Vacation rentals in Cypress Gardens

Guest suite in Winter Haven

4.89 out of 5 average rating, 193 reviews

2 Bedroom Winter Haven Guest Suite

Private lock-off unit. Only shared between your party. Attached to main home , no shared spaces inside. 1st bedroom -Queen bed and sitting area bathroom attached. 2nd bedroom- two twin sized beds Kitchen and living room included and not shared outside of your party. 3 minutes from Winter Haven hospital. Self check in and out. 20 minutes from Legoland. 45 minutes from Disney and Universal This is an older florida neighborhood with a diverse and working class vibe. Located on Lake Maude

Apartment in Winter Haven

4.99 out of 5 average rating, 148 reviews

Florida Penthouse in luxurious mansion!

Stay in your own themed Florida apartment . Tropical, palm trees, beaches ,marine life, flamingos throughout this stunning apartment in a multimillion dollar home. After parking on gated driveway walk up to your own private entrance way to paradise. Keyless entrance. One flight up and your viewing gorgeous lake views second to none. Executive kitchen with everything you need to cook a 5 course meal. Outdoor balcony that will leave you amazed. Opulence, security, with Florida Style awaits you!

4.95 out of 5 average rating, 126 reviews

Legoland Getaway 7 mins • Sleeps 7 • Elevator

Come relax with your whole family in this peaceful home! Our 2 bedroom 2.5 bathroom home is very spacious and can accommodate up to 7 people. Enjoy your day only 7 minutes to LEGOLAND. You will have pool access as well as access to many board games and arcade games within the home. Fun for the whole family! Our home is wheelchair accessible with an elevator that goes between floors so your family can accommodate well if needed! We do not allow parties. The home is strictly no-smoking.

Superhost

4.78 out of 5 average rating, 316 reviews

Florida Oasis w/ Pool near LEGOLAND

We have added a modern twist to the design of this 1950's home with all the modern appliances and finishes. This home is nestled in-between 2 lakes among the Winter Haven Chain of Lakes! The backyard is a Florida Oasis of a great pool and pool deck with plenty of fun available with games for you and the kids, or just enjoy laying peacefully in the sun! 2.5 mile drive from Legoland 3.5 mile drive from Downtown Winter Haven with great restaurants and small town unique shops.

Guesthouse in Lake Hamilton

4.87 out of 5 average rating, 255 reviews

Luxury Cottage Near Legoland & Chain of Lakes

The Old Florida Cottage, in the quaint community of Lake Hamilton, just 5-miles from Legoland, less than an hour from Disney, and minutes away from the only public boat access to Lake Hamilton, is your perfect getaway! Enjoy a fully-equipped kitchen, a luxurious suite and modern bathroom, surrounded by Old Florida decor. We look forward to welcoming you to the cottage, with its own entrance and dedicated parking, located on a quiet street. Your home away from home!

4.92 out of 5 average rating, 177 reviews

Hidden Haven Lakehouse Pool by Legoland

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.

4.75 out of 5 average rating, 24 reviews

Cozy House In Winter Haven

Welcome to our charming Airbnb located in the heart of Winter Haven, FL! This cozy home offers a peaceful retreat with a fully equipped kitchen, comfortable living space, and a private backyard. Perfectly located, it's just minutes away from LEGOLAND Florida and other local attractions. Whether you're here to explore or relax, our inviting space provides a convenient and comfortable home base. Book your stay and experience the best of Winter Haven!

4.98 out of 5 average rating, 100 reviews

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!

5 out of 5 average rating, 58 reviews

Lake*Walk2LEGOLAND*Pool*Putting Green*Dock*Sunsets

"Most beautiful home we’ve ever stayed at. Thank you for your sweet hospitality!" - Jessica "House felt like a spa!" - Kandy Sunset Haven is a luxurious contemporary lake house on beautiful Lake Summit in Winter Haven Florida. From the moment you enter, you are greeted with a view of the lake beyond the pool deck, where many beautiful sunsets can be seen almost nightly. This wonderful home boast an array of amenities for an extraordinary stay.

4.97 out of 5 average rating, 111 reviews

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 9 year old Grandson Dalton. It’s a great spot to relax by the in ground pool and fenced in back yard. Enjoy the outside with your family and cookout. We want you to love The Dalt as much as we do. Located in Winter Haven and Central FL area easy to enjoy the local lakes. Also not too far from other central Fl attractions and beaches from East or West coast.