We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals and condos in Winter Park, FL and nearby

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 1,867 Rentals in the Winter Park Area
loading...
From
$114
Per Night
Winter Park
1 Bedroom, 1 Bathroom, Sleeps 4
14 photos Details
Make Inquiry
From
$850
Per Night
Winter Park
5 Bedrooms, 6 Bathrooms, Sleeps 11
30 photos Details
Make Inquiry
From
$225
Per Night
Winter Park
3 Bedrooms, 2 Bathrooms, Sleeps 7
15 photos Details
Make Inquiry
Also consider
VISTA CAY RESORT - UNIVERSAL, CONVENTION CENTER
2 Bedrooms, sleeps 6
$90 - $110 / night
Orlando New Year's Vacation Rental - 2br/2ba suite
2 Bedrooms, sleeps 6
$159 - $199 / night
Low priced Orlando Disney Vacation Pool Home
3 Bedrooms, sleeps 7
$59 - $85 / night
Orlando Excellent House 3 Bedrooms
Sleeps 4
$127 - $159 / night

The following rentals are within 5 miles of Winter Park, Florida.

From
$99
Per Night
Orlando
3 Bedrooms, 3 Bathrooms, Sleeps 6
22 photos Details
Reviews (1) Make Inquiry
From
$129
Per Night
Orlando
4 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details
Reviews (19) Make Inquiry
From
$189
Per Night
Orlando
6 Bedrooms, 3 Bathrooms, Sleeps 14
15 photos Details
Reviews (9) Make Inquiry
From
$99
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (1) Make Inquiry
From
$139
Per Night
Orlando
5 Bedrooms, 4 Bathrooms, Sleeps 10
12 photos Details
Reviews (1) Make Inquiry
Get the List
From
$85
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (17) Make Inquiry
From
$159
Per Night
Orlando
3 Bedrooms, 4 Bathrooms, Sleeps 8
17 photos Details
Reviews (1) Make Inquiry
From
$214
Per Night
Orlando
2 Bedrooms, Sleeps 6
10 photos Details
Reviews (1) Make Inquiry
From
$70
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
Reviews (1) Make Inquiry
From
$95
Per Night
Orlando
4 Bedrooms, 3 Bathrooms, Sleeps 8
11 photos Details
Reviews (1) Make Inquiry
From
$54
Per Night
Orlando
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
Reviews (1) Make Inquiry
From
$110
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details
Reviews (1) Make Inquiry
From
$120
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 6
27 photos Details
Reviews (2) Make Inquiry
From
$75
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 6
38 photos Details
Reviews (10) Make Inquiry
From
$149
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 8
24 photos Details
Reviews (1) Make Inquiry
From
$130
Per Night
Orlando
4 Bedrooms, 3 Bathrooms, Sleeps 8
17 photos Details
Reviews (3) Make Inquiry
From
$120
Per Night
Orlando
5 Bedrooms, 4 Bathrooms, Sleeps 12
38 photos Details
Reviews (3) Make Inquiry
From
$110
Per Night
Orlando
4 Bedrooms, 3 Bathrooms, Sleeps 8
49 photos Details
Reviews (2) Make Inquiry
From
$247
Per Night
Orlando
4 Bedrooms, Sleeps 9
13 photos Details
Reviews (1) Make Inquiry
From
$185
Per Night
Orlando
6 Bedrooms, 6 Bathrooms, Sleeps 15
45 photos Details
Reviews (1) Make Inquiry
From
$125
Per Night
Orlando
1 Bedroom, 2 Bathrooms, Sleeps 8
44 photos Details
Reviews (1) Make Inquiry
From
$80
Per Night
Orlando
1 Bedroom, 1 Bathroom, Sleeps 4
29 photos Details
Reviews (5) Make Inquiry
From
$83
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 4
11 photos Details
Reviews (15) Make Inquiry
From
$69
Per Night
Orlando
1 Bedroom, 1 Bathroom, Sleeps 4
21 photos Details
Reviews (3) Make Inquiry
From
$179
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (23) Make Inquiry
From
$1,895
Per Week
Orlando
4 Bedrooms, 4 Bathrooms, Sleeps 16
17 photos Details
Reviews (1) Make Inquiry
From
$270
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 8
20 photos Details
Reviews (2) Make Inquiry
From
$189
Per Night
Orlando
3 Bedrooms, 4 Bathrooms, Sleeps 8
16 photos Details
Reviews (26) Make Inquiry
From
$160
Per Night
Orlando
7 Bedrooms, 5 Bathrooms, Sleeps 16
28 photos Details
Reviews (2) Make Inquiry
From
$125
Per Night
Orlando
1 Bedroom, 1 Bathroom, Sleeps 4
10 photos Details
Reviews (1) Make Inquiry
From
$260
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 8
24 photos Details
Reviews (5) Make Inquiry
From
$99
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (2) Make Inquiry
From
$810
Per Week
Orlando
4 Bedrooms, 2 Bathrooms, Sleeps 8
20 photos Details
Reviews (40) Make Inquiry
From
$159
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 8
16 photos Details
Reviews (34) Make Inquiry
From
$109
Per Night
Orlando
2 Bedrooms, 2 Bathrooms, Sleeps 8
24 photos Details
Reviews (3) Make Inquiry
From
$149
Per Night
Orlando
3 Bedrooms, 4 Bathrooms, Sleeps 8
45 photos Details
Reviews (1) Make Inquiry
From
$199
Per Night
Orlando
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (3) Make Inquiry
Go to map view
Book Online(539)
Use filters to find the best results!

Suitability

  • Wheelchair access (161)
  • Elder access (385)
  • Suitable for children (498)
  • Pet friendly (51)
  • Smoking allowed (38)

Amenities

  • Internet (1,208)
  • Air Conditioning (1,180)
  • All pools (803)
  • Other outdoor space (589)
  • Hot Tub (523)
  • View all amenities
Filter search results by:
Book Online(539)

Suitability

  • Wheelchair access (161)
  • Elder access (385)
  • Suitable for children (498)
  • Pet friendly (51)
  • Smoking allowed (38)

Amenities

  • Internet (1,208)
  • Air Conditioning (1,180)
  • All pools (803)
  • Other outdoor space (589)
  • Hot Tub (523)
  • View all amenities