Vacation rentals with outdoor seating in Orangeville

Guesthouse in Orangeville

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

4.96 out of 5 average rating, 382 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Guesthouse in Orangeville

A studio room features a spacious bed with crisp linens and a decorative throw. Comfortable seating areas include armchairs and a small table. Natural light filters in through the windows, enhanced by a ceiling fan overhead. The kitchen and dining area are visible in the background.

4.95 out of 5 average rating, 147 reviews

A bright & stylish urban studio

Come & relax...in privacy. In the "Carriage House" you will be away from the main house, in your own building! Its a 634 square foot studio-style unit, that is unique & intimate. A nice sized kitchen, complete with gas range. Spacious & bright over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for more room. A diner booth for meals, or working at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Apartment in Horning's Mills

A private wooden deck is shown with an umbrella-covered table and four chairs, surrounded by lush greenery. Windows on the building's façade allow natural light, while potted plants add a touch of color, enhancing the outdoor space for relaxation.

4.96 out of 5 average rating, 325 reviews

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and the Bruce Trail. Close to Shelburne, Mansfield, Creemore, Pine River Institue and many excellent restaurants (The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

Guest suite in Orangeville

This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.

4.93 out of 5 average rating, 859 reviews

Hot Tub & Cozy Spring Retreat-Headwaters Retreat

Escape to our rustik-modern queen suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

Shipping container in Puslinch

The exterior of a modern, dark-toned tiny home is framed by trees. A private dock with Adirondack chairs sits by the water, reflecting the structure's warm lights. The tranquil setting is enhanced by the surrounding natural landscape and evening ambiance.

4.99 out of 5 average rating, 105 reviews

Wildwood Tiny Home Escape with Wood Fired Sauna

Welcome to an absolutely unique converted shipping container – Wildwood Tiny Home! This converted shipping container has a big personality! If you and your guests are looking for luxury, nature, peace, serenity, and a chance to escape the city – this getaway is perfect for you! At Wildwood Tiny Home, you can fill your time with hanging out on your own private beach & waterfront dock, enjoying your firepit, beach volleyball, horseshoes, cornhole, badminton, board games, and many more!

4.93 out of 5 average rating, 135 reviews

A modern living area is presented with two light grey sofas facing a glass coffee table, which rests on a decorative rug featuring shades of blue and neutral tones. Natural light enters through two windows, highlighting the stylish wall decor.

Apartment in Shelburne

L&S Comfy Suite

Beautiful inviting space for families as well as individuals. Brand New Fully renovated area with lots of amenities for the whole family. 2 Great size bedroom with queen size beds. Jack And Jill full washroom with an amazing shower that boast body jets. Comes with all the bells and whistles. Open concept with Living room, Dining room, Full Kitchen, Washer and Dryer, free parking, work area ideal for remote work, and lots more…. NO UNREGISTERED GUESTS ARE ALLOWED AS PER HOUSE RULES.

4.97 out of 5 average rating, 379 reviews

The modern tiny home features a black exterior and a large glass front, allowing natural light to illuminate the interior. A simple outdoor seating area with two chairs is visible, surrounded by lush greenery and trees, creating a connection with the serene natural surroundings.

Tiny home in Arthur

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

4.9 out of 5 average rating, 513 reviews

An inviting outdoor space features a wooden pergola with string lights, surrounding a dining table and seating area. A private hot tub is positioned nearby, with lush greenery and vibrant flower arrangements enhancing the serene environment.

Cabin in Erin

Cabin stay and play! 10 mins to Canadian Open!

Take it easy at this unique and tranquil getaway. Located steps from Calerin Golf Course (350 m) and includes many amenities, such as: a BBQ, patio w/ dining area, private hot tub, acres of groomed trails, games galore, pool table, fire pit, comfy queen bed w/ separate heated bunkie with a second queen bed and more! Optional pull out available, please inquire within (fee may apply). 2 km or 5 mins, from the picturesque town of Erin. Lots of restaurants, shops, and plenty to do!

4.98 out of 5 average rating, 164 reviews

A spacious living area features a blue sofa with a light throw, positioned beside a circular coffee table. Wall art adorns the white walls, and natural light filters through a decorative window. A white cabinet and a small plant complete the cozy atmosphere.

Loft in Mono

Hockley Haven

Kick back and relax in this calm, stylish space. Cozy 1 bedroom carriage house loft (appx 650 sq ft) above detached 3 bay garage in serene country setting on 5 acres of pine and cedar with a river running thru it. Pullout couch can accommodate 2 additional people. Walk across the road to Pollinator Garden & Island Lake Trails. 6 min drive to Hockley Valley Resort and Adamo Estate Winery, as well as beautiful downtown Orangeville boasting fabulous restaurants and quaint shops.

