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Winter Garden Rentals

$Pet friendly Botanical Florida house w\/back deck\/fence in heart of Winter Garden$
From $180 per night (USD)
VRBO
Pet friendly Botanical Florida house w\/back deck\/fence in heart of Winter Garden
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Next to Veterans park and West Orange Trail and Historic Downtown Winter Garden, property is private, fenced w/ deck. Tr ...
From $180 per night (USD)
VRBO
From $135 per night (USD)
Expedia
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 $135 per night (USD)
Expedia
$Spacious Winter Garden Home w\/ BBQ, Walk to Dwtn!$
From $124 per night (USD)
VRBO
Spacious Winter Garden Home w\/ BBQ, Walk to Dwtn!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled among a wealth of historical attractions, live entertainment, and outdoor recreation awaits ‘The Strawberry Hous ...
From $124 per night (USD)
VRBO
$Winter Garden Bungalow w\/ Gas Grill, Walk to Dtwn!$
From $113 per night (USD)
Expedia
Winter Garden Bungalow w\/ Gas Grill, Walk to Dtwn!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the historical highlights of Winter Garden just steps from your door when you stay at ‘The Bungalow at The Stra ...
From $113 per night (USD)
Expedia
From $115 per night (USD)
VRBO
Modern Winter Garden Cottage: 16 Mi to Disney
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 $115 per night (USD)
VRBO
From $160 per night (USD)
Expedia
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
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 $160 per night (USD)
Expedia
$Luxury 3BR King\/Queen Free Parking Near Disney$
From $100 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 $100 per night (USD)
VRBO
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Expedia
1 Bedroom Apartment 420738 by Houzlet
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One or more photo(s) has been virtually staged. Under Construction. NOW PRE-LEASING! Move in anticipated for January 15, ...
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Expedia
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Expedia
1 Bedroom Apartment 420740 by Houzlet
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One or more photo(s) has been virtually staged. Under Construction. NOW PRE-LEASING! Move in anticipated for January 15, ...
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Expedia
Click For Pricing
Expedia
2 Bedroom Apartment 420736 by Houzlet
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
One or more photo(s) has been virtually staged. Under Construction. NOW PRE-LEASING! Move in anticipated for January 15, ...
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Expedia
From $99 per night (USD)
VRBO
Chic Studio in Winter Garden
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Uncover Winter Garden's allure at our chic studio apartment! Stroll to downtown's boutiques, cafes, and the lively farme ...
From $99 per night (USD)
VRBO
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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 ...
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Expedia
From $94 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 $94 per night (USD)
VRBO
$Cozy 3 BR\/2 BA Downtown Winter Garden Cottage property.$
From $100 per night (USD)
Expedia
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 $100 per night (USD)
Expedia
From $150 per night (USD)
Expedia
Learn how to camp RV style in this Lux RV which sleeps up to 8 people.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This luxury RV is nestled in downtown Winter Garden near Disney and is fully equipped. RV is plugged in and stationed on ...
From $150 per night (USD)
Expedia
From $130 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 $130 per night (USD)
Expedia
From $183 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 $183 per night (USD)
VRBO
From $60 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 $60 per night (USD)
Expedia
From $184 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 $184 per night (USD)
VRBO
From $63 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 $63 per night (USD)
Expedia
From $89 per night (USD)
VRBO
Cute Studio on the Bike trail
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
Historic Downtown Winter Garden Gem - Explore & Relax! Discover our inviting studio in Downtown Winter Garden. Walk to ...
From $89 per night (USD)
VRBO
From $87 per night (USD)
Expedia
Large Studio Apartment Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy easy access to everything from this perfectly located home base. Located in Historic Downtown Winter Garden, You j ...
From $87 per night (USD)
Expedia
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VRBO
Our RV is located in winter garden near downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
<p>Located in Winter Garden, this welcoming mobile home lets you experience it all. Make short work of the 3-minute driv ...
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VRBO
From $216 per night (USD)
Expedia
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 $216 per night (USD)
Expedia
$Updated Winter Garden Home w\/ Yard & Fire Pit!$
From $163 per night (USD)
VRBO
Updated Winter Garden Home w\/ Yard & Fire Pit!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The best of Winter Garden awaits you at this lovely 2-bedroom, 2-bathroom vacation rental! Located near top attractions ...
