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 $251 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 $251 per night (USD)VRBO
From $205 per night (USD)VRBO
Spacious Winter Garden Home w\/ BBQ, Walk to Dwtn!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Nestled among a wealth of historical attractions, live entertainment, and outdoor recreation awaits ‘The Strawberry Hous ...
From $205 per night (USD)VRBO
From $186 per night (USD)Expedia
Winter Garden Bungalow w\/ Gas Grill, Walk to Dtwn!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the historical highlights of Winter Garden just steps from your door when you stay at ‘The Bungalow at The Stra ...
From $186 per night (USD)Expedia
From $316 per night (USD)VRBO
The Oak View Place..
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A private Suite with seperate entrance and own luxury Bathroom. The Oak View Place is something you will remember forev ...
From $316 per night (USD)VRBO
From $151 per night (USD)Expedia
Modern Winter Garden Cottage: 16 Mi to Disney
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Adventures big or small await at this 1-bedroom, 1-bathroom vacation rental in Winter Garden! This newly renovated cotta ...
From $151 per night (USD)Expedia
From $200 per night (USD)VRBO
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Your Winter Garden retreat begins at this 2-bedroom, 1-bathroom vacation rental cottage offering old Florida charm, hist ...
From $200 per night (USD)VRBO
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4 Bedroom, 3 Bath Home has 2,602 Square Feet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 4 bedroom, 3 bath home has 2,602 square feet of living space with so much more Amenities. Over sized Tub ...
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From $206 per night (USD)VRBO
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 $206 per night (USD)VRBO
From $507 per night (USD)Expedia
WATERFRONTWntrGdnHSE VIEWS Dock Wildlife 13mi Disn
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: Enjoy the breathtaking sunrise views of Lake Apopka from this newly refurbished and well appointed 4 bed, 2.5 b ...
From $507 per night (USD)Expedia
From $279 per night (USD)VRBO
10 mins to theme park! Family size spacious house with loft.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Beautiful spacios house in upscale neighborhood with nearby 5 min walk two mini malls with supermarket, restaurants, pha ...
From $279 per night (USD)VRBO
From $113 per night (USD)Expedia
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)Expedia
From $380 per night (USD)VRBO
Luxury 3BR King\/Queen Free Parking Near Disney
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stay in the heart of it all! Our centrally-located place puts you just minutes from Disney and Universal. Indulge in lux ...
From $380 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
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Luxury 2BDR \/Gated\/Resort Style Pool\/Gym\/FastWifi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Mirella Apartment Homes are centrally located in desirable Windermere FL. It is 20 minutes to Disney, 20 minutes t ...
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Our RV is located in winter garden near downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Guest accommodations at Our RV is located in winter garden near downtown offer air conditioning. Kitchens offer microwav ...
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From $178 per night (USD)VRBO
Luxury 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 $178 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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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 $220 per night (USD)Expedia
Spacious 2BDR Oasis w Resort Style Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our spacious and open floor plan features a large kitchen island, perfect fir cooking up delicious meals and entertainin ...
From $220 per night (USD)Expedia
From $219 per night (USD)VRBO
Downtown 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 $219 per night (USD)VRBO
From $120 per night (USD)VRBO
Private In-Law Suite with a lake view in a gated community
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Here is a spectacular pool home in the gated community of Wesmere! This gated community is conveniently located near are ...
From $120 per night (USD)VRBO
From $278 per night (USD)VRBO
Windermere CasaMirella · 2BR\/Modern\/Fast Wi-Fi\/Pool\/gym\/near Disney Parks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Create your experience as we welcome you to this centrally located Luxury Family, Friend, Travel nurse,and all ...
From $278 per night (USD)VRBO
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2BD Apt+Lake\/FountainView+Balcony, Resort Style Pool, Wi-Fi, Desk, Gym, Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Paradise is home at our apartment in Central Florida. Our resort-style community gives you every opportunity to enjoy a ...
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From $188 per night (USD)VRBO
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 $188 per night (USD)VRBO
From $121 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 $121 per night (USD)Expedia
From $260 per night (USD)VRBO
Large Studio Apartment Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Enjoy easy access to everything from this perfectly located home base. Located in Historic Downtown Winter Garden, You j ...
From $260 per night (USD)VRBO
From $157 per night (USD)Expedia
Cute Studio on the Bike trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Historic Downtown Winter Garden Gem - Explore & Relax! Discover our inviting studio in Downtown Winter Garden. Walk to ...
From $157 per night (USD)Expedia
From $199 per night (USD)VRBO
Cozy Orlando Oasis w\/Resort Style Pool\/Fast WiFi\/Free parking\/Gym\/Close To Parks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Our spacious and open floor plan features a large kitchen island, perfect for cooking up delicious meals and entertainin ...
