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 $286 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 $286 per night (USD)
VRBO
From $270 per night (USD)
Expedia
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 $270 per night (USD)
Expedia
From $217 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 $217 per night (USD)
VRBO
From $288 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 $288 per night (USD)
Expedia
From $211 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 $211 per night (USD)
VRBO
From $233 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 $233 per night (USD)
Expedia
From $346 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 $346 per night (USD)
VRBO
From $304 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 $304 per night (USD)
Expedia
From $511 per night (USD)
VRBO
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Enjoy the breathtaking sunrise views of Lake Apopka from this newly refurbished and well appointed 4 bed, 2.5 ...
From $511 per night (USD)
VRBO
From $110 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 $110 per night (USD)
Expedia
From $277 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 adults and is located a short walk or bike ride to beautiful downtow ...
From $277 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Dtwn Winter Garden Home: 12 Mi to Disney!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Whether you’re looking for a Disney vacation or a charming city escape, this Winter Garden vacation rental is perfect fo ...
From $325 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $328 per night (USD)
VRBO
Beautiful 4 Bedroom Farm House
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 $328 per night (USD)
VRBO
From $515 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 $515 per night (USD)
VRBO
From $162 per night (USD)
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 ...
From $162 per night (USD)
Expedia
From $222 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 $222 per night (USD)
VRBO
From $536 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 $536 per night (USD)
Expedia
From $632 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 $632 per night (USD)
VRBO
From $337 per night (USD)
Expedia
Downtown Winter Garden bungalow with private putting green and fire pit
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 $337 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 *Privat ...
From $202 per night (USD)
VRBO
From $222 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 Ne ...
From $222 per night (USD)
Expedia
From $857 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 $857 per night (USD)
VRBO
From $364 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 $364 per night (USD)
Expedia
From $215 per night (USD)
VRBO
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 $215 per night (USD)
VRBO
From $131 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 $131 per night (USD)
VRBO
From $138 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 $138 per night (USD)
VRBO
From $175 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 $175 per night (USD)
Expedia
From $267 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 $267 per night (USD)
VRBO
From $283 per night (USD)
Expedia
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 $283 per night (USD)
Expedia
From $261 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 $261 per night (USD)
VRBO
From $204 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 $204 per night (USD)
Expedia
From $286 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 $286 per night (USD)
VRBO
From $286 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 $286 per night (USD)
Expedia
From $542 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 $542 per night (USD)
VRBO
From $286 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 $286 per night (USD)
Expedia
From $286 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 $286 per night (USD)
VRBO
From $328 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 $328 per night (USD)
Expedia
From $432 per night (USD)
VRBO
Updated 4-Bedroom Winter Garden House In Golf Cart District 20 Min From Disney
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Stay less than 1 mile away from downtown Winter Garden which is the cutest downtown with many shops and restaurants, whi ...
From $432 per night (USD)
VRBO
From $227 per night (USD)
Expedia
Relaxing retreat w/ pool & BBQ grill
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Summary: Welcome to your relaxing Winter Garden retreat - a cozy base near top attractions, perfect for families & smal ...
From $227 per night (USD)
Expedia
From $552 per night (USD)
VRBO
Luxury Getaway Near Winter Garden Downtown, Disney
Bedrooms:
4
Bathrooms:
7
Sleeps:
16
Escape to this luxury 7BR, 8 Queen Beds, 4 Full bathrooms, Large dinning area, 5,000+ sq ft villa featuring a private tr ...
From $552 per night (USD)
VRBO
From $279 per night (USD)
Expedia
1921 2BD/1BTH Bungalow - Historic Winter Garden, Steps to Plant St, Dogs Welcome
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Nestled in the Historic District of downtown Winter Garden, this restored 1921 Bungalow is just a block to Plant Street ...
From $279 per night (USD)
Expedia
From $400 per night (USD)
VRBO
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the heart of the charming down town Winter Garden. This Second floor, 2 bedroom apartment offers a king siz ...
From $400 per night (USD)
VRBO
From $145 per night (USD)
Expedia
Lovely Studio Apt #1 in Downtown Winter Garden, by Bike Trail
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden ...
From $145 per night (USD)
Expedia
From $158 per night (USD)
VRBO
Cozy Studio Apt #5 by Bike Trail & Historic Downtown Winter Garden
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden ...
From $158 per night (USD)
VRBO
From $154 per night (USD)
Expedia
Large Studio Apt #8 by Bike Trail & Historic Downtown Winter Garden
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Private studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Gard ...
From $154 per night (USD)
Expedia
From $151 per night (USD)
VRBO
Studio Apt #3 in Historic Downtown Winter Garden, across from the Bike Trail
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden attra ...
From $151 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Cute Studio Apt #2 by Bike Trail & Historic Downtown Winter Garden
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden ...
From $190 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Private Studio Apt #7 by Bike Trail & Historic Downtown Winter Garden
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Private studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Gard ...
From $156 per night (USD)
VRBO
From $151 per night (USD)
Expedia
Chic Studio Apt #4 by Bike Trail & Historic Downtown Winter Garden
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden ...
From $151 per night (USD)
Expedia
From $145 per night (USD)
VRBO
Efficiency Apt #6 Near Downtown & Bike Trail
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden ...
From $145 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Cozy 1-bedroom with AC in awesome Winter Garden
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Unwind in Winter Garden at this pleasant apartment. Featuring one cozy bedroom with a king bed, it offers a serene retre ...
From $363 per night (USD)
Expedia

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Winter Garden Rentals

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Results: 52 Rentals