Forrest Hills Rentals
From $342 per night (USD)VRBO
Charming Clean Home near East End Market - Monthly discounts available
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Winter Park home ready for your event, vacation or executive rental. Updated kitchen, granite countertops, wood floors, ...
From $342 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
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 $194 per night (USD)VRBO
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)VRBO
From $162 per night (USD)Expedia
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)Expedia
From $103 per night (USD)VRBO
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)VRBO
From $158 per night (USD)Expedia
Downtown Groovy Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This groovy place to stay is truly one of a kind! Just walking distance from a plethora of Orlando’s most popular eateri ...
From $158 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 $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 $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 $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 $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 $197 per night (USD)Expedia
Eclectic 1 Bedroom Apt in Downtown Orlando. 15mins from Airport & UCF.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Keep it simple at our peaceful and centrally-located 1 bedroom apartment situated in the quaint Mills/50 corridor. We a ...
From $197 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 $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 $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 $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
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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 ...
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 $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
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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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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 $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
From $156 per night (USD)Expedia
Mills 50 District\/Audobon Park Area 2 Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom, one bath 1/2 duplex in prime area of Orlando. Big bedroom has queen bed. Smaller bedroom has a twin and a f ...
From $156 per night (USD)Expedia
From $403 per night (USD)VRBO
Cozy 2-Bedroom Bungalow near Theme Parks & Orlando's Top Michelin-rated spots
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly renovated bungalow in the heart of Orlando's vibrant Mills 50 neighborhood! This charming retreat b ...
From $403 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 $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 $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 $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 $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 $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 $372 per night (USD)Expedia
GardenHouse @AudubonPark Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Take it easy at this unique and tranquil getaway. Located in Orlando's garden district, GardenHouse is conveniently loca ...
From $372 per night (USD)Expedia