Holiday rentals in Winter Springs

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Top-rated holiday rentals in Winter Springs

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Top guest favourite
A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.
Guest house in Longwood
4.97 out of 5 average rating, 116 reviews

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from I-4 makes commuting easy. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not have issues. Grab bars in the bathroom.

Top guest favourite
A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.
Bungalow in Maitland
4.88 out of 5 average rating, 581 reviews

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

Top guest favourite
A spacious outdoor area features a pool surrounded by a tiled patio. Comfortable lounge chairs are neatly arranged around the pool, while decorative planters with blooming flowers add a touch of color. The setting is complemented by manicured lawns and a clear sky.
Flat in Altamonte Springs
4.96 out of 5 average rating, 332 reviews

St.John suite

Luxurious space with PRIVATE ENTRANCE, BATHROOM, and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree lined streets, Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting.

Top guest favourite
A studio-style living space features a spacious bed with neutral bedding, complemented by decorative pillows. A round mirror hangs over a wooden nightstand. The kitchenette area includes a small microwave and cabinetry, while an area rug adds warmth to the wooden floor.
Guest suite in Sanford
4.98 out of 5 average rating, 236 reviews

The Secret Sanctuary in Sanford, 5min from Airport

Welcome to your quiet, spacious, and private sanctuary. Enjoy all new appliances in the full size kitchen, a 50” flat screen TV, and a shaded outdoor area surrounded by greenery. It is located only minutes from the Orlando Sanford International Airport, Historic Downtown Sanford’s restaurants and shops, Lake Monroe’s scenic waterfront, and is centrally located between Florida’s beaches and the amusement parks. **Space is cleaned with EPA approved cleaners, including high touch surfaces**

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, 114 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 spacious outdoor deck is presented with several seating options, including lounge chairs and a dining table. Lush greenery surrounds the area, with a golf course visible in the distance under a bright blue sky scattered with clouds.
Bungalow in Sanford
4.91 out of 5 average rating, 132 reviews

The Golf-view House (Entire House, King bedroom)

This 2/1.5 house is private, clean, and cozy. The open kitchen features stainless steel appliances and provides all necessary cooking wares. The spacious dining/livingroom area receives enough sunlights through the picture windows. Enjoy beautiful golf course view while sitting at the dining table and/or on the humongous outside deck. There is an outdoor dining area and grill on the deck. The house is within 45 minutes from theme parks (Disney & Universal) and beaches (Daytona/New Smyrna).

Guest favourite
Guest house in Sanford
4.95 out of 5 average rating, 168 reviews

Little Hidden Cottage- Near Sanford Airport

Located in Sanford FL, our Hidden Little Cottage is a private studio guest house with its own entrance, features full kitchen & bath room, queen size bed, full size pull out couch & twin size travel bed, & provides flexible self check-in. We are located 7 minutes from the Sanford Airport and Boombah Sports Complex, 10 minutes to Downtown Sanford, I –4 & 4–17. We’re also central to many Central Florida attractions such as Natural Springs, Sandy Beaches, Theme Parks and Historic Districts

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, 285 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.

Top guest favourite
An open-concept studio features a queen bed with crisp white linens and a ceiling fan overhead. A kitchenette with white cabinetry and a dark countertop is present alongside a small dining area. A wall-mounted TV is positioned for viewing from the bed.
Home in Casselberry
5 out of 5 average rating, 9 reviews

Cozy Modern Studio

This private studio has been converted from a garage to a fully equipped studio. A spacious open-concept layout with everything in one stylish and functional space. It features a comfortable sleeping area, a fully equipped kitchen, a private bathroom, and an in-unit washer and dryer—perfect for solo travelers, couples, or digital nomads looking for a quiet, well-equipped place to call home. Disney world - about 1hr Universal studios- about 40min Boombah sports plex - about 25 min

Guest favourite
A serene view of Lake Mary is framed by a large tree and a white post. The sky transitions into vibrant hues as the sun sets, reflecting softly on the water's surface. A lamp illuminates the foreground, enhancing the peaceful lakeside atmosphere.
Guest house in Lake Mary
4.97 out of 5 average rating, 123 reviews

Sunset Cottage in Lake Mary, Florida

Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.

Top guest favourite
Two sparkling glasses filled with a bright orange beverage are placed by the edge of a non-heated swimming pool. The pool area is surrounded by lush greenery and light stone walls, offering a serene outdoor retreat.
Guest suite in Oviedo
4.92 out of 5 average rating, 435 reviews

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

Cozy 2 bedroom guest suite connected to host's primary residence but has its own entrance and there is no shared spaces inside. Living room, 2 separate bedrooms and a full size bath. Amenities include a coffee bar, mini fridge, microwave, TV, Wifi and access to non-heated swimming pool. Host primary residence does overlook the pool area. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Disney: 40 miles

Top guest favourite
A private pool area is enclosed by a screen, featuring a clear blue water surface. Several floats and beach balls are visible on the water, with lounge chairs and lush greenery seen in the background, offering an inviting space for relaxation.
Guest suite in Winter Springs
4.91 out of 5 average rating, 128 reviews

Sierra Suite w/ Pool, Hot tub, and Sauna-Near UCF

Welcome to your home away from home! Our 1 bedroom, 1 bathroom suite offers all the amenities you need for a comfortable and relaxing stay. Enjoy a dip in the pool, soak in the hot tub, or unwind in the sauna. The bedroom has a comfortable queen size bed, and the bathroom has a shower and tub. The suite is perfect for couples or solo travelers looking for a tranquil getaway. We look forward to hosting you!

Popular amenities for Winter Springs holiday rentals

Quick stats about holiday rentals in Winter Springs

  • Total rentals

    80 properties

  • Nightly prices starting at

    £15 before taxes and fees

  • Total number of reviews

    3.4K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    20 properties have a pool