
House vacation rentals in Cypress Gardens
Find and book unique houses on Airbnb
Quick stats about house rentals in Cypress Gardens

Total vacation rentals
Explore 60 vacation rentals in Cypress Gardens

Nightly prices starting at
Cypress Gardens vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

Verified guest reviews
Over 4,150 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Cypress Gardens vacation 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!
Top-rated house rentals in Cypress Gardens
Guests agree: these houses are highly rated for location, cleanliness, and more.

Sunshine on the Lake | Boat Slip+Lakefront Fishing
Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

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)

Spectacular Waterfront Home in Winter Haven
Enjoy a wonderful family get away at this premier waterfront home on the famous Chain of (19) Lakes! Separate yourself from the crowd at this beautiful Cypress Gardens home set on an acre with lush tropical foliage and surrounded by 3 sides of water. Featuring a chef's kitchen, 2 private docks, the "New Florida Pool," 2 hot tubs, fire pit and many more amenities. Enjoy relaxed luxury at its finest. We are just a few minutes to Legoland, restaurants and shopping, but miles from ordinary!

Extra large home! Bring Your Boat & all the Toys!
Bring your boat, skis, fishin’ pole, or any other water toys! We supply ping pong, corn hole, bicycles and other toys! Directly across from Lake Howard boat ramp and 10 minutes from LegoLand! Enjoy this spacious, well-equipped 2300 sf home that has everything you need to enjoy your stay in Winter Haven, aka Chain of Lakes City, a quaint downtown with free parking-- and just a skip away from Disney and Universal. This getaway is an above-average accommodation both in style and comfort!

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!

Beautiful Lake House Boating Fishing near Legoland
Welcome to The Executive Lake House ten minutes from Lego Land in beautiful Winterhaven, Florida. The brand new rental home sits on a lake and offers a dock, with boats, fishing gear and beautiful views of the lake. The home offers one bedroom a full kitchen and laundry and one full bathroom The backyard has a playground and pool area that is ( not) included at this price point. If wanting an additional charge of 20 dollars per night Will be charged. Let me know at booking.

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.

Spacious 3 Bed, 2 Bath Home Near Legoland
Enjoy family vacation in this fresh, clean 3-bedroom, 2-bathroom home. With keyless entry and a private fenced backyard, you'll have everything you need for a comfortable stay. 4 miles from Legoland 1 mile from downtown Locally owned & operated As residents of Winter Haven, we're passionate about sharing our community with you. We're always ready to assist you with any questions or requests during your stay. Book your stay today and discover the charm of Winter Haven!

3/2 House near Legoland w Optional Heated Pool
Relax with the whole family at this peaceful home in Winter Haven 5mins to Legoland and the new Peppa Pig theme park, perfect for your next family vacation! Right across the street from lake Ned park with lake View from the front porch and office, bring your small water toys as there is a public boat ramp across the street. There are many restaurants as well as a Publix grocery store all within 2 miles from the home! Downtown winter haven is a short 10 minute commute.
Popular amenities for Cypress Gardens house rentals
House rentals with a pool

Lake Whistler Beach House with lakefront pool

Villa Resort Club

Waterfront Heated Pool Putting Green Dock Legoland

Relaxing Lakefront Escape • Pool + 150” Theater

Cozy Lakefront Home w/ Pool -7 mins from Legoland

Breathtaking Home

Stylish Lakehome w.HUGE Pool/Arcade/Theater

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

Million-Dollar Sunsets Included

Legoland Pool House with Suite 4br/2bth

Family Winter Haven Retreat w/ Pool & Game Room

Florida Dream Vacation House

Cozy 3 bedrooms 2 bathrooms

4 bdr Family Fun Stay By Legoland/Sealife/Disney

Spacious Winter Haven Retreat w/Pool&Pet Friendly!

Lego-Land Getaway
Private house rentals

Luxury Heated Pool Home, 85 inch TV, King bed

Lake Home w/Heated Pool, Dock, Kayaks & EV Charger

Touch of Paris | Parisian-Inspired Condo Getaway

Perfect retreat for the family near Legoland!

Overlook Joy

Magnolia Farmhouse- Cozy with a Perfect Patio

Relaxing Retreat |Games, Pizza Oven, Massage Chair

Newly remodeled Lakefront Vacation Home
When is the best time to visit Cypress Gardens?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ551 | ﺩ.ﺇ577 | ﺩ.ﺇ577 | ﺩ.ﺇ551 | ﺩ.ﺇ518 | ﺩ.ﺇ521 | ﺩ.ﺇ521 | ﺩ.ﺇ518 | ﺩ.ﺇ496 | ﺩ.ﺇ518 | ﺩ.ﺇ514 | ﺩ.ﺇ544 |
| 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 |
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- Rentals with a fireplace Cypress Gardens
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- Walt Disney World Resort
- Universal Studios Florida
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- Magic Kingdom Park
- SeaWorld Orlando
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- Aquatica
- Disney's Hollywood Studios
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- Tampa Convention Center




