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Winter Springs Vacation Rentals

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    Don't let other travellers get your favourite Winter Springs area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 24 Rentals in Winter Springs
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    Winter Springs
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Winter Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 10 kilometres of Winter Springs.
    Two-Bedroom Gator Cottage1 / 22
    (1)Excellent
    Oviedo
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    The Cottage at Oviedo1 / 39
    (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 May 31, 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 November 21, 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
    Oviedo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Secure Parking
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Patio
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful lake front view: Relax in the spa with your family on our large back patio and watch the gorgeous colors of the sky as the sun dips down over Lake Jesup. Gator Nest is a 3 bedroom 2 bathroom home hosted by Black Hammock Getaway in Oviedo, FL. Perfect for bird watchers, this home is...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Oviedo
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for a new construction Vacation Home Rental, look no further! This Beautiful 4 Bedroom / 3 Bath Town Home was built in 2017 in the stunning community Storey Lake Resort. Beautiful furnishings and all the comforts of home ready to welcome you! The beautiful modern kitchen...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    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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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Washer
    • Patio
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 19, 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, Central Florida 32746
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    Great for large families! Spacious, quiet 5 bedroom 4 bathroom 2-story villa in Oviedo, Florida, available 365 days a year. Close to Black Hammock Airboat Rides and Adventures near beautiful Lake Jesup. Has enough room to comfortably sleep 12 people, bring the whole family! 3000 square feet on 5...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    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
    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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    Amenities & Details
    • Waterfront
    • Secure Parking
    • Porch
    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 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 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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    About this property
    Gator Den Enjoy a warm bath in the master bathroom tub with massaging jets. Huddle up with a loved one on the screened in back porch and watch a breathtaking sunset over the lake. Gator Den is a 3 bedroom, 2 bathroom home in a hidden corner of Oviedo, Fl. Part of Black Hammock Getaway's Vacation...
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    Location Information
    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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    Location Information
    Longwood, Central Florida 32750
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    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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    Location Information
    Oviedo, Central Florida 32765
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    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, Central Florida 32750
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    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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    Location Information
    Longwood, Central Florida 34746
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    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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    Location Information
    Oviedo, Central Florida 32765
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Oviedo
    5 Bedrooms, 3 Bathrooms, Sleeps 20 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 house is centralized to do it ALL! It is 20 minutes from Orlando Airport (MCO), or the Orlando/Sanford Airport (SFB), Downtown Orlando, and Winter Park's famous Park Avenue. It is only 30-45 mins from Disney/SeaWorld/Universal theme parks, shopping the Mall of Millenia or Premium Outlet Malls...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 20
    Longwood
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy an oasis of quiet, comfortable Florida living at this 4-bedroom, 2-bathroom vacation rental house in Longwood! Whether it’s business or pleasure that brings you to town, this charming home boasts a 2,400-square-foot open-concept interior, 2 separate living spaces, an office area and a...
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    Location Information
    Longwood, Central Florida 32779
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    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
    Oviedo
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Private Garden
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Lakeside Sunsets: Cozy, Lakeside 2 bedroom 1.5 bathroom with a den. Located in the middle of Black Hammock Fish Camp right on the majestic Lake Jesup. Comfortably sleeps 4. Features free wifi internet and a smart tv for watching your favorite netflix series. Just feet away from the Lazy...
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    Oviedo, Central Florida 32765
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Lake Mary
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the beautiful city of Lake Mary/Sanford. Located near everything -adjacent city of Orlando, only 15 minutes away from Sanford Airport and a short drive to Daytona Beach. Easy access to Disney, Universal and all major attractions. Wekiva Springs, St John River and Lake Monroe nearby...
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    Lake Mary, Central Florida 32773
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lake Mary
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located close to Orlando, in the Lake Mary/Sanford area, less than 5 minutes from shopping malls, movie theaters and numerous restaurants, with rapid I-4 and SR-417 access. Ideal central location with beaches, amusement parks, springs, all nearby. Up to 6 guests can share a very special getaway in...
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    Lake Mary, Central Florida 32771
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    Treat your family to an unforgettable Florida retreat in Longwood at this fantastic 3-bedroom, 2-bathroom vacation rental home! With 2,600 square feet to kick back in indoors, and a shared yard for the pup to run around, you'll all be relaxed in no time. After Orlando theme park adventures, relax...
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    Longwood, Central Florida 32779
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Longwood
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sunshine State awaits you at this 1-bath Longwood vacation rental studio with a courtyard! Built in the 1970s, 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...
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    Longwood, Central Florida 32779
    Condo/Apartment - 1 Bathroom, Sleeps 3
    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
    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 like Daytona Beach, Disney World, Universal Studios, Park Avenue, and Blue Springs State Park. When not out...
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    Location Information
    Lake Mary, Central Florida 32746
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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