Holiday houses in Lake Ashton

The Modern Retreat by Legoland

Welcome to your perfect family getaway—just 7 minutes from LEGOLAND Florida! This spacious 4-bedroom, 2.5-bath home features 7 comfy beds and plenty of space to relax. Thoughtfully designed for families, it includes toddler essentials, a crib, and even a double stroller—all to make traveling with little ones easier. Clean, stylish, and fully equipped, our home is your worry-free base for a fun and memorable stay. We can’t wait to host your family and help you create lasting memories together!

Lakefront Master Suite with Private Entrance

This peaceful master suite with deck overlooks Little Blue Lake and has relaxing outdoor spaces. The master bedroom has king-sized bed. The attached bathroom has a roomy shower with two shower heads and a soaking tub. The kitchenette area has a Keurig with coffee and tea. Also, a refrigerator/freezer, microwave, toaster oven, air-fryer, cups, dishes and utensils. 7 miles to Bok Tower Gardens. 5 miles to Webber and 3 miles to Warner. 6 miles to Lake Wales Skydiving and Paramotor training.

Luxury 3BR 2Bath•Pool• Game Room• Legoland 4 Min

4 min from Legoland! Enjoy this luxury 3BR/2BA family oasis with a private pool & child safety fence, grill area with outdoor dining, and a fully fenced yard. Game room with air hockey, toys & NEX Playground console. Master king suite with walk-in closet, 2 other queen size beds with pull out twin size trundles, TVs in every room, fireplace, and full kitchen with dining room. Central AC/Heat, washer & dryer, Lake Ned access, and stylish décor - perfect for family fun in the Florida sunshine!

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)

Spectacular Waterfront Home in Winter Haven

Enjoy a wonderful family get away at this premier waterfront home on the famous Chain of (19) Lakes! Separate yourself from the crowd at this beautiful Cypress Gardens home set on an acre with lush tropical foliage and surrounded by 3 sides of water. Featuring a chef's kitchen, 2 private docks, the "New Florida Pool," 2 hot tubs, fire pit and many more amenities. Enjoy relaxed luxury at its finest. We are just a few minutes to Legoland, restaurants and shopping, but miles from ordinary!

*This must be THE PLACE FL*

Your place away from home! Have fun with the whole family at this unique and stylish place. You'll have everything you need to relax and recharge. It is located less than 10 mins away from Legoland, restaurants and convenience stores. This house offer 3 BR and 2 full BA as well as a fully-equipped kitchen. All bedrooms include TV, dresser, closet and memory foam mattress. The Master bedroom has a queen bed, and the other two bedrooms have full size beds. There is wifi and parking available.

Linda Casita de Lake Wales

Cute older house with modern amenities. Located right downtown within a block from the playpark, Lake Wailes lake, walking path, and the historic downtown shopping area. All of the appliances in the home are brand new, as well as the washer and dryer. There is a large TV in the living room, as well as one in each bedroom - each with Roku and Netflix. Each bedroom also has a mini split A/C unit to sleep as cold, or hot, as you like. Parking is in the rear covered carport.

3/2 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.

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.

Relaxing Lakefront Escape • Pool + 150” Theater

Spacious Lake Mabel retreat with a private pool, massive 150-inch movie theater screen, and peaceful lake views with lake access nearby. Just 14 minutes from LEGOLAND, this 2,000 sq ft home is perfect for families or groups. Enjoy fishing, a fenced yard, strength training area, shared laundry room, open living spaces, and a fully stocked kitchen in a quiet lakeside setting. Perfect for relaxing pool days and unforgettable movie nights.

7 - Country Cottage 2bed/1bath - Unit 9

3- Smart TVs w/ YouTube TV + Free WiFi | Covered Front Porch | Living Room with Sofabed Very close to Legoland, Advent Field House and Conference Center, Restaurants, Grocery, and direct canal access to Lake Eloise Perfect for a small family vacation or a fisherman’s retreat, this cozy, well-decorated modular home is part of Cypress Inlet Vacation Homes and Marina located on the beautiful Winter Haven Chain of Lakes.