Winter Garden Rentals
From $165 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 $165 per night (USD)VRBO
From $201 per night (USD)Expedia
Walk to Dtwn: Winter Garden Home w\/ Patio
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Nestled among a wealth of historical attractions, live entertainment, and outdoor recreation awaits ‘The Strawberry Hous ...
From $201 per night (USD)Expedia
From $151 per night (USD)VRBO
Walkable Winter Garden Bungalow: 3 Blocks 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 $151 per night (USD)VRBO
From $152 per night (USD)Expedia
16 Mi to Disney: Cottage w\/ Deck in Winter Garden
- 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 $152 per night (USD)Expedia
From $223 per night (USD)VRBO
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
- 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 $223 per night (USD)VRBO
From $205 per night (USD)Expedia
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 $205 per night (USD)Expedia
From $161 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 $161 per night (USD)VRBO
From $154 per night (USD)Expedia
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 $154 per night (USD)Expedia
From $171 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 $171 per night (USD)VRBO
From $153 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 $153 per night (USD)Expedia
From $159 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 $159 per night (USD)VRBO
From $192 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 $192 per night (USD)Expedia
From $347 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 $347 per night (USD)VRBO
From $199 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 $199 per night (USD)VRBO
From $101 per night (USD)VRBO
2nd Floor Studio Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your ideal urban retreat in the heart of Downtown Winter Garden. Situated just steps away from the bustling d ...
From $101 per night (USD)VRBO
From $116 per night (USD)Expedia
First floor apartment Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your ideal urban retreat in the heart of Downtown Winter Garden. Situated just steps away from the bustling d ...
From $116 per night (USD)Expedia
From $198 per night (USD)VRBO
House 2 Bedrooms \/2 full bathrooms Downtown Winter Garden
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Full renovated house in downtown Winter Garden FL. Welcome to your ideal urban retreat in the h ...
From $198 per night (USD)VRBO
From $210 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 $210 per night (USD)Expedia
From $230 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 $230 per night (USD)VRBO
From $82 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 $82 per night (USD)Expedia
From $203 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 $203 per night (USD)VRBO
From $96 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 $96 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 $106 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 $106 per night (USD)Expedia
From $282 per night (USD)VRBO
Comfy Studio Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our Comfy Studio Apartment in the heart of Winter Garden. You'll be just a short stroll from the vibrant Down ...
From $282 per night (USD)VRBO
From $162 per night (USD)Expedia
Enchanted 2 Bedroom Home near Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This fully furnished villa/duplex is a perfect Orlando/Winter Garden stay! This home gives you the plenty of comfort an ...
From $162 per night (USD)Expedia
From $113 per night (USD)VRBO
Enchanted TINY HOME SUITE near Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your unique Winter Garden experience begins at this enchanted tiny home, 2 blocks away from the golf cart district. Eith ...
From $113 per night (USD)VRBO
From $96 per night (USD)Expedia
Enchanted TINY HOME near Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your WG experience begins at this enchanted tiny home. Either hideaway at this little retreat with what you need to rela ...
From $96 per night (USD)Expedia
From $162 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 $162 per night (USD)VRBO
From $102 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 $102 per night (USD)Expedia
From $174 per night (USD)VRBO
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 $174 per night (USD)VRBO
From $283 per night (USD)Expedia
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 $283 per night (USD)Expedia
From $248 per night (USD)VRBO
Fire Pit & Yard: Updated Winter Garden Home!
- 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 $248 per night (USD)VRBO
From $126 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 $126 per night (USD)Expedia
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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 $272 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 $272 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 $194 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 $194 per night (USD)VRBO
From $546 per night (USD)VRBO
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 $546 per night (USD)VRBO
From $97 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 $97 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 $504 per night (USD)Expedia
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 $504 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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From $162 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 $162 per night (USD)Expedia
Click For PricingVRBO
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 ...
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From $371 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 $371 per night (USD)Expedia
From $775 per night (USD)VRBO
Central Florida's Historic Gem & wedding venue- The Oakland Manor House
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 13
Originally built in the early 1900’s, this gracious manor was carefully renovated, preserving its historic craftsman-sty ...
From $775 per night (USD)VRBO
From $404 per night (USD)Expedia
Luxury Family Escape ● Library ●Near Disney
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Windermere is a charming community ideal for long-term renters, located near Disney World. It features a four-bedroom h ...
From $404 per night (USD)Expedia
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 $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
Click For PricingVRBO
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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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 $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 $193 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 $193 per night (USD)Expedia
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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 $193 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 $193 per night (USD)Expedia