Haven Orlando, Florida Just an hour northeast, Orlando offers world-class entertainment with theme parks, nightlife, and international dining. From the thrills of Universal Studios to peaceful strolls in Leu Gardens, there’s something for everyone. Whether you're staying near the parks or in downtown districts, unwind in a vacation rental in Orlando that places you at the heart of Central Florida’s action. Tampa, Florida About an hour west, Tampa delivers a dynamic blend of city life, culture, and coastal fun. Guests can explore the Florida Aquarium, stroll the Tampa Riverwalk, or enjoy a sunset from Bayshore Boulevard. After a day in the city or on the beach, relax in a vacation rental in Tampa offering both comfort and access to Gulf Coast experiences. Lakeland, Florida Only 30 minutes away, Lakeland charms with historic streets, blooming gardens, and walkable lakeside parks. Visitors can explore the Polk Museum of Art, admire Frank Lloyd Wright’s campus architecture, or browse weekend farmers markets. For a close and cultured stay, book a vacation rental in Lakeland tucked into this artsy Central Florida hub. Kissimmee, Florida Less than an hour north, Kissimmee is a family vacation favorite with resort communities, theme park proximity, and endless entertainment. Ride airboats through swamps, shop at Old Town, or head into Disney in minutes. At day’s end, recharge in a vacation rental in Kissimmee designed for relaxation after high-energy adventures. Davenport, Florida Just 25 minutes from Winter Haven, Davenport is a vacationer’s haven with spacious homes, private pools, and tranquil neighborhoods. It’s an ideal launch point for day trips to Legoland, Disney, or scenic drives across Central Florida. For space and comfort in a quieter setting, settle into a vacation rental in Davenport that blends value and accessibility. Discover enchanting lakeside escapes and thrilling amusement park destinations across the US. Delight in the serene ambiance of this charming destination, surrounded by picturesque lakes. For an unforgettable lakeside retreat, explore airbnb in South Lake Tahoe in California, where the crystalline waters of Lake Tahoe are perfect for sailing and hiking excursions. In Texas, vacation rentals in Marble Falls offer a delightful blend of natural beauty and artistic culture near Lake Marble Falls, renowned for its stunning sunsets. Utah’s majestic Flaming Gorge vacation rentals provide an adventurous escape with rafting and fishing opportunities along its rugged canyon landscapes. Meanwhile, Lake Ozark vacation rentals in Missouri invite you to discover the peaceful surroundings of the Ozarks with access to the Lake of the Ozarks State Park and quaint waterfront villages. For an exhilarating family getaway steeped in fun and excitement, venture beyond the local LEGOLAND to diverse amusement park destinations. Consider Anaheim airbnb options in California, the home of Disneyland and vibrant entertainment districts. In Florida, airbnb in Four Corners situates you near the magical realms of Walt Disney World and Universal Studios. Close to Orlando, Kissimmee vacation rentals place you near lively theme parks and charming local attractions like Old Town. Experience the warmth of a small-town feel with a stay in Davenport, where the proximity to major parks is complemented by serene golf courses and nature reserves.