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Holiday Rentals in Winter Springs

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    Don't let other travellers get your favourite Winter Springs area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 26 Rentals in Winter Springs
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    Winter Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 10 kilometers of Winter Springs.
    Oviedo
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Oviedo
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Oviedo
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Waterfront
    • Wi-Fi
    • Balcony
    • Patio
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This brand new five-bedroom, four-bathroom home sits on 5 acres located just fifteen minutes outside of the City Beautiful, Orlando, and five minutes from SR417. Gator Palace is perfect for large families and groups. Within walking distance of The Black Hammock, this residency comfortably sleeps 12...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    The Cottage at Oviedo1 / 37
    (3)Excellent
    Oviedo
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Grill
    • Housekeeping Included
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2018
    Just spent 3 glorious nights at the Cottage in Oviedo (FL). The Cottage is comfortable, clean, peaceful and I will return there again while visiting family in Oviedo. Every...
    Reviewed 21 November 2017
    While checking hotel prices on Trip Advosor, The Cottage popped up. We needed a room for the night but wanted our college age daughter to join us. She won’t share a hotel room...
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    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...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 bed/2 both Lake Front home1 / 25
    (1)Very good
    Lake Mary
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
    • Washer
    • Patio
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2018
    Just 15 minutes from Sanford this provided us with a convenient central base from which to explore the Real Florida (that is, keeping away from all things with a theme park, as...
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    About this property
    Cozy 3 bedroom 2 bath home on little Lake Mary very quiet and relaxing home in a family oriented community. This 1584 sqft. home, has a magnificent waterfront view; guests will enjoy gazing at Little Lake Mary from multiple rooms of the home. The Open floor plan and entryway draws you into a...
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    Lake Mary, Florida 32746
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oviedo
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This brand new two-bedroom, one-bathroom cottage sits on five acres located just fifteen minutes away from downtown Orlando and five minutes from SR 417. You will be within walking distance of The Black Hammock. This quaint cottage comfortably sleeps four people and can be added as an extension of...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Oviedo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Secure Parking
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely, fully-furnished, three-bedroom, two-bathroom lakefront home is on a large lot in a unique location surrounded by wildlife with a large backyard. Gator's Nest is perfect for summertime relaxation; Enjoy a cool dip in your counter current spa. This vacation home is 5 minutes away from...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Longwood
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our place is in the quiet suburb of Longwood, Florida, 20 minutes from mid-town Orlando. The furnishings and fixtures are new, with beautiful oriental rugs and hardwood floors. Shopping malls, parks, restaurants, groceries and pharmacies are nearby and also brand new Wawa! We are 15 minutes from...
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    Longwood, Florida 32750
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Three-Bedroom Two Bath Lake Jesup Home at Gator Den1 / 21
    (2)Excellent
    Oviedo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Porch
    • Patio
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2018
    We had an amazing weekend at this property. We brought our two dogs, which mainly stayed on the back patio, but it was perfect. The views were amazing from the patio. Within...
    Reviewed 4 January 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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    About this property
    This beautiful three-bedroom, two-bathroom home on Lake Jesup is surrounded by wildlife but also 5 minutes from SR 417 and 15 minutes to downtown Orlando. Gator Den comfortably sleeps six people in its 1,720 square foot layout. This home is perfect for those who love to fish! From your backyard you...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Longwood
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    • Balcony
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you need a beautiful vacation home away from home in centrally located Longwood, Florida between Disney World and Daytona Beach with a concierge service come stay with us. This 1200 Sq feet 2 bedroom 2 bathroom home is elegantly furnished down to the last detail. The living area host deluxe...
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    Longwood, Florida 32750
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Lake Mary
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 4 bedroom/2 bathroom house with laundry room, large fully equipped kitchen, spacious living room, cozy dining area, swimming pool/patio, and more! You will love this cozy home with hardwood floors throughout, and a modern kitchen. Located in Central Lake Mary, minutes away from i-4 and...
