Hooper Park Rentals
From $267 per night (USD)VRBO
Comfy Home in Winter Park, can accommodate up 6 guests!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our home is located in Winter Park and can serve as a central base to live like a local. You can enjoy all of the great ...
From $267 per night (USD)VRBO
From $146 per night (USD)Expedia
A curated stay in the Historic College Quarter
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You'll fall in love with this beautiful historic cottage located in the heart of Winter Park. Filled with charming vinta ...
From $146 per night (USD)Expedia
From $254 per night (USD)VRBO
Modern Mediterranean Oasis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Warm and stylish getaway. Very spacious bedrooms open dining and family room. Relax outside with beautifully lit paved p ...
From $254 per night (USD)VRBO
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Amazing College Park private walled in estate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Amazing private Mediterranean walled estate located across from the historic DubsDread golf course! Centrally located in ...
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From $281 per night (USD)VRBO
Amazing location- walk to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Entire Private Home - 2 bed 2 bath fully furnished unit located just one block from Park Ave in Winter Park. ***Several ...
From $281 per night (USD)VRBO
From $122 per night (USD)Expedia
Tiny Cottage - 3 MI to Downtown w\/Grill & Hammocks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Renovated guest suite using original reclaimed materials to create a modern vintage farmhouse vibe. Centrally l ...
From $122 per night (USD)Expedia
From $162 per night (USD)VRBO
Home away from home in the heart of charming Winter Park!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
You'll fall in love with this beautifully curated historic home located in the heart of Winter Park. Filled with curated ...
From $162 per night (USD)VRBO
From $103 per night (USD)Expedia
Little gem apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You'll fall in love with this little gem located in the heart of Winter Park. Filled with charming vintage furniture and ...
From $103 per night (USD)Expedia
From $548 per night (USD)VRBO
Charming 3-bedroom townhome with AC and WiFi in Winter Park
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Winter Park at this 3-bedroom townhome. With 1 king bed and 2 queen beds, this adorable property is ...
From $548 per night (USD)VRBO
From $77 per night (USD)Expedia
College quater charming Winter Park Historic Dist Rollins College quarters
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
The College Quarters in Winter Park is located in the charming city of Winter Park Historic District. Located within blo ...
From $77 per night (USD)Expedia
From $142 per night (USD)VRBO
Bungalow Near Downtown Orlando, Winter Park, Major Hospitals, and Disney!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming Renovated Studio in Downtown Orlando’s College Park Experience the best of urban and small-town living in this ...
From $142 per night (USD)VRBO
From $229 per night (USD)VRBO
King Room Near Fracture Care Center ORL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This property is located opposite Florida Hospital, 700 metres from the Orlando Science Center. A complimentary hot brea ...
From $229 per night (USD)VRBO
From $109 per night (USD)VRBO
2 Bed 1.5 Bath in Winter Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Property Description Please reference other sites for more detailed ratings and reviews. Spacious 2 bedroom/ 1.5 bath d ...
From $109 per night (USD)VRBO
From $133 per night (USD)VRBO
Lakefront Condo w\/ Sunroom, Office, & Lakeside Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to beautiful Winter Park, Florida and your home away from home in your lakeside, super-convenient 1 bedroom /1 h ...
From $133 per night (USD)VRBO
From $314 per night (USD)VRBO
Charming home 3 blocks from historic Park Avenue & one block from Lake Virginia
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Open kitchen / family room with dining area to comfortable seat 4, dining room and living room, screened in porch for wa ...
From $314 per night (USD)VRBO
From $427 per night (USD)Expedia
Private Luxury Pool \/ Smart-home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Owners have freshly renovated September 2023 Investing over ($75,000) adding the following - Brand new single slope met ...
From $427 per night (USD)Expedia
From $248 per night (USD)VRBO
Stroll to Park Avenue from Vintage Lake-View House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This cozy, quaint Winter Park home was built in 1925. The house has updated appliances and plenty of space. There are tw ...
From $248 per night (USD)VRBO
From $139 per night (USD)VRBO
Cute Guest House In Winter Park Minutes From Downtown in Car
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy our guest house and the new space we created in Oct 2015! The guest house has a kitchenette with two glass burners ...
