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Vacation Rentals in Winter Springs, FL and nearby

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    From
    $150
    / Night
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    1 / 18
    5 of 5 stars (3) Excellent
    Winter Springs
    4 Bedrooms, 3 Bathrooms, Sleeps 6
    other travelers have booked this property
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    From
    $169
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    1 / 20
    5 of 5 stars (5) Excellent
    Winter Springs
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    The following rentals are within 10 miles of Winter Springs, Florida.

    From
    $130
    / Night
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    1 / 19
    5 of 5 stars (1) Excellent
    Sanford
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    From
    $80
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    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 2
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • There Are Tennis...
    • Deck
    • TV
    • Washer
    • Wi-Fi
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • 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
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    Location Information
    Winter Park, Central Florida 32789
    From
    $1,800
    / Month
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    Winter Park
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Patio
    • Satellite TV
    • Dryer
    • Washer
    • Deck
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This property is only available for 6 months lease. Location: Winter Park, College Park, Central-Disney-Orlando Area, Florida, USA No Pets - We love animals but for our guests with allergies, we do not allow pets in our homes. Accommodations: House that will accomodate up to 4 guests, 2 Bedrooms,... View all property information
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    Location Information
    Winter Park, Central Florida 32789
    From
    $125
    / Night
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    Altamonte Springs
    3 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • TV
    • Game Room
    • Deck
    • Washer
    • DVD Player
    • Stereo System
    • Pool Table
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
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    Location Information
    Altamonte Springs, Central Florida 32750
    From
    $167
    / Night
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    1 / 10
    5 of 5 stars (1) Excellent
    Oviedo
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
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    Overview Reviews (1)
    Amenities & Details
    • Waterfront
    • DVD Player
    • Water Views
    • Stereo System
    • Private Fishing...
    • Air Conditioning
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • 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. Extremely secluded yet the house... View all property information
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    Location Information
    Oviedo, Central Florida 32765
    5 of 5 stars Reviewed January 4, 2015
    The house was exactly what we needed. It's a quality home located on Lake Jessup. We liked the location. It's walking distance to the Black Hammock and local Lady Gator bar...
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    $131
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    1 / 22
    5 of 5 stars (1) Excellent
    Alafaya
    4 Bedrooms, 7 Bathrooms, Sleeps 8
    other travelers have booked this property
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    Overview Reviews (1)
    Amenities & Details
    • Pool Table
    • Watersports Nearby
    • Private Outdoor...
    • TV
    • Game Room
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is a great house for families, lots of space. Professionally and tastefully decorated throughout. There is baby equipment, including cot, highchair, stroller, child safety netting across pool (removable). There is also a selection of board games for the whole family. Cable TV, 50' HDTV flat... View all property information
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    Location Information
    Alafaya, Florida 33837
    5 of 5 stars Reviewed July 8, 2015
    Beautiful and amazing home. Nothing too much trouble. The owners, Sue & Dave, even provided an ice box for us to use as there wasn't one at the property. Everything else we could...
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    From
    $130
    / Night
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    Maitland
    2 Bedrooms, 3 Bathrooms, Sleeps 4
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Stereo System
    • DVD Player
    • Fireplace
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    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. Our guests call our home a fun & relaxing... View all property information
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    Location Information
    Maitland, Florida 32751
    From
    $114
    / Night
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    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Dryer
    • Air Conditioning
    • DVD Player
    • Patio
    • Shared Tennis Court
    • TV
    • Washer
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    Winter Park, Central Florida 32792
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    From
    $200
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    Maitland
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    Maitland, Florida 32751
    From
    $77
    / Night
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    Lake Mary
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Waterfront
    • Hot Tub
    • Children's Pool
    • Watersports Nearby
    • Air Conditioning
    • Wi-Fi
    • Pool Table
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • 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. Open kitchen/living/dining room combination with breakfast bar and sliding glass door leading out... View all property information
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    Location Information
    Lake Mary, Florida FL32746
    From
    $200
    / Night
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    Winter Park
    2 Bedrooms, 2 Bathrooms, Sleeps 5
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Watersports Nearby
    • Water Park Nearby
    • Deck
    • There Are Tennis...
