Vacation rentals in Lake Bess

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)

Luxury by Legoland 104

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

Nice little get•a•way

Relax with your family at this peaceful home *** Master bedroom not included ***. Take the kids to Legoland, which is only 5 minutes away, then stop off at one of our many restaurants to get something to eat. If not, stop at the supermarket and grab something to cook is this spacious kitchen. Want something even more quite, drive down to Bok Tower Gardens and enjoy music or yoga, but don't forget the flowers and food. After a long day, relax on the sofa with your favorite drink and a movie.

*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.

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!

4/2 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.

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!

Legoland Splash Escape (pool and hotub)

Relax in the heated pool and hot tub after enjoying theme parks such as Busch Gardens, Disney world, and Universal Studios! LegoLand is 1 mile away! Lego bedroom for kids. Centrally Located in the middle of Florida allows beach trips to both east & west coast. Air-conditioned garage has been turned into a game room with pool table, air hockey and a Miss Pac-man arcade game!

Family Winter Haven Retreat w/ Pool & Game Room

Relax in style at this spacious 3BR Winter Haven home with a private heated pool, game room, and space for up to 10 guests. Just minutes from LEGOLAND, lakes, and local dining, this single-level retreat offers two king bedrooms, a bunk room, and a bonus lounge with a queen sleeper. Enjoy a fully stocked kitchen, Keurig coffee, BBQ grill, and ping pong or pool table fun!

The Haven House

Escape to the heart of Central Florida! Our stylish home is just minutes from Legoland Florida Resort, 42 miles from Walt Disney World, and about an hour from Universal Orlando Resort, SeaWorld, and Busch Gardens. Explore Winter Haven’s beautiful Chain of Lakes, then relax and unwind in a home designed for comfort. We can’t wait to host you!

Stunning Luxury House on the Chain of Lakes

Bring the whole family to this spacious lakefront home with lots of room for fun! We are an established short-term rental property with 5-star reviews but newer to the Airbnb platform. If you are interested in a beautiful property on Winter Haven's famous chain of lakes with plenty of room for family and friends, this house is for you!