From $199 per night (USD)VRBO
From $287 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 $287 per night (USD)VRBO
From $156 per night (USD)VRBO
Chic Studio in Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Uncover Winter Garden's allure at our chic studio apartment! Stroll to downtown's boutiques, cafes, and the lively farme ...
From $156 per night (USD)VRBO
From $253 per night (USD)Expedia
Updated Winter Garden Home w\/ Yard & Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
The best of Winter Garden awaits you at this lovely 2-bedroom, 2-bathroom vacation rental! Located near top attractions ...
From $253 per night (USD)Expedia
From $125 per night (USD)VRBO
Adorable 1-bedroom right on the bike trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy all that Historic Downtown Winter Garden has to offer in this centrally located apartment home. The West Orange Co ...
From $125 per night (USD)VRBO
From $325 per night (USD)Expedia
All-You-Need Studio Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the simplicity of perfection at our studio apartment – your all-in-one retreat in Historic Downtown Winter Gard ...
From $325 per night (USD)Expedia
From $221 per night (USD)VRBO
LUXE Apartment In Winter Garden. Near Disney.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Entire apartment in the prestigious Winter Garden neighborhood. Approximately 30 minutes drive to Disney, Orlando Intern ...
From $221 per night (USD)VRBO
From $195 per night (USD)Expedia
Modern Florida Bungalow: 3 Miles to Winter Garden!
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $195 per night (USD)Expedia
From $391 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 $391 per night (USD)VRBO
From $1076 per night (USD)Expedia
Amaizing Villa Flores w\/hot tub located 30 minutes from Disney land Atractions.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Perfect for family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay, What ...
From $1076 per night (USD)Expedia
From $189 per night (USD)VRBO
Cozy 3 BR\/2 BA Downtown Winter Garden Cottage property.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy three-bedroom cottage with all the comforts of home. Walking/Biking distance away from West Orange Trail and the H ...
From $189 per night (USD)VRBO
From $109 per night (USD)Expedia
Private Studio on the Bike Trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to Winter Garden's historic charm in the comfort of your own private studio. Reserve your stay now and experience ...
From $109 per night (USD)Expedia
From $253 per night (USD)VRBO
Learn how to camp RV style in this Lux RV which sleeps up to 8 people.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the gorgeous landscape that surrounds this luxury RV camper and get the best night sleep you’ve ever had. This ...
From $253 per night (USD)VRBO
From $267 per night (USD)VRBO
King Studio Suite Near Speer Park ORL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This property is 19 km from Disney's Magic Kingdom and 20 km from Amway Center. With a bar, This property has air-condit ...
From $267 per night (USD)VRBO
From $181 per night (USD)VRBO
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 $181 per night (USD)VRBO
From $163 per night (USD)Expedia
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 $163 per night (USD)Expedia
From $290 per night (USD)VRBO
Charming 2-bedroom cottage in enchanting Winter Garden with AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a peaceful stay at this 2-bedroom cottage in Winter Garden. This awesome property features a king bed and a queen ...
From $290 per night (USD)VRBO
From $298 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 $298 per night (USD)VRBO
From $506 per night (USD)VRBO
Luxurious Vacation Home in Beautiful Windermere, 20 Min. to Disney & Universal!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Nestled in Windermere, this lovely house boasts 5 bedrooms including 2 king beds, 1 queen bed, 1 twin bed, 1 murphy bed, ...
From $506 per night (USD)VRBO
From $185 per night (USD)Expedia
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 $185 per night (USD)Expedia
From $202 per night (USD)VRBO
StylishAptWtrGrdnOppLake&Prk&Yrd
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: *Brand new one bedroom apartment near downtown Winter Garden, across from Lake Apopka and Newton Park *Private ...
From $202 per night (USD)VRBO
From $256 per night (USD)Expedia
Charming Studio Apartment Near Downtown and Disney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover the perfect getaway in this delightful studio apartment, ideally located right across from the scenic West Oran ...
From $256 per night (USD)Expedia
From $761 per night (USD)VRBO
(381) Fantastic Home Near Disney 5BD\/5BT\/14P
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to the marvelously mod open living area with expertly-curated furnishings and decor, including comfortable seati ...
From $761 per night (USD)VRBO
From $203 per night (USD)Expedia
FunTropicalTinyHomeGolfCartLake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Escape to our fun tropical Tiny Home, just 1-2 minutes from downtown Winter Garden and across the road from New ...
From $203 per night (USD)Expedia