Holiday rentals with a patio in Winter Park

Find and book unique Holiday Accommodation with Outdoor Verandahs on Airbnb

Quick stats about holiday rentals with a patio in Winter Park

  • Total holiday rentals

    Explore 240 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at $28 AUD per night before taxes and fees

  • Verified guest reviews

    Over 13,620 verified reviews to help you choose

  • Family-friendly holiday rentals

    140 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 90 rentals that welcome pets

  • Holiday rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wi-Fi availability

    230 of Winter Park holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Park rentals

  • 4.9 Average rating

    Winter Park stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Winter Park's top spots, include Orlando Science Center, Harry P. Leu Gardens, and Orlando Museum of Art

Top-rated Holiday Accommodation with Outdoor Verandahs in Winter Park

Guests agree: These Holiday Homes with Outdoor Verandahs are highly rated for location, cleanliness and more.

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Top Guest favourite
Guesthouse in College Park
4.99 out of 5 average rating, 164 reviews

College Park Villa Oasis w/ Botanical Courtyard

TOP 1% ABNB PRIVATE-SAFE-QUIET Villa Oasis central to DT ORL/Eola/Winter Park. Tranquil bamboo lined Cottage provides relaxed setting in much desired COLLEGE PARK neighborhood. Former recording studio @ 2X the living space of most College Park listings. Newly renovated bathroom, kitchen, outdoor space. Guest's own separate residence, bath/laundry room, garden patio and parking. I-4 EZ access to downtown ORL, Winter Park, THEME PARKS, central Fla activities! PLEASE MESSAGE with ANY QUESTIONS!!!

Top Guest favourite
A bright living space features a comfortable sectional sofa adorned with decorative pillows, paired with a light-colored armchair. A wooden coffee table sits on a textured area rug, while a ceiling fan and pendant lighting add modern touches. The kitchen bar is equipped with high stools, enhancing the open layout.
Guesthouse in Orlando
5 out of 5 average rating, 103 reviews

Livingston Hideaway • Walk To Lake Eola • Hot Tub

Welcome to Livingston Hideaway, a charming historic duplex in downtown Orlando, just two blocks from Lake Eola. This private space offers a quiet, residential feel while being steps from dining, nightlife, and events. Perfect for couples or business travelers, it features a private entrance, fenced outdoor area with hot tub and putting green, free parking, and fast Wi-Fi. Thoughtfully updated with modern comforts, Livingston Hideaway blends historic character with walkable downtown convenience.

Top Guest favourite
A spacious living area features a large, deep-seated sectional couch adorned with decorative pillows. A wooden tray rests on the couch. A dining table with chairs is positioned near bright windows, enhancing the natural lighting in the room.
Home in Winter Park
4.97 out of 5 average rating, 198 reviews

Stylish newly updated home in Winter Park

Sleeps 8 people comfortably but can fit 10. This home has VERY CONVENIENT ACCESS TO I-4 making it easy to get to Orlando's most sought after attractions, including Park Avenue, Downtown Orlando, Rollins College, Leu Gardens, Mills Ave, Baldwin Park, College Park, Camping World Stadium, Amway Arena, SunRail, and many hospitals. SHORT WALK to 3 notable restaurants Also nearby: Universal Studios (20 min) Outlet Mall (20 min) International Drive (25 min) Orlando Airport (30 min) Disney (~30-40 min)

Top Guest favourite
A spacious outdoor area features a large pool with crystal-clear water, accompanied by a hot tub and a soothing water fountain. Surrounding the pool, a stone patio hosts multiple seating areas beneath a pergola, providing a serene setting for relaxation.
Home in Orlando
4.97 out of 5 average rating, 104 reviews

Unique Spacious Home w/ Pool near Downtown Orlando

Nestled on a quiet street, 15 mins from Downtown Orlando. This home has a massive pool, hot tub, water fountain, real outdoor and indoor fire place, outdoor patio area w/seating. The Kitchen is equipped with everything you need to make delicious meals, and there are two living areas to provide ample space for relaxation. There is also a designated office area to take work calls. ☀ College Park – 10 mins ☀ Downtown Orlando – 15 mins ☀ Universal Studios – 28 mins ☀ Walt Disney World – 34 mins

Top Guest favourite
A modern kitchenette features light cabinets and a combination of granite countertops. Stainless steel appliances, including a microwave and dishwasher, are visible. Pine wood floors run throughout, contributing to a warm appearance. Natural light fills the room through a window, illuminating the adjoining dining area.
Bungalow in Orlando
4.97 out of 5 average rating, 273 reviews

King/Queen Bungalow w/ porch | central vibey area

Our 1920's historic home is nestled in a quiet neighborhood just a few blocks from everything. The ColonialTown North district of Orlando (also called Mills/50) is a vibrant, central area with exceptional walkability to grocery stores, a trendy bar scene, LOTS of coffee and boba options, foodie restaurants and casual late night eats. When you're ready, retreat to our porch swing and watch the sunset reflect off the trees. We lived in this space for four years and left it just as we crafted it.

