Holiday rentals in Lake Bess

Luxury by Legoland 106

Experience comfort and convenience in this stylish 2-bedroom, 2-bathroom apartment, located less than one mile from the LEGOLAND entrance. Situated in a brand-new 2024 luxury complex, this ground-floor unit offers a seamless blend of relaxation & entertainment, perfect for families and theme park enthusiasts. Amenities & Features: • Resort-style heated pool • State-of-the-art fitness center • Fire pits, BBQ grills, and picnic spaces • LEGOLAND-themed kids’ bedroom for a fun, immersive stay

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!

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.

John Shirley’s Retreat

Welcome to John Shirley’s Retreat. We are pleased to provide you with a home where the entire family can enjoy. There is plenty of room for everyone. Spacious rooms to unwind or a spacious living room and den where you can enjoy each other’s company. You’re in the mood for some outdoor fun? We have large pool in our screened patio. You can also travel 2 miles down the road to visit Legoland and enjoy our local restaurants. This house is fully equipped and ideal for new memories to be made.

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.

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.

Lovely Home on Lilac Lane - Winter Haven

Your family will be close to everything when you stay at this centrally-located place. This house is located in a residential neighborhood and has amenities such as a community pool and neighborhood walking trail. This is house located: -4.7 miles away from Legoland -6 minutes away from multiple Shopping Plazas -20 miles from Lakeland Square Mall -50 miles from Busch Gardens -45 miles from Universal Studios & Volcano Bay -34 miles from Disney World

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.

Luxury Lake Ruby Lakehouse • Dock • Sleeps 8

Unwind with the whole family at this peaceful lakefront retreat on Lake Ruby. Enjoy sunrise views, a private dock, spacious living areas, and a fully stocked kitchen. Three comfortable bedrooms plus a pullout sofa make it perfect for families and groups. Relax, recharge, and create unforgettable memories in a quiet, beautiful setting.