Holiday rentals with a pool in Woolwich

4.84 out of 5 average rating, 147 reviews

A private backyard space features a swimming pool with steps leading in. Comfortable lounge chairs sit nearby on the concrete patio, while vibrant green trees and a well-maintained lawn surround the area. A shaded seating area can be seen in the background.

Home in Waterloo

Entire Guest Unit+Free Parking by Glenbridge Plaza

Located in a prime location in Waterloo, one of the most desirable safe and quiet neighborhoods of Lincoln Heights, this unique place perfectly blends privacy and comfort. Just minutes away from University of Waterloo, Wilfrid Laurier University, Conestoga College, highways (7/8),2 minute walk to Glenbridge Plaza, Zehrs Market (Grocery), CIBC Bank, A&W, Canadian Pizza, pharmacies, etc. It is an 8-minute drive to the St. Jacobs Farmers Market and only a 5-minute drive fromWalmart.Busstop is here

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.

4.92 out of 5 average rating, 819 reviews

HotTub & Cozy Fireplace - Headwaters Retreat

Escape to our rustic-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!

4.95 out of 5 average rating, 186 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

A peaceful , rural, retreat in Ariss. Hot tub, great bird watching. Well situated between Elora, Fergus, St Jacobs and Guelph. Visit Cox Creek Winery, Kissing Bridge, G2G & Cotton Tail hiking/biking trail, snowshoeing, snowmobile trails & Chicopee Ski Resort. Two dogs on the property. Walkout basement, king bed, portable crib (on request) shower, kitchenette, seating area, natural light. Large backyard, firepit, barbeque, outdoor eating area. Keyless, separate, private entry, free parking.

4.99 out of 5 average rating, 97 reviews

Apartment in Waterloo

Charming Hideaway: 1-bedroom Apartment

Whether you’re in town for sports, work, or family, you'll love how the apartment is: Fully Furnished: from kitchen to bedroom, we’ve got you covered. Cozy: Gas fireplace and a queen air mattress for extra guests. Private Entrance: Your own smart lock access. Outdoor Space: Your own private deck with a BBQ. Heated Pool: SHARED pool available mid May to September. Entertainment: Stay connected with WIFI and enjoy Netflix, Prime, and Disney on the Smart Parking: No worries about finding a spot

4.97 out of 5 average rating, 103 reviews

Five alpacas are seen walking across a grassy area in front of a large, restored barn. The barn features a dark roof and wooden siding, with a door visible on the lower level. A clear blue sky and scattered clouds provide a bright backdrop.

Farm stay in Caledonia

Alpaca farm stay and bunkie getaway.

A farm stay on your way to soaking up all that our county has to offer. The bunkie is located next to a restored century barn and an outdoor pool. The property is home to 5 alpacas, mini goats, chickens and our family dog. The bunkie is on a shared property with our home. It's 1 hour from Toronto, 20 minutes from Hamilton, 1-hour from Niagara-on-the-lake and 10 minutes from the historic Ancaster village. Antiquing, hiking, nature tours, golfing, wine tours, farmers markets and more close by.

4.9 out of 5 average rating, 100 reviews

A spacious living room is highlighted by tall wooden ceilings and large windows that invite ample natural light. Two comfortable sofas face each other over a coffee table, with a patterned area rug underfoot. A small fireplace and colorful stained glass add character to the warm design.

Barn in Milton

Five Star Hayloft Suite

This open space home is in the top level of a century-old bank barn. Witness the beautiful architecture while enjoying modern amenities like an open-concept kitchen, projector & movie lounge, and more! Enjoy 180 degree views from the bay window in the living room during your stay. Five Star Ranch offers a year-round getaway in a beautiful country setting. Situated on a working farm, and surrounded by gardens, animals and beautiful forest, it is a perfect destination for seclusion and peace.

The living area features modern furniture with a blue sofa and a wooden coffee table. A piece of wall art depicting floral arrangements is displayed above the sofa. Large windows allow ample natural light and showcase city views.

4.94 out of 5 average rating, 126 reviews

Hydropool Spa HotTub/Bowling Alley/Patio/BBQ/Games

**Hydro spa hot tubs are open! **Fully licensed Airbnb - no hassle during your stay! **Stunning Interior decor, guests'' unique experience **Unmatched amenities in town! you must check out the amenities' pictures **Corner unit with stunning city views ** Location! Heart of Kitchener, centrally located to grocery stores, hip restaurants/bars, cute local shops, parks & happening city life ** 3 mins walk GO Station. 126 Weber St. W **Across Goo-gle Head office w/ LRT rail at doorsteps

4.97 out of 5 average rating, 112 reviews

Home in Alton

Cozy Cabin Vibes - Hot Tub• Firepit• Snowy Retreat

Escape to our riverside cabin this winter—soak in the hot tub under falling snow, curl up by the fire, and enjoy cozy evenings surrounded by nature. Perfect for couples, families, a ski weekend away, girls’ weekends, or a quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

5 out of 5 average rating, 13 reviews

A covered outdoor space is framed by greenery, featuring comfortable seating areas with floral cushions. A wooden deck leads to a hot tub, surrounded by plants. A sign reading 'GARDEN' is visible on the steps, enhancing the inviting atmosphere.

