Winter Garden Villas - Best Villa Winter Garden 2026

ARM53A Historic Downtown Area and Clock of Winter Garden Florida

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Our top choices for Winter Garden villas

1-Bedroom Villa Near Disney w/ Pool & Lazy River

Kissimmee

includes taxes & fees

1 Jun - 2 Jun

Villa Near Disney World and SeaWorld

Kissimmee

Luxury Villa Near Walt Disney World

Kissimmee

includes taxes & fees

1 Jun - 2 Jun

The Farm House - Great Location + Pet Friendly!

Windermere

includes taxes & fees

26 May - 27 May

VedaHive Luxury Villa

Solterra Resort

Nelson

includes taxes & fees

26 May - 27 May

Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater

Haines City

Carmen L.

includes taxes & fees

31 May - 1 Jun

Vista Vibes • Upscale Escape · Lake Dora

Mount Dora

Judy B.

includes taxes & fees

26 May - 27 May

Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees

Clermont

Kathleen S.

includes taxes & fees

26 May - 27 May

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Top Winter Garden Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"Clean and very secure. Planning my next stay there."

Universal's Cabana Bay Beach Resort

8/10 Good

"Seeing that this hotel is themed in the 50's and 60's time era I did not think I would be a fan, but it was the most reasonably priced one out of all the Universal Resorts so I gave it a shot. I am so happy I did! The atmosphere was wonderful! with the dining room playing old commercials to the music, there is also an ice cream shop. They have the biggest gym and arcade I have ever seen in a hotel, they also had character visits in the lobby and a good size souvenir store. The hotel had plenty of choices for dinner and breakfast, the portion sizes of meals were good size. The staff from the front desk, to housekeeping and storing our baggage were all super friendly! I liked the walking distance to Volcano Bay. The shuttles to the parks and City Walk were consistent and convenient. My only suggestion to the hotel would be that when housekeeping is doing their daily turndown service is to check the levels of the conditioner and shampoo as we ran out on day two. The hotel is not in walking distance to any stores which you can pretty much get anything in their souvenir shop or food area but be prepared to pay. Early admission to the parks was definitely a plus. My two grown boys who are 18 and 25 really enjoyed the hotel and we would definitely stay there again!"

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

6/10 Okay

"Overall a decent stay for the low $$$. If you’re not going to be in the room much- however the bathrooms are older and have some wear and tear. The towels are also terrible…breakfast was not edible. The staff was so kind the woman at the front desk at check in was very informative. I wouldn’t stay here again but if you’re on a budget it’s doable"

Vacation Village Orlando, Celebration

4/10 Poor

"Only stayed for one day and had to sleep in a hot box.. when we arrived the thermostat was set to heat so we gave it time to get cool while we got food just to come back and it’s still hot..just to find out AT CHECK OUT that “the circuit breaker” tripped and they gave no accommodation for it…was very unsatisfied."

Homewood Suites by Hilton Orlando at Flamingo Crossings

6/10 Okay

"To start, I accidentally booked a handicapped accessible room and while showering the floor flooded almost all of the way to the door despite there being 2 drains in the floor. To avoid this we had to turn the shower off while washing. However, they were able to get us a new room, but that rooms sink kept clogging as well. Also, the bedding had some dark stains which made me question if the covers were even washed. We specifically booked there for the shuttle service to the parks, but these shuttles don’t run all day and I guess you have to reserve a spot ahead of time to ensure you’ll get a seat. The walk from the parking garage sucks after a long day at the park. There is no direct entrance into the hotel from the garage. You have to walk all of the way to the front. The breakfast was ok, pretty standard. I will say the rooms were spacious which was nice and the air conditioning worked really well. The staff was friendly. The location was great, and the pool was nice, but the chairs were pretty uncomfortable. I’m not sure if we will stay here again in the future. It wasn’t terrible, but it wasn’t what I was expecting either."

Find out more about Winter Garden

Winter Garden Villas information

Number of reviews	408
Accommodation	10950 Villas
Lowest Price	€150
Highest Price	€813

Frequently asked questions

How much do villas in Winter Garden cost?

Villas in Winter Garden cost between €150 and €813 per night. These stays offer the privacy to enjoy your own space at a price that's gentle to your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your villa in Winter Garden with Expedia?

With Expedia, it's easy to find your ideal villa in Winter Garden. Travelling with the kids? Use our helpful filters to search for stays with amenities like a pool and WiFi. If you have a budget, choose how much you're willing to spend and your preferred star rating. We'll help you find the right place in tune with your taste and style.

How can I find cheap villas in Winter Garden?

A great way to get cheap villas in Winter Garden is with Expedia's convenient filter tool. Refine your search results by star rating, budget and amenities to grab awesome bargains in only a click or two.

What is there to do near my villa in Winter Garden?

Whatever your tastes or interests, Winter Garden has lots of things to keep you busy. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on most travellers' sightseeing plans. You shouldn't miss Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you can discover more terrific attractions like these with the money you save.

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Winter Garden Holiday Rentals

Search Villas in Winter Garden

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Garden villas

1-Bedroom Villa Near Disney w/ Pool & Lazy River

Villa Near Disney World and SeaWorld

Luxury Villa Near Walt Disney World

The Farm House - Great Location + Pet Friendly!

VedaHive Luxury Villa

Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater

Vista Vibes • Upscale Escape · Lake Dora

Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees

Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!

Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney

Serenity Now By Shine Villas At Watersong #416 5 Bedroom Villa

Splendid Lake View Villa With Heated Pool/spa Near Disney

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

Rustic Hideaway - Great Location + Pet Friendly!

Upstay Pristine 3BR Home With Private Pool & BBQ

College Park SAFE QUIET PVT Villa - Mins to ORL/Winter Park/Eola FREE PARKING

Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!

Tropical Views 4bdr Sleeps 8. Close to Parks!

Bahama Bay Resort - Ground Floor

Gorgeous VILLA near Disney, Private Heated South Pool

Find holiday rentals that suit your style

Top Winter Garden Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Winter Garden

Winter Garden Villas information

Frequently asked questions

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