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Holiday rentals with a patio in Winter Park

Find and book unique Holiday Accommodation with Outdoor Verandahs on Airbnb

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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Guest favourite
The inviting pool area is framed by a wooden deck, featuring two lounge chairs and a large umbrella for shade. The clear water reflects the blue sky and surrounding greenery, creating a serene atmosphere for relaxation.
Home in Altamonte Springs
4.94 out of 5 average rating, 103 reviews

Orlando Poolside Oasis

Welcome to the Orlando Poolside Oasis!! This property is located in a quiet suburb of Orlando, with easy access to both theme parks and the beaches. This 3 bedroom 2 bathroom pool home will allow you to vacation in comfort and style. We have recently completed many upgrades to the property, including a newly renovated kitchen and bathrooms. We hope you love this property as much as we do! The home is also very baby friendly (crib upon request, stroller, baby bath,etc)!We can’t wait to host you!😊

Top Guest favourite
Guesthouse in College Park
4.99 out of 5 average rating, 156 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 heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.
Home in Lake Formosa
4.97 out of 5 average rating, 147 reviews

Spacious Home with Pool & Hot Tub near Downtown

Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

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
4.98 out of 5 average rating, 183 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 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
4.98 out of 5 average rating, 250 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.

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 Orwin Manor
4.99 out of 5 average rating, 109 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, 113 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.

Superhost
The living area features a modern design with a gray sectional sofa adorned with decorative pillows. A wooden coffee table sits atop a textured area rug, accompanied by a floor lamp and potted plant. A wall-mounted TV and large windows allow natural light to fill the space.
Home in Winter Park
4.84 out of 5 average rating, 151 reviews

𝕊𝕝𝕖𝕖𝕡𝕤 𝟠| 𝕎𝕚𝕟𝕥𝕖𝕣 ℙ𝕒𝕣𝕜|ᴏʀʟᴀɴᴅᴏ

Enjoy this private 2/1 home with stylish decor. The property is very well located! Just a short car ride away from gorgeous Park Avenue and the best restaurants, Rollins College, College Park, downtown (Kia Center, Camping World Stadium, Dr. Phillips Center) and 30 minutes from all major theme parks. ✔ Comfortable 3 x Queen beds + pull out sofa ✔ Full Kitchen ✔ Parking on driveway and free street parking ✔ Smart TV ✔ Washer/Dryer "FREE" ✔ Dining table ✔ High-Speed Wi-Fi

Top Guest favourite
An open living area features a comfortable sofa, decorative pillows, and a coffee table. A flat-screen TV is mounted on a white media unit, with greenery and framed art enhancing the space. Large windows allow natural light to fill the room, complemented by cozy blue curtains.
Home in Colonialtown South
4.95 out of 5 average rating, 192 reviews

Spacious 3BR/2B w/Workspace & Backyard Paradise

Bring the whole group to this great place with lots of room for fun and prime for a relaxing home base for your trip! With open concept common areas, full kitchen, laundry, and games to play, this makes for a super cute and spacious home! The backyard oasis has a hammock plus a patio with furniture, and partial sunshine. Located in a quiet neighborhood blocks from downtown Orlando and close to major attractions and highways. This home is loaded with everything you'll need!

Guest favourite
A charming arched bridge is framed by lush greenery and hanging Spanish moss. The surroundings are filled with trees and plants, creating a serene outdoor space that invites exploration.
Guesthouse in Orlando
4.92 out of 5 average rating, 190 reviews

Jefferson St. Cottage

This cottage is a unique free-standing detached dwelling in the heart of Lawsona Park in the Historic District in downtown Orlando. It sits behind the owner's main house in the back of the lot; privacy is not an issue. The cottage is loaded with all the amenities needed to enjoy your stay. We are close to highways to visit Universal, Disney World, Sea World any more attractions in central Florida. In addition, Uber is a very good option for transportation.

Guest favourite
The exterior of a modern shipping container suite is displayed, featuring large windows that allow natural light to flood the interior. The surrounding landscape includes gravel and low-maintenance foliage, with a small deck leading to the entrance, emphasizing the blend of nature and contemporary design.
Tiny home in College Park
4.94 out of 5 average rating, 176 reviews

Shipping Container Oasis -HotTub- 30 min to Disney

Step into this unique experience: a shipping container transformed into a luxury 1 bedroom 1 bathroom suite. The space is perfect for couples, business travelers, tourists, and families. After a busy day in the parks or shopping, come back to a cozy outdoor paradise with lights strung up under a covered pergola. Lounge on the couch and enjoy a gas fireplace table, grill a meal on the Weber Spirit 2 gas grill, and soak your tired feet in the hot tub.

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
4.96 out of 5 average rating, 108 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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Avg. price$170 AUD$176 AUD$182 AUD$173 AUD$163 AUD$170 AUD$166 AUD$166 AUD$156 AUD$168 AUD$197 AUD$195 AUD
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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 12,870 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

Destinations to explore