Osceola Shores Rentals
- From $146 per night (USD)
VRBO
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)VRBO
- From $400 per night (USD)
Expedia
Best Winter Park Home close to Rollins College, Advent Health & Park Avenue !
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful furnished and fully equipped kitchen 4-bedroom, 3-bath home which sits on a large fenced corner lot in a high ...
From $400 per night (USD)Expedia
- From $124 per night (USD)
VRBO
Stay near Winter Park action at our 2-bedroom apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Winter Park, this charming 2-bedroom apartment offers non-stop chances for unwinding and exploring. Unwi ...
From $124 per night (USD)VRBO
- From $156 per night (USD)
Expedia
Mid Century Luxury, 1 block from Park Ave (#3)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This 2nd floor apartment is nestled under oaks on a quiet cobblestone street in downtown Winter Park. There are only 3 u ...
From $156 per night (USD)Expedia
- From $156 per night (USD)
VRBO
Mid Century Luxury, 1 block from Park Ave (#2)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This ground floor apartment is nestled under oaks on a cobblestone street in downtown Winter Park. There are only 3 unit ...
From $156 per night (USD)VRBO
- Click For Pricing
Expedia
Winter Park Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Simplicity at its finest. I host like I live and like I like to be hosted- with chocolates and snacks and fluffy towels ...
Click For PricingExpedia
- From $244 per night (USD)
VRBO
Cute bungalow minutes walk from Park Avenue.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Just what you have been waiting for; beautiful cottage home in the heart of Winter Park! 2 bedroom/2 bath only steps aw ...
From $244 per night (USD)VRBO
- From $281 per night (USD)
Expedia
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)Expedia
- From $164 per night (USD)
VRBO
Luxury Living Just 3 Blocks From Park Ave!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful Acacia wood flooring, with marble in the bathrooms and porcelain tile in the kitchen. Quartz countertops, ceil ...
From $164 per night (USD)VRBO
- From $172 per night (USD)
Expedia
Winter Park Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy your stay at the Winter Park Oasis! This cozy 2 bedroom private unit, is in a charming and historic neighborhood! ...
From $172 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 $77 per night (USD)
VRBO
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)VRBO
- From $241 per night (USD)
VRBO
Home for Family Thanksgiving
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Our home has high quality furniture, linens, cookware and tableware for your family dinners. There are large and small ...
From $241 per night (USD)VRBO
- 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 $180 per night (USD)
Expedia
Modern Elegance In The Heart Of Winter Park - 2 beds\/2 baths
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Location!!! Beautifully appointed 2 bedroom, 2 bath second floor apartment overlooking a beautiful pool area with balcon ...
From $180 per night (USD)Expedia
- From $219 per night (USD)
VRBO
Just 3 Blocks to Park Ave Shops\/ Restaurants, 2 From The Winter Park Village!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Modern, clean and unique. Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz c ...
From $219 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 $139 per night (USD)
VRBO
Mid Century Modern Cottage in The Heart of Winter Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Furnished Mid Century Modern Short/Long term rental located in charming Olde Winter Park. Two bedrooms and one and half ...
From $139 per night (USD)VRBO
- From $201 per night (USD)
Expedia
Winter Park Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Your backyard oasis awaits you, with queen size 10in memory foam swing mattress, full outdoor kitchen, 65in TV along wit ...
From $201 per night (USD)Expedia
- 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
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $116 per night (USD)
VRBO
Cozy and Chic Winter Park Studio which is conveniently located just for you
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Light, airy, and perfectly appointed studio. Enjoy this fully furnished and centrally-located location. This space provi ...
From $116 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Newly renovated Cottage in the heart of Winter Park's most desired neighborhood.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is the spot, whether you are having an adventure at Walt Disney World or enjoy exploring the cobblestone roads, sho ...
From $242 per night (USD)Expedia
- From $151 per night (USD)
VRBO
LUXURY AND LOCATION!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two block ...
From $151 per night (USD)VRBO
- From $130 per night (USD)
Expedia
Charming 2BR\/2BA Winter Park Cottage, steps from Park Ave
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our charming 2-bedroom, 2-bathroom home nestled in the heart of Winter Park! Located just a short stroll away ...
From $130 per night (USD)Expedia
- 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 $222 per night (USD)
VRBO
Comfortable House in the lovely Winter Park, Olando Fl .
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Easy access to drive in and out, ample parking available. A good open yard space is available at the back of the house f ...
From $222 per night (USD)VRBO
- From $198 per night (USD)
VRBO
Charming Home Winter Park, Near Rollins College, Lake Baldwin Park, Orlando FL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the convenience of this exceptional locale strategically situated just 5-7 minutes away from the vibrant Park A ...
