Holiday rentals with outdoor seating in Winter Park

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Winter Park

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

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Guest favourite

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 favourite

Campervan/Motorhome

5 out of 5 average rating, 37 reviews

Luxurious 42 foot Class A RV on 5 forested acres

Lose yourself on a million dollar forested property in a 350k Luxurious RV pampering you with all leather seating, king size bed, additional queen/full/bunks for 8 guests, hard stone counters and tile flooring with washer/dryer and full size residential refrigerator in unit. Water/ice in door of fridge with convection microwave to cook any of your meals available. Multiple smart TV's throughout. Seating on patio with ping pong, table/chairs. NOTE - SMOKE FREE RV In/Outside and 5 ACRE PROPERTY.

Guest favourite

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, 147 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

4.88 out of 5 average rating, 112 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 favourite

Apartment

4.95 out of 5 average rating, 154 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 favourite

Guest suite

4.97 out of 5 average rating, 316 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 favourite

Campervan/Motorhome

4.97 out of 5 average rating, 172 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

Superhost

Home

4.9 out of 5 average rating, 10 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 favourite

Farm stay

4.99 out of 5 average rating, 110 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

Campervan/Motorhome

4.9 out of 5 average rating, 10 reviews

Fresh Air Camper Van/RV

How would you like to have front row seats to a working sustainable farm, learn about the sustainable pillars and work the farm for crop share compensation? Bring your own RV/Camper Trailer/Van (under 25 feet) to the Farm! Plug into 30/50 amp three-prong electrical hookup and/or 110 watt receptacles. Available 30-foot rock driveway pad for your home on wheels, potable rainwater hookup, two outdoor showers and plenty of room to roam.

Guest favourite

Townhouse

4.91 out of 5 average rating, 183 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