Vacation rentals with outdoor seating in Winter Park

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Winter Park

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage

4.93 out of 5 average rating, 164 reviews

Mills Cottage

Beautiful private upstairs cottage with deck overlooking the lake. It’s near other lakes and dog friendly parks are close. Comfort was the number one reason when choosing furniture and mattresses. Kitchen fully equipped: coffee maker, toaster, microwave, cook top oven, refrigerator, washer/dryer, iron & flat screen TV. Wifi, cable tv, Amazon & Netflix. A dedicated professional work space and desk. Includes light breakfast and snacks. Please note there is an additional charge to use the pool.

Guest favorite

Cottage

4.94 out of 5 average rating, 101 reviews

Cozy Cottage 3 blocks from town

Come as guests, leave as friends. This super-clean 1 bed, 1 bath cottage sleeps up to 4 adults. "Cozy Cottage" is pet friendly and laid back with a super-fast internet connection. Historic Mount Dora is only steps away. Enjoy the many quaint shops, restaurants and regional festivals. The rolling hills and lakeside views give this town its New England seaside charm. Orlando theme parks are only 1 hour away. We are the perfect place to retreat after the hustle and bustle of the theme parks.

Guest favorite

A cozy sleeping area features a spacious bed dressed in white bedding, flanked by vibrant red pillows. Wooden accents create a warm atmosphere, while a bedside lamp provides soft lighting. A window offers views of the surrounding nature, enhancing the inviting space.

Tiny home

4.87 out of 5 average rating, 54 reviews

Lux Tiny Home/RV in Prime Location Dog Friendly

Brand New "Destination RV / Tiny Home" permanently placed on our beautiful property in Longwood/Wekiwa Springs. Enjoy affordable private luxury with all the bells and whistles. Prime location 35 min to MCO, 25 min to Disney & Universal, and less than 10 min to Wekiva Springs State National Park and other local treasures. Perfect for guests wanting access to both the amusement parks and beaches (we are in the middle). Luxury Hotel style mattress. Beach chairs & umbrellas etc. avail to rent.

Superhost

Treehouse

4.88 out of 5 average rating, 148 reviews

The Beehive Treehouse

This one of a kind treehouse will quickly become one of the most booked tree houses on the planet. Unique in every possible way. It started as an art of love during Covid and it quickly became a project that has fought the attention of superstar singers looking to disconnect from everything but being close to everything. Queen bedroom, drawer space, full bathroom, Nespresso coffee maker, 80-inch tv, private balcony overlooking the main wedding venue, outdoor claw tub and custom chandelier.

Superhost

Townhouse

4.87 out of 5 average rating, 118 reviews

Orlando Disney new House at Resort with lake view!

Renewed house in Resort with fantastic lake view and an Amazing Clubhouse. (NO resort fees) | 1 min | Old Town Kissimmee | 3 min | Publix® | 3 min | McDonald's®, Wendy's®, Miller's Ale House® and much more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | Premium Outlet® I-4 | 9 min | DISNEY® AREA (All Parks) | 10 min | ESPN Sports | 10 min | Convention Center | 14 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 60 min | Bush Garden's® | 95 min | Sarasota & Clearwater

Guest favorite

A spacious living area features large glass doors that open to a scenic balcony overlooking the Arnold Palmer PGA golf course. Soft furnishings are complemented by a stylish coffee table and decorative accents. Nearby, a vibrant Star Wars-themed bedroom displays unique decor and multipurpose seating.

Condo

4.95 out of 5 average rating, 156 reviews

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

This modern 3-bedroom luxury condo (with an ELEVATOR right to the door) has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

Guest favorite

A bright living area features large windows with light beige curtains, allowing natural light to fill the space. A vintage dresser is positioned next to a blue upholstered chair adorned with decorative pillows. Warm wooden flooring and an area rug add to the room's cozy atmosphere.

