Winter Park

Winter Park Homestays

Enter your dates to find homestays in Winter Park for a cozy, local feel.

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Popular Homestays in Winter Park

Check out the best homestays in Winter Park for a home-like stay.
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Lakefront Paradise Near Attractions
Lakefront Paradise Near AttractionsLakefront Paradise Near AttractionsLakefront Paradise Near AttractionsLakefront Paradise Near AttractionsLakefront Paradise Near AttractionsLakefront Paradise Near Attractions
59
Hotel near Winter Park Area,Winter Park
Featured facilities: Clothes Dryer
Outstanding
5 reviews
10.0/10
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College quater charming Winter Park Historic Dist Rollins College quarters
College quater charming Winter Park Historic Dist Rollins College quartersCollege quater charming Winter Park Historic Dist Rollins College quartersCollege quater charming Winter Park Historic Dist Rollins College quartersCollege quater charming Winter Park Historic Dist Rollins College quartersCollege quater charming Winter Park Historic Dist Rollins College quartersCollege quater charming Winter Park Historic Dist Rollins College quarters
15
Hotel near Winter Park Area,Winter Park
Featured facilities: Washing Machine
Great
2 reviews
9.0/10
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Winter Park College quarters historic district
0
Hotel near Winter Park Area,Winter Park
The College Quarters in Winter Park is located in the charming city of Winter Park Historic District. Located within blocks. of SunRail stations, shopping, movie theatres, grocery, gas stations, banks, and golf courses, and Rollins College founded in1885 along the shores of Lake VirginiaAbout pets:Pets allowed: dogs and cats less than 50 lbs per pet (limit 2 pets total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
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Winter Park
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Elegant & Spacious Historic Winter Park Home with Pool + Spa
Elegant & Spacious Historic Winter Park Home with Pool + SpaElegant & Spacious Historic Winter Park Home with Pool + SpaElegant & Spacious Historic Winter Park Home with Pool + SpaElegant & Spacious Historic Winter Park Home with Pool + SpaElegant & Spacious Historic Winter Park Home with Pool + SpaElegant & Spacious Historic Winter Park Home with Pool + Spa
29
Hotel near Winter Park Area,Winter Park
Historic Winter Park home, located within a beautiful neighborhood. The home is spacious, charming and elegantly-appointed with serene, lush views. Out back is a gorgeous oasis, featuring a resort-style heated pool and spa, surrounded by a tropical garden. Longer-term inquiries welcome – please reach out directly for more information/pricing.The home is brimming with charm and surrounded by beautiful nature. Charming features, such as hardwood floors throughout, push-button light switches and original windows/doors, give the home character while modern touches like Nest thermostats, Brilliant home automation, Nest-protect smoke detectors, and smart locks bring it into the 21st century. The home also has very reliable internet with a wireless mesh network that extends into the backyard.An oversized front porch with a classic porch swing, sofa, and rocking chairs welcome you to the front entrance. A large, gated driveway accommodates three parking spots and provides access to a private side-entrance. The first story boasts a formal living room with fireplace and cozy seating, a family room with a flat-screen TV (equipped with Apple TV with Netflix, ad-free Hulu and a variety of other apps) and large sectional sofa, a formal dining room, spacious eat-in kitchen (complete with large refrigerator, microwave, dishwasher, and oven), a mud room with a built-in office space and a half bathroom. The second story features four spacious bedrooms and a laundry room right next to the master bedroom. Master suite includes a large walk-in closet, a flatscreen tv with roku, two built-in his-and-hers toiletry stations and a luxurious master bathroom.The master suite has a king-size bed with pillow-top mattress, the second bedroom has a queen bed with pillow-top mattress, the third has full-size bed with memory foam mattress and the fourth bedroom has both a twin-sized bed with memory foam mattress, as well as a convertible sleeper-sofa. Out the back-door is a screened-in porch with an additional dining area. The backyard is centered around a large, resort-style sparkling heated pool and spa. Backyard also includes a summer kitchen with grill, lounge chairs, a hammock, outdoor table and chairs with giant umbrella, and an additional intimate seating area near the spa. In the back corner is a fenced-in, grassy area with a children's playground.All backyard/common areas are shared with the detached, private guest house, which is rented separately. Please inquire if you're interested in renting the guest house as well. Landscape and pool are maintained weekly.About pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
