Holiday rentals in Lake Hamilton

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

Relaxing Retreat |Games, Pizza Oven, 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.

Sunshine on the Lake | Boat Slip+Lakefront Fishing

Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

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)

Classic Cottage in country setting

Relax with the family in this peaceful setting. Short drive to the parks, shopping, restaurants. 10 minutes from Interstate 4. Walmart and Posner Park Shopping Center nearby. Patio area with fire pit and gas grill and lawn chairs. 2 car carport parking on premise. 2 bedroom w/HDTV's, 2 bath, fully furnished kitchen, dishwasher, breakfast nook, dining room, living room w/HDTV. Washer/dryer. Fully fenced 3/4 acre yard with plenty of room for kids to play. Self check in with keypad.

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 Home w/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.

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.

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.