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 in Winter Park, FL

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $166 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travelers to Winter Park are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    1 / 27
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 19
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Show Prices
    1 / 27
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Patio
    • Grill
    • DVD Player
    • Balcony
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Comfortable 1bd/1bath home with convenient location midway between historic Winter Park and Downtown Orlando. Just a hop away from I-4. Within close distance you will find a unique selection of specialty shops, parks, and restaurants for every taste on Edgewater Dr.. Historic Dubdread golf... View all property information
    Location Information
    Winter Park, Central Florida 32789
    5 of 5 bubbles Reviewed November 1, 2016
    Rental for an entire apartment. Full kitchen livingroom and bedroom. Owners are wonderful to work with. We will rent from again. Thanks for your kindnesses.
    5 of 5 bubbles Reviewed April 14, 2016
    While planning to attend a family wedding, my husband and I wanted to find a nice place that was less expensive and more spacious than the hotels that were recommended to us. This...
    See all reviews
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Private Yard
    • Parking
    • Patio
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This is a great little neighborhood chock full of local businesses, great people, nice neighbors and just a nice homey feeling. I can't get enough of the Main Street (Edgewater Dr.) running through, you have everything from some pretty great restaurants, plenty of yoga studios (YAY), to great... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 37
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Patio
    • Washer
    • Private Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Comfortable & Clean 1bd/1bath home with convenient location in historic Winter Park yet very close to Downtown Orlando or the main interstate to get you anywhere quickly. Beautiful Mead Gardens is a block down the road and is no cost to park and walk the gardens or picnic. It is close to nightlife,... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 22
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Patio
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Comfortable & Clean 1bd/1bath home with convenient location in historic Winter Park yet very close to Downtown Orlando or the main interstate to get you anywhere quickly. Beautiful Mead Gardens is a block down the road and is no cost to park and walk the gardens or picnic. Within a very close... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 35
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Lakeside, on the shores of Lake Killarney, is in the exclusive village town of Winter Park (32789). You are 7 min to downtown Orlando, 20 min to Universal/ Disney. A 5,700 sq. ft family estate home with 285 ft of shoreline situated in an eco-sanctuary of rare birds & teeming aquatic life.... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 35
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Washer
    • Air Conditioning
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A beautifully appointed 3 bedroom cottage on 400 acre Lake Fairview. We are central to College Park, Winter Park, and Altamonte Springs giving you the most comprehensive selection of shopping, eateries, and theater selections available in Orlando. Just minutes from from Interstate 4 and the down... View all property information
    Location Information
    Winter Park, Central Florida 32804
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • DVD Player
    • Patio
    • Washer
    • Satellite TV
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32792
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 / 40
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Waterfront
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Perfect spot to enjoy the sunset over our lake, sit by the outdoor fireplace, use the putting green & relax. Or walk to Baldwin Park shops & restaurants (0.8 miles)! Only 10 min drive to Park Ave/Rollins. 35 Min to Disney, 25 to Universal. Enjoy! This adorable mother-in-law cottage/suite has lots... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Satellite TV
    • Air Conditioning
    • Washer
    • Internet Access
    • Patio
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 28
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Central Heating
    • Balcony
    • Terrace
    • Housekeeping...
    • Patio
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Come enjoy the tropical splendor that is Liki Tiki Village Resort Orlando, Florida. Relax in spacious condominiums and accommodations that includes a variety of amenities, including a water park, for the whole family. Liki Tiki Village is located only seven miles from Walt Disney World, SeaWorld,... View all property information
    Location Information
    Winter Park, Central Florida 34787
    1 / 18
    8 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Private Outdoor...
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Summary Less than 15 minutes from Walt Disney World, the exclusive new Retreat community at... View all property information
    Location Information
    Winter Park, Central Florida
    1 / 20
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 18
    8 Bedrooms, 5 Bathrooms, Sleeps 17 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Satellite TV
    • Parking
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Summary Located just 15 minutes from Walt Disney World, this beautiful home offers the perfect... View all property information
    Location Information
    Winter Park, Central Florida
    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    • Parking
    • Washer
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Housekeeping...
    • Patio
    • Washer
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 24
    Studio, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Air Conditioning
    • Patio
    • Satellite TV
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    Get the List
    1 / 14
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Shared Yard
    • Shared Outdoor Pool...
    • Air Conditioning
    • Secure Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This property features The following: Spacious-748 sq ft 1 bed 1 bath Fully furnished-just move in! Great location-Full Sail University next block down, off 436, mins to shopping and schools. Community pool, tennis courts, and play ground. Small dogs ok . Available 01-Aug.2015. Close to all major... View all property information
    Location Information
    Winter Park, Central Florida 32792
    1 / 13
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Patio
    • Parking
    • Satellite TV
    • Washer
    • Internet Access
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 15
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Grill
    • Patio
    • DVD Player
    • Internet Access
    • Hot Tub
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • Grill
    • Private Outdoor...
    • Patio
    • Satellite TV
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Washer
    • Parking
    • Satellite TV
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 24
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Patio
    • Private Outdoor...
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32714
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    • Patio
    • Internet Access
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32792
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Internet Access
    • Patio
    • Air Conditioning
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 18
    8 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Parking
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Top Villas does vacation rentals differently. Book with us and youll get the best homes, at the best prices, from people who really care. Best rate guarantee | Tailor-made service | 24/7 guest support Summary If you are planning a big Orlando vacation with family and friends, this is perfect... View all property information
    Location Information
    Winter Park, Central Florida
    1 / 18
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Satellite TV
    • DVD Player
    • Patio
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Parking
    • Washer
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Balcony
    • Washer
    • DVD Player
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Patio
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Patio
    • Private Outdoor...
    • Air Conditioning
    • Internet Access
    • Grill
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32792
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Patio
    • DVD Player
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Washer
    • Air Conditioning
    • Patio
    • Internet Access
    • Satellite TV
    • Grill
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32792
    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Grill
    • Washer
    • Private Outdoor...
    • Internet Access
    • Patio
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Parking
    • Internet Access
    • Patio
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Winter Park, Central Florida 32789
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Grill
    • Hot Tub
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Nestled between the cities of Winter Park and Orlando, Audubon Park is a gem that recently won the National Main Street Award for its uniqueness! This quiet little street is close to local parks, dining, nightlife, shopping, yoga and more! You’ll love the coziness, in-garden-feeling and locally... View all property information
    Location Information
    Winter Park, Central Florida 32789
    Winter Park Flight and Weather Info
    Airports nearby (1)
    Plan your day of travel
    MCO
    Orlando Intl Airport
    12.2 miles from Winter Park
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    67° 48°
    January
    68° 49°
    February
    72° 53°
    March