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Vacation rentals with a pool in Woolwich

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Woolwich

  • Total vacation rentals

    Explore 60 vacation rentals in Woolwich

  • Nightly prices starting at

    Woolwich vacation rentals start at R 162 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 1,980 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Woolwich vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Woolwich rentals

  • 4.8 Average rating

    Woolwich stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Woolwich

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
Guest suite in Elora-Salem

Private Basement Suite with Heated Pool Near Elora

Welcome to The Salem Hideaway, a private basement suite nestled among the trees in the quiet village of Salem, just minutes from historic Elora. Enjoy your own private entrance, heated pool, fire pit, and peaceful surroundings. We live upstairs, so you may occasionally hear normal household sounds, but we do our best to keep things quiet and ensure you have a relaxing stay. m Minutes from downtown Elora, you’ll be close to shops, restaurants, hiking trails, and everything the area has to offer

4.98 out of 5 average rating, 48 reviews
Top guest favorite
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.

4.95 out of 5 average rating, 213 reviews
Superhost
A serene view of the villa is captured from the edge of the natural spring-fed pond, showcasing its spacious, multi-level design. Surrounding greenery, including trees and landscaped gardens, adds to the tranquility of the setting. Fluffy clouds drift across a bright blue sky.
Villa in Cambridge

Luxury Villa for Accommodation

★★★ SUPERHOST for 6+ years ★★★ Escape to this stunning, secluded villa for exquisite accommodation or hosting memorable events. ✔ Secluded villa on 8.8-acre lot ✔ Private 17 ft deep natural spring-fed pond + hot tub ✔ 4000 sqft living space ✔ Full access ✔ 4 bedrooms, 7 beds ✔ High-end finishes: Offers comfort & elegance. ✔ BBQ ✔ Next to Whistle Bear Golf Club & Langdon Hall (Relais & Châteaux, 5 Diamond dining), Cambridge Mill, walking trails, scenic Blair Creek. ✔ 401 easy access

4.88 out of 5 average rating, 132 reviews
Guest favorite
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

Come escape to the country! This beautifully villa offers a memorable STAYCATION! Step into this stylishly designed oasis and feel yourself unwind. The open concept villa with king bed, sitting area, fireplace and full kitchen seamlessly flows into the outdoor space, where you’ll find plenty of room to unwind and dine al fresco. The private pool is yours to enjoy. Enjoy morning coffee, soak up some rays and as the sun sets, enjoy the propane fire pit for a cozy evening. Minutes away from Elora

4.85 out of 5 average rating, 41 reviews
Top guest favorite
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

4.99 out of 5 average rating, 113 reviews
Superhost
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.

4.87 out of 5 average rating, 111 reviews
Top guest favorite
A vibrant, triangular-shaped house is surrounded by greenery, reflecting in a clear, inviting swimming pool. A shaded seating area with lounge chairs can be seen beside the pool, and large glass doors allow natural light to fill the interior space.
Home in Elora-Salem

Riverside Retreat w Hot Tub, Pool & Sauna in Elora

Are you looking for a Fall Getaway in Elora? Althea Crystal Retreat, located in picturesque Elora, Ontario, has everything you need. For this September 2026: Get 4 nights at 20% off Unwind in one of our unique crystal rooms. Relax by the hot tub, and warm up in the sauna and by the indoor or outdoor fireplace. Go swimming in the beautiful heated pool (closes end of September). Get cozy by our fireplace while you watch TV. Look out to the breathtaking views of the river nearby.

4.97 out of 5 average rating, 35 reviews
Top guest favorite
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

Escape from the noise of the city and relax at our charming, home-away-from home. We are located in Blair (minutes from the 401, Langdon Hall, Roseville Estates, WhistleBear Golf Course and the Gaslight District; just to name a few). You can relax in the beautiful heated pool and welcome to enjoy any of the other outdoor spaces. At night you can cozy up by either of the wood-burning fireplaces, watch tv, listen to music or just chill. Coach House also included in price.

5.0 out of 5 average rating, 28 reviews
Top guest favorite
Guest suite in Kitchener

The Oasis

Enjoy the bright, spacious, and homey cottage vibes with a fully private saltwater pool, hot tub, luscious green yard, fire pit area, and several walking trails out the back gate. Retreat to the spacious walk out basement suite with 70” TV home theater, elliptical trainer, desk space and plenty of windows open to the forest view behind the house. Beautiful Doon neighbourhood within minutes of the 401. Plenty of shopping and eating choices within a few minutes drive.

4.97 out of 5 average rating, 147 reviews
Guest favorite
The exterior of a two-story house showcases a blend of stone and dark wood siding, with a spacious deck accessible from the upper floor. Lush green grass and neatly arranged flower beds surround the home, while a gray sky sets a calm backdrop.
Home in Alton

Cozy Country Spring Getaway | HotTub + Fire Pit

Escape to the countryside this spring 🌸 Unwind in the hot tub or pool, enjoy cozy fires under the stars, and soak in the peaceful charm of Alton. Perfect for a relaxing getaway, girls weekend, or 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

4.96 out of 5 average rating, 130 reviews
Top guest favorite
Guesthouse in Breslau

House on the Hill

What makes The House unique? How about: - a year-round heated indoor pool & sauna - private 2-bedroom + loft guesthouse with private entrance - fully-equipped kitchen - homey living area with electric fireplace - 27 gorgeous acres with 2 ponds - private patio & BBQ There's so much more! Come join your hosts Frances & Rod and experience a country retreat in the middle of the city... all this within 5km to Waterloo Int'nl Airport & 15 min to tri-cities & 401.