From $139 per night (USD)VRBO
From $153 per night (USD)VRBO
Cottage Retreat in the City
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
QUICK LOOK Newly Constructed, 1-Bedroom Cottage in College Park, a quaint downtown Orlando neighborhood Available Night ...
From $153 per night (USD)VRBO
From $133 per night (USD)VRBO
☀️ King Condo w\/ Sunroom, Lakeside Pool and Waterfront Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to beautiful Winter Park, Florida and your home away from home in our trendy, super-convenient 1/1 King bed ...
From $133 per night (USD)VRBO
From $137 per night (USD)VRBO
Cabana style studio apt\/private garden near Rollins and Park Ave. 1 week minim<br><br>
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
About this space Cook in or don't in this private and luxurious yet serene studio, where fun mid century meets old flori ...
From $137 per night (USD)VRBO
From $209 per night (USD)Expedia
THE CLOUD 9 SUITE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
PET FRIENDLY 🐾 Book the Cloud 9 Suite, located in the heart of downtown Winter Park FL and Orlando! Beautifully furnish ...
From $209 per night (USD)Expedia
From $146 per night (USD)VRBO
Home Away from Home- Winter Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy our newly renovated home in Winter Park. We are centrally located and within minutes from Rollins College and Park ...
From $146 per night (USD)VRBO
From $287 per night (USD)Expedia
Total Serenity #2, 2 BDRM, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Enjoy your stay in this cozy, newly remodeled 2 Bedroom 2 bath, 1200 sq ft apartment! Centrally located in the heart of ...
From $287 per night (USD)Expedia
From $171 per night (USD)VRBO
Tranquil & Tiny house
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This recently restored Tiny house has everything you need in such a unique, tranquil and surreal setting in the heart of ...
From $171 per night (USD)VRBO
From $170 per night (USD)Expedia
Cute and Cozy Apartment-B 1 Bedroom Duplex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
ENJOY YOUR STAY IN WINTER PARK IN THIS COZY, NEWLY RENOVATED APARTMENT CENTRALLY LOCATED IN A QUIET NEIGHBORHOOD WITHIN ...
From $170 per night (USD)Expedia
From $309 per night (USD)VRBO
Hidden Oasis #4 2 BDRM, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your stay in this cozy, newly remodeled 2 Bedroom 2 bath, 1200 sq ft apartment! Centrally located in the heart of ...
From $309 per night (USD)VRBO
From $256 per night (USD)Expedia
Peace and the Park #3 -2 BDRM, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy your stay in this huge 1200 square foot newly remodeled 2 Bedroom 2 bath apartment! Centrally located in Winter Pa ...
From $256 per night (USD)Expedia
From $1406 per night (USD)VRBO
LUXURY 5\/4 w Jacuzzi tub Winter Park\/CP Orlando Gem
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 22
Welcome to your perfect Orlando getaway! This stunning new home boasts 5 spacious bedrooms and 4 modern baths, comfortab ...
From $1406 per night (USD)VRBO
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Charming 2-bedroom apartment with AC and WiFi in enchanting Winter Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Located in Winter Park, this apartment is a dream. With 2 nice bedrooms, AC, WiFi, a hair dryer, an iron, and a washing ...
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From $308 per night (USD)VRBO
3-bedroom Bungalow in Welcoming Winter Park with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this marvelous 3-bedroom gem in Orlando. This lovely bungalow features 1 king bed and 2 queen beds, perfect for ...
From $308 per night (USD)VRBO
From $121 per night (USD)VRBO
Winter Park College quarters historic district
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The College Quarters in Winter Park is located in the charming city of Winter Park Historic District. Located within blo ...
From $121 per night (USD)VRBO
From $162 per night (USD)VRBO
Cheerful and stylish 2-bedroom with parking, centrally located
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax in this cheerful, sun-filled home, walking distance to restaurants, shopping, groceries and our favorite local cof ...
From $162 per night (USD)VRBO
From $156 per night (USD)Expedia
Modern, fabulous two-bedroom with parking in Winter Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our newly renovated duplex home is stylish and well-appointed with everything you need for a getaway or a longer visit. ...
