Holiday rentals with a pool in Region of Waterloo

The Oasis

Enjoy the bright, spacious, homey cottage vibes with a fully private saltwater pool **(Open until October 17th) hot tub **(Open until Nov 15th), 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 close by.

Location · Family · TV

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

Family · Location · Access

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.

Location · Value · View

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

Location · Value · Check-in

High Rise 1BR Building with Gorgeous Views

This beautiful condo is located in the brand new Station Park Union Towers. Station Park is one of the newest (and sleekest!) additions to Kitchener -Waterloo's growing skyline. This bright, airy condo is large enough to host 3 guests at a time, and features spectacular city views, a private balcony patio, and floor-to-ceiling windows. It has a fully equipped kitchen, living and dining areas, and a separate bedroom with a King sized bed. You also get access to the fabulous building amenities!

Value · Family · Cleanliness

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.

Family · Location · River

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.

Family · Location · Accuracy

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.

Family · Location · Checkout

Historic Blair Road Coach House and Terrace Suite

Two separate units on stone farmhouse property built in 1837. Located adjacent to Devils Creek and Grand River trail system. 3 bedrooms, 5 beds including a king, 2 kitchens. Minutes to Grand River bluff views, downtown Galt, Hamilton Family Theatre, Langdon Hall, the Old Mill, Whistle Bear Golf Club and Galt Country Club. Coach House and Terrace apartment combined. Lots of parking! Pool open seasonally, approximately May until end of September.

Family · Location · Indoor spaces

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.

Value · Family · Decor

Modern High-Rise Condo w City Views & Balcony

Whether you’re visiting for work or a city getaway, this modern one-bedroom condo offers comfort and convenience in the heart of Kitchener, with beautiful city views. The open-concept layout features a cozy bedroom, sleek bathroom, and a sofa bed—perfect for couples, small groups, or business travelers. Unwind, recharge, and enjoy a seamless stay that truly feels like home. Book your stay today!

Value · Location · Comfort

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. 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.

Value · Location · Accuracy