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Vacation Rentals near Winter Park Tech

901 W Webster Ave, Winter Park, Florida 32789
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    Travelers to Winter Park are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 104 Rentals in Winter Park
    2br - 1000ft2 - Winter Park House1 / 13
    (2)Excellent
    1.9 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    SPACIOUS CONDO CLOSE TO UCF, FULL SAIL & ROLLINS1 / 18
    (1)Poor
    4.6 miles from Winter Park Tech
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Mid Century Luxury, 1 block from Park Ave (#3)1 / 11
    (15)Excellent
    1.1 miles from Winter Park Tech
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Stroll to Park Avenue from Vintage Lake-View House1 / 23
    (27)Excellent
    1.3 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Just Like Home... With A Pool!1 / 23
    4.6 miles from Winter Park Tech
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Cute bungalow minutes walk from Park Avenue.1 / 16
    (7)Excellent
    1.2 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Beautiful Retreat in the Heart of Winter Park - Office, Patio, Hammock and More!1 / 30
    (25)Excellent
    1.8 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Mid Century Luxury, 1 block from Park Ave (#2)1 / 11
    (9)Excellent
    0.6 miles from Winter Park Tech
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Winter Park, Central Florida
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Remodeling? Moving? Attending classes? Be our guest!1 / 16
    (31)Excellent
    2.1 miles from Winter Park Tech
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Winter Park, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Greatest location! Condo with private yard!1 / 19
    1.1 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Cheerful 4-bedroom with large and lush backyard1 / 23
    1.5 miles from Winter Park Tech
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Winter Park, Central Florida
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Million Dollar View on the Lake!1 / 12
    1.6 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
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    Winter Park, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Light, Bright and Full of Delight! 2 Blocks to Park Ave1 / 29
    0.6 miles from Winter Park Tech
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    A curated stay in the Historic College Quarter - 30 days minimum stay -1 / 29
    (16)Excellent
    1.0 miles from Winter Park Tech
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    ☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park1 / 30
    0.4 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
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    • Balcony
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    Winter Park, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Beautiful 3 Br. Condo (441946) by Houzlet1 / 22
    0.7 miles from Winter Park Tech
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool1 / 25
    1.1 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Winter Park, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 1
    Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.1 / 30
    1.2 miles from Winter Park Tech
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Beautiful 3 Br. Townhome (421120) by Houzlet1 / 24
    1.4 miles from Winter Park Tech
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Relaxing, lake-view home near Park Avenue1 / 14
    1.3 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This cozy, quaint Winter Park home was built in 1925. The house has updated appliances and plenty of space. There are two big bedrooms with their own bathroom. Plus two single beds for guests. Do not forget our large dining and living room. We are mere minutes from historic Park Avenue where you...
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Quiet Location, 1BR/1BA APT in Duplex House1 / 13
    4.6 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Winter Park, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Cozy Comfort Just 2 Blocks From Park Ave!1 / 30
    0.4 miles from Winter Park Tech
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow1 / 30
    (24)Excellent
    4.5 miles from Winter Park Tech
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Peace and the Park #3 -2 BDRM, 2 Bath1 / 12
    0.8 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Contemporary Award Winning Hotel w/Rooftop Close to Parks & Rollins College1 / 26
    1.1 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Winter Park, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 1
    Stylish Boutique Guest House1 / 27
    0.8 miles from Winter Park Tech
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Yard
    • Patio
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    About this property
    Indulge the senses in the calming aesthetics of this newly constructed guest house. The residence features room for 4 guests across 2 bedrooms, a large bathroom with a walk-in shower that features dual shower heads & skylight. A desk for remote workers, and plenty of room to spread out across the...
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Amazing location- walk to everything1 / 28
    (18)Excellent
    1.0 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
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    Winter Park, Central Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    ADA Compliant Room in Award Winning Hotel w/Rooftop Pool - Close to Parks!1 / 26
    1.1 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Winter Park, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 1
    NEW * Cozy Retreat Near Lake Killarney in Winter Park1 / 14
    1.3 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College1 / 26
    1.1 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Winter Park, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 1
    Comfy Home in Winter Park, can accommodate up 6 guests!1 / 18
    (6)Very good
    0.9 miles from Winter Park Tech
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    THE CLOUD 9 SUITE1 / 12
    1.4 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Winter Park, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Winter Park Hideaway1 / 16
    2.9 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Breezy Pool Home!1 / 9
    (11)Very good
    3.7 miles from Winter Park Tech
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Mid Century Modern Cottage in The Heart of Winter Park1 / 14
    (16)Excellent
    1.9 miles from Winter Park Tech
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Luxury Living Just 3 Blocks From Park Ave!!!1 / 18
    0.2 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    East End Escape1 / 10
    2.7 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Tranquil & Tiny house1 / 10
    1.4 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Winter Park, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Lakefront Condo w/ Sunroom, Office, & Lakeside Pool1 / 30
    0.5 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Winter Park, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths1 / 30
    0.4 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Winter Park Oasis1 / 11
    (9)Excellent
    1.5 miles from Winter Park Tech
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    ★Quiet Location House➠Minutes Away from Everything1 / 17
    4.6 miles from Winter Park Tech
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Winter Park, Central Florida
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Modern and Romantiv Villa1 / 13
    2.8 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Winter Park, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Private GUEST SUITE near downtown, hospitals & universities in Winter Park FL1 / 21
    2.3 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Winter Park, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 1
    Charming home 3 blocks from historic Park Avenue & one block from Lake Virginia1 / 14
    1.0 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Hidden Oasis #4 2 BDRM, 2 Bath1 / 8
    1.1 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Winter Park, Central Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    You're Pampered Here - Just 3 Blocks From Park Avenue!1 / 30
    0.4 miles from Winter Park Tech
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Terrace
    • Hot Tub
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    Pet friendly
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    Smoking allowed
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    Location Information
    Winter Park, Central Florida
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations1 / 26
    1.1 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Balcony
    • Wi-Fi
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    • Terrace
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    Pet friendly
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    Smoking allowed
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    Location Information
    Winter Park, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 1
    Winter Park Bamboo Loft1 / 12
    1.6 miles from Winter Park Tech
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Winter Park, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Beautiful 2 Story Winter Park Villa1 / 15
    3.5 miles from Winter Park Tech
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Winter Park, Central Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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