Holiday rentals with outdoor seating in Winter Park

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Winter Park

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

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Guest favourite

Guest suite in College Park

4.98 out of 5 average rating, 347 reviews

A SUITE RETREAT with a Garden View in the City

A lovely remodeled in-law suite in a 1920s Mission Styled home in College Park suited for 2 people with a separate entrance, private bath & a little kitchenette.The Suite looks out into a garden to offer a relaxing view. Even though you are in the Downtown area, the suite was designed to offer solitude. We are walking distance to many restaurants & only an easy 5 minute drive to downtown Orlando. I am looking forward to hosting any and all who would like to visit. All are welcome. #STR-1009437

Guest favourite

Tiny home in Baldwin Park

4.95 out of 5 average rating, 208 reviews

Lakefront+Great Reviews+Kayaks+Expresso Coffee

Free to use: - Romantic & Birthday Packages - Propane grill included! - 2 bikes to take into town - 2 kayaks for use on our private lake - 2 paddle boards for use on our private lake Nestled lake front, you have the best view on the property; open your vintage double french doors to view the sunset from your king bed or sunrise over lake and view any of our 51 species of birds. Enjoy a meal cooked on your private gas grill. Spices and grill tools included! Lakefront and Private yard space.

Guest favourite

Rental unit in College Park

4.92 out of 5 average rating, 106 reviews

College Park/Winter Park separate 1 bed/bath 32804

255 sq ft- 1 bedroom w/ queen bed, office space, kitchenette, large bathroom, private entrance in your own yard area. This gem is super clean, the unit is quiet w/ complete blackout in bedroom, bathroom has tons of natural light & 3 shower heads, microwave, fridge & Keurig. Comfy, near I-4 exit 44 Par St. Kia Center 3 mi Airports (MCO) (SFB) 23 mi Orlando Ballet School 1.5 mi AdventHealth Orlando 0.6 mi AdventHealth Winter Park 3.4 Orlando Health & Arnold /Winnie Palmer 3.8 Rollins College 2 mi

Guest favourite

Bungalow in Maitland

4.87 out of 5 average rating, 527 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.

Guest favourite

Guesthouse in College Park

4.94 out of 5 average rating, 108 reviews

Beautiful 1 Bed/1 Bath in College Park Orlando

College Park is a great residential neighborhood of Orlando close to all the action, but also far enough away if you are looking for peace and quiet. There are several bars, breweries, and restaurants within minutes by car and you can also Uber downtown within 5-10 minutes. The Advent Health Hospital is within walking distance just 3 blocks away. Everything from Disney and Theme Parks to nightlife and nature are about a 30 minute drive away. If you need any help deciding what to do, just ask.

Guest favourite

Tiny home in College Park

4.96 out of 5 average rating, 666 reviews

Quiet Shed in Downtown

Nestled behind my 1920s bungalow in one of Orlando’s best neighborhoods, The Shed is a local experience and retreat. Located in the city center, just a 5 min Uber to Amway, Soccer Stadium, and walking distance to the Sun Rail and hospital, you’ll love The Shed, because of its chill vibe and privacy. Perfect for couples, traveling professionals, and those new to Airbnb. Note: I rent my main house so you may see those guests in the backyard. No smoking/vaping allowed. Early check-in @ $20/hr

Guest favourite

Guesthouse in College Park

4.91 out of 5 average rating, 163 reviews

8th Green Cottage - A relaxing oasis in the city

The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located 5 minutes from downtown. Sitting on the historic 1924 Dubsdread golf course. Enjoy the great views, pleasant and quiet neighborhood all with easy access to everything Orlando has to offer. Location is key when traveling and the 8th Green Cottage delivers! Disney, Universal, and Sea World all within a straight shot down I4. Free play Arcade with 3500 games included in spare bedroom Pets are welcome and stay Free.

Guest favourite

Home in Winter Park

4.94 out of 5 average rating, 138 reviews

Modern, Quiet & Cozy - Entire house 2/2

Embrace Tranquil Living in Winter Park, Florida. Located in a quiet neighborhood NE of downtown this recently renovated house is modern, clean, and cozy. Short drive to other great attractions in Orlando. Its central location is minutes away from Park Ave, the University of Central Florida, Rollins College, Full Sail University, Downtown Orlando, MCO Airport, Amway Center, Dr. Phillips, Science Center, Orlando City Stadium, and much more! You need to be at least 18 years old to book.

Guest favourite

Guesthouse in College Park

4.97 out of 5 average rating, 119 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. We are located in College Park of Orlando. The main road here is Edgwater Drive which offers restaurants, bars, and boutique shops. This location is 15 min. from downtown, 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals in central Florida. Also, you are within walking distance from the historic Dubsdread Golf Club and restaurant. Perfect home away from home.

Guest favourite

Tiny home in Spring Lake

4.98 out of 5 average rating, 694 reviews

The Little Treehouse 2 at Country Club of Orlando

With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

Guest favourite

Cottage in Winter Park

4.95 out of 5 average rating, 372 reviews

Winter Park Pearl 6 min drive to historic Park Ave

This Winter Park cottage was built in 1954 with original hardwood flooring. Take a 5 min drive to and through historical Winter Park to access shops and restaurants on the coveted Park Ave. It is the perfect central location to access beaches, Universities, Orlandos events, and the best restaurants. The house is tucked away into a quiet neighborhood with lots of sleepy old big oaks. If you have any questions I am always available, so please ask. My response time is immediate!

Guest favourite

Tiny home in College Park

4.95 out of 5 average rating, 110 reviews

Luxury Container Home 30 min from Disney-Hot tub

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, and soak your tired feet in the hot tub.