House holiday rentals in Winter Springs

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Top-rated house rentals in Winter Springs

Guests agree: these houses are highly rated for location, cleanliness and more.

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Top guest favourite
An outdoor seating area features blue Adirondack chairs and a patterned table, arranged on a concrete patio. Two large trees provide shade, and a swing is visible in the background. The space is accented with decorative rugs and greenery, fostering a relaxed atmosphere.
Home in Sanford
4.93 out of 5 average rating, 254 reviews

Farmhouse-Chic Retreat with a Charming Patio

Guests have full use of the house, including a spacious kitchen. Four bedrooms with memory foam mattresses ensure you can sleep comfortably. The dining room table can seat 6-8. In the living room there’s a comfortable seating area across the room from a large desk - great for those traveling for work! There is a separate laundry room off the back patio. Guests will have complimentary use of detergent. Iron and ironing board are also available for guest use. On the property there’s an occupied mother-in-law apartment - with separate parking and it’s own entrance so that guests staying in the house are not disturbed by the apartment’s full-time occupant. The backyard is also has a dividing fence for house guests’ privacy. As a guest staying at the house you will have privacy, but I’m local nearby and can assist guests at their request. Behind the house is an occupied apartment that has its own entrance, parking, and backyard. Nestled into a cluster of moss-draped oaks, the house is only a short drive from restaurants and shops in Lake Mary and quaint downtown Sanford. The best way to navigate the area is by car. There are several car rental agencies nearby, with the Orlando-Sanford International Airport just 5-7 min drive.

Guest favourite
Two red kayaks are positioned on a tree trunk beside a peaceful lake, reflecting blue skies and lush greenery. A covered patio area is visible, alongside a hot tub, creating an inviting space for relaxation by the water.
Home in Lake Mary
4.86 out of 5 average rating, 337 reviews

Independent Unique Lake guest house/kayaks/jacuzzy

Independent Guest house with a beautiful lake where you can have unlimited kayaking use during your stay as option(2 kayaks). Property is at lake Mary across Country club, close to Sanford, Boombah Sports, Orlando Fl, walking distance to windixie super market, downtown Lake Mary, dunking donuts , near Orlando Sanford International Airport. Walk to many restaurants and entertainment, 30 min to Daytona Beach. Near Wekiva springs. To go to Disney or Universal, we have easy access to I-4 and 4-17.

Superhost
The living area features a bold accent wall and modern furnishings. A yellow sofa is complemented by four accent chairs with striped cushions. A decorative coffee table sits at the center, surrounded by plants and artwork, creating a welcoming atmosphere.
Home in Winter Park
4.81 out of 5 average rating, 154 reviews

Modern 4-Bed Home in Winter Park (FullSail/UCF)

✨ MODERN WINTER PARK RETREAT ✨ 🏡Welcome to our stylish escape in Winter Park. Situated on a half-acre lot in a tranquil neighborhood, this modern 4-bed, 3-bath home is just minutes from Full Sail, UCF, Park Avenue, and Downtown Orlando. With open-concept living, a fully stocked kitchen, a fenced backyard with a basketball court, and high-speed Wi-Fi, this home is perfect for family vacations, group getaways, or business trips. 📝PLEASE NOTE: 🧺 A washer & dryer is now included as an amenity!

Top guest favourite
The exterior of the home features a welcoming front entrance with a gray door and arched window. The pathway is lined with colorful foliage, and tropical plants surround the entrance. A lamp post stands at the forefront, providing soft illumination amidst the lush greenery.
Home in Sanford
4.97 out of 5 average rating, 270 reviews

Clean, cozy home in a GREAT location

This clean, comfortable home is in a peaceful neighborhood and centrally located to everything you may wish to enjoy while on your Central Florida vacation. Literally two to three minutes away from I-4, highway 417 and a multitude of shopping and dining options. Universal Studios, Sea World and Daytona International Speedway are all within about 40 minutes, while Disney World and Kennedy Space Center are about 50 - 60 minutes. Also easy access to Sanford and Orlando International Airports.

Guest favourite
A spacious living area features a large sectional couch and a stylish coffee table. Natural light filters through the windows, highlighting modern décor. An arcade game stands in the background, and a laundry area is visible to the left, contributing to the home's functionality.
Home in Casselberry
4.88 out of 5 average rating, 113 reviews

Cozy 4/2, King Beds, Pergola, Hot Tub & Pool

Newly renovated farmhouse gem centrally located in the beautiful Casselberry / Orlando area. Stylish and thoughtful touches throughout will make you feel right at home. 2 king beds, 1 queen and 1 bunk room (2 doubles & 2 twins) along with an 8' farmhouse table (seats 8) makes this home great for both small & larger groups alike. Complete with a hot tub, amazing walk-in shower, Marvel Arcade, Private patio with pergola outdoor furniture & gas grill, it's great for both the adults and kiddos!

