Hooper Park Rentals
From $248 per night (USD)VRBO
Stroll to Park Avenue from Vintage Lake-View House
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $278 per night (USD)Expedia
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 $278 per night (USD)Expedia
From $362 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 $362 per night (USD)VRBO
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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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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 $147 per night (USD)VRBO
Cottage Retreat in the City
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
QUICK LOOK Recently Constructed, 1-Bedroom Cottage in College Park, a quaint downtown Orlando neighborhood Available Ni ...
From $147 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 $254 per night (USD)Expedia
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)Expedia
From $375 per night (USD)VRBO
Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
- Bedrooms:
- 2
- 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 $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 $482 per night (USD)VRBO
Private Luxury Pool / Smart-home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Owners have freshly renovated September 2023 Investing over ($75,000) adding the following - Brand new single slope met ...
From $482 per night (USD)VRBO
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Amazing College Park private walled in estate
- Bedrooms:
- 3
- 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 $427 per night (USD)Expedia
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)Expedia
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 $162 per night (USD)Expedia
Modern, fabulous two-bedroom with parking in Winter Park
- Bedrooms:
- 1
- 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 $162 per night (USD)Expedia
From $146 per night (USD)VRBO
Home Away from Home- Winter Park
- Bedrooms:
- 1
- 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 $3475 per night (USD)Expedia
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 ...
From $3475 per night (USD)Expedia
From $253 per night (USD)VRBO
Fire Pit + Grill + 2MI to DT + Long Term Stays!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Come and relax in our newly remodeled, stylish home. Moments away from craft beer bars, brewery, AdventHealth O ...
From $253 per night (USD)VRBO
From $271 per night (USD)Expedia
Elegant & Spacious Historic Winter Park Home with Pool + Spa
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Historic Winter Park home, located within a beautiful neighborhood. The home is spacious, charming and elegantly-appoint ...
From $271 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 $1429 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 $1429 per night (USD)VRBO
From $97 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 $97 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 $322 per night (USD)Expedia
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 $322 per night (USD)Expedia
From $170 per night (USD)VRBO
The beautiful Melrose Cottage - 25% monthly rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our Melrose Cottage in Winter Park. This delightfully curated property features 2 bedrooms with a king and qu ...
From $170 per night (USD)VRBO
From $157 per night (USD)VRBO
City Cottage with Mid Century Modern Vibe
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Premium home with Mid Century Modern vibe. Beautiful furnishings and decor to make you feel completely comfortable. Rel ...
From $157 per night (USD)VRBO
From $338 per night (USD)VRBO
Coastal Bungalow ~ Firepit, Pool, Gazebo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay at this elevated coastal retreat with a neutral palette, turquoise accents, and natural wood touches. This 3 bed, 2 ...
From $338 per night (USD)VRBO
From $220 per night (USD)Expedia
Winter Park Gem, 2BR Near Parks, 3MI to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to our cozy and inviting 2-bedroom, 1-bathroom home. This charming property offers a comfortable and co ...
From $220 per night (USD)Expedia
From $2396 per night (USD)VRBO
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 ...
From $2396 per night (USD)VRBO
From $1063 per night (USD)Expedia
5/4 King bed LUX Arcade near WP/CP & DT Orlando
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to your perfect Orlando getaway! This stunning new home boasts 5 spacious bedrooms and 4 modern baths, comfortab ...
From $1063 per night (USD)Expedia
From $256 per night (USD)VRBO
2bd/2ba Remodled near Winter Park/Hospitals/Downtown + fast wifi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Keep it simple at this peaceful and centrally-located home. This special place is close to everything, making it easy to ...
From $256 per night (USD)VRBO