Vacation rentals in Lake Hamilton

Hidden Gem - Hot Tub/ Fire pit/Hammock/Grill Area

Hidden Gem is a peaceful and unique getaway perfect for up to 6 guests looking to relax with family and friends. Soak in the hot tub, fire up the grill, rest in the hammock, and gather around the fire pit under the stars. Located less than a mile from Lake Pierce, you can bring your boat or kayaks for a fun day on the water, with nearby lakes and state parks to explore. Just 20 mins to LEGOLAND and 50 mins to Disney, it's the perfect nature escape with easy access to Central Florida attractions.

Adult-Only Retreat w/ Pool & Spa | 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.

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.

Tranquil Golf Themed Getaway with Lake View!

This stylish 2-bedroom, 2-bathroom condo is a dream retreat for golf lovers. Thoughtfully decorated with a refined golf theme, it features elegant green accents, framed course prints, and subtle touches inspired by the fairway. The open living area flows to a private patio overlooking lush landscapes and lake view, perfect for relaxing after a round. Modern finishes, a fully equipped kitchen, and comfortable bedrooms make this the ideal blend of sport, style, and sophistication.

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.

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.

Lakefront Boho Cottage w/ Fire Pit | Still Waters

Welcome to Still Waters Retreat, a peaceful lakefront cottage just 10 minutes from Lake Myrtle Sports Complex and about 30–35 minutes from Disney (without traffic). Perfect for couples, families, and tournament stays, enjoy calming lake views, golden sunsets, cozy boho interiors, and s’mores by the firepit. Minutes from downtown Lakeland, dining, shopping, major highways, and easy day trips to Orlando or Tampa — serenity without sacrificing convenience.

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!

Cozy 3 bedrooms 2 bathrooms

Relax with the whole family at this peaceful and charming home in Winter Haven.This home is centrally located and is within walking distance to Lake Howard , downtown winter haven and plenty attractions We are located 10 minutes from Legoland, Peppa Pig Park, five minutes to Advent Health Fieldhouse, five minutes to Winterhaven Hospital, 45 minutes to Walt Disney World, SeaWorld and Busch Gardens.

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.