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Vacation Rentals near Rollins College

1000 Holt Ave, Winter Park, Florida 32789-4409
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    Travelers to Winter Park are booking November dates now. Secure your vacation rental today, and have the perfect trip.
    All 42 Rentals in Winter Park
    Winter Park-College Park-Orlando-11 / 27
    (2)Excellent
    1.7 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2br - 1000ft2 - Winter Park House1 / 13
    (2)Excellent
    1.0 miles from Rollins College
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Winter Park-College Park-Orlando -21 / 19
    (2)Average
    1.7 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    1.9 miles from Rollins College
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    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....
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    Winter Park, Central Florida
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Stroll to Park Avenue from Vintage Lake-View House1 / 23
    (26)Excellent
    0.5 miles from Rollins College
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Retreat in the Heart of Winter Park - Office, Patio, Hammock & More!1 / 28
    (21)Excellent
    0.7 miles from Rollins College
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Family home with flexible schedule1 / 16
    (27)Excellent
    1.0 miles from Rollins College
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Winter Park, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Casa Aloma - Elegant Winter Park House with Great Pool and Huge Backyard!!1 / 46
    (154)Excellent
    1.9 miles from Rollins College
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Winter Park, Central Florida
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Just Like Home... With A Pool!1 / 23
    (60)Excellent
    4.1 miles from Rollins College
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Winter Park, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Amazing location- walk to everything1 / 11
    (7)Excellent
    0.3 miles from Rollins College
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Terrace
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    Winter Park, Central Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Chic Lakeside Midcentury Modern Retreat1 / 14
    (2)Excellent
    1.1 miles from Rollins College
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Casa Winter Park1 / 50
    (23)Excellent
    1.9 miles from Rollins College
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Winter Park, Central Florida
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Winter Park charm. Close to Park Ave1 / 9
    (25)Excellent
    1.5 miles from Rollins College
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1.3 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Terrace
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    Winter Park, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    1.0 miles from Rollins College
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Stunning 3 bedroom/2 bathroom custom built 1 story home in the heart of Winter Park, 2 blocks to Park Avenue. 3 bedrooms each with queen beds, one of which is a studio with private bath *NOT SUITABLE FOR EVENTS due to limited parking (3 cars) perfect monthly rental. Unique Benefits Close to...
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    Winter Park, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    HOME AWAY FROM HOME in beautiful Winter Park1 / 12
    (1)Excellent
    2.2 miles from Rollins College
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2021
    Nice house, quite neighborhood. Well stocked kitchen (dishes, condiments, plastics, etc.). Beds were super comfy and the upstairs shower was awesome. Loved fenced in yard for...
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    About this property
    Our house is located in beautiful Orlando, it's close to great restaurants, universities, downtown Winter Park, downtown Orlando, great dining, theme parks, and much more. Get ready to feel at home away from home. Enjoy two private bedrooms, one with a King Size bed, the second a Full-size bed...
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    Winter Park, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    2.2 miles from Rollins College
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When selecting a place to stay during your upcoming trip to beautiful Central Florida, consider a condo-style resort located in the heart of favorite vacation and theme park destination that offers all the conveniences of home while you're away from yours. You can enjoy just that. From full...
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    Orlando, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.6 miles from Rollins College
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Waterfront
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to your personal getaway in the city, where every room has lake views! Only 3 miles from the lively heart of downtown Orlando, endless restaurants and nightlife await! Our gem has direct access to the lake right outside the condo where you can easily fish or simply enjoy the Florida...
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    Orlando, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Modern Tropical Pool Home East Orlando1 / 28
    (1)Excellent
    4.6 miles from Rollins College
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 19, 2017
    My guest and I stayed at this home for a long weekend. Enjoyed every moment. It’s exactly how the picture shows. Very modern and spacious. It’s worth your peace of mind. Thanks...
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    About this property
    Relax in this East Orlando Tropical Modern solar heat pool home. Conveniently close to the 417 expressway. House includes Master Bedroom with a comfortable King size bed, luxury bedding, private bath, dual shower heads and Smart TV. Second bedroom is a queen with luxury bedding Smart TV. 3rd...
