Kid-friendly holiday rentals in Cypress Gardens

4.95 out of 5 average rating, 101 reviews

3/2 House w Heated Pool 5mins to Legoland

Come enjoy our heated pool! Relax with the whole family at this peaceful home in Winter Haven 5mins to Legoland and the new Peppa Pig theme park, perfect for your next family vacation! Right across the street from lake Ned park with lake View from the front porch and office, bring your small water toys as there is a public boat ramp across the street. There are many restaurants as well as a Publix grocery store all within 2 miles from the home! Downtown winter haven is a short 10 minute commute.

4.96 out of 5 average rating, 117 reviews

Glass House• Family Escape Near Legoland!

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.

4.95 out of 5 average rating, 236 reviews

Apartment in Auburndale

Ariana Place - Tree House Like Lakefront Views

An Upstairs Sumptuous Tree house (like) Apt on Lake Ariana Waterfront. Upper Outside Deck with chairs & table. Quiet and tranquil with Hi-Speed Wifi for Business Travelers, Smart Antenna TV and Incredible Views for Romantic Get-Aways. Located near Disney, Legoland & Busch Gardens in Central Florida. Luxurious Bedding, Full Kitchen with Coffee & Wine Bar. One Complimentary Bottle of Cabernet per Stay. Sorry, No Pets. No Smoking inside Apt but allowed on property. Save 5% monthly

Tiny home in Winter Haven

4.92 out of 5 average rating, 113 reviews

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.

4.99 out of 5 average rating, 269 reviews

Cottage in Eagle Lake

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!

4.95 out of 5 average rating, 319 reviews

Spacious 3 Bed, 2 Bath Home Near Legoland

Enjoy family vacation in this fresh, clean 3-bedroom, 2-bathroom home. With keyless entry and a private fenced backyard, you'll have everything you need for a comfortable stay. 4 miles from Legoland 1 mile from downtown Locally owned & operated As residents of Winter Haven, we're passionate about sharing our community with you. We're always ready to assist you with any questions or requests during your stay. Book your stay today and discover the charm of Winter Haven!

4.96 out of 5 average rating, 979 reviews

Treehouse in St. Cloud

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Guesthouse in Lake Hamilton

4.89 out of 5 average rating, 245 reviews

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!

4.91 out of 5 average rating, 175 reviews

Hidden Haven Lakehouse Pool by Legoland

Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

5 out of 5 average rating, 52 reviews

Lake*Walk2LEGOLAND*Pool*Putting Green*Dock*Sunsets

"Most beautiful home we’ve ever stayed at. Thank you for your sweet hospitality!" - Jessica "House felt like a spa!" - Kandy Sunset Haven is a luxurious contemporary lake house on beautiful Lake Summit in Winter Haven Florida. From the moment you enter, you are greeted with a view of the lake beyond the pool deck, where many beautiful sunsets can be seen almost nightly. This wonderful home boast an array of amenities for an extraordinary stay.

4.97 out of 5 average rating, 108 reviews

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.