Vacation rentals with a pool in Woolwich

Find and book unique homes with a pool on Airbnb

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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Superhost

Home in Aldershot

4.85 out of 5 average rating, 40 reviews

Four seasons Pool Retreat

6 bedrooms, 4 washrooms, pool, large, kitchen and family room. Mins from lake, restaurants, shopping, bars, cafes and so much more. Central, yet quiet neighbourhood. Relax and Enjoy our indoor pool available year long. Fully equipped kitchen and family room perfect for a large family. Comfortably sleep in our high-end mattresses in a thought-through decorated home. Hosting has been my passion. Super host 6 years in a row we plan to offer you the same comfort we have provided guests over years

Top guest favorite

A backyard area features a wooden deck with a hot tub and an adjacent pool. Colorful hanging flower baskets add vibrancy, while cozy seating on the upper balcony invites relaxation. Lush greenery complements the stone-paved patio and the well-maintained lawn.

Guest suite in Orangeville

4.92 out of 5 average rating, 754 reviews

Hot Tub & Cozy Getaway - 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!

Superhost

A warm ambiance is created by two vintage-style lamps placed on a rustic, wooden ledge against a textured brick wall. A large mirror reflects natural light from nearby windows, enhancing the room's inviting atmosphere. Decorative objects add a unique touch to the display.

Apartment in Stratford

4.81 out of 5 average rating, 126 reviews

The Palatial - 1500 sq feet of amazing space.

Unique space on two floors, right downtown! Old world character with modern aesthetic. Mid-century modern, IKEA and one-of-kind mix. Downstairs: high ceilings, large living rm, 2 bedrms with desks and closets, kitchenette, and sm bathrm. Upstairs: sunny open space - kitchen, dining and living. 2 Bedrms: compact, with closet + desk. Bathrm+ powder rm. Kids welcome. Comfy beds, down duvets, feather pillows [and non feather]. TV to use as monitor [no cable]. Bring cable to connect to your laptop.

Guest favorite

Home in Aldershot

4.93 out of 5 average rating, 29 reviews

Holiday Retreat with Pool

This unique place has a style all its own. Minutes from lake, steps from restaurants, shopping, bars, cafes and so much more. Central, yet quiet neighbourhood. Relax and Enjoy our large backyard and the pool with family. Our fully equipped kitchen and kitchenette for a large family. Comfortably sleep in our high-end mattresses in a thought-through decorated home. Hosting has been my passion. Super host 6 years in a row we plan to offer you the same comfort we have provided guests over years!

Top guest favorite

A spacious pool area features a clear blue swimming pool surrounded by a concrete deck. Sun loungers are arranged for relaxation, and a fenced backyard includes greenery and flowering trees, providing a peaceful outdoor setting. Natural light brightens the space, enhancing the tranquil ambiance.

Apartment in Ariss

4.96 out of 5 average rating, 157 reviews

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.

Superhost

A bright pool area is surrounded by lush greenery and colorful flowerbeds. A two-story cottage sits in the background, framed by trees. The stone patio features seating arrangements, offering a tranquil view of the inviting water.

Cottage in Cambridge

4.88 out of 5 average rating, 8 reviews

Waterfront home with Pool, Boat Ramp/Canoe/Kayak

This vacation home has beautiful views, southern exposure , flower gardens and greenery all around. Surrounding the pool in the back yard beside the lake there is a flagstone patio area with a campfire pit. A perfect spot for watching dreamy sunsets. There is a fabulous pool 17x36 ft with a big deck surrounding it. A picnic table and BBQ on the upper patio terrace by the cottage, overlooking the lake. We have lots of gathering places to lounge around and relax in the outdoor patio furniture.

Superhost

A clear blue pool is surrounded by neatly arranged lounge chairs and red umbrellas. Lush greenery provides a natural backdrop, creating a private and tranquil setting. Steps lead into the pool, enhancing accessibility for guests enjoying the outdoor space.

Bungalow in Burlington

4.75 out of 5 average rating, 118 reviews

Sleeps 12 ADULT private hot tub pool Walk to Lake

Max 12 ADULTS* - Price varies with # of guests*. (Add correct # for price accuracy.) - Cottage Vibe, Cozy, secluded - POOL June to October - HOT TUB open all year - Ping pong/pool table - AC/furnace. NEW! - BBQ + fuel - Private entrance - Short walk to the lake - Towels: Provided (guests bring beach towels). *ADULTS ONLY. Unfenced pool = RISK to toddlers/non-swimmers. **No parties, events, unregistered guests. ** Pool & Hot Tub close @ 10:30 PM NALOXONE kit avail.

Superhost

Cabin in Fergus

4.88 out of 5 average rating, 107 reviews

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

Featured in Forbes "5 Charming Towns In Ontario" A cottage which has more to offer than a resort. Be it Summer or Winter! Indulge in the longest waterfront view you've ever seen from a cottage, nestled atop a hill. With an array of luxurious amenities, including heated pool, sauna, hot tub, gym, outdoor kitchen, fire pit, and multiple patios, this retreat exceeds all expectations. 4 family rooms, offices, a chef's kitchen, 10-person dining area, your every need is catered to.

Guest favorite

Home in Cambridge

4.9 out of 5 average rating, 264 reviews

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.

Top guest favorite

A private backyard features a sparkling pool surrounded by a spacious patio. A large dining table with bright green chairs is shaded by a vibrant umbrella. Grassy areas and tall trees offer a serene, enclosed atmosphere, enhancing the outdoor living experience.

Home in Erin Mills

5 out of 5 average rating, 17 reviews

Family Oasis with Pool and Hot Tub

Bring the whole family to this great place with lots of room for fun. Enjoy the private backyard with a fenced in pool, trampoline, hot tub, outdoor has fire pit and sitting area. Private parking for two cars. Lots of space to spread out and enjoy. 2 family rooms with tvs, access to laundry, huge kitchen, and large dinning room for family dinners. Family friendly neighbourhood. Restaurants and shopping nearby. Backyard is private and exclusive to you only.

Superhost

A patio area features a large umbrella casting shade over a glass-top table surrounded by cushioned chairs. In the background, a crystal-clear pool glimmers beside lush greenery and a basketball hoop. The inviting space is designed for relaxation and leisure.

Apartment in Burlington

4.82 out of 5 average rating, 146 reviews

Quiet 2-bdrm, family-friendly apt with cont. bfast

Welcome to Pjila'si Home (Mi'kmaq word meaning Welcome, come in and sit down is prounced ep' ee-laa-chi). Great basement apartment, conveniently-located within a 15-minute drive of the beach, forests, farms and the mall. Less than an hour of Niagara Falls, Canada's Wonderland, 5 airports, and downtown Toronto. Continental Breakfast fixings included in your stay which includes pastries, cereal, juice, cheese, fresh fruit, coffee and tea.

Top guest favorite

A spacious swimming pool is surrounded by a solid stone deck. The water glimmers under sunlight, reflecting the clear sky above. Lounge chairs are positioned nearby, with a shaded area visible in the background. The setting invites relaxation and leisure.

Bungalow in Hamilton Beach

4.94 out of 5 average rating, 157 reviews

Lakefront. Pool. Beach. Fire-pit.

A PERFECT COMBINATION OF LOCATION, LUXURY AND LIFESTYLE. This unique, self contained Studio is only steps from the beach and the beach trail. Enjoy unforgettable beach sunrises. This exclusive beach-sand-bar community is centrally located between Toronto and Niagara. It's a hop, skip & a jump to world renowned restaurants, art crawls, fashion, theatre, culture & more. ADULTS ONLY (21>). Long weekends have a 3 night min.