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    Orlando, Central Florida
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    New on the Market!  Spotless Lakeside Home1 / 20
    (1)Excellent
    2.8 miles from Rollins College
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    New on the market, this 3/2 home sits on a quiet tree lined street across from Lake Ivanhoe. The neighborhood is very 'walkable'; with Publix, Starbucks, shops, restaurants and bars all close by. There is easy access to Interstate-4 and Theme Parks with Universal Studios only 10 miles away. The...
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    Orlando, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.8 miles from Rollins College
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    We are Pleased to Present to you our property in the heart of Orlando 5 minutes from Downtown Orlando. La Pela #2, is a comfortable, spacious, townhouse newly and Tastefully Renovated located in a peaceful, very quiet and privately gated community in the Heart of Orlando. This Property is just...
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    Orlando, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Brand New/Free Hot Spa/Free Shuttles/WaterPark/Private PoolXbox/Movie/Game/Grill1 / 65
    (4)Excellent
    4.1 miles from Rollins College
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Children's Pool
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    Pet friendly
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    Reviewed February 9, 2020
    We booked and stayed at this property with my family of 4 plus my parents from Ajax and my brother whom travelled from BC.This place was ideal! The place looks exactly how the...
    Reviewed August 14, 2018
    Thank you for the lovely stay at your beautiful home! The home is exceptional with plenty of space. Pictures of the home are exactly same as we saw during our stay. The location...
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    About this property
    Luxury Vacation Home: Free Shuttle & Fantastic Water Park We offer all our guests free crib, high-chair and Strollers; also free transportation within the resort and free to Disney, Universal and SeaWorld! Resort staff is on-site to provide assistance to guests when needed. Owner and Our Property...
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    Orlando, Central Florida
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    3.4 miles from Rollins College
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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...
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    Maitland, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Home, Sweet Home Orlando1 / 18
    (1)Excellent
    3.0 miles from Rollins College
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Reviewed July 13, 2019
    This is great family-friendly home. The pool and screened in porch was very nice. We had a great time. We will be back.
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    About this property
    Located in a quiet neighborhood NE of downtown, this light & bright, 4br/2 bath, private pool home has easy access to airports, theme parks, Performing Arts, Park Ave, colleges, Daytona & the Space Coast. Relax on a boat tour or have a fun-filled day at one of Orlando's many theme parks. Then come...
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    Aloma, Central Florida
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    4.2 miles from Rollins College
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    About this property
    A two bedroom and two bathroom condo with 1112 square feet of perfection. The condo is located on the 2nd floor. Elevators are located in the middle of the building There is a King bed in the Master Suite and in the second bedroom has two Full-size beds. There is a 42' Flat screen TV in the living...
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    Orlando, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4.8 miles from Rollins College
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    After a fun-filled day exploring area attractions, escape to the brilliantly adorned Two-Bedroom Villa at Westgate Lakes, which offers remarkable spaciousness. Westgate Lakes provides the ideal setting for an unforgettable vacation or business trip with transportation to local theme parks and...
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    Orlando, Central Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    4.8 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Closest to Disney Magic! Located in Lake Buena Vista, Wyndham Bonnet Creek Resort is less than a mile from the gates of Walt Disney World®. You 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...
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    Orlando, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    4.8 miles from Rollins College
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Orlando, Central Florida
    Condo/Apartment - 1 Bathroom, Sleeps 4
    3.7 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Amazing Condo in the beautiful downtown Orlando area - by Lake Eola Walking distance to Publix and 2 min from highways Facilities & Recreation Shared pool Fitness center Near transportation Clubhouse Security & Access Elevator Secured entry Controlled access Additional Features Hardwood floor...
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    Orlando, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    4.8 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Inspired by historic Saratoga Springs—a late-1800s’ New York retreat famous for its spas and horse racing—this charming, Victorian-style Resort hotel is nestled between rolling golf course greens and the shimmering Village Lake. Delight in stately Studios and multi-bedroom Villas, dazzling pools...
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    Orlando, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    4.0 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    A luxurious loft. Pebbles away from Universal Studios and Disney! Equipped with all essential amenities. Our Apartments homes are not Pet or Cigarette friendly. We pride ourselves on being the best hosts! Located in the most popular high rise in the city. The space is surrounded by the night life...
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    Orlando, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    3.4 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Newly constructed, fresh, clean, nicely furnished private apartment with separate access behind my personal home in downtown Orlando. This apartment is located in desirable Thornton Park neighborhood and within a mile of many restaurants, clubs, nightlife, concerts, downtown arena, Dr. Phillips...
