Winter Garden Vacation Rentals from $93: Search Short-Term Rentals

Q: What's the top vacation rental that Winter Garden has to offer?

Formosa Valley Resort by UNE Homes : This vacation home near Winter Garden is equipped with an outdoor pool, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

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Our top choices for Winter Garden vacation rentals

1. StylishAptWtrGrdnOppLake&Prk&Yrd

Winter Garden

Lindsey W.

$181 nightly

Sep 17 - Sep 18

Total with taxes and fees

2. Fire Pit & Yard: Updated Winter Garden Home!

Winter Garden

Patrick O.

$418 nightly

Sep 20 - Sep 21

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

3. Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL

Winter Garden

Steve S.

$298 nightly

Oct 6 - Oct 7

Total with taxes and fees

4. FunTropicalTinyHomeGolfCartLake

Winter Garden

Emily R.

$207 nightly

Sep 20 - Sep 21

Total with taxes and fees

5. Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room

Winter Garden

Anonymous traveler

$349 nightly

Sep 17 - Sep 18

Total with taxes and fees

6. Fire Pit & Yard: Updated Winter Garden Home!

Winter Garden

$444 nightly

Sep 20 - Sep 21

Total with taxes and fees

7. House with large deck, walking distance to Historic Downtown Winter Garden

Winter Garden

Sam M.

$345 nightly

Sep 29 - Sep 30

Total with taxes and fees

8. Cozy 1-bedroom with AC in awesome Winter Garden

Winter Garden

$327 nightly

Sep 21 - Sep 22

Total with taxes and fees

9. The Oak View Place..

Oakland

Libba F.

$249 nightly

Sep 17 - Sep 18

Total with taxes and fees

10. Modern Luxury Stay | 20 min to Disney

Winter Garden

$388 nightly

Oct 9 - Oct 10

Total with taxes and fees

11. WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

Winter Garden

Tim S.

$512 nightly

Sep 20 - Sep 21

Total with taxes and fees

12. Upstay - Condo w Hot Tub and Pool - Near Disney

Winter Garden

$232 nightly

Sep 20 - Sep 21

Total with taxes and fees

13. Upstay: Condo Near Disney w Pool, Sauna

Winter Garden

"The unit was very clean and organized when we arrived. All the amenities and appliances that come with the unit worked amazing. The only exception was the WiFi. It was a bit slow, however this could be easily fixed and should not discourage from booking this property. Being at the pool was the highlight of staying at this property. It was clean and came with fun pool sized amenities like pool basketball and connect 4. Being in the lobby was also fun with the ping pong table and pool table. The...

Nancy

$215 nightly

Sep 21 - Sep 22

Total with taxes and fees

14. Family Fun Condo Pool and Sauna near Disney

Winter Garden

John and Dawn R.

$259 nightly

Sep 19 - Sep 20

Total with taxes and fees

15. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden

$241 nightly

Sep 17 - Sep 18

Total with taxes and fees

16. Studio Near Disney World Resort with Pools + more

Kissimmee

$192 nightly

Sep 20 - Sep 21

Total with taxes and fees

17. 1-Bedroom Villa Near Disney w/ Pool & Lazy River

Kissimmee

$220 nightly

Sep 20 - Sep 21

Total with taxes and fees

18. Upstay: Resort Style Condo w Pool, Sauna

Winter Garden

Ashlynn D.

$216 nightly

Sep 17 - Sep 18

Total with taxes and fees

19. Upstay - Condo w Pool and More - Near Disney

Winter Garden

SHARLA B.

