
House holiday rentals in Winter Garden
Find and book unique houses on Airbnb
Quick stats about house rentals in Winter Garden

Total holiday rentals
Explore 70 holiday rentals in Winter Garden

Nightly prices starting at
Winter Garden holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 3,300 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
70 of Winter Garden holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Garden rentals

4.8 Average rating
Winter Garden stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated house rentals in Winter Garden
Guests agree: these houses are highly rated for location, cleanliness and more.

Downtown Bungalow with fire pit and putting green
This 1920's home has been fully updated to include new kitchen, bath, fixtures, appliances, and more. The home has 2 bedrooms with one having a king bed and the other a queen bed. Beds feature super comfy Tuft & Needle mattresses ! Kitchen covers all of your basic cooking needs, has stainless appliances, refrigerator with ice maker, and Keurig coffee maker. The dining table comfortably seats 4 and is perfect for a meal or to use as a work space. New full size washer and dryer in carport laundry room. Grab a bottle of wine from Tony's less than 1 block away and relax in the screened-in front porch. Depending on the season grab a Valencia orange off the citrus tree in the back yard. You can use the entire home! There are 2 spacious bedrooms, 1 bath, dining room, kitchen, and a full washer and dryer in the laundry room (located in the carport). Owners live less than a mile away and are available as needed. We can meet you if you need anything! Just a few short steps from the famous Farmer's Market, Crooked Can Brewing, the Plant Street Market, the West Orange Bike Trail, Garden Theater, countless restaurants, and all that Downtown Winter Garden has to offer. This historic home is the perfect escape from the bustle of the tourist district, less than 30 minutes to Disney World, 25 minutes to Universal Studios, 30 minutes to Sea World. You can easily walk the 1 block to Plant St where most of the amenities of Downtown Winter Garden are located. You'll be just 25 minutes from Universal Studios and I-Drive via the Turnpike and 25 minutes from Disney via hwy 429. Also if you are into biking you can rent them at Wheel Works or the West Orange trail head and hit the famous West Orange Trail. There is a 2 car covered carport on site. Across the street from an elementary school so during the school year, there is some traffic in the morning and afternoon. Please be mindful and a good neighbor!

The Legacy House - your home away from home.
Just a block away from the South Lake Bike Trail System, 18 minutes from beautiful Lake Minneola, and a mere 20 miles from the Disney Parks, and 5 minutes from the Bella Collina wedding venue, this peaceful neighborhood home will be a perfect spot to rest after a full day of fun. This is an ideal spot if you're coming for cycling events, fishing competitions, a wedding or simply to enjoy the most beautiful part of Florida! We hope you chose to book with us; it would be our pleasure to host you!

Spacious Home with Pool & Hot Tub near Downtown
Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

The Perfect Home - Heated Pool - Next to Universal
This luxurious, modern, completely remodeled single-family home with HEATED pool and spacious FULLY FENCED backyard in one of Orlando's best neighborhood! Centrally located from all Orlando has to offer: ☆ 1.7 miles from Universal Studios ☆ 2.6 miles to Restaurant Row ☆ 4.5 miles to Orange County Convention Center ☆ 6.5 miles to Seaworld ☆ 10 miles to Disney World This home offers upscale living space with stunning outdoor area to kick back and enjoy after a long day at the parks.

Lake Front Home with private Dock on Lake Louisa
Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow cleaning and disinfecting of the house

Cozy Winter Garden Home 20 MINUTES FROM DISNEY
Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.

★★Casa en la Pequeña Loma ★★ 4 beds ★ jacuzzi
Enjoy this charming remodeled home with 3 bedrooms, 2 bathrooms, and a JACUZZI waiting for your and your family. Each room has a TV. The kitchen has all you need to make a home cook dinner after a really fun day!!! A minute walking distance to VANDERGRIFT CENTRAL PARK which features: Baseball Fields (Lighted), Basketball Court, Volleyball, Boardwalk, Concession Stand, Fishing Dock, Football Field, Non-Motorized Boat Launch, Parking, Picnic Tables, Playground, Restrooms

Spacious Bungalow with Pool and Courtyard
Whether you seek relaxation or adventure, this house offers the best of both worlds! Relax in this spacious bungalow with a courtyard, pool, hot tub, and fire pit! Take a short walk to downtown Clermont and discover the charming shops, restaurants, and breweries! Explore the sights and attractions that Central Florida has to offer! Whether you crave the vibrancy of downtown or the tranquility of your own oasis, this property offers the best of both worlds!