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Stylish Boutique Guest house in Winter Park
Stylish Boutique Guest house in Winter ParkStylish Boutique Guest house in Winter ParkStylish Boutique Guest house in Winter ParkStylish Boutique Guest house in Winter ParkStylish Boutique Guest house in Winter ParkStylish Boutique Guest house in Winter Park
35
Hotel near Winter Park Area,Winter Park
Indulge the senses in the calming aesthetics of this newly constructed guest house. The residence features room for 4 guests across 2 bedrooms, a large bathroom with a walk-in shower that features dual shower heads & skylight. A desk for remote workers, and plenty of room to spread out across the common (indoor & outdoor) areas.Your modern kitchen is fully stocked with basic cooking essential’s, a cozy living room with a smart tv, dining room with skylight.Tastefully decorated with minimalist design, this guest house is fully equipped to be your home-away-from-home.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Smoking is not allowed inside the property and if you do, it will result in $250 additional cleaning charge and possible eviction..NO CANDLES. None. Instead, we provide flameless, battery-operated candles for you to use.”,Make sure to TURN OFF OUTDOOR LIGHTS if don’t use it. No loud gatherings after 10:30pm. Please respect the space & keep it clean..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Outstanding
49 reviews
10.0/10
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Winter Park charm. Close to Park Ave
Winter Park charm. Close to Park AveWinter Park charm. Close to Park AveWinter Park charm. Close to Park AveWinter Park charm. Close to Park AveWinter Park charm. Close to Park Ave
9
Hotel near Winter Park Area,Winter Park
Featured facilities: Clothes Dryer
Outstanding
9.8/10
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LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
26
Hotel near Winter Park Area,Winter Park
Featured facilities: Clothes Dryer
Outstanding
3 reviews
10.0/10
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Winter Park Oasis
Winter Park OasisWinter Park OasisWinter Park OasisWinter Park OasisWinter Park OasisWinter Park Oasis
11
Hotel near Winter Park Area,Winter Park
Enjoy your stay at the Winter Park Oasis! This cozy 2 bedroom private unit, is in a charming and historic neighborhood! This Oasis is a short drive from park ave restaurants, Rollins college, downtown Orlando and our beautiful beaches. Wifi and 2 car parking is included.Wake up in this bright bungalow, located right in the heart of Winter Park. I love the atmosphere in my neighborhood, you will find unique architecture, good restaurants, and beautiful local parks.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 20.About events:No events allowed.
Amazing
3 reviews
9.4/10
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LUXURY AND LOCATION!!!
0
Hotel near Winter Park Area,Winter Park
Featured facilities: Kitchen, Washing Machine
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Winter Park Oasis
Winter Park OasisWinter Park OasisWinter Park OasisWinter Park OasisWinter Park OasisWinter Park Oasis
10
Hotel near Winter Park Area,Winter Park
Your backyard oasis awaits you, with queen size 10in memory foam swing mattress, full outdoor kitchen, 65in TV along with a 2 hole putting green and flower wall. You can relax and enjoy the warm florida winters with a nice bbq.Walking distance to phelps park, 1 mile from park ave, 1.5 mile from Rollins college and plenty more.About pets:Pets allowed.Pets are allowed with a $100 pet fee applied.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.No smoking inside or around the property.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.No parties or events are allowed at anytime..
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Frequently Asked Questions

What are some good hotels near Rollins Museum of Art in Winter Park?

For Winter Park hotels near Rollins Museum of Art, many travelers recommend The Alfond Inn (from IDR 4,997,601), Park Plaza Hotel Orlando - Winter Park (from IDR 2,836,285) and SpringHill Suites by Marriott Winter Park (from IDR 3,494,793) for their great location and service.

What are the must-visit spots in Winter Park?

Which neighborhoods in Winter Park are best for tourists to stay in?

Popular areas highly recommended by visitors to Winter Park include Winter Park Area.