Guest favourite
The exterior of the house showcases a striking blend of wood and stone finishes, featuring large windows that illuminate the interior. An expansive, clear blue pool reflects the sky, with a bridge extending over the water leading to the main entrance.
Villa in Orlando
4.95 out of 5 average rating, 124 reviews

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

Welcome to our stunning lakefront resort, where luxury meets tranquility! Dive into our expansive 100,000-gallon pool, enjoying a refreshing swim surrounded by breathtaking views. Inside, our tastefully designed space features midcentury modern amenities ensuring you have everything for a perfect getaway. Each bedroom offers serene views and plush bedding for a restful night’s sleep. Whether you seek adventure or relaxation, this is your ideal getaway. Book now for unforgettable memories!

Top Guest favourite
A stylish kitchen is equipped with modern stainless steel appliances, including a refrigerator and microwave. A central island features two metallic stools, and the cabinetry is finished in a soft gray. A small potted plant adds a touch of greenery to the space.
Guesthouse in Orlando
4.99 out of 5 average rating, 125 reviews

Location, Location, Location!

Enjoy a stylish experience at this centrally-located Guest House. It is located in an excellent area close to the downtown Orlando, excellent restaurants, and much more. It is fully furnished and equipped with new appliances (washer and dryer included) and furniture. It is located minutes from Winter Park, Downtown Orlando and theme parks. Downtown Orlando 3 miles (6 min) Advent Health Hospital 0.6 miles (2 min) Walt Disney World 20 miles (23 min) Universal Studios 11 miles (18 min)

Top Guest favourite
The screened-in pool area features a tranquil pool with a soft blue hue, surrounded by white decking. A small table holds a lit lantern beside two lounge chairs, providing a serene space for relaxation under the evening sky.
Home in Maitland
4.99 out of 5 average rating, 124 reviews

Florida Poolside Paradise a Great Place to Unwind!

Welcome to our exquisite 4-bedroom vacation rental in the heart of Maitland, Florida – a true gem where luxury meets convenience. This upscale home boasts fine furnishings and a private pool, making it the ideal retreat for families or groups seeking both comfort and style during their Sunshine State getaway. The house is located in a residential neighborhood with plenty of restaurants and shopping within a 5 minute drive. Convenient location off Rt 436. and half hour to the airport.

Top Guest favourite
Guesthouse in Orlando
4.99 out of 5 average rating, 170 reviews

Baldwin Park Guest House

Welcome to the Baldwin Park Guesthouse! This private sanctuary features modern day comforts including a large screen SmartTV and private garden patio. It the perfect place for a romantic getaway or a solo trip to the area. Stroll over to explore Baldwin Park or visit beautiful downtown Winter Park (don’t miss the scenic boat tour). Orlando International Airport the and the area attractions are just a short drive away. We look forward to welcoming you to the guesthouse soon!

Superhost
A scenic hot tub is surrounded by a stone patio and lush greenery, providing a serene outdoor space. Features include decorative tile accents and a gentle water feature, contributing to a calming atmosphere. Comfortable seating is positioned nearby for relaxation.
Home in Azalea Park
4.89 out of 5 average rating, 222 reviews

Hot Tub, Fire Pit, Private Backyard, King Bed

Welcome to our home centrally located between Downtown Orlando, UCF, Orlando Airport, and near to the parks. Our 2 bed 1.5 bath home with an additional sleeper sofa is a great vacation spot for your next visit to Central Florida. Beaches, Disney, the Amway Center, Dr. Phillips Center, UCF and so much more. Our home is a quiet place to rest your head at night or enjoy a relaxing beverage in our custom hot tub after a long day enjoying all Orlando has to offer.

Guest favourite
An outdoor space features a heated pool and a hot tub, surrounded by stone masonry. A custom bar, crafted from wood, is visible alongside tropical plants. Two built-in TVs are fitted above the bar area, enhancing the outdoor living experience.
Home in Orlando
4.92 out of 5 average rating, 165 reviews

Stunning Orlando Getaway w/Spa & Heated Pool

The whole group will enjoy easy access to everything from this centrally located Orlando location. This 1950s beautifully designed space has all modern amenities with an amazing outdoor living space. Located in College Park situated close to many amenities Orlando has to offer. Only 9 Minutes to downtown Orlando or 15 Minutes to Universal. The Acre & The Cottage Wedding venues are both within Walking Distance. Dubsdread is only 4 Minutes Away.

Top Guest favourite
A serene bedroom features a spacious bed dressed in crisp white linens, flanked by modern bedside lamps. A vibrant floral accent wall adds a pop of color, while light filters through plantation shutters, creating a calming atmosphere.
Home in College Park
4.97 out of 5 average rating, 115 reviews

Yale House in College Park 2 mi from Downtown

Yale House is a charming, historic 1927 home. This happy place is a stylish mix of nostalgia and modern life. The home is only steps away from shops & restaurants. The full kitchen and laundry have everything one needs for longer stays and includes a dedicated workspace with ethernet. There is wifi & 3 streaming TV’s with a huge comfy couch. Driveway parking for two cars. Two bedroom choices provide for a peaceful rest.

Popular amenities for Winter Park Holiday Houses with Outdoor Verandahs

When is the best time to visit Winter Park?

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