From $163 per night (USD)
VRBO
From $88 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 $88 per night (USD)
Expedia
From $418 per night (USD)
VRBO
WATERFRONTWinterGdnHSE+VIEWS+Dock+Wildlife+Firepit
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Enjoy the breathtaking sunrise views of Lake Apopka from this newly refurbished and well appointed 4 bed, 2.5 b ...
From $418 per night (USD)
VRBO
From $166 per night (USD)
VRBO
Large 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 $166 per night (USD)
VRBO
From $87 per night (USD)
VRBO
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 $87 per night (USD)
VRBO
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Expedia
4 Bedroom Single_family 421312 by Houzlet
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
You're going to love this home! The spacious kitchen is exquisite with gorgeous cabinetry, contemporary counters, and st ...
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Expedia
From $200 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 $200 per night (USD)
VRBO
$Water-View Oasis w\/spacious wrap around screened in balcony- mins from beach$
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Expedia
Water-View Oasis w\/spacious wrap around screened in balcony- mins from beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Waterviews to die for! Spacious open floor living area. Large Island in kitchen, with water views from bedroom, living r ...
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Expedia
$Beautiful 4 Bedroom Farm House\n$
From $245 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 $245 per night (USD)
VRBO
From $600 per night (USD)
Expedia
30 minutes to Disney Atractions
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Perfect for family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay, What ...
From $600 per night (USD)
Expedia
$Luxury 2BDR \/Gated\/Resort Style Pool\/Gym\/FastWifi$
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VRBO
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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VRBO
From $161 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 $161 per night (USD)
Expedia
$Windermere CasaMirella · 2BR\/Modern\/Fast Wi-Fi\/Pool\/gym\/near Disney Parks$
From $134 per night (USD)
VRBO
Windermere CasaMirella · 2BR\/Modern\/Fast Wi-Fi\/Pool\/gym\/near Disney Parks
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Create your experience as we welcome you to this centrally located Luxury Family, Friend, Travel nurse,and all ...
From $134 per night (USD)
VRBO
From $319 per night (USD)
Expedia
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 $319 per night (USD)
Expedia
From $67 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 $67 per night (USD)
VRBO
From $165 per night (USD)
VRBO
2BR Orlando Oasis: Balcony, Cozy, Great Amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to our 2 bedroom apartment in Windermere, FL! Perfectly located within walking distance to shops, parks, and a g ...
From $165 per night (USD)
VRBO
From $275 per night (USD)
VRBO
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 $275 per night (USD)
VRBO
From $200 per night (USD)
Expedia
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 ...
From $200 per night (USD)
Expedia
Click For Pricing
VRBO
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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VRBO
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Expedia
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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Expedia
$Tranquil Oasis - Pool - Gym- Kid\/Pet Friendly$
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VRBO
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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VRBO
From $175 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 $175 per night (USD)
Expedia
$2BD Apt+Lake\/FountainView+Balcony, Resort Style Pool, Wi-Fi, Desk, Gym, Kitchen$
Click For Pricing
VRBO
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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VRBO
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Expedia
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 ...
Click For Pricing
Expedia
From $199 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 $199 per night (USD)
VRBO
From $129 per night (USD)
Expedia
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 $129 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Windermere Two Bedroom Updated Townhouse Water View,Close to Disney, A+ Location
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Renovated 2 bedroom, 2.5 bath townhome in a very safe and desirable community. This townhome is across the street from ...
From $229 per night (USD)
VRBO
$Cozy Orlando Oasis w\/Resort Style Pool\/Fast WiFi\/Free parking\/Gym\/Close To Parks$
From $146 per night (USD)
Expedia
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 $146 per night (USD)
Expedia
From $104 per night (USD)
VRBO
Cozy & Comfy Lakeview 1BD in Central Orlando
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your luxurious retreat in the heart of Windermere! This 1BD apartment is centrally located to all the area's ...
From $104 per night (USD)
VRBO

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Winter Garden Rentals

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Results: 53 Rentals