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.

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Guest favourite
Home in Waterloo
4.86 out of 5 average rating, 125 reviews

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

Superhost
Home in Hamilton Beach
4.9 out of 5 average rating, 105 reviews

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 favourite
Guest suite in Orangeville
4.92 out of 5 average rating, 794 reviews

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!

Top guest favourite
Flat in Ariss
4.96 out of 5 average rating, 176 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.

Top guest favourite
Flat in Waterloo
4.99 out of 5 average rating, 87 reviews

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

Guest favourite
Apartment in Kitchener
4.97 out of 5 average rating, 114 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

Top guest favourite
Home in Elora
4.96 out of 5 average rating, 24 reviews

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

Top guest favourite
Home in Alton
4.97 out of 5 average rating, 106 reviews

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

Top guest favourite
Flat in Kitchener
5 out of 5 average rating, 13 reviews

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.

Cabin in Fergus
4.84 out of 5 average rating, 123 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.

Top guest favourite
Home in Cambridge
5 out of 5 average rating, 20 reviews

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.

Guest favourite
Guest house in Erin
4.96 out of 5 average rating, 133 reviews

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

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