A castle entrance with flags and banners, including a LEGO Kingdoms banner.

Winter Haven cottage rentals

We found 15 cottage rentals — enter your dates for availability

Explore Winter Haven cottage rentals

Image of The Russell Lake House

Premier Host

The Russell Lake House

Sleeps 4 · 1 bedroom · 1 bathroom

Image of Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Sleeps 3 · 2 bedrooms · 1 bathroom

Image of Lake Ida Beach Resort

Lake Ida Beach Resort

Sleeps 4 · 1 bedroom

Image of Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sleeps 8 · 2 bedrooms · 1+ bathroom

Image of Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!

Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!

Sleeps 6 · 2 bedrooms · 2 bathrooms

Image of Charming Historic Cottage with Cozy Porch and Garden Retreat

Premier Host

Charming Historic Cottage with Cozy Porch and Garden Retreat

Sleeps 4 · 2 bedrooms · 1 bathroom

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