Winter Garden Vacation Rentals
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Our top choices for Winter Garden vacation rentals
1. Upstay Large Family Condo w Pool, Sauna
Upstay Large Family Condo w Pool, SaunaWinter Garden
$210 nightly
The price is $236
Dec 9 - Dec 10
Total with taxes and fees
2. Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOLWinter Garden
9.8 out of 10, Exceptional, (24 reviews)
"The property was perfect for our week with family"
Steve S.
$308 nightly
The price is $343
Nov 17 - Nov 18
Total with taxes and fees
3. Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness roomWinter Garden
10.0 out of 10, Exceptional, (9 reviews)
"The house is absolutely beautiful! We stayed for two nights and had a wonderful experience. Communication with the host was excellent throughout our stay. We really enjoyed our time there and would definitely recommend this place!"
isaac
$344 nightly
The price is $384
Dec 1 - Dec 2
Total with taxes and fees
4. StylishAptWtrGrdnOppLake&Prk&Yrd
StylishAptWtrGrdnOppLake&Prk&YrdWinter Garden
9.8 out of 10, Exceptional, (26 reviews)
"Great place to stay! "
Lindsey W.
$174 nightly
The price is $186
Nov 18 - Nov 19
Total with taxes and fees
5. The Garden Luxe Retreat
The Garden Luxe RetreatWinter Garden
10.0 out of 10, Exceptional, (4 reviews)
"Great place to stay. Very clean and had everything we needed. Great location to go to Winter Garden downtown area with many excellent places to dine.3rd floor walkup was a little difficult moving in and out but there was parking right near the door. "
Corey K.
$393 nightly
The price is $393
Nov 29 - Nov 30
Total with taxes and fees
6. Upstay - Condo Near Disney w Pool-spa-sauna-games
Upstay - Condo Near Disney w Pool-spa-sauna-gamesWinter Garden
$214 nightly
The price is $241
Nov 30 - Dec 1
Total with taxes and fees
7. Family Fun Condo Pool and Sauna near Disney
Family Fun Condo Pool and Sauna near DisneyWinter Garden
9.6 out of 10, Exceptional, (5 reviews)
"Love the place and it was close to all the parks. Only thing was the fans in the room didn’t work but overall it was great."
Adolat
$225 nightly
The price is $253
Nov 17 - Nov 18
Total with taxes and fees
8. FunTropicalTinyHomeGolfCartLake
FunTropicalTinyHomeGolfCartLakeWinter Garden
9.4 out of 10, Exceptional, (11 reviews)
"We had a great time! The host was spectacular. Our accommodations were very clean and comfortable! "
Emily R.
$196 nightly
The price is $211
Nov 17 - Nov 18
Total with taxes and fees
9. Fire Pit & Yard: Updated Winter Garden Home!
Fire Pit & Yard: Updated Winter Garden Home!Winter Garden
$444 nightly
The price is $499
Nov 15 - Nov 16
Total with taxes and fees
10. Cozy 1-bedroom with AC in awesome Winter Garden
Cozy 1-bedroom with AC in awesome Winter GardenWinter Garden
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay and had a great experience. Gina communicated with us right away, so we knew how to check in or had any questions answered. The property is very cute and looks new and was spotless. The location of the property is great as well. Downtown Winter Garden is adorable with great restaurants and is an easy drive down Plant St. It also was very convenient to where we were visiting in Ocoee and Orlando.We had everything we needed, highly recommend this property, and would stay there...
Anonymous traveler
$332 nightly
The price is $370
Nov 17 - Nov 18
Total with taxes and fees
11. Upstay: Stylish 3BR Condo w Pationear Disney
Upstay: Stylish 3BR Condo w Pationear DisneyWinter Garden
10.0 out of 10, Exceptional, (1 review)
"The room was great, spacious, clean, just what we needed. All the amenities were as promised. We loved the stay."
Ismael
$201 nightly
The price is $226
Nov 30 - Dec 1
Total with taxes and fees
12. Fire Pit & Yard: Updated Winter Garden Home!
Fire Pit & Yard: Updated Winter Garden Home!Winter Garden
9.6 out of 10, Exceptional, (12 reviews)
"Amazing House! Would stay again anytime!"
Patrick O.
$428 nightly
The price is $478
Nov 15 - Nov 16
Total with taxes and fees
13. Winter Garden Family-friendly Condo w Resort Pool
Winter Garden Family-friendly Condo w Resort PoolWinter Garden
$235 nightly
The price is $264
Nov 30 - Dec 1
Total with taxes and fees
14. Family-Friendly 2BR Condo w Resort Pool & Sauna
Family-Friendly 2BR Condo w Resort Pool & SaunaWinter Garden
$221 nightly
The price is $248
Nov 30 - Dec 1
Total with taxes and fees
15. Upstay: Stylish 3BR Condo w Patio—near Disney
Upstay: Stylish 3BR Condo w Patio—near DisneyWinter Garden
$235 nightly
The price is $264
Nov 29 - Nov 30
Total with taxes and fees
16. Modern 3BR Condo Near Disney- Pool and Hot Tub
Modern 3BR Condo Near Disney- Pool and Hot TubWinter Garden
$226 nightly
The price is $226
Nov 17 - Nov 18
Total with taxes and fees
17. Upstay - Condo w Pool - Near Disney!
Upstay - Condo w Pool - Near Disney!Winter Garden
10.0 out of 10, Exceptional, (2 reviews)
"It was a very nice condo. "
Mellodie L.
$258 nightly
The price is $292
Nov 19 - Nov 20
Total with taxes and fees
18. Upstay: 3BR Family Condo w Pool & Sauna
Upstay: 3BR Family Condo w Pool & SaunaWinter Garden
$235 nightly
The price is $264
Nov 30 - Dec 1
Total with taxes and fees
19. Upstay Disney Pet Friendly Condo w Pool Spa Games
Upstay Disney Pet Friendly Condo w Pool Spa GamesWinter Garden
10.0 out of 10, Exceptional, (1 review)
$222 nightly
The price is $250
Nov 30 - Dec 1
Total with taxes and fees
20. Modern Pet-Friendly 2BR Condo—6 mins from Disney
Modern Pet-Friendly 2BR Condo—6 mins from DisneyWinter Garden
10.0 out of 10, Exceptional, (1 review)
"I was very impressed pictures did no justice, it was extremely clean, host was friendly and easy to access."
Tay T.
$226 nightly
The price is $254
Nov 30 - Dec 1
Total with taxes and fees
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
Home2 Suites by Hilton Orlando at Flamingo Crossings
10/10 Excellent
Price trends for vacation rentals in Winter Garden
Less expensive | More expensive | This month | Next month |
|---|---|---|---|
April | February | $235 | $284 |
Month | Price |
|---|---|
January | $287 |
February | $293 |
March | $221 |
April | $202 |
May | $202 |
June | $220 |
July | $217 |
August | $213 |
September | $219 |
October | $223 |
November | $235 |
December | $284 |
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Winter Garden. Select dates and complete search for nightly totals inclusive of taxes and fees.
Find out more about Winter Garden
Everything you need to know about Winter Garden vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Garden vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Garden vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Winter Garden vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Winter Garden. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Garden in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $89 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Winter Garden rentals
At Expedia, we put the best Winter Garden vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Winter Garden rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Garden vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Garden. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
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