HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled

Make a holiday apartment in Winter Park your home away from home

Located in a leafy suburb of Orlando, a Winter Park holiday apartment or villa is an ideal base for enjoying everything the metropolitan area has to offer, while providing a scenic and serene retreat from the hustle and bustle in the evenings. Planned and developed as a resort town at the turn of the 20th century, the brick-cobbled streets surrounding the rentals in Winter Park encourage strolling and browsing; perhaps stopping for a meal in one of the many upscale restaurants. With a wide range of villas, apartments, cabins and lodges to choose from, HomeAway offers Winter Park holiday accommodation to suit every taste.

Things to do

-Festivals: The annual Bach Festival is held every autumn at Winter Park's Rollins College Campus; a must if tourists have a passion for choral and classical music. March's Sidewalk Art Festival is one of the country's most prestigious, as is November's Winter Park Concours d'Elegance, for lovers of combustion-powered artistry of the four-wheeled variety.

-Gardens: Mead Botanical Garden encompasses 47 acres of parkland, and is typically within walking distance of most Winter Park holiday rentals. It boasts a number of ecosystems to explore by foot on the boardwalk, or by bicycle on the bike trails. A 300 seater amphitheatre also anchors this urban oasis, along with a discovery barn, butterfly garden and a recreation centre.

-History: Many of the buildings surrounding rentals in Winter Park are over 100 years old, which is a real rarity in the US with their propensity for constant urban renewal. They shoulder tree-shaded and brick-cobbled streets, and abut the Venetian canals, blending elegantly with picturesque lakes and meticulous parks.

-Theme Parks: While Winter Park holiday rentals are sited in a peaceful, quaint town, Orlando has some of the most exciting theme parks in the world. From behemoths like Disney World, Universal Studios and Sea World, to smaller parks like Legoland, the Kennedy Space Centre Visitor Complex, the Holy Land Experience and Gatorland, tourists can easily do a theme park a day!

-Nightlife: Eating out is typically quite high end in Winter Park, matching the atmosphere of this quaint and elegant town. From French bistros to tapas bars, BBQ joints to fusion fare, there's a venue for every taste and budget, but the tendency is towards fine dining. Bars and nightclubs are equally cosmopolitan.

Weather in Winter Park

Winter Park has a typical Florida subtropical climate, with warm, dry winters and long, hot summers, encouraging the eponymous notion of the town as a winter destination. Rain falls mainly during the summer as heavy thunderstorms, breaking the humidity and also helping to keep things cooler than inland areas further north. Temperatures from June to September top out at around the mid-30°C mark, while winter maximums hover around 22°C: it’s about the same as a British summer.

Travel to Winter Park

Travel to Winter Park is a cinch as Orlando International Airport is only 14 miles away. Unusually for Florida, visitors could feasibly get around on Orlando's public transport. This is often undesirable, however, especially during the summer with the heat, humidity, and frequent cloudbursts. Fly/drive is still preferable, despite Orlando's extensive public transport system. There is an Amtrak station in Winter Park itself, if guests fancy an iconic American train journey, though Amtrak is a national network rather than a local one.

