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Holiday Rentals in Winter Springs, FL

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    ₹ 10,575 Average
    ₹ 67,000+
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    1 / 18
    5 of 5 stars (3) Excellent
    Winter Springs
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 20
    5 of 5 stars (5) Excellent
    Winter Springs
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    The following rentals are within 15 kilometres of Winter Springs, Florida.

    1 / 16
    5 of 5 stars (1) Excellent
    Sanford
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 10
    5 of 5 stars (1) Excellent
    Altamonte Springs
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • 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
    5 of 5 stars Reviewed 12 June 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...
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    1 / 27
    5 of 5 stars (1) Excellent
    Sanford
    4 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
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    • 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
    5 of 5 stars Reviewed 25 February 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...
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    1 / 13
    Winter Park
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Balcony
    • Patio
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Satellite TV
    • Parking
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    • 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
    1 / 27
    5 of 5 stars (1) Excellent
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Washer
    • Satellite TV
    • Patio
    • Grill
    • DVD Player
    • Balcony
    • 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
    5 of 5 stars Reviewed 15 April 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...
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    1 / 40
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Waterfront
    • Patio
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    • 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
    1 / 26
    Oviedo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
    • Parking
    • Air Conditioning
    • Patio
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    • 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
    1 / 17
    Maitland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • 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
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    1 / 35
    Winter Park
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • 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
    1 / 17
    Altamonte Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • 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
    1 / 19
    5 of 5 stars (1) Excellent
    Sanford
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • 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
    5 of 5 stars Reviewed 27 June 2016
    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...
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    1 / 17
    Winter Park
    8 Bedrooms, 5 Bathrooms, Sleeps 17 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • ?
    About this property
    Summary Located just 15 minutes from Walt Disney World, this beautiful home offers the perfect luxury environment for family and friends to share a vacation of a lifetime! With a spacious open layout living space, and two floors of bedrooms, there's comfort, privacy and luxury for 3 or 4 families... View all property information
    Location Information
    Winter Park, Central Florida
    1 / 13
    Oviedo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Minutes to Disney/Daytona Beach/UCF 5 Acre Gated Property and The Cottage is nestled on this property Secluded but close to everything Entire Cottage for your enjoyment. Between Orlando and Daytona Beach. easy I-4/417 access close by. Beautiful Get Away/private gated 5 acres. Cottage Comfy King... View all property information
    Location Information
    Oviedo, Central Florida
    1 / 17
    Winter Park
    8 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • ?
    About this property
    Summary Less than 15 minutes from Walt Disney World, the exclusive new Retreat community at Champions Gate offers luxury travelers, the perfect place to call home during their magical vacation in the Sunshine State! With a stylish and modern design, this 8 bedroom luxury pool home offers space... View all property information
    Location Information
    Winter Park, Central Florida
    1 / 19
    Oviedo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Air Conditioning
    • Hot Tub
    • Private Garden
    • 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
    1 / 35
    Winter Park
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • 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
    1 / 18
    Maitland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • 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
    1 / 24
    Chuluota
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Washer
    • Patio
    • Porch
    • Grill
    • Internet Access
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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
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    1 / 17
    1 of 5 stars (1) Terrible
    Winter Park
    8 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • ?
    About this property
    Summary If you are planning a big Orlando vacation with family and friends, this is perfect for you! Designed purely for large groups of fun seeking visitors, this 8 Bedroom home offers the opportunity to save on accommodation costs, without giving up any comfort, space or style. The added... View all property information
    Location Information
    Winter Park, Central Florida
    1 / 17
    Alafaya
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • ?
    About this property
    If golf is your thing then all our luxury vacation rentals on the Shire at West Haven are within minutes of some of the best courses in Orlando. The nearest course is Champions Gate which currently offers two Greg Norman designed layouts called the National and International with a third course on... View all property information
    Location Information
    Alafaya, Florida
    1 / 14
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • DVD Player
    • Shared Garden
    • Shared Outdoor Pool...
    • Air Conditioning
    • Secure Parking
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    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
    1 / 24
    Altamonte Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
    • Internet Access
    • Parking
    • Patio
    • Satellite TV
    • Washer
    • Air Conditioning
    • Grill
    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
    1 / 19
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • 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
    1 / 22
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Patio
    • Washer
    • Wi-Fi
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    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
    1 / 24
    Fern Park
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Satellite TV
    • Porch
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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
    1 / 28
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Central Heating
    • Balcony
    • Terrace
    • Housekeeping...
    • Patio
    • Hot Tub
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    • 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
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    Winter Park, Central Florida
    1 / 27
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    Your own private unit includes 1 master bedroom with Queen bed Full Kitchen with stove, refrigerator, microwave, coffee maker 32" flat screen tv. Access to Washer/dryer Comfortable & Clean 1bd/1bath home with convenient location in historic Winter Park yet very close to Downtown Orlando or the... View all property information
    Location Information
    Winter Park, Central Florida
    1 / 37
    Winter Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • 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
    1 / 24
    Altamonte Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Internet Access
    • Grill
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    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Have the Altamonte Springs trip of a lifetime with this upscale 3-bedroom, 2-bath vacation rental home, which sleeps 6. Offering wonderful amenities such as a swimming pool, screened-in porch and a central Florida location minutes from popular Orlando attractions, this quaint residence has... View all property information
    Location Information
    Altamonte Springs, Central Florida
    1 / 36
    Lake Mary
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • 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
    1 / 30
    Winter Park
    5 Bedrooms, 6 Bathrooms, Sleeps 11 | Quick View
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    • Sauna
    • Waterfront
    • Hot Tub
    • Private Outdoor...
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    • 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