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 Orlando

4.98 out of 5 average rating, 303 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

26 Jan – 2 Feb

$160 NZD per night

Guest favourite

Guest suite in Altamonte Springs

4.97 out of 5 average rating, 301 reviews

St. Hemingway Suite

Very tranquil Romantic room 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 to Spring Valley

18–25 Sep

$183 NZD per night

Guest favourite

Bungalow in Maitland

4.86 out of 5 average rating, 490 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.

9–16 Oct

$179 NZD per night

Guest favourite

Guest suite in Winter Park

4.96 out of 5 average rating, 245 reviews

Atmospheric Studio in the Garden

Enjoy a little piece of Florida's lush paradise. Full studio suite lives elegantly & comfortably for longer-term stays. We've taken such pride in the opportunity to allow old Florida to intersect with compelling modern design and styling. Relax in this fully furnished studio apartment with kitchenette nestled among a verdant garden. Home boasts modern kitchen, comfy memory foam bed, separate shower and bath & spacious living and entertaining areas. Available for stays of one month or longer.

15–22 Jun

$238 NZD per night

Guest favourite

Guesthouse in Orlando

4.91 out of 5 average rating, 144 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.

17–24 Oct

$277 NZD per night

Guest favourite

Home in Winter Park

4.94 out of 5 average rating, 109 reviews

Modern, Quiet & Cozy - Entire house /Winter park

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.

28 Sep – 5 Oct

$315 NZD per night

Guest favourite

Tiny home in Orlando

4.98 out of 5 average rating, 638 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.

28 Oct – 4 Nov

$252 NZD per night

Guest favourite

Cottage in Winter Park

4.95 out of 5 average rating, 342 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!

14–21 May

$365 NZD per night

Guest favourite

Guesthouse in Orlando

4.93 out of 5 average rating, 227 reviews

Bungalow Near Downtown Orlando - No Cleaning Fee!

🌟 Newly Renovated Gem! 🏡 Nestled behind our 1950’s bungalow in Downtown Orlando's charming College Park district. Explore urban living with a small-town vibe! 🚲 Bike along brick tree-lined streets to award-winning restaurants, boutique shops, local breweries, and vibrant farmers markets! Nearby: 🌳 Winter Park: 10 mins 🏙️ Downtown Orlando: 10 mins 🛣️ I4: 2 mins 🏰 Disney and Universal: 20-30 mins 🏥 Hospital: 5 mins Experience the best of Orlando just moments away! ✨

2–9 Jun

$261 NZD per night

Guest favourite

Treehouse in Saint Cloud

4.97 out of 5 average rating, 790 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. For a video tour type the following link into your browser: https://tinyurl.com/a72vevp5 There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; meemaws-country -cottage which sleeps six.

6–13 Apr

$326 NZD per night

Guest favourite

Guesthouse in Orlando

4.95 out of 5 average rating, 132 reviews

Jefferson St. Cottage

This cottage is a unique free-standing detached dwelling in the heart of Lawsona Park (Historic Downtown Orlando). It sits behind the owner's main house in the back of the lot. The cottage is newly updated with all the amenities to give guests a perfect secluded area near bars, eateries, parks as well as easy access to highways to visit Universal, Disney World, Sea World any more attractions in central Florida.

26 Apr – 3 May

$200 NZD per night

Guest favourite

Guesthouse in Maitland

4.98 out of 5 average rating, 117 reviews

Private 1-bd Mid-Century Guesthouse

Welcome to our tranquil & private 1-bd Mid-Century Modern Guesthouse. The space has a separate entrance and keyless access. Full kitchen, living room, bedroom and bathroom. Centrally located in Florida, our guesthouse offers easy access to the surrounding areas. Lots of museums, nature walks, parks & fantastic places to eat. Book now & experience the love & care we have put into our property!

11–18 Jan

$206 NZD per night