
Holiday 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

Cozy Fall HotTub 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!

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

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

Riverside Retreat /w Hot Tub & Sauna in Elora
Are you looking for the perfect summer escape? Althea Crystal Retreat in picturesque Elora, Ontario, has what you need! Take advantage of our special offers: Save up to 22% off stays booked during Monster Month. Enjoy: Early Bird & Last Minute Discounts. Offers are valid for our full-house accommodation until December 2025 Unwind in one of our unique crystal rooms. Relax by the pool and hot tub, and warm up in the sauna. Feeling Adventurous? Go kayaking in our backyard with our kayaks

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

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.

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.

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.

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.
Popular amenities for Woolwich rentals with a pool
House rentals with a pool

Modern Luxury House w/EV Charger & Heated Pool

Cottage Ambiance Private

Four seasons Pool Retreat

The Bayfront Flat - Harbour Views + Private Pool!

Estate, Secluded On the Grand River.

Relax in Hot Tub, Sauna & Swim Pool - Stunning 6BR

Arts Home @ Limeridge | Cozy Autumn Luxury Escape

Chalet by hiking trail and ski hill
Apartment 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 holiday rentals with a pool

Stargazer Dome

Cozy Private Suite with Year-Round Hot Tub

Milton Home- a Family Oasis

Luxurious Home | Hot Tub & Pool | Sleeps 8

Cozy Retreat • Heated Pool • Fireplace • Workspace

Classy Basement - 2 Bedroom in Burlington

High Rise 1BR Building w Gorgeous Views

21st- floor Luxury & City Views
Quick stats about holiday rentals with a pool in Woolwich
Total rentals
30 properties
Nightly prices starting at
$13 SGD before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
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- Rentals with pools Regional Municipality of Waterloo
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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
- Royal Botanical Gardens
- Bayfront Park
- 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
- Galt Country Club Limited
- Art Gallery of Hamilton
- Mount Nemo Golf Club