Holiday rentals in Cypress Gardens

The Paradise Hide Away

This is a beautiful and private place newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! Talk to me if you need different check in/out times? Dogs are allowed with permission. There is a $200 fully refundable pet security deposit to cover any damages that may occur since Airbnb doesn’t cover damages caused by pets plus a non refundable pet fee of $50 per pet for every 1-7 day period and must be paid before checking in !

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)

*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.

Simple Apartment in quiet suburb

This property is about 1 hour from Tampa & Orlando, away from traffic and noise. This 1 bedroom apartment offers a comfortable bed with simple amenities. We are not far from many attractions such as Disney, Universal Studios, LegoLand, Busch Gardens, Seaworld, and more. The property has its own private entrance to come and go as you wish. Pickelball are courts nearby as well as grocery stores, local coffee shops, and local restaurants - all within 5 min. driving distance of the property.

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. 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. (Additional guests must be pre-approved). Free boat parking and boat rental available. House is connected to the main home with a private keyless touchpad for contactless entry. Pet friendly with prior approval and pet deposit.

Ariana Place - Tree House Like Lakefront Views

An Upstairs Sumptuous Tree house (like) Apt on Lake Ariana Waterfront. Upper Outside Deck with chairs & table. Quiet and tranquil with Hi-Speed Wifi for Business Travelers, Smart Antenna TV and Incredible Views for Romantic Get-Aways. Located near Disney, Legoland & Busch Gardens in Central Florida. Luxurious Bedding, Full Kitchen with Coffee & Wine Bar. One Complimentary Bottle of Cabernet per Stay. Sorry, No Pets. No Smoking inside Apt but allowed on property. Save 5% monthly

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!

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.

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)

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 10 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.

4 a Tiny House w/ Bunk Bed in Quiet Marina Unit 14

Our cozy tiny house is perfect for when less is more :-). An intimate space for a long reflective weekend or a more affordable option for a few days with the kids at nearby Legoland. Offering a queen-size Murphy bed and two additional single-size bunk beds, the Cypress Inlet Tiny House can comfortably accommodate up to four people. Equipped with a mini-fridge, a microwave, and a Keurig duo (drip & pod) coffee maker.