Winter Haven is a lakeside Central Florida city built around a beautiful Chain of Lakes — think boating, fishing, waterfront parks, a walkable historic downtown with restaurants and markets, and family-friendly draws like LEGOLAND — all lending themselves to relaxed, affordable multi-week stays that still feel interesting.
You’re centrally located about 35–40 miles from Orlando (theme parks, big-city dining and an international airport) and ~45 miles from Tampa (beaches, pro sports and nightlife), with nearby Lakeland (~20 miles) adding extra restaurants and cultural options — a quiet home base with easy weekend variety.