Family-friendly holiday rentals in Winter Haven

Near Disney/Kid-Friendly/Disney-Themed/Water Park

Your magical vacation starts here! Just 15 minutes from Disney World, this beautiful, family-friendly home offers luxury, themed rooms, and fun, perfect for creating unforgettable memories. The home is located in the ChampionsGate area. It has 3 bedrooms, 2.5 bathrooms, modern furniture, and super fast internet. You will have free access to the Enclaves at Festival amenities center which features a large beach-entry pool, kids water park, beach volleyball, mini-golf, restaurant, and gym.

Adorable Agave Suite w/ private pool and entrance

Relax & unwind in The Agave Suite, located in a peaceful lake town. This will be your “shome” away from home. Upon entry of the the property you will find a private entrance, covered parking, private screened in pool and mature trees. Your guesthouse comes equipped with 1 cozy queen size bed, pull-out sofa bed, walk-in shower, kitchenette, smart tv, wifi and more. Looking to explore? We are centrally located to your nearest parks & Florida attractions. Close to fishing docks & bike trails.

Simple Apartment in quiet suburb

This property is about 1 hour from Tampa & Orlando, away from traffic and noise. This 1 bedroom apartment offers a comfortable bed with simple amenities. We are not far from many attractions such as Disney, Universal Studios, LegoLand, Busch Gardens, Seaworld, and more. The property has its own private entrance to come and go as you wish. Pickelball are courts nearby as well as grocery stores, local coffee shops, and local restaurants - all within 5 min. driving distance of the property.

Studio apt in Historic area of Lakeland

This second story studio is on our homes property. It has a Queen bed, bathroom and kitchen. It is nestled in the historic area of Lakeland, one block in from The "Frank Lloyd Wright" designed Florida Southern college, tours are available! Our Cobblestone streets take you to our neighborhood restaurants, the art museum, library, Hollis garden, we are between two lakes-Hollingsworth it has a great walking/running path, and Lake Morton a bird paradise. All within walking distance.

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 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!

Adorable 1 bedroom Guesthouse near Lego Land

This is a beautiful and private place offers a queen size bed, newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! We are located less than 8.6 miles from Legoland & under 6.2 miles from the Lake Myrtle Sports complex. Winter Haven is halfway between Orlando and Tampa. Around 29 miles to Disney World, Universal and Sea World. Around 38 miles to Bush Gardens, Dali museum, Aquarium and much more!

Cute & Cozy in Winter Haven, Florida

The guesthouse Cute & Cozy is private yet adjacent to the main house (owner lives) and has its own entrance. Located in central Florida, between Orlando and Tampa; 3 miles from Legoland, 5-10 minute walk from shopping and restaurants on Cypress Gardens Blvd. The Cute & Cozy is also in a great location from Florida's amazing beaches, just under 2 hours east or west. Maybe an hour drive to Disney, SeaWorld and Universal (depends traffic)

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 10 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.

4 a Tiny House w/ Bunk Bed in Quiet Marina Unit 14

Our cozy tiny house is perfect for when less is more :-). An intimate space for a long reflective weekend or a more affordable option for a few days with the kids at nearby Legoland. Offering a queen-size Murphy bed and two additional single-size bunk beds, the Cypress Inlet Tiny House can comfortably accommodate up to four people. Equipped with a mini-fridge, a microwave, and a Keurig duo (drip & pod) coffee maker.