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    Orlando, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    2.4 miles from Rollins College
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    Temporary Rental single family home 5 mins from Disney property. Beautiful well mainted single story home in quiet upscale neighborhood. 2 bedrooms and 3 bathrooms (master bedroom queen bed and second bedroom twin bed). Entire home furnished and very clean. 5 mins from Publix Plaza at Lakes of...
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    Orlando, Central Florida
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    4.1 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Urban cool meets childhood fancy in this downtown boutique bungalow in the Country Club of Orlando. The Little Treehouse is the perfect Central Florida getaway for two in this separate 260 sq. ft. second floor renovated 1926 carriage house. Conveniently located five minutes from Downtown Orlando,...
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    Orlando, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Westgate Town Center Resort1 / 10
    (8)Average
    4.8 miles from Rollins College
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed March 19, 2019
    We have stayed at the Westgate Villas and Town Center several times and have never been disappointed. It is a challenge to swim in ALL of their pools during the week, because we...
    Reviewed April 20, 2017
    Check in was long process. By the time we got to the desk we had waited 30-45 minutes. Have the gentleman are information, license and credit card and requested rooms together...
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    About this property
    Está situado a solo 1,6 km de 1.6 km de Walt Disney World, y a pocos minutos del Universal Studios y SeaWorld, estos apartamentos son el lugar perfecto para una familia Orlando. Westgate Town Center Resort cómodas, apartamento totalmente amueblado. Los alojamientos disponen de zona de cocina o...
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    Location Information
    Orlando, Central Florida
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
    2.8 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    Enjoy the convenience and privacy of a centrally situated affordable condo-away-from-home all for yourself and the family. Easy access to airport, Disney attractions, major malls, beaches and all the excitement Orlando has to offer. Walk to nearby restaurants, groceries, gym and most other...
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    Location Information
    Maitland, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    The Shed in Downtown Orlando1 / 7
    (1)Excellent
    2.4 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 26, 2019
    We stayed here for one night after a family vacation in order to be closer to the airport for an early-morning flight and to take a breather after a week together. The check-in...
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    About this property
    Nestled behind my 1920's bungalow in one of Orlando’s best neighborhoods, The Shed is a local experience like no other. Around the corner from the Orlando Science Center, a $7 Uber to Amway, Orlando City Stadium, or walking distance to the Sun Rail, you’ll love The Shed because of its chill vibe,...
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    Location Information
    Orlando, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    4.1 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Start your Florida vacation out right at this 1-bedroom, 1-bathroom Fern Park vacation rental guesthome. Perfect for small families and couples, this unit sits within an easy drive of the highway - trips to downtown Orlando or Disney Parks will be a breeze! New updates to this property include an...
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    Location Information
    Fern Park, Central Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    2.5 miles from Rollins College
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Washer
    • Patio
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the heart of the desirable College Park area, this updated 2-bed, 1-bath vacation rental is the perfect homebase for your next stay in downtown Orlando. The duplex offers privacy for 4 with convenience to local restaurants and retail shops 5 blocks away. Spend mornings on your patio and...
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    Location Information
    Fairvilla, Central Florida
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    4.9 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Entry: Private entry suite w/lake & park frontage; parking spaces; WiFi, porch w/TV & seating, huge shaded yard, security alarm & video survielance 24/7. Livingroom: Enter from front porch through private door into large porcelain tiled livingroom/full kitchen/dining area combo/wall mounted big...
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    Location Information
    Orlando, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    3.7 miles from Rollins College
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Yard
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New Luxury Apartment. Our location is a newly luxury apartment . All Amenities listed above this listing is included.. This space is also near by grocery stores & everything you can name . This unit is 15-20 mins away from Universal, Disney , MCO. 5 mins away from Walmart , 3 mins away from Publix...
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    Location Information
    Orlando, Central Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    3.5 miles from Rollins College
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Yard
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PET, FAMILY friendly . GO ORLANDO CITY / PRIDE! Freshly renovated home with all the upgrades of modern comfort. Centrally located in the Downtown Orlando Thornton Park area. Zen decor is very relaxing and tranquil. Just renovated with new bamboo floors, solid wood cabinets in the kitchen, quartz...
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    Location Information
    Orlando, Central Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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