Winter Garden Holiday Rentals from AU$307: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Winter Garden has to offer?

Formosa Valley Resort by UNE Homes : This holiday home rental outside 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 holiday rentals

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

1. StylishAptWtrGrdnOppLake&Prk&Yrd

Winter Garden

Lindsey W.

includes taxes & fees

18 Nov - 19 Nov

2. FunTropicalTinyHomeGolfCartLake

Winter Garden

Emily R.

includes taxes & fees

12 Nov - 13 Nov

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

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

Winter Garden

Steve S.

includes taxes & fees

11 Nov - 12 Nov

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

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

Winter Garden

isaac

includes taxes & fees

1 Dec - 2 Dec

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

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

Winter Garden

includes taxes & fees

11 Nov - 12 Nov

6. Upstay: Stylish 3BR Condo w Pationear Disney

Winter Garden

Ismael

includes taxes & fees

29 Nov - 30 Nov

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

7. 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 traveller

includes taxes & fees

8 Dec - 9 Dec

8. Upstay Stylish 3BR Condo w Patio Near Disney

Winter Garden

includes taxes & fees

6 Dec - 7 Dec

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

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

Winter Garden

Patrick O.

includes taxes & fees

11 Nov - 12 Nov

A spacious living area with a dining table, chairs, a sofa, and a kitchen in the background.

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

Winter Garden

Thomas C.

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

Winter Garden

includes taxes & fees

18 Nov - 19 Nov

Discover the winding lazy river, perfect for a refreshing float on a sunny day.

12. Studio Near Disney World Resort with Pools + more

Kissimmee

includes taxes & fees

30 Nov - 1 Dec

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

includes taxes & fees

11 Nov - 12 Nov

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.

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

Winter Garden

includes taxes & fees

8 Dec - 9 Dec

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

Winter Garden

includes taxes & fees

8 Dec - 9 Dec

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

16. Upstay Large Family Condo w Pool, Sauna

Winter Garden

includes taxes & fees

11 Nov - 12 Nov

Stunning Aerial View Of The Property Surrounded By Nature

17. Family Fun Condo Pool and Sauna near Disney

Winter Garden

John and Dawn R.

includes taxes & fees

18 Nov - 19 Nov

18. Upstay - Condo Near Disney w Pool Hot tub Sauna

Winter Garden

includes taxes & fees

17 Nov - 18 Nov

A balcony with a ceiling fan, a white cushioned chair, a small table, and a potted plant.

19. Upstay - Pet-Friendly Condo - Sauna, Pool

Winter Garden

KELLEE

includes taxes & fees

18 Nov - 19 Nov

20. Upstay Modern 2BR Condo Near Disney

Winter Garden

includes taxes & fees

8 Dec - 9 Dec

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Find holiday rentals that suit your style

Top Winter Garden Hotel Reviews

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

10/10 Excellent

Jade

A large hotel with multiple floors, a central courtyard, and a reflective water feature.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

10/10 Excellent

Amiel

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

10/10 Excellent

Kerryn

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Bay Lake

10/10 Excellent

Vincent

An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

10/10 Excellent

Kim Louise

A swimming pool with a slide and a small waterfall feature, surrounded by lounge chairs and umbrellas.

Homewood Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

10/10 Excellent

Amiel

A pool area with lounge chairs, a fire pit, and palm trees.

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Bay Lake

10/10 Excellent

Jane

A swimming pool with a rock formation centerpiece, lounge chairs, and umbrellas.

Hilton Vacation Club Aqua Sol Orlando West

Winter Garden

10/10 Excellent

Brad

A resort with multiple swimming pools, lounge areas, and a view of the sea.

The Grove Resort & Water Park Orlando

Winter Garden

10/10 Excellent

Amar

A spacious lobby with a high ceiling, two exits, and comfortable seating areas with tables and chairs.

Hilton Vacation Club Polynesian Isles Kissimmee

Kissimmee

10/10 Excellent

Fantastic place for our 3 weeks for 4 in a 2 bed place. Had 2 bathrooms and excellent kitchen with dishwasher and own laundry. Great staff and easy location to all Disney and Universal at a fraction of the cost of their properties. Apartment was huge and plenty of space. Only cleaned once a week but this was fine as we are used to doing it ourselves and also felt much less intrusive and could just "feel at home". Thanks Polynesian team!

Mark

Find out more about Winter Garden

Everything you need to know about Winter Garden holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Garden holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Winter Garden holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter Garden holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter Garden holiday rentals we have selected for you start as low as AU$307 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winter Garden rentals

At Expedia, we put the best Winter Garden holiday 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 holiday.

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.

Frequently Asked Questions

Can I find a holiday rental in Winter Garden?

Yes, there are holiday rentals in Winter Garden close to Surfari Water Park, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Winter Garden has to offer?

Formosa Valley Resort by UNE Homes: This holiday home rental outside 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 holiday rentals are there in Winter Garden?

With 6 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Winter Garden?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Garden. Holiday rentals feature amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.

Winter Garden Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Garden holiday rentals

1. StylishAptWtrGrdnOppLake&Prk&Yrd

2. FunTropicalTinyHomeGolfCartLake

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

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

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

6. Upstay: Stylish 3BR Condo w Pationear Disney

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

8. Upstay Stylish 3BR Condo w Patio Near Disney

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

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

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

12. Studio Near Disney World Resort with Pools + more

13. Winter Garden Family-friendly Condo w Resort Pool

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

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

16. Upstay Large Family Condo w Pool, Sauna

17. Family Fun Condo Pool and Sauna near Disney

18. Upstay - Condo Near Disney w Pool Hot tub Sauna

19. Upstay - Pet-Friendly Condo - Sauna, Pool

20. Upstay Modern 2BR Condo Near Disney

Find holiday rentals that suit your style

Top Winter Garden Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

Find out more about Winter Garden

Winter Garden holiday rentals: An excellent choice for every season

How to find incredible deals on Winter Garden rentals

Frequently Asked Questions

Can I find a holiday rental in Winter Garden?

What are some of the best holiday rentals that Winter Garden has to offer?

How many holiday rentals are there in Winter Garden?

What can I see and do in Winter Garden?

What are holiday rentals like in Winter Garden?