4.95 out of 5 average rating, 235 reviews

The spacious bedroom features a king bed with a striped blanket and a decorative area rug. Large windows allow natural light, which brightens the neutral walls. French doors lead to an outdoor area, complemented by a seating arrangement and a wooden furniture set.

Place to stay in Mono

Rural Estate Coach House Apartment

Peaceful secluded guest house in forest property 5 minutes from Orangeville. We have three active dogs who often demand attention! Can be arranged as a two bedroom with privacy or a one bedroom with extra room. King bed in the large bedroom. Double futon in the sitting room. Fabulous bathroom with views. The guest house is 70 feet from main house. Quiet, nice forest walks. NOT a 'corporate Airbnb' - managed by owner. Near Bruce Trail and Hockley.

Guest suite in Orangeville

A cozy living area features a light-colored sofa with decorative cushions, a coffee table, and a wall-mounted television. A slim electric fireplace is situated beneath the TV. To the rear, a fully equipped kitchen can be seen, enhancing the space's functionality.

5 out of 5 average rating, 195 reviews

Garden Studio Apartment

Enjoy a stylish experience at this centrally located place. Newly renovated 1 bdrm walkout apartment located in our home in downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Enjoy evenings on your own patio in a private backyard overlooking the garden. Enjoy walks on the Island lake Conservation Park.. Dine at any of the many fine restaurants or cook at meal in your own fully equipped kitchen.

4.99 out of 5 average rating, 145 reviews

A private detached apartment is visible nestled among tall trees and lush greenery. The wooden exterior of the structure blends harmoniously with the natural surroundings. A pathway leads towards the entrance, framed by a vibrant landscape of ferns and colorful shrubs.

Guest suite in Caledon

Casa Caledon-Secluded Suite Surrounded by Nature

Take it easy at this unique and tranquil getaway on 3 acres of land The suite is close to conservation areas Cheltenham Badlands, Fork of the Credit and Terra Cotta Bruce trail, golf courses, restaurants, bakeries, butchers, farm produce and city needs are close Each season is wonderful Spring/summer has lush forests, the pond and fire pit Fall walks with the beautiful colours Winter has a white blanket and access to winter sports

Popular amenities for Orangeville outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.94 out of 5 average rating, 524 reviews

Two light blue chairs are positioned near a tranquil lake, with a bottle of wine and a glass resting on a wooden table. A sign displaying 'LIVE THE LIFE YOU'VE IMAGINED' is set upright on the ground, surrounded by greenery and soft grass.

Home in Cambridge

Shades Mill Lake - Unit 1 of 2. 3rd Bed available.

4.99 out of 5 average rating, 171 reviews

The exterior of a log house is presented, showcasing a large balcony with flower boxes and a well-maintained garden featuring a pond. Lush greenery surrounds the property, complemented by a paved driveway and a striking wooden design that enhances its rustic charm.

Home in West Montrose

Austrian Log house

4.93 out of 5 average rating, 165 reviews

An open concept game room features a polished pool table at the center, with a bar area equipped with stools to one side. Large windows allow natural light to fill the space, while a mounted TV and comfortable sectional couch create an inviting entertainment area.

Home in Badjeros

JJ’s small town country retreat

4.95 out of 5 average rating, 298 reviews

The exterior of a charming stone cottage is showcased, featuring a sloped roof and a welcoming front entrance. Lush greenery and flowering shrubs enhance the garden area, while a decorative street lamp stands next to the path leading to the cottage.

Home in Elora

Nolahouse Charming Bungalow in the Heart of Elora

4.99 out of 5 average rating, 204 reviews

A modern living area features a sleek brown leather couch with decorative pillows, positioned across from a dark wooden coffee table. Bright natural light enters through large bay windows, complemented by light-filtering curtains. A decorative wall map and a large green plant add character to the space.

Home in York

Welcome to Greenhills, a Charming Home w/ Parking

4.98 out of 5 average rating, 165 reviews

A modern home with a striking design features large reflective windows and a mix of black and stone exterior elements. A driveway leads to a garage, with a sleek car parked nearby. The front lawn is well-maintained, bordered by a sidewalk and trees.

Home in Islington

Basement Apartment - New Build!

4.97 out of 5 average rating, 178 reviews

A stylish living room is presented, featuring a neutral color palette, comfortable seating, and modern decor. A large window allows natural light to fill the space, while a flat-screen TV is mounted on a textured wood panel. Decorative accents include a coffee table adorned with books and a floral arrangement.

Home in Elora

Limestone I ...A unique experience downtown Elora.

5 out of 5 average rating, 108 reviews

A vintage schoolhouse stands in the background, showcasing its distinctive architecture and large windows. In the foreground, a well-crafted bike rack holds several bicycles under a shaded canopy, surrounded by autumn foliage and a gravel pathway.

