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Historic Downtown Bungalow w/piano

NO PET OR CLEANING FEES. The Daugherty House, a refurbished, downtown Lakeland, 1918 historic, 3 bed, 2 bath bungalow, between Lake Mirror and Lake Morton, features a 1907 upright piano, beautiful bedrooms with new mattresses and box springs, a spacious rocking chair front porch, cozy Florida room with a fold out couch, a gas fireplace, and memorabilia from Lakeland's history. The home's filled with antiques and modern conveniences, and the kitchen has all your cooking needs. CLICK SHOW MORE.

Magical Pool Villa-close to Disney Game/movie Room

The magic starts the moment you walk through the door—and the memories will last a lifetime! ✨ Our themed vacation home features Mickey Mouse, Toy Story, Frozen, Star Wars and Minion rooms with motion-activated songs, UV artwork, and LED lighting. Enjoy a private pool with color-changing lights, BBQ area, sun loungers, and a fun-filled game room with air hockey and arcade games. Designed to delight kids and adults alike with immersive sights, sounds, and magical details throughout the home!

Matty’s Citrus Connection

You are going to love this Citrus themed hideaway with its Old Florida feel that takes you back to simpler times. Rest and relax in this backyard paradise while enjoying all that Lakeland has to offer. Whether you choose a relaxing day enjoying the many local activities , take a day trip to a beautiful Florida-beach , or decide to visit one of Florida’s theme parks , this is the place to stay . We are centrally located and have quick access to Polk Pkwy , so your adventures are unlimited .

Extra large home! Bring Your Boat & all the Toys!

Bring your boat, skis, fishin’ pole, or any other water toys! We supply ping pong, corn hole, bicycles and other toys! Directly across from Lake Howard boat ramp and 10 minutes from LegoLand! Enjoy this spacious, well-equipped 2300 sf home that has everything you need to enjoy your stay in Winter Haven, aka Chain of Lakes City, a quaint downtown with free parking-- and just a skip away from Disney and Universal. This getaway is an above-average accommodation both in style and comfort!

Cozy Castle

Step back 100 years in this beautifully restored Spanish Gothic home in the heart of Winter Haven. Featuring rich architectural details, elegant furnishings, and modern comforts, this unique retreat offers a memorable stay. Centrally located near Polk County attractions including LEGOLAND, Bok Tower Gardens, Lake Myrtle Sports Complex, Florida Southern College, Winter Haven Airport, and the Chain-of-Lakes. Perfect for families, couples, or extended stays seeking charm and convenience.

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!

4/2 House near Legoland w Optional 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.

Family Home, Legoland, Group-Friendly, 8 Beds

Nestled near Lake Howard in Winter Haven, Chain of Lakes Villa is an elegant 4BR, 2BA retreat designed for families, couples, and groups. Enjoy a fenced backyard with lush landscaping, dedicated workspace, and a fully equipped kitchen with a Keurig. Family-friendly amenities include a crib, high chair, and toys. Guest Favorite: “The home is beautiful and spacious, only wish we would have stayed longer!” Smart lock self check-in; exterior cameras for your security.

KokomoVilla: 4BR Southern Dunes Pool Home

Southern Dunes vacation rental in Haines City, Florida, KokomoVilla is a spacious 4-bedroom, 3-bath pool home overlooking Southern Dunes Golf & Country Club. This family-friendly vacation rental sleeps up to 10 guests and features a private screened pool, golf course views, and a prime location between Disney and Legoland. Ideal for golf trips, family vacations, and extended Central Florida stays, KokomoVilla offers comfort, convenience, and resort-style relaxation.

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

Beautiful Lake House Boating Fishing near Legoland

Welcome to The Executive Lake House 15 minutes from Lego Land in beautiful Winterhaven, Florida. The brand new rental home sits on a lake and offers a dock, with boats, fishing gear and beautiful views of the lake. The home offers 2 bedrooms and a kids loft. A full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is on the property in backyard and is shared with other guests who may be staying here.

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 11 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.