Winter Garden, FL Vacation Homes from AED 176

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Our top choices for Winter Garden vacation homes

1. FunTropicalTinyHomeGolfCartLake

Winter Garden

Emily R.

AED 729 total

includes taxes & fees

12 Nov - 13 Nov

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

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

Winter Garden

Patrick O.

AED 1,758 total

includes taxes & fees

12 Nov - 13 Nov

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

3. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden

AED 971 total

includes taxes & fees

17 Nov - 18 Nov

A covered outdoor swimming pool with lounge chairs and a hot tub.

4. Private Spacious Room in Home, with Pool-The Oasis Room

Clermont

Juan m.

AED 366 total

includes taxes & fees

12 Nov - 13 Nov

A front door with a glass panel, a wreath, and a doormat with a welcoming message.

5. Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!

College Park

Kevin G.

AED 649 total

includes taxes & fees

16 Nov - 17 Nov

A decorative stone fountain with a twisted base, surrounded by vibrant red flowers and tropical foliage, set against a backdrop of a pool and palm trees.

6. Maple Leaf Inn & Suites

Kissimmee

Alex

AED 246 total

includes taxes & fees

12 Nov - 13 Nov

7. Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

Apopka

Naiviv

AED 486 total

includes taxes & fees

16 Nov - 17 Nov

A house with a porch, a door with a sign, and two chairs.

8. Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.

West Lakes District

chelsea

AED 540 total

includes taxes & fees

16 Nov - 17 Nov

A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

9. CUTE and COZY studio w/ jacuzzi!

Azalea Park

Lindsay W.

AED 629 total

includes taxes & fees

12 Nov - 13 Nov

A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

10. Midway between Disney and the Gulf beaches

Polk City

Herb

AED 771 total

includes taxes & fees

21 Nov - 22 Nov

11. Charming 2-bedroom apartment in house with AC, WiFi included

Apopka

Kevin S.

AED 478 total

includes taxes & fees

15 Nov - 16 Nov

A bed with white bedding and two blue pillows with a coral reef design, a tall green plant beside the bed, and a window with grey curtains in the background.

12. Studio in the heart of Orlando

Azalea Park

Matthew

AED 551 total

includes taxes & fees

17 Nov - 18 Nov

A modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

13. Sunshine Escape Guesthouse ☀

Orlando

Robin R.

AED 596 total

includes taxes & fees

17 Nov - 18 Nov

A suburban house with a garage, a driveway, and well-maintained landscaping.

14. Cozy private Room Close to Theme Parks and Airport

Southchase

Anthony S.

AED 445 total

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with a large island, double sinks, and a view to the outside.

15. Sunset Greens Villa

Reunion

Richard

AED 1,401 total

includes taxes & fees

17 Nov - 18 Nov

A modern living room with a sofa, coffee table, and a TV mounted on the wall.

16. 5Br Davenport Home W/ Pool & Private Hot Tub

Solterra Resort

AED 2,438 total

includes taxes & fees

9 Dec - 10 Dec

A modern kitchen with dark cabinets, stainless steel appliances, a black refrigerator, a microwave, and a bar area with white bar stools.

17. 3BR townhouse at Fiesta Key in kissimmee

Kissimmee

AED 1,288 total

includes taxes & fees

29 Nov - 30 Nov

A modern living room with a sofa, red chairs, a dining table with a vase of flowers, and a TV displaying a movie poster.

18. Tiny tropical Orlando Univesal-Disney

Orlando

Allison C.

AED 733 total

includes taxes & fees

16 Nov - 17 Nov

A compact kitchen with white cabinets, a microwave, and a stove. There is a dining area with a black table, white plates, and a vase of flowers.

19. Entire Guest House in Orlando, Florida

Tangelo Park

James V.

AED 499 total

includes taxes & fees

16 Nov - 17 Nov

A spacious living room with a ceiling fan, a door, a window with blinds, and a patterned rug.

20. Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Azalea Park

River

AED 974 total

includes taxes & fees

12 Nov - 13 Nov

View all properties

Learn more about Winter Garden

Stroll the charming brick-lined streets of historic downtown where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre.

See all hotels in Winter Garden

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

Top reviews in Winter Garden

A swimming pool with a hot tub, surrounded by lush tropical plants and a covered seating area.

Allamanda Holiday Home 4 Bedroom

Seasons

10/10 Excellent

Steven

A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

Luxury House - Sleeps 8 Golf Disney Family Fun

Ventura

8/10 Good

myron

Shake Shack Heated Pool & Hot Tub

Kissimmee

10/10 Excellent

Keith

A water park with a pool, slides, and a water fountain.

Luxury 6BR Villa w Pool Jacuzzi Fun in Orlando

Kissimmee

10/10 Excellent

Great Experience – Highly Recommended! I had a wonderful experience from start to finish. The host, Luciana, was incredibly attentive throughout the entire process—clear communication, quick responses, and a welcoming attitude. The property itself was in excellent condition: very clean, comfortable, and well-maintained. It had everything we needed for a great stay. We visit Orlando frequently, and I would absolutely consider booking this place again in the future. Highly recommended!

eddy

Search Vacation Homes in Winter Garden

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Winter Garden vacation homes

1. FunTropicalTinyHomeGolfCartLake

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

3. Winter Garden Family-friendly Condo w Resort Pool

4. Private Spacious Room in Home, with Pool-The Oasis Room

5. Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!

6. Maple Leaf Inn & Suites

7. Charming 1-bedroom mother-in-law suite w/ full kitchen in delightful Apopka

8. Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.

9. CUTE and COZY studio w/ jacuzzi!

10. Midway between Disney and the Gulf beaches

11. Charming 2-bedroom apartment in house with AC, WiFi included

12. Studio in the heart of Orlando

13. Sunshine Escape Guesthouse ☀

14. Cozy private Room Close to Theme Parks and Airport

15. Sunset Greens Villa

16. 5Br Davenport Home W/ Pool & Private Hot Tub

17. 3BR townhouse at Fiesta Key in kissimmee

18. Tiny tropical Orlando Univesal-Disney

19. Entire Guest House in Orlando, Florida

20. Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Learn more about Winter Garden

Top reviews in Winter Garden

Allamanda Holiday Home 4 Bedroom

10/10 Excellent