Charmont Rentals
- 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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $197 per night (USD)
VRBO
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)VRBO
- From $131 per night (USD)
VRBO
Landing at Azul Baldwin Park Apartments - 1 Bedroom in Northeast Orlando
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Azul Baldwin Park Apartments is a lively property in the Northeast Orlando neighborhood of Orlando where Landing offers ...
From $131 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 $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 $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 $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 $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 $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 $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 $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 $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 $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 $120 per night (USD)
VRBO
Landing at Azul Baldwin Park Apartments - 1 Bedroom in Northeast Orlando
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Azul Baldwin Park Apartments is a lively property in the Northeast Orlando neighborhood of Orlando where Landing offers ...
From $120 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 $126 per night (USD)
VRBO
Quaint Key West Pool Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Historic Winter Park Florida. Central Florida's gem Winter Park is filled with history, whimsy and magic as i ...
From $126 per night (USD)VRBO
- From $372 per night (USD)
VRBO
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)VRBO