Winter Garden Vacation Rentals from ￥9,333: Search Short-Term Rentals

A brick building with a clock tower and a sign that reads "Winter Garden."

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Our top choices for Winter Garden vacation rentals

A multi-story building with a corner tower, surrounded by palm trees and greenery.

1. Upstay Large Family Condo w Pool, Sauna

Winter Garden

￥38,086 total

includes taxes & fees

Dec 8 - Dec 9

A TopGolf facility with a brightly lit driving range, a well-lit entrance, and a parking area.

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

Winter Garden

Steve S.

￥54,822 total

includes taxes & fees

Nov 17 - Nov 18

A modern lounge area with a curved sofa, a round coffee table, and a TV mounted on the wall.

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

Winter Garden

isaac

￥62,799 total

includes taxes & fees

Nov 16 - Nov 17

4. StylishAptWtrGrdnOppLake&Prk&Yrd

Winter Garden

Lindsey W.

￥31,036 total

includes taxes & fees

Nov 19 - Nov 20

A modern living room with a pool table, a sofa, a coffee table, and a large window with a view.

5. The Garden Luxe Retreat

Winter Garden

Corey K.

An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

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

Winter Garden

￥38,460 total

includes taxes & fees

Nov 30 - Dec 1

Stunning Aerial View Of The Property Surrounded By Nature

7. Family Fun Condo Pool and Sauna near Disney

Winter Garden

Adolat

￥40,436 total

includes taxes & fees

Nov 17 - Nov 18

A wooden deck with a seating area, a table, and a covered structure with a sign reading "TIMBERWOLE".

8. FunTropicalTinyHomeGolfCartLake

Winter Garden

Emily R.

￥34,909 total

includes taxes & fees

Nov 17 - Nov 18

A house with a brick patio, outdoor seating, and a small garden.

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

Winter Garden

￥79,744 total

includes taxes & fees

Nov 15 - Nov 16

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

￥59,382 total

includes taxes & fees

Nov 17 - Nov 18

11. Upstay: Stylish 3BR Condo w Pationear Disney

Winter Garden

Ismael

￥37,105 total

includes taxes & fees

Nov 30 - Dec 1

A porch with a white railing, a blue door, and a potted plant.

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

Winter Garden

Patrick O.

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

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

Winter Garden

￥51,027 total

includes taxes & fees

Nov 20 - Nov 21

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

Winter Garden

￥42,207 total

includes taxes & fees

Nov 29 - Nov 30

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

Winter Garden

￥36,303 total

includes taxes & fees

Nov 29 - Nov 30

17. Upstay - Condo w Pool - Near Disney!

Winter Garden

Mellodie L.

￥46,592 total

includes taxes & fees

Nov 19 - Nov 20

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

Winter Garden

19. Upstay Disney Pet Friendly Condo w Pool Spa Games

Winter Garden

￥39,871 total

includes taxes & fees

Nov 30 - Dec 1

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.

￥64,254 total

includes taxes & fees

Nov 20 - Nov 21

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Find vacation 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

Amy Dawn

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

We had an excellent stay! The hotel is clean, modern, and very well-appointed, with comfortable rooms that made us feel right at home. Traveling with our toddler, we found everything to be exceptional—the accommodations were spacious and family-friendly. The free breakfast was a fantastic bonus, with a variety of options, including some vegan-friendly choices, which we really appreciated. The staff was welcoming and attentive, ensuring we had everything we needed for a great stay. We would...

Nicolette

A large indoor swimming pool surrounded by lounge chairs and umbrellas, with a hotel building in the background.

Rosen Shingle Creek

Orlando

10/10 Excellent

Narciso

A spacious lobby with a leather sofa, a bar area with stools, and a seating area with tables and chairs.

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

10/10 Excellent

Chris

A stone wall, a brown sofa with orange and yellow cushions, a glass table with a fire feature, and a wooden door with decorative glass panels.

The Delaney Hotel

South Orange

10/10 Excellent

Chelsea

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

Bharat

A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.

Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

10/10 Excellent

Joel

A multi-story hotel with a central courtyard, large windows, and a mix of balconies and arches.

Homewood Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

10/10 Excellent

The property was amazing it is 10 mins away from Disney parks and 5 mins away from the Disney entrance gates. There is a target, 5-below, lime fresh Mexican grill, and a Starbucks at walking distance. The pool is very large and amazing for kids. The hotel rooms are very large with pull couches, comfortable beds, and a fully stocked kitchen perfect cooking. The hotel staff is on another level they offer top-tier service at all hours. The free breakfast is great. Parking is 20 dollars per day and...

Jada

A resort with multiple swimming pools, a large central pool, and a lake.

Embassy Suites By Hilton Orlando Sunset Walk

Kissimmee

10/10 Excellent

This property gave me international resort vibes in Florida. It really was an oasis. I had a two bedroom and our party was five, three were children. The entire property is clean. The staff from the front desk to the support staff were polite and professional. Great location, if you only want to drive a couple of minutes for access to restaurants, you're in a perfect location. It's also not too far out from the theme parks. TIP: There is a $40 daily resort fee that will be deducted from your...

Serene

A resort pool area with a winding pool design, lounge chairs, and palm trees.

Kompose Boutique Resort at Theme Parks

Kissimmee

10/10 Excellent

Patrik

A modern building with a distinctive facade featuring circular windows and a reflective water feature in front.

Universal's Stella Nova Resort

Orlando

10/10 Excellent

A multi-story hotel with a prominent red sign, a well-lit entrance, and a landscaped front yard.

Hampton Inn & Suites Orlando Airport @ Gateway Village

Airport North

10/10 Excellent

Christine

A hotel room with a bed, bedside table, lamp, and a view of the sky through a window.

Hyatt House Orlando International Drive

International Drive District

10/10 Excellent

jordan

A spacious lobby with a central seating area, a reception desk, and a visible staircase leading to other floors.

Pestana Orlando Suites - Lake Buena Vista

Orlando

10/10 Excellent

Christopher

A swimming pool surrounded by lounge chairs and umbrellas, with a hotel building in the background.

Universal's Endless Summer Resort - Surfside Inn and Suites

International Drive District

10/10 Excellent

The beginning of a great stay started with Carmen at the front desk. We felt welcomed, informed and appreciated. I read reviews about the hot water, but we had no problem; the shower was great with adequate hot water. The rooms were clean and cleaned daily. The mattresses isn’t plush but I slept well. The shuttle to City Walk and Universal Studios theme parks and early entry into parks was a plus. The restaurant and Starbucks on property were convenient. The property is in a great location and...

Tanya

Find out more about Winter Garden

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Look no further and take a look at our great range of rental properties in Winter Garden!

Winter Garden Vacation Rentals

Change your mind

Treat yourself

Be picky

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

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

Find out more about Winter Garden