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 Springs, FL and nearby

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
    Change Dates
    Price
    per night
    |||
    |||
    $0
    $169 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travelers get your favorite Winter Springs area vacation rental. You're so close to securing your perfect getaway. Book today.
    Applied filters:
    Nearby
    Clear All
    1 / 18
    5 of 5 stars (3) Excellent
    Winter Springs
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 / 20
    5 of 5 stars (5) Excellent
    Winter Springs
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices

    The following rentals are within 10 miles of Winter Springs, Florida.

    Winter Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Winter Park
    5 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautiful Custom Built Home in the heart of Winter Park... This well appointed home features Brazilian Cherry hardwood flooring; extensive crown molding; plantation shutters and decorative columns accent the foyer, formal living and dining rooms. Private, first floor master suite features a... View all property information
    Location Information
    Winter Park, Central Florida 32789
    Oviedo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Hot Tub
    • Private Yard
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    this house has a unique location, in the middle of the wild life but only 5 minutes from the 417 15 minutes from downtow Orlando 40 minutes from Disney sea world universal studio... 30 minute from Orlando airport 15 minutes from Sanford airport direct access to the lake and fishing from the front... View all property information
    Location Information
    Oviedo, Central Florida 32765
    1 / 27
    5 of 5 stars (1) Excellent
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Grill
    • Balcony
    • Washer
    • Porch
    • 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 stars 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
    Winter Park
    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
    Winter Park
    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
    Maitland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Washer
    • DVD Player
    • Patio
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Close to everything. Minutes off major highway I-4. 2 bedrooms, 2 baths. Large living area, fully stocked kitchen, laundry, dinning room, great private porch & pool area. Plus outdoor shower. 30-40 minutes to attractions. 60 minutes to the beaches.<BR>Our guests call our home a fun & relaxing... View all property information
    Location Information
    Maitland, Florida 32751
    Oviedo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Parking
    • Air Conditioning
    • Patio
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Spacious single-story 1,742 sq foot house on beautiful Lake Jesup. The perfect place to relax with wide water views and covered lanai. Gourmet granite kitchen, tv and wifi. Luxurious master bath with messaging bathtub. Boat ramp access and the perfect fishing spot. Secluded yet the house is only 5... View all property information
    Location Information
    Oviedo, Central Florida 32765
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    Winter Park
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Satellite TV
    • Parking
    • Children's Pool
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Three bedroom house located in one of the most exclusive neighborhoods in Winter Park. House is surrounded by million dollar homes. Large master bedroom downstairs and two bedrooms upstairs. Community pool and small water park for the kids is located a short walking distance away. Famous Park... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 27
    5 of 5 stars (1) Excellent
    Sanford
    4 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Waterfront
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A quiet house with a large cabin feel, tucked away from the hustle and bustle of Orlando and Daytona Beach but is within short driving distances from some of Florida's amazing springs and nature walks! The house boast an amazing view of the Saint John's river, the Lake Monroe Conservation area, and... View all property information
    Location Information
    Sanford, Central Florida 32771
    5 of 5 stars Reviewed February 25, 2016
    The most beautiful and relaxing mini-vacation I have ever taken with the family. The house was immaculate and well stocked. Annemarie is the best hostess ever! always available...
    See all reviews
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    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
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    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 / 10
    5 of 5 stars (1) Excellent
    Altamonte Springs
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Porch
    • Parking
    • Patio
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located in Altamonte Springs, near Maitland, Winter Park, just minutes North of Orlando. Giving an expansive selection of Shopping, Malls, Restuarants, and Theatres available within 2 miles. Close to many Golf courses. Just blocks from Interstate 4. 30 minutes to Sea World, Universal and Disney's... View all property information
    Location Information
    Altamonte Springs, Central Florida 32750
    5 of 5 stars Reviewed June 12, 2016
    We had to make an unexpected visit to the area for a death in the family. Owner was great to deal with especially with such short notice. The house was great. Plenty of...
    See all reviews
    Winter Park
    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 / 17
    Winter Park
    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 / 19
    5 of 5 stars (1) Excellent
    Sanford
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Porch