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    Lake Mary, Florida 32746
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Oviedo
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • Private Garden
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated two-bedroom, one-bathroom home in beautiful Oviedo is located just fifteen minutes away from downtown Orlando and five minutes from SR 417. Gator Lodge is perfect for a fishing getaway! You will be within walking distance of The Black Hammock where you can store your boat in...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Oviedo
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Children's Pool
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very warm, cozy, and clean. The house located is a very nice quiet neighborhood close to UCF(university of central Florida), Disney, Universal studios, Beaches, NASA(Kennedy space center) and many more.. 5 minutes from UCF (University of Central Florida), Panera bread,Starbucks. 10 minutes from...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Oviedo
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Patio
    • Air Conditioning
    • Washer
    • Terrace
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great for family reunions: Huge, brand new 6 bedroom, 5 bathroom 2 story house with 3 master bedrooms in beautiful Oviedo. Features free wi-fi internet, 55 inch flat screen tv in the living room, marble countertops, and all brand new appliances. Pets considered on a case by case basis, please...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Longwood
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Storey Lake Resort and this stunning 4 bedroom, 3 bathroom, 1,914 sq. ft. rental located near the theme parks in Orlando, Florida. This rental has attained the prestigious “Grand” status for having an upgraded professional furniture package. This vacation rental has all the comforts of...
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    Longwood, Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Oviedo
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2-Bedroom, 1-Bathroom Cottage On 5-Acres This brand new two-bedroom, one-bathroom cottage sits on five acres located just fifteen minutes away from downtown Orlando and five minutes from SR 417. Gator Cove is perfect for a small family of 4 or 2 couples. You will be within walking distance of The...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lake Mary
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Parking
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have the Sunshine State retreat of a lifetime at this alluring 4-bedroom, 2-bath Lake Mary vacation rental house. Your vacation begins the moment you arrive at the bright residence, surrounded by a vibrant green lawn and verdant tropical plantings that lead you right up to the front door. Boasting...
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    Lake Mary, Florida 32746
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Longwood
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Patio
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With more than 4,300 square feet of high-end interior space and an elegant lanai with a pool, fountain, and spa, this Longwood vacation rental house promises an unbeatable Florida getaway. The spacious 4-bedroom, 5-bathroom home is set 15 minutes from Lake Jesup and 45 minutes from Daytona Beach...
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    Longwood, Florida 32779
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Longwood
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the lush wetlands of Longwood when you stay at this charming 4-bedroom, 2-bathroom vacation rental home! Located in the northern suburbs of Orlando, the home boasts 2 living and dining areas, a fully equipped kitchen, and furnished screened-in porch! Take advantage of the plentiful outdoor...
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    Longwood, Florida 32779
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Longwood
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that the backyard is not accessible to guests at this time ** Enjoy an oasis of quiet, comfortable Florida living at this 4-bedroom, 2-bath vacation rental house in Longwood! The charming home boasts an impressive 2,400-square-foot interior with an open-concept design, 2 separate...
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    Longwood, Florida 32779
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Longwood
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • DVD Player
    • Patio
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay ** Treat your family to an unforgettable Florida retreat in Longwood at this fantastic 3-bed, 2-bath vacation rental home for 9! After Orlando theme park...
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    Longwood, Florida 32779
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Longwood
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for European paradise, you don't have to travel across the pond - make your way to this Longwood vacation rental unit instead! This 2-bed, 1-bath condo sleeps 4 and will feel more like your very own English manor; with over 1,000-square-foot interior dappled with inspiring...
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    Longwood, Florida 32750
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Longwood
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sunshine State awaits you at this 1-bath Longwood vacation rental studio! Built in the 1970’s, this home maintains its charm while offering modern and updated amenities. With comfortable accommodations for 2 adults and 2 small children, it’s great for a couples’ retreat or small family getaway....
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    Longwood, Florida 32779
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    Oviedo
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Grill
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My home is in a small, quiet, kid-friendly neighborhood. It is 5 minutes from UCF, 25 from Orlando & the airports, & 40 from Disney & beaches. It is close enough to do it all but not so close that you get caught up in all the stress and hectic pace! We have a 55' UHD TV with Netflix & Amazon Prime,...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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    Lake Mary
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Balcony
    • Patio
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Please note that the homeowner lives on site, in the attached unit with some shared outdoor amenities** Experience the best of Lake Mary when you stay at this vacation rental apartment for 5! The 2-bedroom, 1-bathroom home sits on a quiet, private piece of land but is close to great attractions...
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    Lake Mary, Florida 32746
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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