
House vacation rentals in Cypress Gardens
Find and book unique houses on Airbnb
Top-rated house rentals in Cypress Gardens
Guests agree: these houses are highly rated for location, cleanliness, and more.

Fishing Lakefront Paradise w/ Boat Slip & Parking!
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

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!

*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.

Harmony Place - W/ Pool - Near Walt Disney
Welcome to Harmony Place, your perfect getaway! Relax and unwind with the whole family at this serene retreat. This stunning home features a private pool, 3 spacious bedrooms, and 2 bathrooms, comfortably accommodating up to 9 guests. Located in the exclusive Crescent Lakes community in Kissimmee, Florida, you’ll be just 11 miles from Walt Disney World, 22 miles from Universal Studios, and 18 miles from SeaWorld Orlando. Enjoy nearby dining and shopping options for added convenience!

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.

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 two bedrooms, 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.

Freshly Renovated Home
Cute older house with modern amenities. Located right downtown within a block from the playpark, Lake Wailes lake, walking path, and the historic downtown shopping area. All of the appliances in the home are brand new, as well as the washer and dryer. There is a large TV in the living room, as well as one in each bedroom - each with Roku and Netflix. Each bedroom also has a mini split A/C unit to sleep as cold, or hot, as you like. Parking is in the rear covered carport.

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!

Legoland Lakeside Splash 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 Historic Area Retreat!
Welcome to our charming one-bedroom short-term rental nestled in the scenic Lake Morton Historic District and conveniently located near the prestigious Florida Southern College. This thoughtfully designed accommodation offers a perfect blend of modern comfort and historic charm. Situated just a stone's throw away from the beautiful Lake Hollingsworth and Lake Morton our property provides an easy access to leisurely strolls around the lake and jogging trails.

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!
Popular amenities for Cypress Gardens house rentals
House rentals with a pool

KokomoVilla Pool Home at Southern Dunes

Mickey's Lakefront Villa at Sunset Lakes

Waterfront Wizarding Near Universal's Harry Potter

Awesome Vacation Home w/ Private Heated Pool/Spa

Fantastic Water Front Home on the Chain of Lakes

Breathtaking Home

Heated pool/hot tub, near Legoland, Disney,

John Shirley’s Retreat
Weekly house rentals

Modern 3br home

1937 family lakehouse kids and pet friendly

Legoland Pool House with Suite 4br/2bth

Sunset Lakefront Home | Hot Tub, Private Dock

Lake House by Legoland + Loft & Private Dock

Private Ranch Style Home on Lake

Cozy Lakefront Home w/ Pool -7 mins from Legoland

Tranquil Haven, Near Disney
Private house rentals

Majors House #5 - 1BR / 1.5BA

Encanto At Auburndale

Kid-friendly Home w/ Pool & BBQ

Hidden Gem - Hot Tub/ Fire pit/Hammock/Grill Area

Overlook Joy

Luxury Modern Home In S Lakeland

Newly remodeled House 3BR/2BA

Live your best Florida life!
When is the best time to visit Cypress Gardens?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R2,539 ZAR | R2,658 ZAR | R2,658 ZAR | R2,539 ZAR | R2,387 ZAR | R2,404 ZAR | R2,404 ZAR | R2,387 ZAR | R2,285 ZAR | R2,387 ZAR | R2,590 ZAR | R2,827 ZAR |
| 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 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 R339 ZAR per night before taxes and fees

Verified guest reviews
Over 3,630 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
30 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!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- Saint Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Key West Vacation rentals
- Rentals with lake access Cypress Gardens
- Rentals with a fire pit Cypress Gardens
- Rentals with a fireplace Cypress Gardens
- Pet-friendly rentals Cypress Gardens
- Rentals with a patio Cypress Gardens
- Rentals with pools Cypress Gardens
- Family-friendly rentals Cypress Gardens
- Rentals with outdoor seating Cypress Gardens
- Rentals with a washer and dryer Cypress Gardens
- Waterfront rentals Cypress Gardens
- Hotel rooms Cypress Gardens
- House rentals Polk County
- House rentals Florida
- House rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Disney's Animal Kingdom Theme Park
- Old Town Kissimmee
- Walt Disney World Resort Golf
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Discovery Cove
- Aquatica
- Amalie Arena
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ZooTampa at Lowry Park
- ChampionsGate Golf Club