$258 nightly

Sep 24 - Sep 25

Total with taxes and fees

20. Upstay Disney Pet Friendly Condo w Pool Spa Games

Winter Garden

$215 nightly

Sep 21 - Sep 22

Total with taxes and fees

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Top Winter Garden Hotel Reviews

Universal's Cabana Bay Beach Resort

8/10 Good

"Great stay, had an upgrade to a suite brilliant will definitely book again"

Kompose Boutique Resort at Theme Parks

8/10 Good

"Overall a great hotel for the money. Staff were excellent. Rooms were very clean and beds were comfortable. Very little furniture in the room and the shower was only partially closed allowing water to spill onto the floor and cold air to enter. Elevators are very far from most of the rooms. Breakfast was better than most hotels I have stayed at. I would definitely stay at this hotel again."

Marriott's Grande Vista

8/10 Good

"Marriott has a great location with close proximity to Sea World. I was a bit surprised by the amount of the required deposit ($500) at check in.. In addition to the $30 per day self-parking charge (valet is NOT available); I was out of $750 at check in. That meant I essentially paid for my stay once online and then at check in I paid about 85% of that price AGAIN in deposits and parking fees. Also I was SHOCKED to find house-keeping was an ADDITIONAL fee on top of all of this. I thought for a five night stay there would be at least ONE housekeeping session included.. NOT AT ALL. Aside from the absolute nickel and dime fees for EVERYTHING and the VERY aggressive sales pressure to buy their timeshares package. The room was great. The location very convenient. Just be prepared for a substantial deposit when you stay here and beware that they are VERY aggressive in trying to get you to their timeshare sales presentation. A plus is also that their pools stay open until 11pm and they have multiple pools on site."

Price trends for vacation rentals in Winter Garden

Less expensive	More expensive	Next month
April	February	$223

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 $93 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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Things to do in Winter Garden

Frequently asked questions

Can I find a vacation rental in Winter Garden?

Yes, we offer vacation rentals in Winter Garden close to Surfari Water Park, or you can go with a more remote option if you'd like a relaxing place to stay. Tourists who visit Winter Garden speak highly of the fun-filled theme parks and array of shops. While you're here, grab a bite or have a drink at the top-notch restaurants.

What's the top vacation rental that Winter Garden has to offer?

Formosa Valley Resort by UNE Homes: This vacation home near Winter Garden is equipped with an outdoor pool, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

How many vacation rentals are there in Winter Garden?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Winter Garden stay.

What can I see and do in Winter Garden?

Family-friendly attractions include Surfari Water Park and Central Florida Railroad Museum, whereas Lake Louisa State Park and West Orange Trail are a couple of great spots to enjoy the outdoors. Universal Studios Florida and Universal Orlando Resort are other popular places to visit in the area.

What are vacation rentals like in Winter Garden?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Winter Garden. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips.

Winter Garden Vacation Rentals

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Check prices for these dates

Our top choices for Winter Garden vacation rentals

1. StylishAptWtrGrdnOppLake&Prk&Yrd

2. Fire Pit & Yard: Updated Winter Garden Home!

3. Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL

4. FunTropicalTinyHomeGolfCartLake

5. Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room

6. Fire Pit & Yard: Updated Winter Garden Home!

7. House with large deck, walking distance to Historic Downtown Winter Garden

8. Cozy 1-bedroom with AC in awesome Winter Garden

9. The Oak View Place..

10. Modern Luxury Stay | 20 min to Disney

11. WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

12. Upstay - Condo w Hot Tub and Pool - Near Disney

13. Upstay: Condo Near Disney w Pool, Sauna

14. Family Fun Condo Pool and Sauna near Disney

15. Winter Garden Family-friendly Condo w Resort Pool

16. Studio Near Disney World Resort with Pools + more

17. 1-Bedroom Villa Near Disney w/ Pool & Lazy River

18. Upstay: Resort Style Condo w Pool, Sauna

19. Upstay - Condo w Pool and More - Near Disney

20. Upstay Disney Pet Friendly Condo w Pool Spa Games

Find vacation rentals that suit your style

Top Winter Garden Hotel Reviews

Universal's Cabana Bay Beach Resort

Price trends for vacation rentals in Winter Garden

Find out more about Winter Garden

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

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