Virginia Heights Rentals
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 $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 $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 $244 per night (USD)Expedia
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)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 $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 $156 per night (USD)VRBO
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)VRBO
From $156 per night (USD)Expedia
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)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
From $194 per night (USD)Expedia
GREAT LOCATION 🏡
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Location, location, location - this immaculate Olde Winter Park home is ready for you to relax and enjoy Winter Park and ...
From $194 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 $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 $426 per night (USD)VRBO
Ideal Location, Charming 4 bedroom home w Lap Pool, fenced yard, month discounts
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Traditional Old Winter Park home ready for your event, special occasion, vacation, wedding, golf weekend, or executive r ...
From $426 per night (USD)VRBO
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 $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 $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 $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 $287 per night (USD)VRBO
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)VRBO
From $171 per night (USD)Expedia
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)Expedia
From $170 per night (USD)VRBO
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)VRBO
From $309 per night (USD)Expedia
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)Expedia
From $256 per night (USD)VRBO
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)VRBO
From $151 per night (USD)Expedia
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)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 $308 per night (USD)Expedia
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)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
From $286 per night (USD)VRBO
LUXURY 𝕄𝕚𝕕 ℂ𝕖𝕟𝕥𝕦𝕣𝕪 𝕄𝕠𝕕𝕖𝕣𝕟 ᴠᴀᴄᴀᴛɪᴏɴ in 𝒲𝒾𝓃𝓉𝑒𝓇 𝒫𝒶𝓇𝓀
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
NEW CONSTRUCTION Luxury Home north of Downtown Orlando in the heart of Winter Park steps from Winter Park Village near t ...
From $286 per night (USD)VRBO
Click For PricingVRBO
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 PricingVRBO
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 $173 per night (USD)VRBO
Quaint Winter Park East End Market Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our Winter Park home behind East End Market ! You will fall in love with this area which is full of friendly ...
From $173 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)VRBO
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)VRBO
From $248 per night (USD)Expedia
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)Expedia
From $169 per night (USD)VRBO
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)VRBO
From $253 per night (USD)Expedia
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)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
From $153 per night (USD)Expedia
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)Expedia
From $104 per night (USD)VRBO
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)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 $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)Expedia
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)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
Click For PricingExpedia
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 ...
Click For PricingExpedia
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 $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
From $208 per night (USD)VRBO
Modern and fabulous tropical oasis, central to everything!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Make memories at this unique and family-friendly property in the heart of Audubon Park. Hang out in a tropical garden sh ...
From $208 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 $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)VRBO
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)VRBO
From $321 per night (USD)Expedia
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)Expedia
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 $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