Holiday Homes in Winter Garden

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Winter Garden holiday homes

Private kitchen

Welcoming clean 3-bedroom house in cozy neighborhood in Oakland FL

Welcoming clean 3-bedroom house in cozy neighborhood in Oakland FL
Killarney
The price is €599
includes taxes & fees
5 Jun - 6 Jun
Welcoming clean 3-bedroom house in cozy neighborhood in Oakland FL
Exterior

Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
Winter Garden Family-friendly Condo w Resort Pool
Interior

Central Florida's Historic Gem & wedding venue- The Oakland Manor House

Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Oakland
10.0 out of 10, Exceptional, (1 review)
"We had a spectacular time at the Oakland Manor House. It's a gorgeous, historic home filled with both handsome antiques and comfortable sofas and beds. The kitchen is fully stocked and a joy to use to make meals if you're so inclined. The bathrooms were very clean and well appointed with bath products and hair dryers for use. They even had coffee beans and a grinder for use. Very nice gestures. It was spotless and located in a lovely, safe neighborhood. We had a celebration of our wedding with...
United States
Kristen R.
The price is €1,019
includes taxes & fees
7 Jun - 8 Jun
Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Lobby sitting area

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,252 reviews)
"I love the location of this place."
United States
William
The Berkley, Orlando
Towels, soap, shampoo, toilet paper

Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Apopka
10.0 out of 10, Exceptional, (2 reviews)
"Was great! Thank you "
United States
Jade L.
The price is €108
includes taxes & fees
12 Jun - 13 Jun
Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka
Exterior

Charming 2-bedroom apartment in house with AC, WiFi included

Charming 2-bedroom apartment in house with AC, WiFi included
Apopka
9.8 out of 10, Exceptional, (30 reviews)
"Very nice neighborhood and great accommodations. "
United States
Kevin S.
The price is €136
includes taxes & fees
7 Jun - 8 Jun
Charming 2-bedroom apartment in house with AC, WiFi included
Interior entrance

Family Friendly Davenport Pool Villa

Family Friendly Davenport Pool Villa
4.0 star property
Florida Pines
The price is €457
includes taxes & fees
6 Jun - 7 Jun
Family Friendly Davenport Pool Villa
Exterior

Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Orlando
8.6 out of 10, Excellent, (114 reviews)
"Host was amazing to work with and the house was as clean and easy to use and access. Would recommend to anyone going to Orlando for a vacation…"
United States
David Judy B.
The price is €423
includes taxes & fees
5 Jun - 6 Jun
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
1 bedroom, desk, WiFi, bed sheets

Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
United States
Matthew
The price is €153
includes taxes & fees
16 Jun - 17 Jun
Studio in the heart of Orlando
Front of property

4 Bedroom Pool Home

4 Bedroom Pool Home
4.0 star property
Florida Pines
9.2 out of 10, Wonderful, (23 reviews)
"Great location near parks"
United States
donneeka
The price is €292
includes taxes & fees
27 Jun - 28 Jun
4 Bedroom Pool Home
Outdoor pool

Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (71 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is €59
includes taxes & fees
16 Jun - 17 Jun
Maple Leaf Inn & Suites
Smart TV

Rose's Lakeview

Rose's Lakeview
Orlando
9.0 out of 10, Wonderful, (20 reviews)
"Fantastic place. Really independent, the backyard has an excellent view and a nice breeze I highly recommend this place. "
United States
Yves
The price is €365
includes taxes & fees
7 Jun - 8 Jun
Rose's Lakeview
Living room

Doppio Westside

Doppio Westside
4.0 star property
Davenport
9.4 out of 10, Exceptional, (45 reviews)
"Great place to stay. Very clean and the inside of the place was beautiful and spacious."
United States
David
The price is €456
includes taxes & fees
9 Jun - 10 Jun
Doppio Westside
Fridge, microwave, oven, stovetop

Stylish & Cozy King Bed Retreat @ Baldwin Park

Stylish & Cozy King Bed Retreat @ Baldwin Park
Orlando
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful, attentive host! The property was exactly as advertised… clean and well equipped. I would highly recommend this property."
United States
Tom B.
The price is €309
includes taxes & fees
6 Jun - 7 Jun
Stylish & Cozy King Bed Retreat @ Baldwin Park
Family House | Restaurant

Crofton Springs House 4 Bedroom

Crofton Springs House 4 Bedroom
3.5 star property
Providence
10.0 out of 10, Exceptional, (1 review)
The price is €476
includes taxes & fees
15 Jun - 16 Jun
Crofton Springs House 4 Bedroom
3 bedrooms, desk, iron/ironing board, free WiFi

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (49 reviews)
"The house was very clean and the owner was very prompt in answering our one question. The A/C worked great. "
United States
Michael
The price is €218
includes taxes & fees
8 Jun - 9 Jun
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Smart TV, ping pong

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Azalea Park
9.6 out of 10, Exceptional, (24 reviews)
"Quiet neighborhood, good location."
United States
River
The price is €242
includes taxes & fees
5 Jun - 6 Jun
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Interior

It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando

It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando
Kissimmee
9.8 out of 10, Exceptional, (35 reviews)
"The house and location was exactly what the description and pictures described. Rosangela is a great hostess and very welcoming and a pleasure to have worked with. "
United States
Janene B.
The price is €281
includes taxes & fees
8 Jun - 9 Jun
It’s only 15 minutes drive to Disney World and the amazing outlets in Orlando
Fridge, microwave, stovetop, dishwasher

Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
Rosemont
9.4 out of 10, Exceptional, (30 reviews)
"This is a great location for those traveling with families. It was close enough to the main Orlando attractions and great room for 7 people. Very clean and host is amazing at communicating."
United States
Kassandra H.
The price is €444
includes taxes & fees
8 Jun - 9 Jun
Chic Orlando Family Getaway w/ Fenced Yard!
Interior

Kissimmee Retreat with Jacuzzi and Games

Kissimmee Retreat with Jacuzzi and Games
Kissimmee
Kissimmee Retreat with Jacuzzi and Games
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Garden Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

6/10 Okay
"The property was nice. The check in line was crazy long never experienced that before. We use the resort as a home base to access the surrounding theme parks around Orlando. Didn't interact with staff that much but when we did it was good. We spent one day at the surfari water park it was OK. Lazy river need cleaning. There were trash along the side of the pool. Water slide was great kids like it. The room we got was good but it had alot of lint dust. We wiped it down but it didn't help. Maybe because it was recently renovated. Property has construction going on during our stay at the resort (May 29 - June 2)."
henton 4-night trip
Posted less than an hour ago
The Grove Resort & Water Park Orlando

Find out more about Winter Garden

Winter Garden Holiday Homes information

Number of reviews
2,608
Accommodation
28819 Holiday Homes
Lowest Price
€59
Highest Price
€1,019