Search Vacation Homes in Winter Garden

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Browse Select Winter Garden Vacation Homes

Peaceful Private and near everything
This family-friendly Winter Garden vacation home is located on the waterfront, within 3 mi (5 km) of Lake Butler and Orange County National Golf Club. Magic ...
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Peaceful Private and near everything
 Vista Del Lago Hidden Gem! 5 Miles From Disneyworld's Front Door, Orlando
The price is $69 per night from Oct 25 to Oct 25
Located in Winter Garden, this family-friendly vacation home is 2.7 mi (4.4 km) from Island H2O Live!, and within 6 mi (10 km) of Lake Davenport and Highland ...
5/5 Exceptional! (45 reviews)
Quiet and convenient
"This is the perfect retreat. Easy access to theme parks and entertainment, close to shopping and restaurants, but not in the middle of hustle and bustle. We would definitely recommend this property for your family get away."

Reviewed on Oct 19, 2021

Vista Del Lago Hidden Gem! 5 Miles From Disneyworld's Front Door, Orlando
Chill out in a relaxing 3 bed/2 bath home, with lake views, near to Disney
Located on the waterfront, this family-friendly vacation home is within 6 mi (10 km) of Island H2O Live!, Disney's Blizzard Beach Water Park, and Disney's Winter ...
4.7/5 Exceptional! (33 reviews)
👍
"Perfect for us while down visiting with family"

Reviewed on Aug 1, 2021

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Chill out in a relaxing 3 bed/2 bath home, with lake views, near to Disney
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Luxurious Orange Lakes River Island
Located in Winter Garden, this family-friendly vacation home is 1.2 mi (2 km) from Island H2O Live!, and within 6 mi (10 km) of Disney's Animal Kingdom® Theme ...
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Luxurious Orange Lakes River Island
Winter / Summer Vacation Home
This family-friendly Winter Garden vacation home is located by the sea, 1.9 mi (3.1 km) from Island H2O Live!, and within 6 mi (10 km) of Lake Davenport and ...
4.7/5 Exceptional! (38 reviews)
Only one negative
"The only thing I can really say negative is the master beed needs a new mattress. It is worn out and you feel like you are lying in a hole"

Reviewed on Sep 7, 2021

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Winter / Summer Vacation Home
3 Bed 3 Bath Full Service Resort & Water Park Near Disney
Situated in Winter Garden, this vacation home is within 9 mi (15 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Orange County National ...
4/5 Very Good! (2 reviews)
"Very clean"

Reviewed on Jul 10, 2021

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3 Bed 3 Bath Full Service Resort & Water Park Near Disney
Disney Backyard Oasis
Winter Garden, FL
The price is $120 per night from Oct 23 to Oct 23
Set in Winter Garden, this family-friendly vacation home is within 6 mi (10 km) of Island H2O Live!, Disney's Blizzard Beach Water Park, and Disney's Winter ...
4.9/5 Exceptional! (17 reviews)
Beautiful home
"It was a great experience, but the bed were very hard. Overall nice complex!!"

Reviewed on Sep 11, 2021

Disney Backyard Oasis
Modern Bungalow w/ Gas BBQ, Short Walk to Downtown
Situated in Winter Garden, this vacation home is within a 10-minute walk of Winter Garden Art Association, Garden Theatre, and Winter Garden Heritage Museum. ...
4.9/5 Exceptional! (16 reviews)
Winter Garden Cozy House
"We loved the little house. Safe neighborhood, very nice finishes, and decor. The bed was so comfortable! There was only a shower so that was a challenge with a toddler. Also there were no doors between the living and bedrooms or bed and bathroom. That made sleeping arrangements and privacy more difficult ..."

Reviewed on Jul 14, 2021

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Modern Bungalow w/ Gas BBQ, Short Walk to Downtown
Near Disney - Spacious 3BR - Pool and Hot Tub!
The price is $77 per night from Oct 25 to Oct 25
Situated in Winter Garden, this romantic vacation home is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Orange County ...
Near Disney - Spacious 3BR - Pool and Hot Tub!
Cute House by the Lake near Disney World
Located in Vista del Lago, this vacation home is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Disney's Blizzard Beach Water Park. Disney's Winter ...
5/5 Exceptional! (28 reviews)
Very relaxing and comfortable.
"The place where we stayed was beautiful & scenic with a great view of the lake. The home felt inviting and relaxing. It was clean, neat and pet friendly with a real sense of being a home away from home. Really quite comfortable. The owner - John was very courteous, helpful and just a call away should ..."

Reviewed on Oct 12, 2021

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Cute House by the Lake near Disney World
Waterfront Luxury Airstream on An Orange Grove
Situated on the waterfront, this vacation home is within 6 mi (10 km) of Hancock Park, Kings Ridge South, and Lake Butler. Lake Louisa State Park and AdventHealth ...
5/5 Exceptional! (1 review)
Perfect weekend getaway
"Beautiful property. Peaceful and serene. Airstream was spotlessly clean. Everything you need for short stay. Fantastic view. Simply put - amazing. Hope to go back again."

