Vacation rentals in Lake Ashton

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)

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

** New Construction ** Breathtaking view of lake, private dock (2 kayaks for guests included), beach/swim area, outdoor shower, large private balcony w/gas grill and gorgeous sunsets! 2 Bedrooms each w/walk in closet, two full baths, full kitchen w/all amenities. All new furnishings, (3) 4K Smart TV's, FAST free wifi. Gorgeous location, quiet street, private free parking, 2 private entrances. Villa is detached from main house. Near Disney, LegoLand, Bok Tower. WEEKLY & MONTLY DISCOUNTS

La Casita Redonda (The little round house)

Enjoy a memorable visit when you stay in this unique and historical place in Lake Wales, FL. Constructed in 1936 this home is nestled within a quiet and friendly neighborhood just minutes from the downtown area and just a short walk to Lake Wailes itself. Although the current owner updated the home with practical renovations, the peculiar house still has the character and features from the time it was built, features that once granted it a place among the pages of Ripley’s Believe it or Not.

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.

Bamboo Bus -Sauna/Pool/Fire pit/Grill

Bamboo Bus is a unique, romantic and tranquil spa like getaway, perfect for relaxing with your significant other, family or friends. Enjoy the pool, unwind in the barrel sauna, grill your favorite meals and gather around the fire pit for s’mores under the stars. Located less than a mile from Lake Pierce, bring your kayaks and explore nearby lakes and state parks. Just 20 mins to LEGOLAND and 50 mins to Disney, it’s the perfect peaceful escape with easy access to Central Florida attractions.

*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.

Private lake front retreat!

Relax with the whole family at our Winter Haven residence located on Lake Mirror! Enjoy your lake days boating, fishing, kayaking or relaxing. Our outdoor space includes a private dock, 22x22 paved covered patio, 14x8 heated swim spa, outdoor dining space, outdoor TV's for entertainment, paddle boards, and kayak's. In the kitchen, we have a full coffee bar, juicer, brand new appliances and more! This stunning newly renovated 3-bedroom, 2- bathroom vacation home is a water-skiers paradise!

Lakefront Heated Pool, Spa & Dock | Near Legoland

Relax at this lakefront getaway with a heated saltwater pool, hot tub, and private dock—perfect for families or small groups near LEGOLAND Florida and just minutes from downtown Winter Haven. Sunset Haven sits on Lake Howard with water views throughout and bright, open living spaces designed for gathering. Two private suites with attached baths add comfort for couples or extended families. Designed for 8 guests—ideal for relaxed lake days, slow mornings, and sunset evenings by the water.

Waterfront*Pool*Putting Green*Dock*Legoland*8 Beds

Sunset Haven is a luxurious, contemporary 3,581-square-foot lakefront home set on nearly one acre along the shores of beautiful Lake Summit, part of Winter Haven’s famous Chain of Lakes. From the moment you step inside, your eye is drawn through the home to sweeping lake views beyond the pool deck, where breathtaking sunsets can be enjoyed almost every evening. Thoughtfully designed, this exceptional residence offers an impressive array of amenities for a truly unforgettable stay.

Roe Family Lake House (Lake Mcleod)

We can't wait for you to enjoy our fully renovated, family friendly lake house. It's a happy home that provides a wonderful backdrop to any vacation. Centrally located to many Florida destinations- Legoland is only 7 miles away, Disney World is 35 miles away, and you are less than 50 miles from Tampa. The house is located on over an acre of lakefront property. The lake has a public boat launch if your family enjoys water sports or fishing or use the kayaks we provide on site!

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.

2 - Ships Ahoy Bungalow 2 bed/2 bath - Unit 17

Florida’s lakes and biggest attractions are calling you and your family to stay at this vacation rental in Winter Haven! From Legoland and Disney World to the famous Chain of Lakes and golf courses galore, this charming home in Cypress Inlet is minutes from it all. Take your boat out on Lake Eloise, through a private canal right outside the home, or take the kiddos to SeaWorld, a short drive away, before returning to this 2-bedroom 2-bath home.