Family-friendly holiday rentals in Winter Haven

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Just 6 miles to Legoland! This stylish home is perfect for vacation. 2 ensuite bedrooms, 2 additional rooms and 2 additional semi private sleeping areas there is room for everyone. Every space is newly furnished with stylish pieces and comfortable beds. The pool area is fully screened so you can enjoy the Florida weather without the bugs. The open concept space is perfect for large groups and families and the kitchen is ready for you to make a meal. A laundry room houses a washer and dryer.

Legoland Getaway 7 mins • Sleeps 7 • Elevator

Come relax with your whole family in this peaceful home! Our 2 bedroom 2.5 bathroom home is very spacious and can accommodate up to 7 people. Enjoy your day only 7 minutes to LEGOLAND. You will have pool access as well as access to many board games and arcade games within the home. Fun for the whole family! Our home is wheelchair accessible with an elevator that goes between floors so your family can accommodate well if needed! We do not allow parties. The home is strictly no-smoking.

Tiny Lego Home

Tiny Lego home just 12 minutes from Legoland/Peppa pig. Everything to keep the kids entertained. Massive playground and dining/ grilling area, Large outdoor Lego building area, Indoors every thing Lego. Wall legos, table legos and more. If you like Legos this is the place to stay. The kids will be in Lego heaven! Recently added swimming pool with deck and soccer field in playground area. The outdoor playground park is a shared space for any guests who may be staying at complex.

Roe Family Lake House (Lake Mcleod)

We can't wait for you to enjoy our fully renovated, family friendly lake house. It's a happy home that provides a wonderful backdrop to any vacation. Centrally located to many Florida destinations- Legoland is only 7 miles away, Disney World is 35 miles away, and you are less than 50 miles from Tampa. The house is located on over an acre of lakefront property. The lake has a public boat launch if your family enjoys water sports or fishing or use the kayaks we provide on site!

The Russell Lake House

This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Ample off street parking, quiet neighborhood with a private entrance for guests. **** we are in the process of rebuilding the dock so it will be unavailable until further notice ****

Luxury Cottage Near Legoland & Chain of Lakes

The Old Florida Cottage, in the quaint community of Lake Hamilton, just 5-miles from Legoland, less than an hour from Disney, and minutes away from the only public boat access to Lake Hamilton, is your perfect getaway! Enjoy a fully-equipped kitchen, a luxurious suite and modern bathroom, surrounded by Old Florida decor. We look forward to welcoming you to the cottage, with its own entrance and dedicated parking, located on a quiet street. Your home away from home!

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 9 year old Grandson Dalton. It’s a great spot to relax by the in ground pool and fenced in back yard. Enjoy the outside with your family and cookout. We want you to love The Dalt as much as we do. Located in Winter Haven and Central FL area easy to enjoy the local lakes. Also not too far from other central Fl attractions and beaches from East or West coast.

Brutus Way Cottage, a cosy hide away

Enjoy a quick get away at Brutus Way Cottage. It is located to the rear of Lili Haven Bed N Breakfast. On your picturesque drive around Lake Howard, with its walking trail, you will take a right onto a quaint curvy lane known as S. Lake Cannon Drive NW . Be my guest at the cottage surrounded by flowers ; the cottage is nestled in the trees to the back past the Iron gates. Use of the Laundry room available upon request.

3 - Lake Life House 1 bed/1bath - Unit 15

Whether you’re planning to try your hand at fishing in the region’s world-famous Chain of Lakes or scheming up a surprise family retreat to Legoland with the kiddos, this Winter Haven home is ideally located for your getaway! With 1 bedroom, 1 bathroom and access to a boat ramp on a private canal to Lake Eloise. This vacation rental makes it easy to experience the Florida lake life.