Reviewed on Oct 11, 2021

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Waterfront Luxury Airstream on An Orange Grove
Pool home near all Central Florida attractions with a coffee bar
This family-friendly Winter Garden vacation home is located in a rural location, 1.3 mi (2.1 km) from Oakland Nature Preserve, and within 6 mi (10 km) of Central ...
5/5 Exceptional! (6 reviews)
THIS PLACE IS GREAT!!!!!
"This is the nicest place we have stayed at by far on VRBO. The location is perfect. 25 minutes for Disney, 5 minutes from the downtown area. The host are very accomodating. From the games for children to play to the swimming pool in the screened in area, I could not have asked for a cleaner well ..."

Reviewed on Oct 6, 2021

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Pool home near all Central Florida attractions with a coffee bar
Spacious Winter Garden Home w/ BBQ, Walk to Dwtn!
Situated in Winter Garden, this vacation home is within a 10-minute walk of Winter Garden Art Association and Garden Theatre. Winter Garden Heritage Museum and ...
4.9/5 Exceptional! (8 reviews)
Excellent Property
"Comfortable, very clean and beautifully decorated! Very short drive or walk to Downtown Winter Garden."

Reviewed on Jun 15, 2021

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Spacious Winter Garden Home w/ BBQ, Walk to Dwtn!
NEW! Winter Garden House w/ Lanai + Pool Access!
Located in Vista del Lago, this vacation home is within 9 mi (15 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Orange County National ...
5/5 Exceptional! (1 review)
Great place to stay!!!
"The home was very clean and had so many wonderful decorations. The view from the Lani was incredible and the home had a ton of amenities that we could use. The kitchen was fully stocked and had everything we needed to enjoy ourselves!! This is the BEST place we have ever rented and the value is ..."

Reviewed on Aug 5, 2021

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NEW! Winter Garden House w/ Lanai + Pool Access!
Two-Bedroom Villa at Orange lake Resort
Located in Orange Lake, this vacation home is 1.3 mi (2 km) from Island H2O Live! and within 9 mi (15 km) of Lake Davenport and Disney's Animal Kingdom® Theme ...
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Two-Bedroom Villa at Orange lake Resort
Liki Tiki Fun Close to Orlando
Located in Winter Garden, this family-friendly vacation home is 2.7 mi (4.3 km) from Lake Davenport, and within 6 mi (10 km) of Island H2O Live! and Highland ...
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Liki Tiki Fun Close to Orlando
2 bd/2 bath Cozy Florida Home
Located in the center of Winter Garden, this family-friendly vacation home is within a 10-minute walk of Winter Garden Art Association, Garden Theatre, and Winter ...
5/5 Exceptional! (1 review)
Loved it 😍
"The home was absolutely beautiful the owner was so sweet and nice to my family I would love to stay their again it was better than the Marriott that I stayed in a month ago. 🥰"

Reviewed on Apr 18, 2021

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2 bd/2 bath Cozy Florida Home
 4 bedroom, 3 bath home has 2,602 square feet
Situated in Winter Garden, this vacation home is 1.4 mi (2.3 km) from Lake Butler and within 6 mi (10 km) of Winter Garden Art Association and Winter Garden ...
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4 bedroom, 3 bath home has 2,602 square feet
Less than 8 minutes to Disney's Animal Kingdom
Located on the waterfront, this family-friendly vacation home is within 6 mi (10 km) of Island H2O Live!, Disney's Blizzard Beach Water Park, and Disney's Winter ...
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Less than 8 minutes to Disney's Animal Kingdom
Upscale 3BR Near Disney - Pool and Hot Tub
The price is $71 per night from Oct 25 to Oct 25
Situated in Winter Garden, this vacation home is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Orange County National ...
Upscale 3BR Near Disney - Pool and Hot Tub
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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.

Other property types in Winter Garden

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
The price is $179 per night from Nov 7 to Nov 7
4.4/5 Excellent! (5,457 reviews)
"There was not anything we didn’t like. The staff was second to none."

Reviewed on Oct 21, 2021

The Grove Resort & Water Park Orlando
Liki Tiki Village by Diamond Resorts

Liki Tiki Village by Diamond Resorts

3.5 out of 5
17777 Bali Blvd, Winter Garden, FL
The price is $65 per night from Oct 31 to Oct 31
4.1/5 Very Good! (3,191 reviews)
"For a weekend family getaway is great ..fun water poolfor the kids..the rooms are nice....what i didnt like was the delay at check in to hotel resort"

Reviewed on Oct 19, 2021

Liki Tiki Village by Diamond Resorts
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave, Winter Garden, FL
The price is $114 per night from Oct 24 to Oct 24
4.7/5 Exceptional! (330 reviews)
"Great, affordable hotel close to Disney! Very clean and hotel staff was very friendly and accommodating. Will definitely recommend this place 👍"

Reviewed on Oct 19, 2021

Home2 Suites by Hilton Orlando at Flamingo Crossings
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.

Booking Tips to Find the Best Winter Garden Vacation Homes


How much does it cost to rent a vacation home in Winter Garden?

You can find incredible Winter Garden vacation homes for all types of budgets: between $65 and $179 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Winter Garden?

If you are looking for a great deal on your vacation home in Winter Garden, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Winter Garden?

There are 22 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Winter Garden?

Begin by entering your trip dates to see what type of Winter Garden rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Winter Garden?

Booking Winter Garden vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Winter Garden rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Winter Garden along with your vacation property, into a Winter Garden vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

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