4.97 out of 5 average rating, 225 reviews
Guest favorite
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.
Condo in Kitchener

Resort Condo with Bowling and Spa Hot Tub

Stunning 2BR/2BA corner suite in the heart of Kitchener, directly across from Google Kitchener Downtown. Enjoy city views, a fully equipped space for up to 7 guests, and amazing amenities like a hot tub, bowling alley, sauna, rooftop patio & gym. Includes free parking. This fully licensed Airbnb offers a seamless, worry-free stay in a vibrant, walkable neighborhood with easy access to the LRT and GO Station.

4.92 out of 5 average rating, 150 reviews

Popular amenities for Woolwich rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
A spacious living area features a stone fireplace with a wooden mantel as its focal point. Comfortable seating, including a sectional sofa and armchairs, surrounds a glass coffee table. Natural light filters through large windows, complemented by warm wooden accents on the ceiling.
Home in Kitchener

Chalet by hiking trail and ski hill

4.93 out of 5 average rating, 81 reviews
Superhost
Home in Erin

Indoor Pool • Hot Tub • Heated Dome • 40 min GTA

4.75 out of 5 average rating, 32 reviews
Top guest favorite
Home in Hamilton

City Meets Forest Year Round Tree House Retreat

5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Cheltenham

Indoor Pool & Hot Tub Villa | Sleeps 14

4.95 out of 5 average rating, 22 reviews
Top guest favorite
A private backyard is showcased, featuring a heated saltwater pool with inviting blue water. A shaded seating area is set under a large umbrella, surrounded by lush greenery and vibrant yellow flowers. The exterior wall of the home is adorned with light-colored siding, complementing the tranquil setting.
Home in Hamilton

The Bayfront - Harbour Views + Private Pool!

4.91 out of 5 average rating, 81 reviews
Guest favorite
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.
Home in Elora-Salem

Estate, Secluded On the Grand River.

4.92 out of 5 average rating, 102 reviews
Guest favorite
A sparkling pool reflects the blue sky, surrounded by lush greenery and colorful flowers. A potted plant with vibrant pink blooms sits in the foreground, adding a touch of color to the tranquil outdoor space.
Home in Waterloo

Retreat with Luxury in this 4-bed, 4-bath home

5.0 out of 5 average rating, 5 reviews
Home in Saint Clements

St. Clement’s Vacation AIR BnB

4.67 out of 5 average rating, 24 reviews

Condo rentals with a pool

Guest favorite
A modern living area showcases a dark sectional sofa, complemented by a round coffee table atop a light rug. Large glass doors provide access to a balcony, while a television stands on a white media console adorned with decorative items and potted plants.
Condo in Kitchener

Lux Condo by Downtown Kitchener

4.88 out of 5 average rating, 43 reviews
Superhost
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

4.88 out of 5 average rating, 42 reviews
Guest favorite
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.
Condo in Kitchener

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

4.88 out of 5 average rating, 34 reviews
Condo in Kitchener

LuxCondo in the downtown kitchener uptown waterloo

4.85 out of 5 average rating, 34 reviews
Condo in Kitchener

City Views | Pool, Gym, Bowling, Games Room & More

4.75 out of 5 average rating, 12 reviews
Condo in Kitchener

Luxe Suite With Home Cinema - Gym, Bowling, Pool

4.69 out of 5 average rating, 59 reviewsA 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.
Condo in Kitchener

*Modern* 1 Bed Condo Station Park

4.7 out of 5 average rating, 47 reviews
Condo in Kitchener

@ Kitchener ON | 1 bed 1 bath | 5 * Condo apt !

New place to stay

Other vacation rentals with a pool

Top guest favorite
A stone farmhouse is set against a clear blue sky, with a saltwater pool in the foreground. The pool area is bordered by lush greenery and features lounge chairs arranged on a flagstone patio. The reflection of the house is visible on the pool's surface.
Farm stay in Guelph/Eramosa

Luxe B&B - Pool, Firepit, Hot Tub & Farm Animals

4.98 out of 5 average rating, 83 reviews
Guest favorite
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

4.97 out of 5 average rating, 36 reviews
Guest favorite
Apartment in Kitchener

City Views at Station Park + Swim Spa + Hot Tub

4.89 out of 5 average rating, 9 reviews
Guest favorite
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”

4.85 out of 5 average rating, 20 reviews
Guest favorite
Guesthouse in Cambridge

Historic Blair Road Coach House and Terrace Suite

5.0 out of 5 average rating, 11 reviews
Guest favorite
Guesthouse in New Dundee

Stunning Loft with Pool & Fire Pit

5.0 out of 5 average rating, 36 reviews
Guest favorite
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

4.87 out of 5 average rating, 95 reviews
Guest favorite
The living area features a modern sofa with colorful accent pillows, a glass coffee table, and a flat-screen TV. A dining table is positioned by the large floor-to-ceiling windows, which provide ample natural light and showcase vibrant city views.
Apartment in Kitchener

High Rise 1BR Building with Gorgeous Views

4.86 out of 5 average rating, 64 reviews

When is the best time to visit Woolwich?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 1,326 ZARR 1,342 ZARR 1,488 ZARR 1,471 ZARR 1,471 ZARR 1,488 ZARR 1,391 ZARR 1,471 ZARR 1,358 ZARR 1,423 ZARR 1,245 ZARR 1,310 ZAR
Avg. temp-5°C-5°C0°C7°C13°C19°C21°C20°C16°C10°C4°C-2°C

Destinations to explore