Winter Garden, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Winter Garden, Florida on RentalSaver.com!

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 $204 per night (USD)
VRBO
Walk to Dtwn: Winter Garden Home w/ Patio
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled among a wealth of historical attractions, live entertainment, and outdoor recreation awaits ‘The Strawberry Hous ...
From $204 per night (USD)
VRBO
From $182 per night (USD)
VRBO
Walkable Winter Garden Bungalow: 3 Blocks 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 $182 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 $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
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Expedia
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 ...
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Expedia
From $146 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 $146 per night (USD)
VRBO
From $174 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 $174 per night (USD)
Expedia
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)
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 $166 per night (USD)
Expedia
From $232 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 $232 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 $112 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 $112 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 $209 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 $209 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
From $103 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 $103 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 $74 per night (USD)
VRBO
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)
VRBO
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 $195 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 $195 per night (USD)
VRBO
From $341 per night (USD)
Expedia
(381) Fantastic Home Near Disney 5BD/5BT/14P
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
Welcome to Your Dream Vacation Home! Step into this modern five-bedroom home, nestled in the exclusive Encore Resort (n ...
From $341 per night (USD)
Expedia
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VRBO
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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VRBO
From $242 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 $242 per night (USD)
Expedia
From $117 per night (USD)
VRBO
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 $117 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 $266 per night (USD)
VRBO
Fire Pit & Yard: Updated Winter Garden Home!
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 $266 per night (USD)
VRBO
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Expedia
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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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 $537 per night (USD)
Expedia
WATERFRONTWntrGdnHSE VIEWS Dock Wildlife 13mi Disn
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 $537 per night (USD)
Expedia
From $189 per night (USD)
VRBO
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)
VRBO
From $289 per night (USD)
Expedia
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 $289 per night (USD)
Expedia
From $506 per night (USD)
VRBO
Luxurious Vacation Home in Beautiful Windermere, 20 Min. to Disney & Universal!
Bedrooms:
2
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
$Beautiful 4 Bedroom Farm House\n$
From $264 per night (USD)
Expedia
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)
Expedia
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
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)
Expedia
From $241 per night (USD)
VRBO
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)
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
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VRBO
Luxury 2BDR /Gated/Resort Style Pool/Gym/FastWifi
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
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 $351 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 $351 per night (USD)
Expedia
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 $404 per night (USD)
Expedia
Luxury Family Escape ● Library ●Near Disney
Bedrooms:
2
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 $253 per night (USD)
VRBO
Mermaid Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Mermaid room will be sure to please anyone who dreams of being a mermaid or under the sea. This room is themed after ...
From $253 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Peacock Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This charming mini suite offers a cozy yet refined retreat, thoughtfully designed for both comfort and functionality. It ...
From $253 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Grace Suite in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The suite features a luxurious king-sized bed, perfect for relaxing in comfort after a long day. Indulge in the ultimate ...
From $482 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Speakeasy Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step back in time with this uniquely themed suite, thoughtfully designed to reflect the elegance and intrigue of the Pro ...
From $253 per night (USD)
Expedia
From $253 per night (USD)
VRBO
Sage Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Sage Room is a thoughtfully designed mini suite featuring a private bath, cozy sitting room, queen bedroom, and two ...
From $253 per night (USD)
VRBO
From $188 per night (USD)
Expedia
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)
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 Pricing
VRBO
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 ...
Click For Pricing
VRBO
Click For Pricing
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
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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
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Expedia
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 ...
Click For Pricing
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 $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 $268 per night (USD)
VRBO
Peace in the Garden - Home in Winter Garden
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Welcome to Peace in the Garden, your serene home away from home in beautiful Winter Garden, Florida. Tucked awa ...
From $268 per night (USD)
VRBO

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Winter Garden Rentals

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Results: 57 Rentals