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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Winter Garden villas

Outdoor dining

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

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

Luxury Villa Near Walt Disney World

Luxury Villa Near Walt Disney World
Kissimmee
Luxury Villa Near Walt Disney World
Outdoor dining

Villa Near Disney World and SeaWorld

Villa Near Disney World and SeaWorld
Kissimmee
Villa Near Disney World and SeaWorld
Exterior

Amazing Villa with south facing pool and conservation view

Amazing Villa with south facing pool and conservation view
Watersong
9.8 out of 10, Exceptional, (217 reviews)
"House set up, privacy. Host communication was great. "
United States
Tiffani H.
The price is NZ$863
includes taxes & fees
5 May - 6 May
Amazing Villa with south facing pool and conservation view
Exterior

Tiny Hamptons, No Pet Fees, Main Floor Bed

Tiny Hamptons, No Pet Fees, Main Floor Bed
Clermont
10.0 out of 10, Exceptional, (17 reviews)
"Very clean and has everything you need."
United States
Kathleen S.
The price is NZ$500
includes taxes & fees
13 May - 14 May
Tiny Hamptons, No Pet Fees, Main Floor Bed
Outdoor dining

VedaHive Luxury Villa

VedaHive Luxury Villa
3.0 star property
Solterra Resort
7.0 out of 10, Good, (10 reviews)
"Room was clean, place was nice and quiet. "
United States
Abi
The price is NZ$289
includes taxes & fees
1 May - 2 May
VedaHive Luxury Villa
Microwave, oven, stovetop, dishwasher

Vista Vibes • Effortless Luxury Near Lake Dora

Vista Vibes • Effortless Luxury Near Lake Dora
Mount Dora
10.0 out of 10, Exceptional, (2 reviews)
"Perfect location for us, "
United States
Judy B.
The price is NZ$468
includes taxes & fees
7 May - 8 May
Vista Vibes • Effortless Luxury Near Lake Dora
TV

Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
Rustic Hideaway - Great Location + Pet Friendly!
Indoor pool

7BR Lakefront | Pool & Hot Tub

7BR Lakefront | Pool & Hot Tub
Edgewood
9.8 out of 10, Exceptional, (21 reviews)
"We had a nice stay, and Paul was very attentive!"
United States
Susan M.
7BR Lakefront | Pool & Hot Tub
Property grounds

Luxury Tiny by Tiny Hamptons - Chef’s Kitchen

Luxury Tiny by Tiny Hamptons - Chef’s Kitchen
Clermont
10.0 out of 10, Exceptional, (9 reviews)
"Nice accommodations, easy check in, great communications, clean and nice."
United States
John W.
The price is NZ$577
includes taxes & fees
1 May - 2 May
Luxury Tiny by Tiny Hamptons - Chef’s Kitchen
A heated pool

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

Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater
Haines City
8.8 out of 10, Excellent, (86 reviews)
"Our family had a wonderful stay at this property. Everything was lovely. Communication with the owner was quick and very responsive. The home is very roomy and the rooms were all very nice. The movie room was a nice bonus! The pool was great; added pool heat since we stayed in late December and ot was well worth it. Overall great rental!"
United States
Carmen L.
The price is NZ$691
includes taxes & fees
11 May - 12 May
Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater
Exterior

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

College Park SAFE QUIET PVT Villa - Mins to ORL/Winter Park/Eola FREE PARKING
College Park
10.0 out of 10, Exceptional, (27 reviews)
"Great place and super nice host. Definitely recommend this place if you're ever in Orlando"
United States
Keri G.
The price is NZ$307
includes taxes & fees
16 May - 17 May
College Park SAFE QUIET PVT Villa - Mins to ORL/Winter Park/Eola FREE PARKING
Villa, 5 Bedrooms | Exterior

5 Bed Bliss At Solterra By Shine Villas 121 5 Bedroom Villa

5 Bed Bliss At Solterra By Shine Villas 121 5 Bedroom Villa
3.0 star property
Solterra Resort
The price is NZ$1,163
includes taxes & fees
5 May - 6 May
5 Bed Bliss At Solterra By Shine Villas 121 5 Bedroom Villa
Exterior

Completely Renovated 3/2 Close to Disney parks

Completely Renovated 3/2 Close to Disney parks
Royal Palm Bay
10.0 out of 10, Exceptional, (28 reviews)
"15 mins drive to Disney, We enjoyed our stay, clean as advertised, Owner communicates in detail, Will definitely rebook this Villa. "
United States
Elisa
The price is NZ$422
includes taxes & fees
5 May - 6 May
Completely Renovated 3/2 Close to Disney parks
Exterior

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

Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Trafalgar Village
8.8 out of 10, Excellent, (9 reviews)
"House was big enough for the whole family nice pool great area "
United States
Chrystal S.
The price is NZ$797
includes taxes & fees
3 May - 4 May
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
A heated pool

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

Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
Kissimmee
8.8 out of 10, Excellent, (88 reviews)
"The home needs a thorough cleaning."
United States
May V.
The price is NZ$1,604
includes taxes & fees
1 May - 2 May
Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
Outdoor pool, a heated pool, pool loungers

Splendid Lake View Villa With Heated Pool/spa Near Disney

Splendid Lake View Villa With Heated Pool/spa Near Disney
Loughman
9.4 out of 10, Exceptional, (54 reviews)
"beautiful stay will defiantly recommend! host was very accommodating! "
United States
sura l.
The price is NZ$1,135
includes taxes & fees
5 May - 6 May
Splendid Lake View Villa With Heated Pool/spa Near Disney
Interior

The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is NZ$918
includes taxes & fees
3 May - 4 May
The Farm House - Great Location + Pet Friendly!
Villa (3 Bedrooms) | Interior

Upstay Pristine 3BR Home With Private Pool & BBQ

Upstay Pristine 3BR Home With Private Pool & BBQ
3.0 star property
Clermont
The price is NZ$516
includes taxes & fees
5 May - 6 May
Upstay Pristine 3BR Home With Private Pool & BBQ
Exterior

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Altamonte Springs
9.2 out of 10, Wonderful, (5 reviews)
"The stay was great. There was a slight smell of a chemical odor but not overwhelming. The bed was comfy with clean sheets and there were enough clean towels. Made friends with the local cat. Overall, its was a great stay!"
United States
Marty H.
The price is NZ$315
includes taxes & fees
11 May - 12 May
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Garden Hotel Reviews

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

6/10 Okay
"I don't eat breakfast "
Menachem 2-night trip
Posted 1 hour ago
Rosen Inn at Pointe Orlando

Find out more about Winter Garden

Winter Garden Villas information

Number of reviews
502
Accommodation
10979 Villas
Lowest Price
NZ$289
Highest Price
NZ$1,604

Frequently asked questions

How much do villas in Winter Garden cost?
Villas in Winter Garden cost between NZ$289 and NZ$1,604 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.
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.