Winter Garden Rentals
From $160 per night (USD)VRBO
Waterfront Luxury Airstream on An Orange Grove
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Escape to a 100+ Orange Grove in Winter Garden with stunning sunsets, rabbits hopping around the yard, and coyotes howli ...
From $160 per night (USD)VRBO
From $275 per night (USD)VRBO
Mid Century Hipster
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious and professionally decorated 3/2 on huge fenced lot with large shade trees in front. Plenty of room for both sm ...
From $275 per night (USD)VRBO
From $162 per night (USD)VRBO
16 Mi to Disney: Cottage w/ Deck in Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Adventures big or small await at this 1-bedroom, 1-bathroom vacation rental in Winter Garden! This newly renovated cotta ...
From $162 per night (USD)VRBO
From $189 per night (USD)Expedia
Enchanted 3 Bedroom Home near Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
On vacation, relocating, or you just need temporary housing, this home gives you the flexibility and the convenience you ...
From $189 per night (USD)Expedia
From $219 per night (USD)VRBO
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your Winter Garden retreat begins at this 2-bedroom, 1-bathroom vacation rental cottage offering old Florida charm, hist ...
From $219 per night (USD)VRBO
From $232 per night (USD)Expedia
House with large deck, walking distance to Historic Downtown Winter Garden
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This completely renovated 2/2 Bungalow is the essence of the Winter Garden experience. Large, inviting living room with ...
From $232 per night (USD)Expedia
From $113 per night (USD)VRBO
Cute & Cozy in Winter Garden FL.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
This memorable place is anything but ordinary. Conveniently located in Central Florida with many attractions nearby. A m ...
From $113 per night (USD)VRBO
From $74 per night (USD)Expedia
Modern Private Room With Private Entrance
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located room in Winter Garden, brand new queen size bed with pillow top ma ...
From $74 per night (USD)Expedia
From $204 per night (USD)VRBO
Spacious garage apartment in Winter Garden that sleeps four.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This 2BR, 1BA light-filled gem can accommodate four people and is located a short walk or bike ride to beautiful downtow ...
From $204 per night (USD)VRBO
From $335 per night (USD)Expedia
3 Bed Stylish Oasis+Fast WiFi+Pool+Gym
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Step into the comfort of this inviting 2BR 2Bath apartment in the upscale Casa Mirella in Windermere, FL. It promises a ...
From $335 per night (USD)Expedia
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Boho Oasis 20 min from disney, universal, & more
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our spacious and open floor plan features a large kitchen island, perfect for cooking up delicious meals and entertainin ...
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Stay A While
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our secluded away from home. Minutes away to supermarket, shopping stores, and 25 minutes away from theme par ...
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A place with a view
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our secluded away from home. Minutes away to supermarkets, shopping stores, dining and 25 minutes away from t ...
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Tranquil Oasis - Pool - Gym- Kid/Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax with the whole family at this peaceful place to stay. Listing Description Our spacious and open floor plan featu ...
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From $224 per night (USD)VRBO
Dtwn Winter Garden Home: 12 Mi to Disney!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Whether you’re looking for a Disney vacation or a charming city escape, this Winter Garden vacation rental is perfect fo ...
From $224 per night (USD)VRBO
From $169 per night (USD)Expedia
1BDR+Peaceful Stay+FastWifi+ Free Parking+Pool+Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our spacious and open floor plan features a large kitchen island, perfect for cooking up delicious meals and entertainin ...
From $169 per night (USD)Expedia
From $264 per night (USD)VRBO
Beautiful 4 Bedroom Farm House\n
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Quaint 4 bedrooms 2 bath farm house with modern vibe. Can sleep upto 11 guests. Indoor workout area. Fully equipped kitc ...
From $264 per night (USD)VRBO
From $199 per night (USD)VRBO
Modern Florida Bungalow: 3 Miles to Winter Garden!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This charming 2-bedroom, 2-bath vacation rental in the historic town of Oakland is the perfect hideaway for your next fa ...
From $199 per night (USD)VRBO
From $351 per night (USD)VRBO
Orlando 20 Guest Villa Centrally Located with Game Room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 20
Your family will be close to everything when you stay at this centrally-located place located in downtown Windermere! 4 ...
From $351 per night (USD)VRBO
From $146 per night (USD)Expedia
Quaint 1Br/Ba entire guest house in heart of Hist. Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Experience Winter Garden like a local in this 1-bedroom apartment. Private Dwelling, personal covered parking, picturesq ...
From $146 per night (USD)Expedia
From $174 per night (USD)VRBO
1921 Winter Garden home 22 min from Magic Kingdom & 15 min walking to Plant ST
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Beautifully renovated 1921 bungalow, less than 15 min walk to Plant St. farmers market, brewery, restaurants and boutiq ...
From $174 per night (USD)VRBO
From $357 per night (USD)VRBO
Eclectic Escape: Disney Proximity
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our Eclectic Orlando Retreat! Just 25 minutes from Disney, our spacious and uniquely decorated home offers a ...
From $357 per night (USD)VRBO
From $166 per night (USD)VRBO
Experience charming downtown Winter Garden! 1 block from it all!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This 1920's home in the heart of downtown Winter Garden has everything you need! The home has 2 bedrooms, one with a ki ...
From $166 per night (USD)VRBO
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FunTropicalTinyHomeGolfCartLake
- Bedrooms:
- 1
- Bathrooms:
- 7
- Sleeps:
- 5
Summary: Escape to our fun tropical Tiny Home, just 1-2 minutes from downtown Winter Garden and across the road from New ...
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From $913 per night (USD)VRBO
Central Florida's Historic Gem & wedding venue- The Oakland Manor House
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 13
Originally built in the early 1900’s, this gracious manor was carefully renovated, preserving its historic craftsman-sty ...
From $913 per night (USD)VRBO
From $156 per night (USD)VRBO
LUX BROWNSTONE in downtown Winter Garden FL 6 month minimum stay required
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This special place is close to everything. Just a few minutes walk to the coffee shops where you can enjoy a quite mor ...
From $156 per night (USD)VRBO
From $242 per night (USD)VRBO
The Garden Luxe Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedroom | 2 Bath | Prime Winter Garden Location | Near Disney & Universal Nestled in the heart of charming Winter Gar ...
From $242 per night (USD)VRBO
From $241 per night (USD)Expedia
Winter Garden Charm, Near Disney
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedroom | 2 Bath | Prime Winter Garden Location | Near Disney & Universal Nestled in the heart of charming Winter Gar ...
From $241 per night (USD)Expedia
From $241 per night (USD)VRBO
Emerald Grove - Close to Disney
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedroom | 2 Bath | Prime Winter Garden Location | Near Disney & Universal Nestled in the heart of charming Winter Gard ...
From $241 per night (USD)VRBO
From $103 per night (USD)Expedia
Cozy Studio in Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Historic Downtown Winter Garden location with Disney & Universal Minutes Away! Charming studio in Downtown Winter Garde ...
From $103 per night (USD)Expedia
From $188 per night (USD)VRBO
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This lovely ground floor NO Steps to climb apartment in Winter Garden Down Town area is a peaceful retreat for guests on ...
From $188 per night (USD)VRBO
From $190 per night (USD)Expedia
Just Renovated! Cozy 2BR Close to Disney
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Located in Winter Garden, enjoy what this 2-bedroom mobile home has to offer. With 1 queen bed, 1 full bed, and 1 twin b ...
From $190 per night (USD)Expedia