Windsong Rentals
From $146 per night (USD)VRBO
Charming Clean Home near East End Market Large fenced yard - 25% off thirty days
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Winter Park home ready for your event, vacation or executive rental. Updated kitchen, granite countertops, wood floors, ...
From $146 per night (USD)VRBO
From $362 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 $362 per night (USD)Expedia
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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 ...
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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 $387 per night (USD)VRBO
Casa Winter Park
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Winter Park accommodates the need for personal space while enjoying, at the same time, the gathering with several f ...
From $387 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
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 $172 per night (USD)VRBO
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)VRBO
From $200 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 $200 per night (USD)Expedia
From $1058 per night (USD)VRBO
Stunning Luxury Home in Artsy Winter Park featuring Nintendo-Themed Game Room!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
Newly redesigned and just 40 minutes from the theme parks, Atlantic Oasis is an award-winning, custom-built resort-style ...
From $1058 per night (USD)VRBO
From $71 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 $71 per night (USD)Expedia
From $152 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 $152 per night (USD)VRBO
From $204 per night (USD)VRBO
Ideal Location, Charming 4 bedroom home w Pool, fenced yard, 40% off thirty days
- 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 $204 per night (USD)VRBO
From $220 per night (USD)VRBO
Winter Park Bungalow & Outdoor Oasis - Rollins College, Park Ave & Fenced Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming bungalow in the heart of Winter Park's upscale Forest Hills neighborhood is the perfect retreat for your n ...
From $220 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 $206 per night (USD)VRBO
Great Family Home
- 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 $206 per night (USD)VRBO
From $248 per night (USD)Expedia
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)Expedia
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 $136 per night (USD)Expedia
Quaint Key West Pool Bungalow
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience Winter Park like a local in this superb 1-bedroom bungalow. This enchanting property offers all the comforts ...
From $136 per night (USD)Expedia
From $382 per night (USD)VRBO
Amazing lakefront mid-modern 3-bed Winter Park home surrounded by Natural Beauty
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience Winter Park like a local in this 3 bedroom 2.5 bath home. The bedrooms feature 2 queen beds and 1 king bed, e ...
From $382 per night (USD)VRBO
From $77 per night (USD)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 ...
From $77 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 $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 $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
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- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
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Click For PricingExpedia
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
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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 ...
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From $371 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 $371 per night (USD)VRBO
From $371 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 $371 per night (USD)VRBO
From $407 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 $407 per night (USD)VRBO
From $380 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 $380 per night (USD)VRBO
From $414 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 $414 per night (USD)VRBO
From $439 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 $439 per night (USD)VRBO
From $487 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 $487 per night (USD)VRBO
From $447 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 $447 per night (USD)VRBO
From $13267 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 $13267 per night (USD)VRBO
From $240 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 $240 per night (USD)VRBO
From $136 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 $136 per night (USD)VRBO
From $161 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 $161 per night (USD)VRBO