Vacation rentals in Winter Haven

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)

Newly remodeled House 3BR/2BA

Centrally located in Winter Haven, FL and within minutes to Legoland. Only a 45-60 minute drive to local theme parks Disney and Busch Gardens. West/East Coast Florida Beaches are only a 90 minute drive. This newly remodeled 3/2 is a very spacious and accommodating home to any family wanting to get away on a peaceful vacation or weekend retreat. Quiet neighborhood with no HOA and within walking distance to several downtown restaurants, grocery stores, and shopping establishments.

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.

Fantastic Water Front Home on the Chain of Lakes

We are sharing our dream home with you! This home offers one of the best open layouts in Winter Haven. Great open kitchen with granite counter tops, stainless steel appliances, and numerous appliances. The large TV room features a Samsung smart 65" TV that connects to the Lanai/Pool area. A must see to believe! Numerous pictures provided to allow your mind to wonder. My interaction with you will be based on you. We have keypad entry for your convenience. I am here for you though!

Tiny Lego Home

Tiny Lego home just 12 minutes from Legoland/Peppa pig. Everything to keep the kids entertained. Massive playground and dining/ grilling area, Large outdoor Lego building area, Indoors every thing Lego. Wall legos, table legos and more. If you like Legos this is the place to stay. The kids will be in Lego heaven! Recently added swimming pool with deck and soccer field in playground area. The outdoor playground park is a shared space for any guests who may be staying at complex.

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!

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.

Cozy 2-bedroom guesthouse on the lake

Enjoy a relaxing getaway on the beautiful Lake Ariana. Two bedrooms with queen beds comfortably accommodating four adults. Fully equipped kitchen and full bathroom with tub. Laundry room with washer and dryer. Private parking with plenty of room for boat or jet skis. Private entry with hosts on premises. Camera at exterior door for security. The guesthouse is behind the main home. There is not a view of the lake from inside the guesthouse.

3 - Lake Life House 1 bed/1bath - Unit 15

Whether you’re planning to try your hand at fishing in the region’s world-famous Chain of Lakes or scheming up a surprise family retreat to Legoland with the kiddos, this Winter Haven home is ideally located for your getaway! With 1 bedroom, 1 bathroom and access to a boat ramp on a private canal to Lake Eloise. This vacation rental makes it easy to experience the Florida lake life.

7 mins to Legoland /Pool Access/Elevator

Come relax with your family in this peaceful 2BR/2.5BA home, just 7 minutes from LEGOLAND®. Sleeps up to 7 guests, with pool access, board games, and arcade fun for all ages! Wheelchair accessible with elevator between floors. No parties, no smoking. Primary guest must be 25+ and present during stay; ID may be required.