
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.

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

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

Hot Tub Fall Colours 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!

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 mid-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.

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.

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

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!

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

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

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.

The Captain's Cottage at Willow Pond
You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

Historic Blair Road Coach House
Nestled on stone farmhouse property built in 1837. Located adjacent to Devils Creek and Grand River trail system. Minutes to Grand River bluff views, downtown Galt, Hamilton Family Theatre, Langdon Hall, the Old Mill, Whistle Bear Golf Club and Galt Country Club. Brand new, completely separate, thoughtfully designed & decorated, 2 bedroom, (3 bed including a King), 2 bath, guest house with spacious and private cedar deck, forest views and lots of parking.
Popular amenities for Woolwich rentals with a pool
House rentals with a pool

Modern Luxury House w/EV Charger & Heated Pool

Cozy Bungalow near the lake

Unique Old Church House

The Bayfront Flat - Harbour Views + Private Pool!

Private cottage heated pool/HotTub/Games 20 Acre

Riverside Retreat /w Hot Tub & Sauna in Elora

Luxurious Home | Hot Tub & Pool | Sleeps 8

Cozy Retreat • Heated Pool • Fireplace • Workspace
Condo rentals with a pool

Cozy Space

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

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

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

LuxCondo in the downtown kitchener uptown waterloo

Bright & Modern Downtown Stay w/ Pool & Gym

Highrise King Condo With Home Cinema -Free Parking

Luxurious Lakeview Condo in Burlington
Other vacation rentals with a pool

Rustic Farmhouse w/ pool, tennis court on 100 Acre

Luxury Hockley Estate Spa

Fall Into Savings – Book Now & Save Big!

Stunning Family Retreat, 1hr from TO, Sleeps 15

Private Laid-back Luxury

The Portal, An Off Grid Cabin in the Tree of Peace

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

Newly Renovated! 1200 sq foot private apartment
Quick stats about vacation rentals with a pool in Woolwich
Total rentals
40 properties
Nightly prices starting at
€ 9 before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Port Credit
- Whistle Bear Golf Club
- Victoria Park
- Royal Woodbine Golf Club
- Dundas Valley Golf & Curling Club Ltd
- Hockley Valley Resort - Golf, Spa and Ski
- Bingemans Big Splash
- Bayfront Park
- Royal Botanical Gardens
- TPC Toronto at Osprey Valley
- Glen Abbey Golf Club
- Rockway Golf Course
- Caledon Country Club
- Mount Chinguacousy
- Glen Eden
- Hamilton Golf and Country Club
- RattleSnake Point Golf Club
- Credit Valley Golf and Country Club
- Centennial Park Ski Chalet
- Wet'n'Wild Toronto
- Chicopee
- Art Gallery of Hamilton
- Galt Country Club Limited
- Mount Nemo Golf Club