Excellent! 4.6/5
(12 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
House #450575vb
12
Viewed 25 times in the last 48 hours
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Bungalow #780146vb
4
Viewed 29 times in the last 48 hours
Exceptional! 5/5
(15 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Separate Toilet
  • Sleeps 2
Bungalow #444585vb
15
Viewed 27 times in the last 48 hours
Wonderful! 4.8/5
(52 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 10
House #981770
52
Viewed 44 times in the last 48 hours
Excellent! 4.4/5
(16 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 3
Bungalow #3993910
16
Viewed 46 times in the last 48 hours
  • 4 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 8
House #885924vb
4
Viewed 42 times in the last 48 hours
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 5
Cottage #919138vb
2
Viewed 5 times in the last 48 hours
  • 2 BR
  • 2 BA
  • Sleeps 5
Bungalow #322808vb
24
  • 1 BR
  • 1 BA
  • Sleeps 2
Apartment #683231vb
7
Exceptional! 5/5
(10 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 6
House #823160vb
10
Viewed 41 times in the last 48 hours
Excellent! 4.6/5
(31 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 9
House #929474
31
Viewed 39 times in the last 48 hours
  • 1 BR
  • 1 BA
  • Sleeps 2
House #1069947vb
Viewed 8 times in the last 48 hours
Wonderful! 4.8/5
(21 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
House #3023348
21
Viewed 24 times in the last 48 hours
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
House #1027239vb
Viewed 5 times in the last 48 hours
Exceptional! 5/5
(20 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
Cottage #669117vb
20
Viewed 22 times in the last 48 hours
Wonderful! 4.8/5
(30 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 9
House #929471
30
Viewed 26 times in the last 48 hours
  • 1 BR
  • 1 BA
  • Sleeps 2
Studio #493118vb
28
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
House #990123vb
2
Viewed 16 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 5
House #952054vb
3
Viewed 60 times in the last 48 hours
Wonderful! 4.9/5
(11 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #243102
11
Viewed 12 times in the last 48 hours
Excellent! 4.7/5
(6 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Studio #4245895
6
Viewed 29 times in the last 48 hours
Wonderful! 4.8/5
(4 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 8
House #901305vb
4
Viewed 13 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 6
House #4303470
6
Viewed 63 times in the last 48 hours
Wonderful! 4.8/5
(6 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 7
House #3166620
6
Viewed 43 times in the last 48 hours
Exceptional! 5/5
(12 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
House #3023034
12
Viewed 18 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 7
House #1030436vb
1
Viewed 10 times in the last 48 hours
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
Apartment #1069352vb
Viewed 16 times in the last 48 hours
  • 1 BR
  • 1 BA
  • Sleeps 2
Guest House #1033184vb
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 6
Apartment #1046545vb
Viewed 40 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 6
Condo #724660vb
2
Viewed 6 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
House #1091039vb
Viewed 14 times in the last 48 hours
  • 2 BR
  • 2 BA
  • Sleeps 4
House #1060352vb
Viewed 8 times in the last 48 hours
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
House #1097929vb
Viewed 36 times in the last 48 hours
  • 2 BR
  • 1 BA
  • Sleeps 4
House #1056448vb
Viewed 9 times in the last 48 hours
  • 4 BR
  • 2 BA
  • Sleeps 8
House #319653vb
10
  • 2 BR
  • 1 BA
  • Sleeps 4
House #338205vb
9
  • 4 BR
  • 2 BA
  • Sleeps 10
House #694235vb
Viewed 26 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
House #1114809vb
Viewed 9 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
House #1114391vb
Viewed 23 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
House #1114504vb
Viewed 12 times in the last 48 hours
Excellent! 4.7/5
(128 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Hotel #3905183
128
Viewed 837 times in the last 48 hours
Excellent! 4.6/5
(37 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 10
Condo #4141115
37
Viewed 481 times in the last 48 hours
Very Good! 4/5
(15 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #507153vb
15
Viewed 74 times in the last 48 hours
Wonderful! 4.8/5
(9 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #792993vb
9
Viewed 85 times in the last 48 hours
Wonderful! 4.8/5
(66 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 10
Villa #34854vb
66
Viewed 514 times in the last 48 hours
Wonderful! 4.9/5
(89 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #964487
89
Viewed 196 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 8
House #3569183
45
Excellent! 4.6/5
(53 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 9
Villa #56513
53
Viewed 84 times in the last 48 hours
Excellent! 4.7/5
(43 reviews)
avg/night
  • 1 BR
  • 2 BA
  • Sleeps 6
Condo #512028vb
43
Viewed 192 times in the last 48 hours
Excellent! 4.7/5
(46 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 10
Hotel #3905188
46
Viewed 429 times in the last 48 hours

Winter Park Holiday Rentals & Homes (300+)

 

Recent Reviews

One Week Getaway

5 of 5
The physical location (about 20-25 minutes from Universal) was not our first choice, but in the end, it was really our only choice. The house, the land, the lake made for the perfect combination of peace and quiet that we ultimately sought out. After a long day at the parks, returning to the house was something we looked forward to... take a dip, lounge in the wonderfully manicured backyard, grill on the back porch. RInse, wash, repeat... we found ourselves in this pattern almost everyday. Despite the owners being in the UK, they were extremely attentive when a minor glitch popped up. Rest assured they have locals taking great care to ensure that all our needs were met and in a timely fashion. If your kids need to see Mickey every waking moment of every day, then by all means stay on site at Disney, but if you would also like to enjoy YOUR vacation, this is not a treat to miss out on.
  • Review Submitted: Feb 04, 2010
  • Date of Stay: Jan 2010