Top guest favourite
The living area features a modern sectional sofa arranged around a textured coffee table. A colorful area rug adds warmth. A dining table with black chairs is set nearby, illuminated by pendant lights. Large windows provide ample natural light, and contemporary wall art enhances the ambiance.
Home in Orlando
4.94 out of 5 average rating, 119 reviews

Luxurious and modern cottage near UCF

This is peaceful and quiet place in a country seating yet in the middle of the city. It has been renovated and decorated in a luxurious and modern style by professionals. It’s better than the pictures. From here you can easily access the theme parks, beaches, downtown Orlando and all mayor attractions. Disney 24 miles. Universal studios 21 mi. Sea World 18 mi. Airport 12 mi. Beaches 50 mi. Downtown Orlando 15 mi. UCF 2.4 mi. And tons of restaurants! Come and experience Florida at its best

Guest favourite
A refreshing pool is captured, with sunlight sparkling on the water's surface. The stone-accented summer kitchen with a wooden pergola is visible in the background, along with plants and seating, creating a relaxed outdoor setting.
Home in Casselberry
4.92 out of 5 average rating, 118 reviews

Villa with Guest House & Pool-Patio

Welcome to this Amazing House Pool-Patio with 4 Bedrooms + 2 Bathrooms and optional guest house. Luxury and true gem with covered summer kitchen, covered pergola, garage for two cars and a large driveway. 30 Minutes distance to Universal, Sea World, Volcano Bay and others. UCF in 15 minutes and Daytona beach/Cape Canaveral in 50’. Great restaurants and shops. The house is conveniently located and accessible for all attractions in Central Orlando. Airport is 25 minutes. SAFE NEIGHBORHOOD

Top guest favourite
A screened-in pool area features a clear blue pool surrounded by landscaped greenery. A stone waterfall adds a natural touch, complemented by decorative plants and a Zen-inspired statue. Sunlight filters through the trees, enhancing the tranquil ambiance.
Home in Longwood
4.97 out of 5 average rating, 102 reviews

Relaxing 3-Bedroom Pool Getaway

This is a 3-bedroom 2-bath home, bathroom in the main bedroom connects directly to the pool. Accommodates comfortably up to 6 people. We have a wide range of amenities including wifi, TV, covered pool, fully equipped kitchen, and more! This is located in a quiet neighborhood located 30 minutes from Universal Studios, Sea World, and Disney World. The home comes with pool toys, board games, a space for an outdoor bar! The outdoor space is enclosed to keep out mosquitos and other pests.

Guest favourite
The image depicts a calm lake at sunset, with reflections of clouds and colors mirrored in the water. In the foreground, a fishing boat is anchored, positioned near the lake's serene shoreline surrounded by lush greenery.
Home in Longwood
4.94 out of 5 average rating, 145 reviews

Pvt Fishing lk , Pets,Nature, Pool,garage

No HOA. Private 20 acre lake property, with fishing boats and trolling motors, canoes , peaceful boardwalk / dock. Large extra parking for trailers or work trucks. Fishing gear / poles. 2 car garage for safely storing whatever you bring. Fishing gear, tools, bikes, Harley's. Located near Seminole Trail, parks, sun-rail station. 45-60 min from the beach or the attractions DISNEY, UNIVERSAL STUDIOS, close to Lake Mary, Sanford, Wekiva Springs, Daytona 500, Bike week, 20 min from Boombah

Guest favourite
A spacious living area features a modern sectional sofa arranged facing a stone fireplace. Large glass doors provide natural light and views of the outdoor space. Decorative plants and a wall-mounted mirror add elegance to the cozy atmosphere.
Home in Maitland
4.87 out of 5 average rating, 133 reviews

Bonheur Ala Maison

Bonheur A la Maison is the home that offers a beautiful, comfortable, spacious, convenient and all around happy feeling with the little extras and attention to detail to make you feel like you're basking in a lot of luxury for a simple price! Its everything you need from your blow dryer, to your plush robe and from your USB outlets at all bedsides to your built in wireless speakers for your music of choice. We tried to think of it all. Conveniently located near lots of shops and parks!

Top guest favourite
The cottage exterior features a charming yellow facade with a metal roof, surrounded by lush greenery and a mix of plants. A patio area is visible, offering a shaded umbrella and seating amidst a peaceful outdoor setting, complemented by a small koi pond.
Home in Oviedo
4.96 out of 5 average rating, 288 reviews

Cute cottage near UCF & trails. No cleaning fee

Our cottage is nestled behind Oviedo’s oldest home. The cottage boasts lots of windows with a beautiful view of the outdoors. Inside the cottage is a queen-size bed, table for 2-4, kitchenette with refrigerator, toaster and microwave, TV with Netflix and Prime, plus WiFi. There is a tall claw foot tub which can be difficult for people with mobility issues. The cottage is connected to the main house but has its own entrance and guests have complete privacy. There are no shared spaces.

Guest favourite
A modern kitchen features white cabinets and stainless steel appliances, complemented by granite countertops. A large island with seating is positioned centrally, while the dining area is visible through glass doors leading to the backyard.
Home in Longwood
4.93 out of 5 average rating, 236 reviews

Cozy 3 Bedroom Home, Great location!!

Equipped with one camera near the keypad facing the front door and is recording 24/7 , and perfectly situated in an ideal location. The marble countertops and stainless steel appliances create a dreamlike setting. The fenced backyard features a barbecue grill, smart TVs, and board games. Note: we charge an event fee; do not book without discussing and paying the fee. Minutes from I-4, Wekiwa Springs State Park, Disney, and Downtown Orlando. Book this exquisite sanctuary today.

Popular amenities for house rentals in Winter Springs

When is the best time to visit Winter Springs?

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Avg. price$182 SGD$195 SGD$199 SGD$193 SGD$195 SGD$176 SGD$186 SGD$181 SGD$155 SGD$202 SGD$199 SGD$182 SGD
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Quick stats about house rentals in Winter Springs

  • Total holiday rentals

    Explore 50 holiday rentals in Winter Springs

  • Nightly prices starting at

    Winter Springs holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,860 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Winter Springs holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Springs rentals

  • 4.8 Average rating

    Winter Springs stays are highly rated by guests – averaging 4.8 out of 5!