From $198 per night (USD)VRBO
- From $162 per night (USD)
Expedia
Cozy 4-bedroom house with WiFi, AC in peaceful Winter Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this lovely house in Winter Park. With 4 bedrooms, including 3 queen beds and 1 king bed, this fantastic prop ...
From $162 per night (USD)Expedia
- From $101 per night (USD)
VRBO
Florida Vacation Rental ~ 6 Mi to Downtown Orlando
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Soak up the Florida sun and explore the Orlando area with ease from this 2-bed, 1-bath vacation rental in Winter Park! Y ...
From $101 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 $153 per night (USD)
VRBO
LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This duplex unit is cozy and comfortable. It's updated with all new appliances, is tastefully decorated and has very com ...
From $153 per night (USD)VRBO
- From $104 per night (USD)
Expedia
Cozy Comfort Just 2 Blocks From Park Ave!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This duplex unit is cozy and comfortable. It's updated with all new appliances, is tastefully decorated and has very com ...
From $104 per night (USD)Expedia
- From $122 per night (USD)
VRBO
Walk The Downtown Village of Winter Park!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a downstairs end apartment with a back door that opens directly onto the pool deck near the hot tub. The apartme ...
From $122 per night (USD)VRBO
- Click For Pricing
Expedia
A DEAL By The Month! Walk to Rollins & Park Ave
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
It's your own private one-room structure with a private entrance next to a parking space. It's much like a hotel room in ...
Click For PricingExpedia
- From $253 per night (USD)
VRBO
You're Pampered Here - Just 3 Blocks From Park Avenue!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Modern, clean and unique. Fastest internet speed available: 139MBPS download and 21.5 MBPS upload! Second floor penthous ...
From $253 per night (USD)VRBO
- From $130 per night (USD)
Expedia
Light, Bright and Full of Delight! 2 Blocks to Park Ave
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this PRIVATE and Sparkling clean entire home, first floor 2 bedroom/1 full bath luxury apartment near Park Avenue! ...
From $130 per night (USD)Expedia
- From $144 per night (USD)
VRBO
Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a downstairs end apartment with a back door that opens directly onto the pool deck near the hot tub. The apartme ...
From $144 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Contemporary Award Winning Hotel w\/Rooftop Close to Parks & Rollins College
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our 323 square foot King Room is appointed with handsome contemporary furnishings, including an armoire, mini fridge, fl ...
From $550 per night (USD)VRBO
- From $578 per night (USD)
VRBO
ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our Classic King ADA is wheelchair-accessible. The room is appointed with handsome contemporary furnishings, including a ...
From $578 per night (USD)VRBO
- From $588 per night (USD)
VRBO
Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Classic King with Balcony room measures 323 square feet and has the added feature of a balcony with French doors tha ...
From $588 per night (USD)VRBO
- From $552 per night (USD)
VRBO
Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our Classic Queen room is 358 square feet and appointed with two pillowtop Queen size beds, luxury linens and handsome c ...
From $552 per night (USD)VRBO
- From $589 per night (USD)
VRBO
Private Balcony - Award Winning Accommodations w\/Rooftop Pool, Close to Parks!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our Classic Queen with Balcony room is 358 square feet and appointed with two pillowtop Queen size beds, luxury linens a ...
From $589 per night (USD)VRBO
- From $586 per night (USD)
VRBO
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our Premier ADA Queen is a larger room at 448 square feet and is wheelchair-accessible. The room features an additional ...
From $586 per night (USD)VRBO
- From $632 per night (USD)
VRBO
Large Room Award Winning Hotel w\/Rooftop Pool - Close to Parks & Rollins College
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our Parlor King is a larger room at 435 square feet and features a separate Parlor seating area with a sleeper sofa and ...
From $632 per night (USD)VRBO
- From $594 per night (USD)
VRBO
ADA Compliant Room in Award Winning Hotel w\/Rooftop Pool - Close to Parks!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our Premier ADA Queen is a larger room at 448 square feet and is wheelchair-accessible. The room features an additional ...
From $594 per night (USD)VRBO
- From $204 per night (USD)
VRBO
Coastal Feel - Modern Appeal
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 bedroom 2 bath, 1350 sqft detached home Family friendly layout with master bedroom suite, shared bedroom (2 twin beds) ...
From $204 per night (USD)VRBO
- From $1942 per night (USD)
VRBO
Queen Room Near All Saints Episcopal Church ORL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Winter Park, Florida, This property offers free WiFi and an outdoor pool. Rollins College is located 650 metr ...
From $1942 per night (USD)VRBO