Apartment in Kitchener

The little resort II. “ the hideaway”

It’s a unique space , perfect to work anywhere in tri-cities close to st jacobs and Elora. The lower floor is cozy. It’s has its own entrance .. Feels like home. Lots of character. Covered patios to bbq. ID required with photo Perfect to visit the area and enjoy the grand river. we only use thieves natural cleaning products,and no scents on sheets,towels A deposit is required if not a previous bnb guest. Private areas to chill. Toilet paper to get started and coffee,tea and cream.

4.96 out of 5 average rating, 46 reviews

A modern living area features a white media console with a speaker and decorative elements, accompanied by a flat-screen TV displaying the word 'WELCOME.' Natural light enhances the space, while a potted plant is nestled in a woven basket beside the console.

Apartment in Kitchener

21st- floor Luxury & City Views

Welcome to your Sky-High Escape. Located on the 21st floor in the Heart of Kitchener Waterloo. This stylish 1-Bedroom Condo offers stunning views, a comfy Queen sized bed, a full Kitchen with State of the Art appliances , high speed internet, and a smart tv with access to the following subscriptions ; Netflix, Amazon Prime, Disney+ and Crave. The Building Amenities include a Gym, Pool, Lounge area and terrace with BBQ. Whether you're here for work or play, you're right at home.

A modern living area features a sleek kitchen with stainless steel appliances, a stylish couch, and a flat-screen TV mounted on the wall. Large glass doors open to a balcony, allowing natural light to fill the space. A small dining table is set for two beside the kitchen.

4.92 out of 5 average rating, 25 reviews

LuxCondo in the downtown kitchener uptown waterloo

Modern and Sophisticated 1+1 apartment in the heart of Kitchener Downtown and Uptown Waterloo. It features modern furniture, a fully equipped kitchen, and a balcony with stunning sunset views. Enjoy exclusive amenities like a bowling alley, spa, pool table, and hydro swimming pool. The apartment comfortably sleeps 3 with two cozy beds. Located steps from top bars and restaurants, this apartment offers a blend of luxury and convenience. Perfect for business or leisure stays.

Guest suite in Centre Wellington

A refreshing saltwater pool features an elegant waterfall edge, with water cascading gently into the pool below. Two lounge chairs are positioned under a bright umbrella, surrounded by lush greenery, providing a tranquil space for relaxation.

5 out of 5 average rating, 27 reviews

Cozy Private Suite with Year-Round Hot Tub

Welcome to The Salem Hideaway – your private, peaceful retreat tucked among the trees in the quiet village of Salem, just moments from historic Elora. Surrounded by forest and just steps from Irvin Creek, this cozy getaway is perfect for relaxing in nature. Enjoy the peaceful setting as you soak in the hot tub or swim in the pool, take a walk through the woods with a warm drink, or unwind by the fire pit while listening to the creek nearby. minutes from downtown Elora

Popular amenities for Woolwich rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Burlington

4.67 out of 5 average rating, 15 reviews

Beautiful 4 bed Retreat Between Niagra & Toronto

Home in Milton

Cottage Ambiance Private

4.83 out of 5 average rating, 36 reviews

Home in Hamilton

The Bayfront Flat - Harbour Views + Private Pool!

4.94 out of 5 average rating, 16 reviews

A charming brick exterior of a two-story home is surrounded by lush greenery and well-maintained landscaping. Two garages are visible, and a wide driveway leads to the front entrance. The setting features a clear blue sky and vibrant natural surroundings.

Home in Brantford

Brant Paradise. Where luxury meets country charm.

Home in Centre Wellington

The entrance of a renovated stone home is framed by lush greenery and colorful flower beds. A wide, paved pathway leads to the front door, flanked by stone steps, while large windows allow natural light to fill the interior, showcasing the property's unique architectural features.

4.93 out of 5 average rating, 96 reviews

Estate, Secluded On the Grand River.

4.96 out of 5 average rating, 25 reviews

Home in Elora

Riverside Retreat /w Hot Tub & Sauna in Elora

4.75 out of 5 average rating, 8 reviews

A serene backyard scene is depicted with a private swimming pool reflecting the colorful sunset sky. Comfortable lounge chairs are arranged around the pool area, surrounded by landscaped greenery and a grassy expanse, creating an inviting space for relaxation and gatherings.

