Holiday rentals with a pool in Woolwich

4.85 out of 5 average rating, 138 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

4.91 out of 5 average rating, 107 reviews

A spacious living area is highlighted by a light-colored sectional couch, complemented by decorative cushions. A coffee table with a sailboat decor piece sits in the center. The open layout connects to a modern kitchen, featuring sleek appliances and bright lighting.

Home in Hamilton Beach

The Nautical Nook | Luxury Beach House

Welcome to "The Nautical Nook" - where luxury meets comfort. Indulge in our spacious and majestic 5-BR house, just steps from the beach. Enjoy 2 Cali king beds + 3 queen beds, 2 large comfy couches, games, 2 workstations, wifi and EV Charger. Explore our massive & majestic 16k sq ft private backyard paradise. The house also includes private seperate entrance walkout units. Enjoy 2 kitchens, 2 living areas, laundry etc. Close to restaurants, trails, activities and more. A great fit for all guests

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, 807 reviews

Cozy Hot Tub & 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, 183 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, 95 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, 102 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.

4.95 out of 5 average rating, 328 reviews

A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.

Cabin in Mono

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

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, 121 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, 111 reviews

Home in Alton

Stylish 3BR | Hot Tub • Firepit • Cozy Fall Escape

Welcome to your relaxing escape in the heart of Alton—a cheerful and spacious 3-bedroom, 1.5-bathroom home backing onto the beautiful Credit River. Perfect for families, friend groups, wedding guests, or anyone craving peace, nature, and comfort. • 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

4.95 out of 5 average rating, 39 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.

4.91 out of 5 average rating, 279 reviews

An open Great Room features a black leather sofa and a coffee table positioned on a textured area rug. Large windows allow natural light, and a decorative plant trails along the wall. Dining chairs surround a circular table, complementing the inviting layout.

Home in Cambridge

Spacious Bungalow Guest House

Welcome to our stylish, modern, guest house nestled in a private country setting. Enjoy all of the updated conveniences while experiencing rustic surroundings. Peaceful and stress free for the whole family. Located minutes to the City of Cambridge. Note: The pool is outdoor and is generally open by Victoria Day weekend (3rd weekend in May) until Labour Day weekend (last weekend in August), but if it is warm earlier or later we may extend that by a few weeks. Please inquire.

Popular amenities for Woolwich rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 19 reviews

An open-concept kitchen and living area features light hardwood flooring and contemporary furnishings. A white leather sofa complements a wooden coffee table, while a large kitchen island with bar stools is highlighted. A dining table accommodates six, and colorful tile accents add character to the space.

Home in Burlington

Modern Luxury House w/EV Charger & Heated Pool

4.85 out of 5 average rating, 27 reviews

A spacious living area showcases a large gray sectional sofa adorned with yellow and patterned cushions. A round coffee table sits at the center, complemented by an accent table. Bright stained glass windows and indoor plants enhance the room's charm, while a blend of antique and modern decor is visible.

Home in Caledonia

Unique Old Church House

Home in Aldershot Central

The indoor pool area is illuminated by natural light from skylights and large windows. A landscaped view can be seen outside, enhancing the serene atmosphere. An HD TV is mounted on the wall, while comfortable seating is arranged beside the pool, creating a cozy environment.

4.75 out of 5 average rating, 65 reviews

Four seasons Pool Retreat near downtown!

4.82 out of 5 average rating, 34 reviews

Home in Hamilton

The Bayfront Flat - Harbour Views + Private Pool!

4.77 out of 5 average rating, 31 reviews

An outdoor area is visible with a private pool surrounded by a spacious patio. Red seating is arranged near the pool, along with a shaded area under an umbrella. The cottage, characterized by a combination of brick and wood siding, is set against a backdrop of lush trees.

Home in Orangeville

Private cottage heated pool/HotTub/Games 20 Acre

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.

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

Condo rentals with a pool

The living area features a modern design with a blue sofa, two soft armchairs, and a coffee table. A desk is positioned nearby, and a large artwork adds a touch of color to the wall. Natural light streams through the glass doors leading to a balcony.

4.64 out of 5 average rating, 36 reviews

Perfectly Located in Kitchener

Condo in Burlington

Cozy Space

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.

4.91 out of 5 average rating, 11 reviews

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

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.

4.78 out of 5 average rating, 18 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.

4.84 out of 5 average rating, 25 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

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

4.86 out of 5 average rating, 29 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

4.77 out of 5 average rating, 91 reviews

The image displays an open-plan living area equipped with a modern kitchen on one side and a dining table with four chairs on the other. A plush sofa sits in the center, complemented by a chic coffee table, creating a warm and inviting space for relaxation.

Apartment in Balfour

Hamilton Haven | Tempurpedic Bed, Porch + Smart TV

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

5 out of 5 average rating, 55 reviews

A light-filled living area features a spacious grey sectional sofa positioned on a cozy white rug. An orange wooden coffee table adds a pop of color, while built-in shelves display books and decorative items. The open design provides a view into the adjacent kitchen and dining space.

Bungalow in Orangeville

Stunning Family Retreat, 1hr from TO, Sleeps 15

4.83 out of 5 average rating, 24 reviews

A private pool is framed by a spacious patio and surrounded by well-maintained greenery. The villa stands nearby, featuring large windows that overlook the serene outdoor area. A natural stone sits on the patio, adding to the tranquil ambiance.

Guesthouse in Fergus

Country Villa Fergus Elora

Apartment in Guelph-Eramosa

A historic stone house stands amidst lush greenery, featuring large, deep windows and a welcoming entryway framed by vibrant flower pots. The architectural details, including decorative cornices and a pitched roof, highlight its charming character in a serene outdoor setting.

4.94 out of 5 average rating, 16 reviews

Private 2-bed Apt in Gorgeous Historic Home w/pool