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.
dd/mm/yyyy dd/mm/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
    $242 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Winter Park are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    1 / 28
    5 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Payment Protection
    1 / 27
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    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
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other traveller 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 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 theatre selections available in Orlando. Just minutes from from Interstate 4 and the down town area... View all property information
    Location Information
    Winter Park, Central Florida 32804
    1 / 26
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    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 / 37
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Patio
    • Washer
    • Private Garden
    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 / 14
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Shared Garden
    • 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 / 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 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Grill
    • Parking
    • Balcony
    • Air Conditioning
    • Terrace
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Family friendly layout with master bedroom suite, shared bedroom (2 twin beds), main living room furnished with modern elegance. Kitchen with modern conveniences: all top line stainless steel appliances stove top, oven, dishwasher, fridge. Granite countertops and marble floors. Sunroom set up for a... View all property information
    Location Information
    Winter Park, Central Florida 32789
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    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 / 17
    8 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    REF: TOP VILLAS – Championsgate 57 All of our villas here at Top Villas are professionally managed by an onsite property team to ensure you have a perfect stay, Call us today 24/7 for an instant quote, availability, special deals or if you have any questions, regarding our amazing villa in... View all property information
    Location Information
    Winter Park, Central Florida
    1 / 17
    8 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    REF: TOP VILLAS – Championsgate 58 All of our villas here at Top Villas are professionally managed by an onsite property team to ensure you have a perfect stay, Call us today 24/7 for an instant quote, availability, special deals or if you have any questions, regarding our amazing villa in... View all property information
    Location Information
    Winter Park, Central Florida
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Private Garden
    • 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 / 17
    8 Bedrooms, 5 Bathrooms, Sleeps 17 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    REF: TOP VILLAS – Championsgate 56 All of our villas here at Top Villas are professionally managed by an onsite property team to ensure you have a perfect stay, Call us today 24/7 for an instant quote, availability, special deals or if you have any questions, regarding our amazing villa in... View all property information
    Location Information
    Winter Park, Central Florida
    1 / 30
    5 Bedrooms, 6 Bathrooms, Sleeps 11 | Quick View
    Enquire for rates
    Amenities & Details
    • Sauna
    • Waterfront
    • Hot Tub
    • Private Outdoor...
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    CONTACT REAL ESTATE AGENT NINA MARTINOV FOR MORE INFO AND BOOKING!!! The Orange County city of Winter Park, situated north of Orlando, was once considered a winter resort. Today, the arts- and culture-filled city includes Rollins College and the Charles Hosmer Morse Museum of Natural Art.... View all property information
    Location Information
    Winter Park, Central Florida 32789