Holiday rentals with a pool in Woolwich

Find and book unique homes with a pool on Airbnb

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Popular amenities for Woolwich rentals with a pool

House rentals with a pool

Superhost
Home in Burlington
5 out of 5 average rating, 13 reviews

Modern Luxury House w/EV Charger & Heated Pool

DidiRating, 5 stars7 months ago
Our stay at this Airbnb in Burlington, Ontario, was truly a home away from home. From the moment we arrived, we felt completely at ease in this beautiful and peaceful space. The home itself is lovely, with warm, inviting decor and thoughtful touches that made us feel instantly comfortable. The location in Burlington was ideal for us as a family. We enjoyed exploring the nearby , taking peaceful walks along the waterfront, and visiting the local parks. Burlington’s small-town charm paired with its scenic beauty was a perfect match for our family’s needs. The hosts were exceptional—always responsive and so kind, which really enhanced our experience. They went above and beyond to ensure we had everything we needed, and their hospitality made us feel genuinely welcomed. We left with wonderful memories, and we wouldn’t hesitate to stay here again on future visits to Burlington. Highly recommended for families or anyone seeking a peaceful retreat in a beautiful area
Superhost
Home in Aldershot
4.82 out of 5 average rating, 45 reviews

Four seasons Pool Retreat

PatrickRating, 5 stars3 weeks ago
Great value for the money for a place to stay in Burlington. It looked exactly like the pictures. The kids loved having an indoor pool! Thanks for letting us stay!
Superhost
Home in Mono
4.55 out of 5 average rating, 11 reviews

Luxury Hockley Estate Spa

ScottRating, 5 stars2 weeks ago
It was a great location and hosted a large group. Very nice place in a remote area, giving us the feeling of an outdoor oasis.
Superhost
Home in Orangeville
4.67 out of 5 average rating, 15 reviews

Private cottage heated pool/HotTub/Games 20 Acre

DrewRating, 5 stars3 weeks ago
A great spot for a short escape from the city! Amazing property! Very private. Owner and maintence team were procative and prompt. Would have liked to see a book with general instructions on the property. We had to discover where the outdoor couch cushions were stored for example, I also feel the pool being 'not ready' was a bit of a bait and switch with the rental. It was not clear on how the property managers would like us to handle garbage and there was no ideal place to put the bags. We ended up putting them in the mudroom area (as oudoors would only be a larger mistake given local wildlife) Linnens were clean, Kitchen and the whole property is very nice and well mantained. A great spot for a short escape from the city. Would rent again! Thank you for a wonderful stay.
Guest favourite
Home in Waterloo
4.85 out of 5 average rating, 93 reviews

Entire Guest Unit+Free Parking by Glenbridge Plaza

JovinnRating, 5 stars1 week ago
Had a great stay - the place is equipped with everything you’d need and we enjoyed watching a movie on the big tv! It was a suite in a home that was very clean. The neighbourhood was quiet and safe also. Had a great stay!
Top Guest favourite
Home in Ancaster
5 out of 5 average rating, 16 reviews

Loft Apartment

ShannonRating, 5 stars1 week ago
This cozy studio was the perfect get away for us. We felt relaxed, at ease and comfortable. Milena is a gracious host, the home is stunning, welcoming and it was very well stocked with everything we needed, just like home. It was the perfect location for us to hike the waterfall trails, experience the Botanical gardens and visit with family and friends in Hamilton and Burlington. Will certainly book again for future vacations.
Guest favourite
Home in Elora
4.92 out of 5 average rating, 12 reviews