From $156 per night (USD)Expedia
From $248 per night (USD)VRBO
Peaceful Retreat #1 -2B \/2B Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everything that a small to large group of 8 could ask for. Centrally located in the heart of Winter Park. A short walk o ...
From $248 per night (USD)VRBO
From $169 per night (USD)Expedia
Comfy and Charming -A 1 Bedroom Duplex Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
ENJOY YOUR STAY IN WINTER PARK IN THIS COMFY, NEWLY RENOVATED APARTMENT CENTRALLY LOCATED IN A QUIET NEIGHBORHOOD WITHIN ...
From $169 per night (USD)Expedia
From $427 per night (USD)VRBO
Greatest location! Condo with private yard!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Location, Location, Location!!! Greatest location! Well appointed condo -one block from Park Avenue! This is a Downstair ...
From $427 per night (USD)VRBO
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Mills House @WP. Sleeps 11 Renovated. Queen beds
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Enjoy a stylish experience at this centrally-located place. MillsHouse is conveniently located for a foodie adventure. T ...
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Advent health all white unit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to my charming 2 bedroom 2 bathroom home in the heart of Orlando FL located right of the I4 highway exit Princet ...
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Click For PricingExpedia
Cottage on Cornell - Quaint & Cozy w\/Outdoor Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Newly renovated guest suite using original reclaimed materials to create a modern vintage farmhouse vibe. Centrally loca ...
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Click For PricingVRBO
NEW! ☀Bungalow+Patio+FirePit! Close to Everything!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You will love it here! This trendy winter park home will feel like home! Well equipped with all your essentials (Soaps+ ...
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From $213 per night (USD)Expedia
CHARMING - Cozy Retreat Near Lake Killarney in Winter Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come and stay awhile at the Killarney Retreat, built in the 50s, tucked away from the hub of city, yet just a short driv ...
From $213 per night (USD)Expedia
From $238 per night (USD)VRBO
Fire Pit + Grill + 2MI to DT + Long Term Stays!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: Come and relax in our newly remodeled, stylish home. Moments away from craft beer bars, brewery, AdventHealth O ...
From $238 per night (USD)VRBO
From $450 per night (USD)VRBO
Cozy lakeside cottage in the heart of Orlando.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This lakeside Cottage with amazing views is conveniently located within minutes to Winter Park, Downtown Orlando, and Ro ...
From $450 per night (USD)VRBO
From $289 per night (USD)VRBO
Elegant & Spacious Historic Winter Park Home with Pool + Spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Historic Winter Park home, located within a beautiful neighborhood. The home is spacious, charming and elegantly-appoint ...
From $289 per night (USD)VRBO
From $375 per night (USD)VRBO
Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
One month minimum to rent (30 nights). A hidden gem, this meticulous sun-filled 3 BR + Office/2.5 bath home offers ult ...
From $375 per night (USD)VRBO
From $238 per night (USD)VRBO
3BR - 3BA : Location, Location, Location : Rose Isle\/Beverly Shores Neighborhood
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
As you drive into the established and highly desirable neighborhood of Beverly Shores / Rose Isle, you will be embraced ...
From $238 per night (USD)VRBO
From $147 per night (USD)Expedia
Private Poolside Guest House In Winter Park\/Orlando
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful and comfortable two-story cottage/detached guest house, centrally-located within an historic neighborhood. Loc ...
From $147 per night (USD)Expedia
From $321 per night (USD)VRBO
Cheerful 4-bedroom with large and lush backyard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your family will be close to everything when you stay at this centrally-located place. Close to multiple interstate entr ...
From $321 per night (USD)VRBO
From $442 per night (USD)VRBO
Enjoy more space and relax in Downtown Orlando !!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Take advantage of our fast and free WiFi, free hot breakfast, free coffee, free parking and free weekday newspapers thro ...
From $442 per night (USD)VRBO
From $228 per night (USD)VRBO
Tiny Home - 3 MI to Downtown & Winter Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Welcome to our charming 2 bedroom house in the heart of Winter Park, Florida! This beautiful home is the perfec ...
From $228 per night (USD)VRBO