Mead Garden Rentals
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 $198 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 $198 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 $267 per night (USD)Expedia
Comfy Home in Winter Park, can accommodate up 6 guests!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our home is located in Winter Park and can serve as a central base to live like a local. You can enjoy all of the great ...
From $267 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 $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
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Charming 3-bedroom townhome with AC and WiFi in Winter Park
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Winter Park at this 3-bedroom townhome. With 1 king bed and 2 queen beds, this adorable property is ...
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From $76 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 $76 per night (USD)Expedia
From $142 per night (USD)VRBO
Bungalow Near Downtown Orlando, Winter Park, Major Hospitals, and Disney!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming Renovated Studio in Downtown Orlando’s College Park Experience the best of urban and small-town living in this ...
From $142 per night (USD)VRBO
From $169 per night (USD)VRBO
City Cottage with Mid Century Modern Vibe
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Premium home with Mid Century Modern vibe. Beautiful furnishings and decor to make you feel completely comfortable. Rel ...
From $169 per night (USD)VRBO
From $219 per night (USD)VRBO
King Room Near Fracture Care Center ORL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This property is located opposite Florida Hospital, 700 metres from the Orlando Science Center. A complimentary hot brea ...
From $219 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 $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)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 $197 per night (USD)VRBO
From $208 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 $208 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 $183 per night (USD)VRBO
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 $183 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 $209 per night (USD)VRBO
THE CLOUD 9 SUITE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
PET FRIENDLY 🐾 Book the Cloud 9 Suite, located in the heart of downtown Winter Park FL and Orlando! Beautifully furnish ...
From $209 per night (USD)VRBO
From $146 per night (USD)Expedia
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)Expedia
From $1884 per night (USD)VRBO
LUXURY 5\/4 w Jacuzzi tub Winter Park\/CP Orlando Gem
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 22
Welcome to your perfect Orlando getaway! This stunning new home boasts 5 spacious bedrooms and 4 modern baths, comfortab ...
From $1884 per night (USD)VRBO
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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 ...
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From $150 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 $150 per night (USD)VRBO
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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 ...
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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
From $324 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 $324 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 $162 per night (USD)Expedia
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 $162 per night (USD)Expedia
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 $342 per night (USD)Expedia
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 ...
From $342 per night (USD)Expedia
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Advent health all white unit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to my charming 2 bedroom 2 bathroom home in the heart of Orlando FL located right of the I4 highway exit Princet ...
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From $144 per night (USD)Expedia
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)Expedia
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Cottage on Cornell - Quaint & Cozy w\/Outdoor Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Newly renovated guest suite using original reclaimed materials to create a modern vintage farmhouse vibe. Centrally loca ...
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From $122 per night (USD)Expedia
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)Expedia
From $246 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 $246 per night (USD)VRBO
From $115 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 $115 per night (USD)Expedia
From $120 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 $120 per night (USD)VRBO
From $182 per night (USD)Expedia
The beautiful Melrose Cottage
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our Melrose Cottage in Winter Park. This delightfully curated property features 2 bedrooms with a king and qu ...
From $182 per night (USD)Expedia
From $271 per night (USD)VRBO
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 $271 per night (USD)VRBO
From $446 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 $446 per night (USD)VRBO
From $11422 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 $11422 per night (USD)VRBO
From $373 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 $373 per night (USD)VRBO
From $375 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 $375 per night (USD)VRBO
From $408 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 $408 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 $442 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 $442 per night (USD)VRBO
From $488 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 $488 per night (USD)VRBO
From $449 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 $449 per night (USD)VRBO
From $147 per night (USD)Expedia
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)Expedia
From $341 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 $341 per night (USD)VRBO
From $153 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 $153 per night (USD)VRBO
From $442 per night (USD)VRBO
Enjoy more space and relax in Downtown Orlando !!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Take advantage of our fast and free WiFi, free hot breakfast, free coffee, free parking and free weekday newspapers thro ...
From $442 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