Riverside Retreat /w Pool,Hot Tub & Sauna in Elora

ShannonRating, 5 stars3 weeks ago
The Crystal Retreat was really a fun vacation spot, and especially interesting as architecture buffs. The house is a custom home built in 1978 with the plans framed and on display. It is a unique and beautiful house with so much to enjoy on the property. We managed to check off everything over the course of four days, but needed at least that much time to get to all the pretty and relaxing spots throughout. From getting cozy with a movie with a tv that spins to face all the various lounging nooks, to diving in the pool, canoeing to the Elora Quarry, vegging out by the fire pit, we did it all and are thankful to Djurdjica for sharing her special home.
Top Guest favourite
Home in Cambridge
5 out of 5 average rating, 13 reviews

Under the Whispering Pines

ValerieRating, 5 stars2 months ago
We had a wonderful stay with family for my son’s graduation. Communication with Niki was prompt and helpful. The pool house was a wonderful surprise and we spent most of our time there although there were two other living areas. The home is warm, clean, and meticulously designed, with small touches throughout (soft sheets, candle light, dimmers, heated floor in master bath etc). Incredible fireplaces, plenty of glasses and dishes, and a Sonos sound system for the music lovers like us. All perfect for a celebratory weekend!

Condo rentals with a pool

Guest favourite
Condo in Kitchener
4.92 out of 5 average rating, 49 reviews

1 BR with City Views, near Go Transit, Tech centre

LisaRating, 5 stars3 weeks ago
I could not have asked for a better stay in Kitchener! The apartment was comfortable and had everything you need for a pleasant stay and the view is amazin. Super well located, just minutes from uptown Waterloo or downtown Kitchener and at walking distance from the train station. Nicole was also very responsive and helpful! Overall, one of the best airbnb stays I've had!
Guest favourite
Condo in Waterloo
4.88 out of 5 average rating, 85 reviews

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

HosannaRating, 5 stars1 week ago
Second time booking Wendy’s place and it was such a great experience again!
Guest favourite
Condo in Kitchener
4.92 out of 5 average rating, 13 reviews

LuxCondo in the downtown kitchener uptown waterloo

JackieRating, 5 stars1 day ago
I appreciated having a few things in the kitchen that I could use on the first night until I got to the grocery store. Central Fresh Market is a walking distance from the condo for individuals that enjoy some home cooking while on vacation. The pool and bowling area was a great hit for those rainy days. Thank you for responding quickly whenever we contacted you with questions
Superhost
Condo in Kitchener
4.6 out of 5 average rating, 10 reviews

Bright & Modern Downtown Stay w/ Pool & Gym

KendraRating, 5 stars3 weeks ago
We had a wonderful stay at Michael's airbnb. Everything was exactly as he listed. The place is stunning. The condo has lots of great amenities. We had an issue with the coffee maker and Michael went above and beyond to help resolve the issue. Thanks for hosting us. We will be back soon!
Superhost
Condo in Kitchener
4.94 out of 5 average rating, 18 reviews

Highrise King Condo With Home Cinema -Free Parking

RojdarRating, 5 stars2 months ago
Everything was very clean and comfortable definitely recommend this spot.
Superhost
Condo in Burlington
4.88 out of 5 average rating, 52 reviews

Modern Luxury Condo - Go Station, Gym, Pool+

JohnRating, 5 stars5 months ago
Our Go To Place to stay in Burlington. Stephanie goes above and beyond in terms of responsiveness. Being so close to the GO TRAIN made commutes to Union Station a breeze. Will definitely be staying again.
Superhost
Condo in Waterloo
4.92 out of 5 average rating, 25 reviews

The Laundry Rooms, Waterloo - Two Bedroom Suite

KimRating, 5 stars7 months ago
Our 2nd stay at The Laundry Rooms! We loved it. Clean, bright and great location. Love the 2 bed and 2 bath set up and the amenities were great. We will be back!!
Superhost
Condo in Kitchener
4.54 out of 5 average rating, 24 reviews

Perfectly Located in Kitchener

DawsonRating, 5 stars1 week ago
Was a great visit !

Quick stats about holiday rentals with a pool in Woolwich

  • Total rentals

    50 properties

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 properties include access to Wi-Fi

Destinations to explore