Home in New Hamburg

The Heart of New Hamburg - Picturesque Modern Home

Apartment rentals with outdoor seating

4.93 out of 5 average rating, 263 reviews

The exterior of the home is shown, featuring a welcoming entrance with a covered porch. Lush greenery surrounds the property, and a paved driveway leads to a garage. A sign reading 'WELCOME' is prominently displayed above, adding to the inviting atmosphere.

Apartment in Guelph

Cozy and comfortable 1 Bedroom Apartment Guelph

4.95 out of 5 average rating, 518 reviews

A corner of the living room showcases a 55” 4K smart TV mounted on the wall above a stylish fireplace. A comfortable rocking chair with a 'welcome' sign is placed beside a vibrant artwork featuring flowers. A wooden coffee table and decorative items add character to the space.

Apartment in Elora

Devin's Dream

4.95 out of 5 average rating, 110 reviews

A sunset over the water is portrayed, with a golden sun reflecting on the calm surface. The horizon features a silhouette of trees, creating a serene atmosphere. Soft waves ripple gently in the foreground, enhancing the tranquil setting.

Apartment in Toronto

Toronto Island Wonderland View

4.98 out of 5 average rating, 158 reviews

A cozy living area features a light grey sofa and a plush dark blue chair, arranged around a small white TV stand facing a flat screen television. A decorative rug covers the floor, and a dining table with two chairs is positioned nearby, complemented by a vase of flowers.

Apartment in Oakville

Bright, Spacious, Quiet 2 bedroom - Licensed

4.99 out of 5 average rating, 291 reviews

An open-concept living area features a modern kitchen with white cabinetry and stainless steel appliances. A dark blue accent wall highlights a television mounted above a wooden console. A circular marble coffee table is placed in front of a comfortable seating area with a sofa.

Apartment in Elora

The Evelyn Suites - Suite B - Small Pied-à-Terre

4.93 out of 5 average rating, 240 reviews

The exterior of a light-colored home is visible among tall trees, featuring large screened porch windows that invite natural light. A path lined with greenery leads to the entrance, enhancing the sense of seclusion near the Grand River.

Apartment in Fergus

Riverside Retreat

4.95 out of 5 average rating, 195 reviews

A welcoming porch features a blue exterior with white trim, adorned by potted plants and lush greenery. Rocking chairs are positioned on the porch, providing a comfortable space to relax. The pathway is lined with stones, leading from the driveway to the entrance.

Apartment in Ariss

Rural Retreat, near to Elora

4.89 out of 5 average rating, 122 reviews

A modern living space features a comfortable couch positioned in front of a wall-mounted television. A dining area with sleek white chairs is visible, along with a cozy bed beyond a sliding door. Natural light is softly illuminated by recessed lighting.

Apartment in Barrie

The Chieftain Suite

Condo rentals with outdoor seating

4.98 out of 5 average rating, 101 reviews

Stunning 1BR w Pool ~ Free Parking & Self Check-In

5 out of 5 average rating, 132 reviews

A bright and airy living space features large corner windows that offer expansive views of the city. A modern sectional couch is paired with a light rug, while a flat-screen television is mounted on the wall. Lush green plants add a touch of nature to the inviting décor.

Condo in Yorkdale

The Penty: Luxurious Penthouse with Pool, Hot Tub

4.84 out of 5 average rating, 627 reviews

A serene sleeping area features a king-sized bed with layered bedding, including pillows and a textured throw. A forest-themed mural enhances the atmosphere, while soft lighting illuminates the room. A contrasting dark wall adds depth, and a closet space is visible in the corner.

Condo in Elora

(E) Elora Riverside Nook

4.98 out of 5 average rating, 123 reviews

A modern living area features a spacious, cozy sectional sofa with decorative pillows. A large window offers views of the city skyline and access to a balcony adorned with patio furniture. Natural light fills the room, complementing the contemporary decor and wooden flooring.

Condo in Liberty Village

Central condo in heart of Liberty Village +parking

4.93 out of 5 average rating, 178 reviews

A spacious living area is furnished with a comfortable sectional sofa and a coffee table, complemented by an area rug. Natural light floods in from a large window, illuminating the modern kitchen with wood cabinetry and bar seating in the background.

Condo in Elora

Riverview...A Gorgeous Condo on the Grand

4.95 out of 5 average rating, 501 reviews

Lovely Open Concept Friday Harbor Resort Condo

A modern living area is presented, featuring a pull-out couch draped with a light gray blanket. A glass-top coffee table is centered on a striped rug. Adjacent, a sleek entertainment unit is visible with a large television. Natural light is filtered through sheer curtains.

4.87 out of 5 average rating, 324 reviews

Resort Condo in Friday Harbour

An open living area features a deep green sofa, a round coffee table, and a warm rug on light wood flooring. Natural light floods through large glass doors adorned with teal curtains, framed by plants and decorative wall art, creating a cozy and vibrant atmosphere.