Holiday rentals in Lake Hamilton

Adult-Only Getaway w/ Mermaid Pool | 18+, Private

🔒⛓️🗝️ Adults only. Ready to turn your vacation into an experience? Explore your fantasies at our romantic getaway, featuring four themed bedroom options* designed to inspire you. Bring your fave toys, experiment with our spicy 🌶️ amenities, or peruse our shop to bring home a little extra to keep the fire going after you leave. You will love our mermaid pool 🧜🏿‍♀️, jetted spa, & stone meditation deck while you soak up the sun or stargaze. 🌟 Your next adventure awaits. (*1 per 2 guests)

New Modern Guest House! Great location. Smoke-Free

New, modern, well located Guest House, with private entrance for your complete privacy; we are 3 minutes away from Port 27, 10 min away from Legoland, 40 min out from the major Parks and one hour from Bush Garden Tampa. One bedroom, one bathroom, living room with kitchenette (No Stove), Hotel Style Suite. Up to 4 guest, room with a queen bed and a sofa bed in the living area. Wi-fi included. Parking for one car. Is a quiet and comfy guest house separated by a door from the rest of the house

Legoland or Work Retreat w/ Games & Massage Chair

Enjoy the perfect blend of relaxation and entertainment in this completely renovated home. Whether unwinding in the leather reclining sofas, enjoying the massage chair, sipping coffee on the enclosed deck, or gathering around the outdoor bonfire, this home offers a cozy escape for families and friends. We have a beautiful kitchen with drip and Kurig coffee provided. A Webber grill + wood pizza over! We have a large game barn with retro video games, putt putt, basketball, darts, and foosball.

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!

Breathtaking Home

New two story home with private pool, patio, barbecue area & game room. Surrounded by parks, gardens, tranquil lakes & walkways with breathtaking views. Resort amenities located right across the street with an amazing clubhouse (private owned), Bar & Grill restaurant, water park, arcade and gym (extra fee), soccer & football field, & event center for parties & weddings. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

Legoland Lakehouse Canoe & Kayak Retreat

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.

Charming Lakeside Cottage

Escape to our cozy lakeside cottage, featuring a dock that’s perfect for watching sunrises, fishing, and launching your kayak. The property is on Lake Howard, which is part of the Winter Haven Chain of Lakes. Inside, you’ll find a fully equipped kitchen and comfortable living space for unwinding. Located just a short drive from the excitement of Legoland and Disney World, you can easily explore the area’s attractions while having a peaceful haven to return to.

Lake View, Game Room, 10 min Legoland

Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor games designed w/ family fun in mind! Only 3 min to charming downtown Winter Haven shopping & restaurants, 10 min to Legoland, 30 min to historic downtown Lakeland, & conveniently located between Tampa & Orlando (45 min to Disney & just 60 min to Tampa). We can't wait for you to enjoy the beautiful lakes of Winter Haven at The Elby!

Cozy 2-bedroom guesthouse on the lake

Enjoy a relaxing getaway on the beautiful Lake Ariana. Two bedrooms with queen beds comfortably accommodating four adults. Fully equipped kitchen and full bathroom with tub. Laundry room with washer and dryer. Private parking with plenty of room for boat or jet skis. Private entry with hosts on premises. Camera at exterior door for security. The guesthouse is behind the main home. There is not a view of the lake from inside the guesthouse.

Lake Home | Heated Pool, Dock, Kayaks & EV Charger

Come to Lake Hamilton’s luxurious lake house and let the sunsets take your breath away as you relax and enjoy making memories at our gorgeous Mediterranean home! No detail has been missed with gorgeous travertine tile and crown moulding throughout the home. The kitchen is full of natural light with three skylights that stream in the Florida sunshine! There is a fabulous patio door that opens wall to wall to bring the outside in!

Renovated Lakefront Luxury retreat by Legoland

Wake up to stunning lake views in this beautifully renovated 3BR/2BA home. Enjoy an open-concept layout, chef’s kitchen, cozy fireplace, and a covered deck overlooking the water. Fish, kayak, or unwind under the stars on your private lakefront lot. Close to Disney, Busch Gardens, Legoland, and the new Port 27 waterfront entertainment area—this peaceful retreat blends modern luxury with Florida serenity.

Quiet Condo Getaway in Grenelefe

Relaxation at its finest in this serene 1BR, 1BA condo —perfect for couples, friends, or small families. Nestled within the trees and quiet community of Grenelefe, yet just minutes from shops, dining, and local attractions. Enjoy a cozy living space, full kitchen, and all the essentials for a comfortable stay. Ideal for a restful getaway with easy access to everything you need.