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This custom built Floating Bungalow is built for a simple, relaxed, yet luxurious vacation. It has a stainless steel full size refrigerator, range, and dishwasher, granite countertops, hardwood floors, full size shower and a flush toilet (an uncommon feature on a boat). It has a queen size bed and... View all property information
    Location Information
    Sanford, Central Florida 32771
    5 of 5 stars Reviewed 4 weeks ago
    Very delightful place. Top quality everything. Owner met us and suggested things to do and places to go. Great place to stay. Gotta go back. Having the boat off the porch was...
    See all reviews
    1 / 17
    Winter Park
    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
    Winter Park
    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
    Get the List
    1 / 16
    5 of 5 stars (1) Excellent
    Sanford
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Balcony
    • Terrace
    • Satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    COMPLETELY RENOVATED BUNGALO WITH QUEEN SIZE BEDS IN BOTH BEDROOMS. ALL NEW FURNITURE AND BEDDING. COMPLETELY NEW KITCHEN AND BATHROOM. WASHER AND DRYER IN LAUNDRY ROOM. LARGE BACK YARD. NICE FRONT PORCH WITH VIEWS OF CITY PARK. REAR DECK WITH GRILLE. FIRST TIME ON THE MARKET SINCE COMPLETE... View all property information
    Location Information
    Sanford, Central Florida 32771
    5 of 5 stars Reviewed April 2, 2016
    Absolutely loved our time spent in this adorable 2 BR Bungalow. Newly remodeled with high end kitchen and entertainment but still held on to the essence of the historic...
    See all reviews
    Winter Park
    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
    Altamonte Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Balcony
    • Washer
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This house has over 1700-sq and sleeps up to 8 people comfortably. Master bedroom as a new queen size bed and separate bathroom with private entrance. Second bedroom has a new double bed that sleeps 2. Third bedroom has 2 new single beds. Fourth room has a leather futon, plus we can add another... View all property information
    Location Information
    Altamonte Springs, Central Florida 32701
    Maitland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautiful 3 bedroom, 2 full bathrooms home is located in a lovely and quiet community. Close to shops, restaurants, just minutes away from Winter Park. Great for Disney vacations, corporate housing, holidays, UCF, or just to relax in sunny Florida. While in Florida this is your lovely home to... View all property information
    Location Information
    Maitland, Florida 32751
    Altamonte Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Patio
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    MONTHLY RATES For 4 weeks or longer $2200 - $2400. ASK Owner FOR QUOTE! You will love our 1950s home in the Beautiful Bear Lakes Area and we can't wait to welcome our Guests! We purchased this home in January 2012 and transformed it into a beautiful jewel. We put in all the modern conveniences... View all property information
    Location Information
    Altamonte Springs, Central Florida 32703
    Lake Mary
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Children's Pool
    • Hot Tub
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This cozy top floor condo with vaulted ceiling has one bedroom with walk in closet and one bathroom with shower/bath and is located in the gated, amenity-filled community of Regency Park at Lake Mary.<BR><BR>Open kitchen/living/dining room combination with breakfast bar and sliding glass door... View all property information
    Location Information
    Lake Mary, Florida FL32746
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Washer
    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
    Fern Park
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Porch
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Recent upgrades! The property has new carpets, counter tops, 46" flat screen TV in the living room, new paint on kitchen cabinets, DVD player and entertainment center. For your next Florida getaway, come escape to this charming Fern Park vacation rental home. Offering wonderful amenities, such as... View all property information
    Location Information
    Fern Park, Florida 32730
    Chuluota
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Patio
    • Porch
    • Grill
    • Internet Access
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Luminous sunshine and fond memories await you at this spectacular 3-bedroom, 2-bathroom Orlando home! With sleeping accommodations for 8 guests, modern amenities and a tranquil screened porch, this centrally located dwelling won’t disappoint! Situated amidst lush greenery and shimmering... View all property information
    Location Information
    Chuluota, Florida 32826
    1 / 17
    Winter Park
    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
    Lake Mary
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Parking
    • DVD Player
    • Balcony
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Closest to Disney Magic! Located in Lake Buena Vista, Wyndham Bonnet Creek Resort is mere minutes from the gates of Walt Disney World®. You'll will enjoy a very rewarding stay on site. From the full activities calendar to special touches like the tranquil Lazy River, beautiful pool and private... View all property information
    Location Information
    Lake Mary, Florida 32830
    Winter Park
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Patio
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Furnished with original furniture from the 1950's era in a home built in 1955 with original wood floors, bathroom tile, plaster walls and kitchen cabinetry. Clean lines, simple and comfortable. FURNISHED Mid Century Modern Short/Long term rental located in Olde Winter Park. Two bedroom/ one and... View all property information
    Location Information
    Winter Park, Central Florida 32789
    1 / 30
    Winter Park
    5 Bedrooms, 6 Bathrooms, Sleeps 11 | Quick View
    Inquire 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