
House holiday 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.

Southern Dunes Villa - Pool - Golf - near Disney
Stunning executive home with a south facing screened in-ground pool overlooking the 2nd hole of the Southern Dunes Golf Course. 13 miles from LEGOLAND, 22 miles from DISNEY, 29 miles from UNIVERSAL, this is the perfect place to relax after a busy day at the parks. Impeccably maintained, our villa features upgraded furniture, electronics, mattresses and flooring. Southern Dunes is a gated golf community that prides itself on the quality of its golf course & the security & beauty of its homes.

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

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.

Gorgeous Gem in the Heart of Lakeland
LOCATION, LOCATION! This gorgeous, spacious, newly renovated home is located on one of the most desired and safest streets in all of Lakeland, and steps away from the beautiful Lake Hollingsworth and Trail. Close to the lake, and a short drive to downtown Lakeland, this gem is in the perfect location! This home features zero gravity beds, a gourmet kitchen, private laundry, smart TVs and WiFi, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

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.

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.

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!

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.

Charming Lakefront Cottage with Stunning Views
Welcome to our lake house retreat in Lakeland, Florida. You can enjoy a peaceful getaway with beautiful sunset views and tranquil waters during the evenings, and still visit major cities such as Orlando and Tampa during the day which are less than an hour away. Minutes from Southeastern University, Florida Southern, Lake Hollingsworth, and other attractions in the Lakeland area.
Popular amenities for house rentals in Cypress Gardens
House rentals with a pool

KokomoVilla Pool Home at Southern Dunes

Cozy Tiny Home Resort Life Near Disney

Stylish Villa with Free Pool Heat

Harmony Place - W/ Pool - Near Walt Disney

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

Fantastic Water Front Home on the Chain of Lakes

Heated pool/hot tub, near Legoland, Disney,

DisneyWorld 15min!Themed 4 BD home w/private pool!
Weekly house rentals

Modern 3br home

Adult-Only Getaway w/ Mermaid Pool | 18+, Private

2 Free waterparks luxury 3 bedrooms townhouse

Pet friendly Central Florida Bungalow

Private Ranch Style Home on Lake

Waterfront*Heated Pool*Putting Green*Dock*Legoland

Kid-friendly Home w/ Pool & BBQ

Winter Haven Waterfront Retreat
Private house rentals

30 minutes to Disney and Universal Studios

Casa Breeze - Cozy, Luxurious & Close to Disney

Karen’s Happy House

Southern Dunes Lakeview Poolhome

Cozy Retreat in the city

4/2 New Spacious Home Heated Pool Option added

Hidden đź’Ž Minimalist Design | Lego+Disney

Juliana Jewel on Lake Juliana
When is the best time to visit Cypress Gardens?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ÂŁ110 | ÂŁ115 | ÂŁ115 | ÂŁ110 | ÂŁ103 | ÂŁ104 | ÂŁ104 | ÂŁ103 | ÂŁ99 | ÂŁ103 | ÂŁ112 | ÂŁ122 |
| 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 holiday rentals
Explore 70 holiday rentals in Cypress Gardens

Nightly prices starting at
Cypress Gardens holiday rentals start at ÂŁ15 per night before taxes and fees

Verified guest reviews
Over 3,900 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Cypress Gardens holiday rentals include wifi 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 Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Family-friendly rentals Cypress Gardens
- Rentals with a firepit Cypress Gardens
- Rentals with a patio Cypress Gardens
- Rentals with pools Cypress Gardens
- Rentals with lake access Cypress Gardens
- Rentals with a fireplace Cypress Gardens
- Pet-friendly rentals Cypress Gardens
- Rentals with a washing machine and dryer Cypress Gardens
- Waterfront rentals Cypress Gardens
- Rentals with outdoor seating 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
- Give Kids the World Village
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Discovery Cove
- Magic Kingdom Park
- Busch Gardens Tampa Bay
- ESPN Wide World of Sports
- Disney's Animal Kingdom Theme Park
- Epcot
- Old Town
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Amalie Arena
- Aquatica
- Bluegreen Vacations Fountains, Ascend Resort Collection
- Disney's Hollywood Studios
- Island H2O Live!
- ICON Park