    • Wi-Fi
    • Washer
    • Air Conditioning
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    Winter Park, Central Florida 32789
    From
    $259
    / Night
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    Winter Park
    3 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Housekeeping...
    • Wi-Fi
    • Deck
    • Fireplace
    • TV
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    3 Bedrooms \ 3 Baths Very Large Living Area, Pool & Patio - Sleeps 10 This beautiful home is located in a nice secluded neighborhood community in the Winter Park area. From the moment you walk in the door you will be impressed with the extra-large living room area and the wide open kitchen space... View all property information
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    Location Information
    Winter Park, Central Florida 32792
    From
    $269
    / Night
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    Winter Park
    3 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Private Outdoor...
    • TV
    • Housekeeping...
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This must see property is located close to everything in Downtown Winter Park area! Updated with the newest appliances, furniture and electronics on the market. You will find everything you need to create that one of a kind experience with all the comforts of feeling right at home. The open floor... View all property information
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    Location Information
    Winter Park, Central Florida 32792
    From
    $200
    / Night
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    Altamonte Springs
    4 Bedrooms, 2 Bathrooms, Sleeps 9
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Washer
    • DVD Player
    • Patio
    • Dryer
    • Refrigerator
    • Air Conditioning
    • Stove
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    4 bedroom pool home just North of Orlando located on a quiet cul-de-sac. Easy access to the airports and train stations. 10 minutes from downtown Orlando. 40 minutes from Disney. Come enjoy the Florida Lifestyle away from all the traffic and noise. Altamonte Springs has been voted one of the top... View all property information
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    Location Information
    Altamonte Springs, Central Florida 32714
    From
    $159
    / Night
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    Sanford
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • TV
    • Waterfront
    • Watersports Nearby
    • Wi-Fi
    • Air Conditioning
    • Water Views
    • Shared Outdoor Pool...
    • Private Fishing...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • 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
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    Location Information
    Sanford, Central Florida 32771
    From
    $115
    / Night
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    1 / 31
    Lake Mary
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Satellite TV
    • Dryer
    • Washer
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    3 bed 3 bath town home with splash pool Beautifully and professionally decorated 3 bedroom 3 bath town home, with splash pool next to the club house across the street. Located in the Serenity section of the Dream development and is a conveniently located, afford-ably priced community that is just a... View all property information
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    Location Information
    Lake Mary, Florida 33146
    From
    $350
    / Night
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    1 / 17
    Winter Park
    8 Bedrooms, 5 Bathrooms, Sleeps 16
    Overview Make Inquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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
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    Location Information
    Winter Park, Central Florida
    From
    $350
    / Night
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    1 / 17
    Winter Park
    8 Bedrooms, 5 Bathrooms, Sleeps 16
    Overview Make Inquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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
    Make Inquiry
    Location Information
    Winter Park, Central Florida
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    From
    $115
    / Night
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    1 / 28
    Heathrow
    3 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Private Outdoor...
    • Dryer
    • Washer
    • Satellite TV
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    3 bed 3 bath town home with splash pool Close to club house. Located in the Serenity section of the Dream development and is a conveniently located, afford-ably priced community that is just a few miles to the gates of Disney. You will love this vacation home with granite counter tops and stainless... View all property information
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    Location Information
    Heathrow, Florida 34714
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    $350
    / Night
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    1 / 17
    Winter Park
    8 Bedrooms, 5 Bathrooms, Sleeps 16
    Overview Make Inquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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
    Make Inquiry
    Location Information
    Winter Park, Central Florida
    From
    $1,250
    / Night
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    1 / 30
    Winter Park
    5 Bedrooms, 6 Bathrooms, Sleeps 11
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Water Views
    • Satellite TV
    • Internet Access
    • Sauna
    • Waterfront
    • Private Outdoor...
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    Winter Park, Central Florida 32789