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 Family icon

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.

Cancel Clear Filters Apply Filters
More Filters

Price Per Night

£ £

Bedrooms

Bathrooms

Payment Options

Property Type

Popular Searches

Facilities

Location Type

Local Area

Property Details

Clear Filters
Use filters to narrow your search results!
Viewed 111 times in the last 48 hours
  • 3 BR House
  • 3 BA
  • 2000 sq ft
Wonderful! 4.8/5
(73 reviews)
avg/night
73
Viewed 19 times in the last 48 hours
  • 2 BR House
  • 2 BA
  • 1020 sq ft
avg/night
Premier Partner
2
Viewed 26 times in the last 48 hours
  • 1 BR Studio
  • 1 BA
  • 320 sq ft
Wonderful! 4.8/5
(8 reviews)
avg/night
8
Viewed 10 times in the last 48 hours
  • 4 BR House
  • 2 BA
  • 2099 sq ft
Exceptional! 5/5
(8 reviews)
avg/night
Premier Partner
8
Viewed 8 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1900 sq ft
Exceptional! 5/5
(15 reviews)
avg/night
15
Viewed 28 times in the last 48 hours
  • 1 BR House
  • 1 BA
avg/night
3
Viewed 14 times in the last 48 hours
  • 2 BR House
  • 2 BA
  • 2500 sq ft
Exceptional! 5/5
(9 reviews)
avg/night
Premier Partner
9
Viewed 27 times in the last 48 hours
  • 3 BR House
  • 2 BA
Wonderful! 4.9/5
(11 reviews)
avg/night
11
Viewed 7 times in the last 48 hours
  • 2 BR Bungalow
  • 1 BA
  • 1400 sq ft
Excellent! 4.7/5
(9 reviews)
avg/night
Premier Partner
9
Viewed 85 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1500 sq ft
avg/night
4
Viewed 10 times in the last 48 hours
  • 1 BR Bungalow
  • 1 BA
  • Separate Toilet
  • 1000 sq ft
Exceptional! 5/5
(22 reviews)
avg/night
Premier Partner
22
Viewed 39 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1800 sq ft
Excellent! 4.7/5
(37 reviews)
avg/night
37
Viewed 25 times in the last 48 hours
  • 2 BR Bungalow
  • 1 BA
Excellent! 4.6/5
(29 reviews)
avg/night
29
Viewed 21 times in the last 48 hours
  • 4 BR House
  • 2 BA
  • 2200 sq ft
Wonderful! 4.9/5
(27 reviews)
avg/night
27
Viewed 10 times in the last 48 hours
  • 2 BR Cottage
  • 1 BA
  • 1000 sq ft
avg/night
4
Viewed 25 times in the last 48 hours
  • 3 BR House
  • 3 BA
  • Separate Toilet
  • 1800 sq ft
Wonderful! 4.8/5
(43 reviews)
avg/night
43
Viewed 30 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • Separate Toilet
Exceptional! 5/5
(20 reviews)
avg/night
20
Viewed 10 times in the last 48 hours
  • 2 BR House
  • 2 BA
Excellent! 4.7/5
(6 reviews)
avg/night
6
Viewed 5 times in the last 48 hours
  • 2 BR House
  • 2 BA
  • 1500 sq ft
Excellent! 4.7/5
(26 reviews)
avg/night
Premier Partner
26
Viewed 21 times in the last 48 hours
  • 1 BR House
  • 1 BA
  • 701 sq ft
Excellent! 4.6/5
(5 reviews)
avg/night
5
Viewed 7 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • 700 sq ft
Wonderful! 4.9/5
(10 reviews)
avg/night
10
Viewed 7 times in the last 48 hours
  • 2 BR Cottage
  • 2 BA
  • 1950 sq ft
Exceptional! 5/5
(25 reviews)
avg/night
25
  • 1 BR House
  • 1 BA
  • 1 sq ft
avg/night
1
Viewed 7 times in the last 48 hours
  • 1 BR Cottage
  • 1 BA
avg/night
Viewed 10 times in the last 48 hours
  • 3 BR Condo
  • 2 BA
  • 1700 sq ft
avg/night
2
  • 1 BR House
  • 1 BA
  • 700 sq ft
avg/night
2
  • 1 BR Condo
  • 1 BA
View details for price
Viewed 22 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • Separate Toilet
  • 1900 sq ft
avg/night
Premier Partner
7
Viewed 6 times in the last 48 hours
  • 1 BR House
  • 1 BA
  • 250 sq ft
avg/night
Viewed 26 times in the last 48 hours
  • 2 BR House
  • 2 BA
  • 1400 sq ft
avg/night
3
Viewed 10 times in the last 48 hours
  • 3 BR House
  • 1 BA
  • 1200 sq ft
Wonderful! 4.8/5
(8 reviews)
avg/night
8
Viewed 5 times in the last 48 hours
  • 1 BR House
  • 1 BA
  • 900 sq ft
avg/night
4
Viewed 11 times in the last 48 hours
  • 2 BR House
  • 2 BA
  • 1350 sq ft
Excellent! 4.7/5
(15 reviews)
avg/night
15
  • 3 BR House
  • 2 BA
  • Separate Toilet
  • 2635 sq ft
avg/night
Viewed 5 times in the last 48 hours
  • 1 BR House
  • 1 BA
  • 900 sq ft
avg/night
Viewed 6 times in the last 48 hours
  • 1 BR House
  • 1 BA
  • 700 sq ft
avg/night
Viewed 7 times in the last 48 hours
  • 2 BR House
  • 1 BA
  • 950 sq ft
Exceptional! 5/5
(9 reviews)
avg/night
9
Viewed 164 times in the last 48 hours
  • 5 BR Villa
  • 5 BA
  • 3000 sq ft
avg/night
1
Viewed 160 times in the last 48 hours
  • 3 BR House
  • 2 BA
avg/night
Viewed 61 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • Separate Toilet
  • 3100 sq ft
avg/night
Viewed 74 times in the last 48 hours
  • 5 BR Villa
  • 5 BA
avg/night
1
Viewed 189 times in the last 48 hours
  • 6 BR House
  • 5 BA
  • Separate Toilet
  • 2900 sq ft
Excellent! 4.7/5
(46 reviews)
avg/night
46
Viewed 35 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1305 sq ft
Excellent! 4.5/5
(13 reviews)
avg/night
Premier Partner
13
Viewed 217 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1900 sq ft
Wonderful! 4.9/5
(9 reviews)
avg/night
Premier Partner
9
Viewed 37 times in the last 48 hours
  • 1 BR House
  • 1 BA
  • 500 sq ft
Wonderful! 4.9/5
(12 reviews)
avg/night
Premier Partner
12
Viewed 76 times in the last 48 hours
  • 4 BR House
  • 2 BA
  • Separate Toilet
  • 3200 sq ft
Excellent! 4.6/5
(34 reviews)
avg/night
34
Viewed 87 times in the last 48 hours
  • 6 BR House
  • 4 BA
  • Separate Toilets
  • 4000 sq ft
Wonderful! 4.8/5
(38 reviews)
avg/night
38
Viewed 41 times in the last 48 hours
  • 3 BR House
  • 3 BA
  • 2400 sq ft
Wonderful! 4.8/5
(48 reviews)
avg/night
48
Viewed 36 times in the last 48 hours
  • 3 BR Apartment
  • 2 BA
avg/night
Premier Partner
2
Viewed 40 times in the last 48 hours
  • 2 BR Apartment
  • 2 BA
avg/night
Premier Partner
1

Winter Park Holiday Homes & Rentals (300+)