Winter Garden Vacation Rentals from $89: Search Short-Term Rentals

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

Formosa Valley Resort by UNE Homes : You might like this vacation home rental near Winter Garden. It 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

A balcony with a view of a natural landscape, a chair, and a table.

1. Upstay Large Family Condo w Pool, Sauna

Winter Garden

$208 nightly

Dec 2 - Dec 3

Total with taxes and fees

A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a refrigerator.

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

Winter Garden

Steve S.

$310 nightly

Nov 17 - Nov 18

Total with taxes and fees

A spacious lobby with a high ceiling, exposed brick walls, and modern lighting fixtures.

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

Winter Garden

isaac

$349 nightly

Nov 16 - Nov 17

Total with taxes and fees

An aerial view of a coastal property with a swimming pool, tennis courts, and a marina.

4. StylishAptWtrGrdnOppLake&Prk&Yrd

Winter Garden

Lindsey W.

$175 nightly

Nov 18 - Nov 19

Total with taxes and fees

A spacious living area with a modern sofa set, a coffee table, and a decorative vase.

5. The Garden Luxe Retreat

Winter Garden

Corey K.

$393 nightly

Nov 29 - Nov 30

Total with taxes and fees

A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.

6. Upstay - Condo Near Disney w Pool-spa-sauna-games

Winter Garden

$214 nightly

Nov 30 - Dec 1

Total with taxes and fees

Stunning Aerial View Of The Property Surrounded By Nature

7. Family Fun Condo Pool and Sauna near Disney

Winter Garden

Adolat

$237 nightly

Nov 29 - Nov 30

Total with taxes and fees

8. FunTropicalTinyHomeGolfCartLake

Winter Garden

Emily R.

$191 nightly

Nov 16 - Nov 17

Total with taxes and fees

A living room with a sectional sofa, a wooden coffee table, and a ceiling fan.

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

Winter Garden

$444 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern interior with a curved sectional sofa, a round coffee table with a plant, and a brick wall.

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

Winter Garden

"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

$336 nightly

Nov 29 - Nov 30

Total with taxes and fees

11. Upstay: Stylish 3BR Condo w Pationear Disney

Winter Garden

Ismael

$203 nightly

Nov 30 - Dec 1

Total with taxes and fees

A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

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

Winter Garden

Patrick O.

$428 nightly

Nov 15 - Nov 16

Total with taxes and fees

Aerial View Of The Resort-Style Complex Featuring A Large Pool And Serene Surroundings

13. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden

$234 nightly

Nov 17 - Nov 18

Total with taxes and fees

14. Family-Friendly 2BR Condo w Resort Pool & Sauna

Winter Garden

$221 nightly

Nov 30 - Dec 1

Total with taxes and fees

15. Upstay: Stylish 3BR Condo w Patio—near Disney

Winter Garden

$237 nightly

Nov 30 - Dec 1

Total with taxes and fees

16. Modern 3BR Condo Near Disney- Pool and Hot Tub

Winter Garden

$227 nightly

Nov 17 - Nov 18

Total with taxes and fees

17. Upstay - Condo w Pool - Near Disney!

Winter Garden

Mellodie L.

$260 nightly

Nov 19 - Nov 20

Total with taxes and fees

18. Upstay: 3BR Family Condo w Pool & Sauna

Winter Garden

$235 nightly

Nov 29 - Nov 30

Total with taxes and fees

19. Upstay Disney Pet Friendly Condo w Pool Spa Games

Winter Garden

$222 nightly

Nov 30 - Dec 1

Total with taxes and fees

A spacious living room with a sofa, a coffee table, and a TV. There are large windows with curtains, a balcony, and a ceiling fan.

20. Modern Pet-Friendly 2BR Condo—6 mins from Disney

Winter Garden

Tay T.

$235 nightly

Nov 29 - Nov 30

Total with taxes and fees

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Top Winter Garden Hotel Reviews

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent

"The staff were amazing. Ismael at the front desk was training, but was doing a wonderful job. All other front desk staff were also very helpful and very friendly. I truly appreciated that. Breakfast was good, although my partner wanted the diced potatoes every day and they switched out certain items each day."

Homewood Suites by Hilton Orlando at Flamingo Crossings

8/10 Good

"Great hotel. The room was pretty good. I didn't love bed but other than that is was good. The breakfast was very nice and the pool was great for kids. A big water slide and lots of fun. It's also in a shopping district area with a target, coffee places, gas stations and restaurants all within walking distance. That was great! We were able to pick up all the supplies we needed for our room and get dinner while walking around the beautiful area."

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent

"Where to begin on our magical experience here!?! This was my mom's first trip to Florida and we hoped that by already experiencing Hilton Vacation properties that this one would live up to the others, and it did! What extraordinary staff! Graham, our director of food and beverages, took extra special care of this vegetarian with a modified "Avocado Club" instead of turkey, two types of sauces (garlic and cilantro aiolis), blue cheese and a delicious side salad. The fried chicken Nashville hot was such a winner that it was ordered two days in a row, along with the smash burger (my normally small eater ate the whole thing!). Goran was our bartender and made us feel like we were on a cruise - so friendly and kind. Lots of activities - Frank was super patient with paddle boats and bikes, Guillerme was great with mini golf and slime. Pools had a little something for everyone - main pool behind the lobby is heated and there is a hot tub as well. Kids area had multiple water slides that adults loved too. Shallow areas to be close to the action, read a book and keep an eye on things too! Gym was fabulous - spacious, plenty of weights, 2 treads (never a wait) - would love if there was a Peloton there. Rooms are super clean - 2 bedroom is especially spacious with 2 baths. We were in the 1100 building and overlooked the wooded area - super peaceful to hear birds and watch butterflies while enjoying a cup of coffee."

Evermore Orlando Resort

10/10 Excellent

"We came to celebrate my husband's 60th birthday, just the two of us, and stayed in a beautiful four-bedroom flat. At check-in, I had booked the Bayfront online and initially received a city view we didn't understand the mishap., however the staff let us know there was a complimentary upgrade to the Bayfront, which was wonderful💕 My husband was delighted with the experience. We did need some air freshener in the apartment but otherwise it was clean.👌 The service was excellent. 🥰The staff made my husband feel amazing. surprising him with champagne, and a few appetizers.. They were all so kind and made us feel special. We will definitely return.🌟💕❤️💕"

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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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: You might like this vacation home rental near Winter Garden. It 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. Upstay Large Family Condo w Pool, Sauna

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

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

4. StylishAptWtrGrdnOppLake&Prk&Yrd

5. The Garden Luxe Retreat

6. Upstay - Condo Near Disney w Pool-spa-sauna-games

7. Family Fun Condo Pool and Sauna near Disney

8. FunTropicalTinyHomeGolfCartLake

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

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

11. Upstay: Stylish 3BR Condo w Pationear Disney

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

13. Winter Garden Family-friendly Condo w Resort Pool

14. Family-Friendly 2BR Condo w Resort Pool & Sauna

15. Upstay: Stylish 3BR Condo w Patio—near Disney

16. Modern 3BR Condo Near Disney- Pool and Hot Tub

17. Upstay - Condo w Pool - Near Disney!

18. Upstay: 3BR Family Condo w Pool & Sauna

19. Upstay Disney Pet Friendly Condo w Pool Spa Games

20. Modern Pet-Friendly 2BR Condo—6 mins from Disney

Find vacation rentals that suit your style

Top Winter Garden Hotel Reviews

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

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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