Holiday rentals in Winter Haven

Winter Oasis

Escape to Winter Oasis, a serene retreat between Tampa and Orlando. Nestled in Winter Haven, our cozy guesthouse offers a haven for travelers seeking tranquility near major attractions. Whether you're exploring Disney's magic, enjoying Universal Studios' thrills, or simply unwinding in central Florida's beauty, our guesthouse is your perfect base. Relax in the comfortable outdoor area, cook in the fully equipped kitchen, or enjoy drinks on the private patio. Book your stay at Winter Oasis today!

Cozy Family Home Near Legoland

Relax with the fam after a fun day at LEGOLAND (just 4 miles away!) or Disney World (36 miles) in our cozy home complete with a well-stocked kitchen, fully-fenced backyard, and comfortable beds. We are proudly pet friendly! Spend a day on the famous Chain of Lakes (24 canal-connected lakes), catch a free ski show on Lake Silver, wander downtown to shop, or toast a pint at Union Taproom. Winter Haven is centrally located between Tampa and Orlando with plenty of fun nearby for the whole family.

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)

Kid-friendly Home w/ Pool & BBQ

Enjoy a delightful stay in our Renovated 3BD house for your Winter Haven trip. The unit is equipped with dryer, washer, Wi-Fi, fully equipped kitchen, baby proofed, and BBQ to make your stay comfortable. Enjoy the private pool, free parking, and large patio. Our house is 20 mins away from LEGOLAND and 50 mins away from Disney Parks and attractions. Discover Winter Haven’s chain of lakes with all the water sports and its surroundings in the best way. We look forward to hosting you!

Lakefront Home on the Winter Haven Chain O’Lakes!

Completely renovated 2 Bedroom, 1.5 bath home location on beautiful Lake Roy on the Winter Haven Chain O’Lakes. This is a mother-in-law suite that is connected to the main home. One bedroom on the lower level with a queen bed. Second story with king bed and twin bed. Full bath located upstairs). Comfortably sleeps 5. Dog welcome with prior approval and pet fee. Boat parking at dock. Boat rental available at Central Florida Water Sports. Private entry with keyless touchpad.

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!

Adorable 1 bedroom Guesthouse near Lego Land

This is a beautiful and private place offers a queen size bed, newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! We are located less than 8.6 miles from Legoland & under 6.2 miles from the Lake Myrtle Sports complex. Winter Haven is halfway between Orlando and Tampa. Around 29 miles to Disney World, Universal and Sea World. Around 38 miles to Bush Gardens, Dali museum, Aquarium and much more!

Private Poolside Villa

Lovely, private, poolside villa. The apartment is inside a completely enclosed, block walled pool deck. It provides privacy & your own personal oasis! Due to the proximity to the pool, my place is best suited for adults. I will only host young ones 13 & older that are proficient swimmers. The apartment is behind my personal home with no connecting doors. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

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.

Cute & Cozy in Winter Haven, Florida

The guesthouse Cute & Cozy is private yet adjacent to the main house (owner lives) and has its own entrance. Located in central Florida, between Orlando and Tampa; 3 miles from Legoland, 5-10 minute walk from shopping and restaurants on Cypress Gardens Blvd. The Cute & Cozy is also in a great location from Florida's amazing beaches, just under 2 hours east or west. Maybe an hour drive to Disney, SeaWorld and Universal (depends traffic)

Million-Dollar Sunsets Included

The best part of this cottage is the lakeside setting on Lake Howard, where evenings end with truly unforgettable sunsets. The space is fully furnished, quiet, and intentionally designed with soft pink, feminine details that feel cozy, calming, and welcoming. Guests love the walkable downtown location, the peaceful atmosphere despite being close to everything, and the convenience of being less than a mile from Winter Haven Hospital.

2 Bedroom Apartment near Legoland and Disney

This Private Studio features 2 bedrooms, kitchenette with dining area, private bath, walk-in closet, own entrance and from the Main Studio bedroom a large Balcony with Spectacular lake views. The Kitchenette with dining table and the bathroom is located in between of the 2 Bedrooms. The second Bedroom is only 10'x10' with a Queen bed and Wardrobe. Early Check in or late check outs are not available