Home in Kitchener

Luxurious Home | Hot Tub & Pool | Sleeps 8

5 out of 5 average rating, 21 reviews

A spacious outdoor area features a heated pool surrounded by a tiled deck. Comfortable seating is arranged under large umbrellas, alongside a dining set and a barbecue grill. Lush greenery and potted plants enhance the relaxing atmosphere of the space.

Home in Cambridge

Under the Whispering Pines

Condo rentals with a pool

5 out of 5 average rating, 17 reviews

A clear view of the inviting pool surface, featuring a textured pattern in calming shades of blue. The image conveys a welcoming atmosphere with a bright, reflective quality enhanced by the surrounding environment.

Condo in Waterloo

1BR+*TheKorner@Circa1877-One Bedroom+Suite

4.88 out of 5 average rating, 100 reviews

A modern kitchen is showcased with light wood cabinetry and white countertops. Stainless steel appliances are provided, including a built-in oven. Two stylish black stools are positioned at the island, inviting casual dining. Ambient lighting illuminates the workspace, enhancing functionality.

Condo in Waterloo

Cozy 1BR Condo w/ Insuite LDRY, Gym & Free Parking

A modern living area features a cozy armchair and a small dining table beside large glass doors that lead to a balcony. Natural light fills the space, highlighting the subtle color palette. A flat-screen TV is mounted on the wall, and greenery adds a touch of freshness.

4.92 out of 5 average rating, 13 reviews

City Views & Private Balcony | Gym, Pool & More!

Condo in Corktown

Hamilton condo, 1 hour to Toronto or Niagara Falls

A bright living area features a modern sofa and a wooden coffee table atop a soft rug. Floor-to-ceiling windows invite natural light and provide access to a private balcony. A large flat-screen TV is mounted on the wall, complemented by decorative plants.

4.79 out of 5 average rating, 19 reviews

Bright & Modern Downtown Stay w/ Pool & Gym

A spacious living area features a large, comfortable L-shaped couch complemented by decorative cushions. A 68" HD Smart TV is mounted on the wall, and expansive floor-to-ceiling windows provide a bright view of downtown Kitchener, enhancing the room's airy feel.

4.83 out of 5 average rating, 30 reviews

Highrise King Condo With Home Cinema -Free Parking

4.92 out of 5 average rating, 36 reviews

A stylish living area is presented with a green sofa and two textured chairs surrounding a light wood coffee table. A large television is mounted on the wall, and vibrant tropical wallpaper adds a splash of color. Ample natural light enters through two large windows.

Condo in Waterloo

The Laundry Rooms, Waterloo - Two Bedroom Suite

A modern open-concept space features a well-equipped kitchen on the left and a cozy seating area with a sofa and television. Large glass doors lead to a private balcony, allowing natural light to fill the room. Light wood flooring adds warmth to the environment.

4.72 out of 5 average rating, 36 reviews

*Modern* 1 Bed Condo Station Park

Other holiday rentals with a pool

An aerial view of the cottage showcases its spacious layout amidst lush greenery along the waterfront. The surrounding trees provide a natural habitat, and features such as multiple patios and a fire pit are visible, creating an inviting outdoor space.

Cabin in Fergus

4.85 out of 5 average rating, 132 reviews

Luxury Oasis!! Heated Pool☆Sauna ☆Hot tub☆4Patios

Apartment in Milton

5 out of 5 average rating, 3 reviews

Stunning 2 bedroom condo in Milton near Hwy 401

4.96 out of 5 average rating, 24 reviews

The historic farmhouse is set against a backdrop of lush greenery and flowering plants. The white exterior features traditional architecture, including multiple windows and a gabled roof. A vibrant sky with scattered clouds complements the serene outdoor setting.

Farm stay in Milton

Rustic Farmhouse w/ pool, tennis court on 100 Acre

4.87 out of 5 average rating, 30 reviews

A spacious farmhouse with a stone exterior is surrounded by greenery. A large deck extends from the house, with a hot tub situated below it. A tall tree stands in the foreground, partially obscuring the view of the property.

Farm stay in Puslinch

KJ's Farmhouse w/SwimSpa Retreat

A charming stone cottage is surrounded by lush greenery, with a sloped lawn leading to a welcoming front porch. The structure features a red front door and large windows, framed by well-kept shrubs and trees, creating a serene outdoor environment.

Cottage in Woodstock

4.76 out of 5 average rating, 63 reviews

Stone Cottage in the heart of Dairy Country

4.93 out of 5 average rating, 42 reviews

A clear view of a private heated pool is presented, surrounded by a green patio. A striped chair and glass table are visible in the foreground, with a blue waterslide and shaded seating area observed in the background.

Bungalow in Milton

Milton Home- a Family Oasis