Guest suite

4.97 out of 5 average rating, 322 reviews

St. Hemingway Suite

Very tranquil Romantic Suites with views and access to large lake. PRIVATE ENTRANCE and private bathroom. Amenities include, private dock, pool, large manicured lawns, private parking, breakfast kitchenette and much more. Close to theme parks and beaches. Ample shopping and award winning restaurants very nearby. Peaceful setting to read, do Yoga, enjoy quiet moments by the lake, watch the boats sail by or watch the sun rise. Peace and tranquility at its best. We welcome you

Guest favorite

A colorful interior of the pop-up camper features a cozy seating area with vibrant orange cushions. Soft lighting is provided by a stylish lamp. The kitchenette is visible, equipped with essential appliances, and patterned rugs add texture to the space. Natural light filters through the patterned curtains.

Camper/RV

4.97 out of 5 average rating, 190 reviews

Fireplace, Heated King Bed, FREE Kayaks and Bikes!

Electrical Fireplace! Heated King Bed! Private Outdoor Shower! Outdoor Fire Pit for Smore's! Free Kayaks! Free Bikes! Free Paddle Boards! Free Cuban Expresso Coffee! MINUTES TO: 12 Kia Center 10 Downtown Orlando 10 Winter Park 4 Baldwin Park 45 Disney 35 Universal Studios 35 Sea World WHY STAY HERE -2PM Check in 12PM Check out -Free use of bikes for trails and town exploring -Heated King Bed! -Free paddle boards & kayaks for our lake -Fire pit for cooler nights

Guest favorite

Home

4.93 out of 5 average rating, 14 reviews

Southern Dunes / Legoland / Golf / Disney

Welcome to your charming Florida retreat! This golf course front 4-bedroom, 3-bathroom home features a private pool and patio, spacious living areas, and a fully equipped kitchen. Enjoy comfort with cozy bedrooms and family-friendly amenities. Located minutes from local attractions, golf courses, and just a short drive from Disney World and Legoland, this home offers the perfect blend of relaxation and convenience. Book your stay today for an unforgettable Florida getaway!

Guest favorite

A covered swing hangs from a sturdy wooden frame, positioned near a fire pit surrounded by a circular stone border. Red chairs are arranged nearby, with trees and a rustic fence in the background, creating a serene outdoor setting.

Farm stay

4.99 out of 5 average rating, 115 reviews

Slice of paradise ranch and outdoor quality time.

A quiet country retreat., pet the horses & goats, enjoy the sunken large fire pit surrounded by nature. See wild deer, turkey, black bear, racoons, eagles and more. Majestic live oaks and of space to let the kids or pets run free. Enjoy the covered picnic area and swing near the fire or have a BBQ at our resort style outdoor entertaining area. No city lights here, see the stars in their full glory while relaxing at fire pit and swing for 2. Springs, canoeing 5 mins away.

Superhost

Home

4.89 out of 5 average rating, 9 reviews

PuraVida Urban Lakehouse+Bungalow - Full Property

Welcome to our Pura Vida jungle-inspired urban lake house, nestled in the heart of Orlando! Combining tropical tranquility with modern luxury, this unique retreat offers the perfect escape for travelers seeking a serene atmosphere just minutes from the city's attractions. **NO PARTY OF ANY KIND OR EVENT ALLOWED** Circular driveway makes for free and easy parking. Located 15 min from the airport, 15 min to Universal, 30 min to Disney, and 50 min to Cocoa Beach.

Guest favorite

Aerial view of a sprawling resort pool area featuring a lazy river, water slide, and lush landscaping. Multiple lounge chairs line the poolside, while a shaded tiki hut offers respite. A serene lake reflects the clear blue sky, enhancing the resort's inviting atmosphere.

Townhouse

4.91 out of 5 average rating, 188 reviews

I-Gated Resort-5 miles to Disney-2 FREE Water Park

Is this home booked? We have more! Click on the circular profile image, then scroll down till you see James's Listings. Gated/24 hour security. Resort living with 2 main clubhouses and a few other extra quieter pools, playground and a soccer field. 10 min to Disney 15 min to Universal 10 min to the Convention Center Within a 5 min drive: Publix Grocery Walmart Target 10-15 restaurants