
Family-friendly holiday rentals in Cypress Gardens
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Cypress Gardens
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

3/2 Great Family Home Near Legoland
Enjoy easy access to Legoland (4 mi) & charming Downtown (1 mi) from this centrally-located home. Designed to make you feel right at home during your family getaway, the whole home is private to you. We are pet friendly! Featuring a kitchen ready to make a home meal, a fully fenced private back yard, keyless entry, & free, ample parking for multiple cars and a trailer. Street parking is also allowed. Locally owned & operated. We are excited to share our city and provide exceptional service

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)

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.

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.

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.

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.

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.

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.

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.
Popular amenities for Cypress Gardens family-friendly rentals
Family-friendly home rentals with a hot tub

4mi to Disney | Games | Private Pool

Charming Tiny House on 5 acres with POOL/ HOT TUB

Magical Disney House-Pool & Hot Tub,Free Waterpark

Themed Disney Villa | Pool | Arcade | Resort ºoº

Mickey Fantasia Family Friendly w/accessibility

Fantastic Water Front Home on the Chain of Lakes

There is no other place you want to be than here.

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5
Family- and pet-friendly home rentals

Classic Cottage in country setting

Million-Dollar Sunsets Included

The Paradise Hide Away

three bedroom family house, near legoland

3.5 Acre Modern Country Farmhouse |23 mi to Disney

2 King Beds + Fireplace + Fenced Yard Retreat

Bamboo Bus -Sauna/ Pool/Fire pit/Grill

Amazing Villa near DisneyWorld FREE heated-pool
Family-friendly home rentals with a pool

Legoland Pool House with Suite 4br/2bth

Luxury by Legoland 106

Waterfront Heated Pool Putting Green Dock Legoland

Florida Dream Vacation House

Stylish Lakehome w.HUGE Pool/Arcade/Theater

Lakefront home w/heated pool minutes from Legoland

Escape Comfort Property

Magical Family Fun House Near Disney Luxury Villa
When is the best time to visit Cypress Gardens?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $219 AUD | $229 AUD | $234 AUD | $218 AUD | $206 AUD | $210 AUD | $207 AUD | $206 AUD | $199 AUD | $213 AUD | $213 AUD | $219 AUD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about holiday rentals that are family-friendly in Cypress Gardens

Total holiday rentals
Explore 70 holiday rentals in Cypress Gardens

Nightly prices starting at
Cypress Gardens holiday rentals start at $132 AUD per night before taxes and fees

Verified guest reviews
Over 4,310 verified reviews to help you choose

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Cypress Gardens holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Cypress Gardens rentals

4.9 Average rating
Cypress Gardens stays are highly rated by guests—averaging 4.9 out of 5!
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- Family-friendly rentals United States
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Magic Kingdom Park
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Busch Gardens Tampa Bay
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Amalie Arena
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!