Stylish Lakeview Home for Triathletes/ Family 380
Experience tranquility at this stylish and inviting Lakeview hideaway. Embrace the comfort promised by our tastefully furnished interiors, supplemented by stunning lake vistas- a perfect sanctuary for leisurely vacations or rigorous triathlon trainings. Triathletes will adore the home's strategic location near running paths, open swimming spots and bike-friendly paths. Our fully complete kitchen is at your disposal to nourish your training regime.

Downtown Winter Garden, Florida
Charming two bedroom, one bathroom home just three blocks from downtown Winter Garden Florida. Across the street from the West Orange Bike Trail and walking distance to restaurants, Splash pond, shopping and Farmers Market. The back yard is shaded by a 100 year old live oak tree. There is a “no pet policy” at the house. We do not accept guests under the age of 12. There are NO cameras on or around the property. I respect the privacy of my guests.

Lakeview Sunsets with Loft Escape West of Orlando
We are proud to announce No Smoking on premises property. This Duplex A Lake house overlooks Starke Lake in Central Florida. Great fishing, magnificent sunsets and Disney fireworks every night . Close to Disney 19 miles & 12 miles to Universal & 14 miles to Downtown Orlando. Other activities include air boating, Cape Cape Canaveral and centrally located just 1 hour from ocean or gulf. Please NO SMOKING on premises.

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Enjoy the breathtaking sunrise views of Lake Apopka from this newly refurbished and well appointed 4 bed, 2.5 bath vacation home in Winter Garden, Fl. While the house offers total tranquility and relaxation, it is only a short drive from Orlando’s numerous theme parks (Universal Studios 20 min, Disney World 30 min) and all other local attractions (Mall of Millenia and premium outlet malls 20 min drive)
Popular amenities for house rentals in Winter Garden
House rentals with a pool

Private Pool Oasis w/Xbox, Fireplace, Projector

Pool & Spa Oasis/Golf Retreat/Near Disney/3BR Home

Paradise pool home /5 Min Universal /13 min Disney

Recharging Lakeview Oasis w/Pool centrally located

Harmony | Heated Pool | 10 min Universal & Epic.

Pool + Heated spa Family friendly King suite Oasis

Spacious Getaway ~ Heated LED Pool & Ping Pong

Modern Tropical House Heated Salt Pool
Weekly house rentals

MVV7485 - 3BR townhouse with Hot Tub

Entire clean comfortable house

Your Enchanted Home Near Downtown Winter Garden

Winter Garden Cottage w\fence

Lakefront in West Orlando Florida

Rural Home Near the Springs

Downtown Winter Garden Luxury Retreat (NO Parties)

Lakefront Home•screened deck, dock•Long Stays OK
Private house rentals

Water Front Haven

Pool & Jacuzzi+Cinema+Games+Fire Pit | Near Disney

Sunshine on Seminole

1921 Winter Garden home 22 min from Magic Kingdom

Orlando/Downtown/GameRoom/Disney/Tikihut/MiniGolf

1921 Bungalow in Historic Downtown Winter Garden

Exquisite Luxury Home Minutes from All Theme Parks

Orlando, Peaceful Waterfront property !
When is the best time to visit Winter Garden?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £95 | £99 | £93 | £96 | £95 | £96 | £74 | £74 | £66 | £83 | £91 | £97 |
| 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 |
Destinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Panama City Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Hollywood Holiday rentals
- Savannah Holiday rentals
- Jacksonville Holiday rentals
- Hilton Head Island Holiday rentals
- Kissimmee Holiday rentals
- Walt Disney World Resort
- Orange County Convention Center
- SeaWorld Orlando
- Disney Springs
- Orlando / Kissimmee KOA
- Universal's Volcano Bay
- Epcot
- Camping World Stadium
- Kia Center
- Disney's Animal Kingdom Theme Park
- University of Central Florida
- Discovery Cove
- Tinker Field
- Old Town
- LEGOLAND Florida Resort
- Reunion Resort Golf Courses - Palmer & Watson
- Disney's Hollywood Studios
- ChampionsGate Golf Club
- ICON Park
- Aquatica
- Epperson Lagoon
- Island H2O Live!
- Ocala National Forest
- Blue Spring State Park





