Holiday rentals with a pool in Oakville

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Oakville

  • Total holiday rentals

    Explore 40 holiday rentals in Oakville

  • Nightly prices starting at

    Oakville holiday rentals start at $71 NZD per night before taxes and fees

  • Verified guest reviews

    Over 630 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Oakville holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oakville rentals

  • 4.8 Average rating

    Oakville stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Oakville

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Superhost
Home in Burlington
4.83 out of 5 average rating, 12 reviews

3 bedroom home close to downtown with Pool!

This unique home offers its own charm, just minutes from the lake and walking distance to restaurants, shopping, cafes, and more. A quiet yet central neighborhood. Relax in our backyard and pool with your family. Our kitchen and kitchenette are fully equipped for a large family. Enjoy the comfort of high-end mattresses in a thoughtfully decorated home. Hosting is my passion, and as a Super host for six years in a row, we’re committed to providing you the same comfort we’ve offered our guests!

Guest favourite
An open-concept kitchen and living area features light hardwood flooring and contemporary furnishings. A white leather sofa complements a wooden coffee table, while a large kitchen island with bar stools is highlighted. A dining table accommodates six, and colorful tile accents add character to the space.
Home in Burlington
5 out of 5 average rating, 21 reviews

Modern Luxury House w/EV Charger & Heated Pool

Modern, clean, detached home in Burlington, perfect for families. * Open-concept design with ultra fast WiFi (1GBPS) and reliable mesh WiFi * 3 bedroom w/Two king beds for comfort & space * L2 electric car charger (NEMA 14-30) & 3-car private parking * Centrally located: 32 mins to Toronto, 30 mins to wine country * Palmer neighborhood: Top 10 family-friendly (Zoocasa 2023), #1 community (Maclean’s 2019) Relax by the heated saltwater pool (May - October) or cozy up by the Indoor gas fireplace.

Guest favourite
The image features a diamond-shaped solar-heated swimming pool reflecting the soft colors of sunset. Comfortable blue lounge chairs are positioned nearby, overlooking a serene lake. The distant skyline can be faintly seen across the water, blending into the horizon.
Home in Hamilton
4.81 out of 5 average rating, 119 reviews

California Chic +Breathe +Unwind +Restore

Enter through the grand foyer with a winding staircase, pass the kitchen, and step into the relaxing backyard featuring an in-ground, diamond-shaped, solar-heated swimming pool and a stunning lake. The view of the lake is beautiful! The area is quiet and scenic, with the soothing sounds of the lake lulling you to sleep. You are just 30 minutes away from Niagara Falls and 1 hour from Toronto. On a clear day, you can even see the Toronto skyline. It's the perfect place for a group or family of 9.

Guest favourite
A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.
Guesthouse in Mississauga
4.89 out of 5 average rating, 108 reviews

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

YES Hot tub and heated pool are open! Forget your worries in this spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. **25+ ID & waiver req**

Top Guest favourite
A modern living area features a large window with expansive views of the cityscape and surrounding landscape. A flat-screen television is mounted on the wall opposite a comfortable sofa and a coffee table, creating a welcoming space for relaxation.
Apartment in Mississauga
4.95 out of 5 average rating, 183 reviews

Luxury Stay w/phenomenal view!

Enjoy a stylish experience at this centrally located property. Sunset lovers are going to love this one! Starbucks, restaurants, grocery shops, dentists, pharmacies, and much more ON THE MAIN FLOOR. Walking distance to Mississauga’s largest mall Square one. 15 mins drive from airport. 20 mins drive to Downtown Toronto. Lakeshore south view from balcony. Gym, swimming pool, jacuzzi, sauna, piano room, cards room, stretching room, outdoor bbq, and much more in this unique one of a kind property.

Top Guest favourite
A bright and airy living space features large corner windows that offer expansive views of the city. A modern sectional couch is paired with a light rug, while a flat-screen television is mounted on the wall. Lush green plants add a touch of nature to the inviting décor.
Condo in Yorkdale
5 out of 5 average rating, 145 reviews

The Penty: Luxurious Penthouse with Pool, Hot Tub

Welcome to our modern & luxurious corner penthouse! Stylishly designed with lush greenery and upscale touches, this bright space offers comfort, elegance, and a relaxed tropical vibe. Take in stunning panoramic city views and unwind with premium amenities including an outdoor pool, hot tub, and steam room sauna. Just a 15-min drive to downtown. Public transit at the doorstep. 10-min drive to Rogers Stadium. Perfect for discerning guests seeking an elevated stay in Toronto’s vibrant urban core

Top Guest favourite
Guest suite in Mississauga
4.92 out of 5 average rating, 171 reviews

Full apt on Upper floor near HWY - S Mississauga

Get the privacy & convenience of a hotel and comfort of a home. Many of our guests are repeat guests as they find a lot of value in staying here. In Lorne Park in S. Mississauga, the apartment is on the upper floor of a house with a separate entrance. One minute to QEW, 17 minutes from the airport, & 20 minutes to downtown Toronto, this spacious apartment is self-sufficient with a new, full kitchen with appliances, bathroom, laundry & parking. Ideal for all types of stays. No smoking please.

Superhost
The indoor swimming pool area features a tiled pool surrounded by natural light from large skylights. Two colorful floats are positioned on the water surface, and glass doors provide a view of the outdoors, enhancing the open and airy feel of the space.
Villa in Toronto
4.92 out of 5 average rating, 209 reviews

Toronto Vacation | ➊ The One Toronto Villa

The One is a unique luxurious private midle-century modern villa escape in the center of north Toronto. Having a stunning and spacious lawn for events and social gathering, this modern house is featured a thermostatic indoor swimming pool. Being inspired from a farmhouse building, the house offering a traditional touch on the vintage furniture and a rustic interior that gives a warm and cozy feelings. It is a great escape from the hustle and bustle of city life without going out of town.

Guest favourite
Bungalow in Burlington
4.74 out of 5 average rating, 140 reviews

FIFA Cottage Monthly avail. 12 Max Hot Tub Pool

Max 12 ADULTS* *Unfenced pool = NOT suitable for toddlers & non-swimmers. Young adult (13yrs.+) swimmers welcome. Inquire re weekend or weekly availability. - COTTAGE-Vibe Secluded - POOL OPEN mid-June to Oct. - HOT TUB all year - Ping pong/pool table - AC/furnace - BBQ+fuel - Private enter. - Short walk to lake - Towels avail, guests bring BEACH towels, lawn chairs NO parties, events, unregistered guests. Pool & Hot Tub close @ 10:30 PM NALOXONE kit avail.

Top Guest favourite
A backyard seating area is viewed, featuring a dark outdoor sectional couch with a black coffee table placed on a striped rug. Surrounding the heated saltwater pool are lounge chairs and lush greenery, creating a serene outdoor space.
Guesthouse in Brampton
5 out of 5 average rating, 109 reviews

Bright and Airy Guest Suite with Pool

Large windows, high ceilings, fresh modern decor, cedar sauna, fitness room and backyard pool best describes our Garden Suite. Spoil yourself in everything this space has to offer. Featuring a comfy queen size bed sheeted with luxury cotton and down duvet. A large queen pull-out couch offers space for extra sleepers. Take some time to refine your culinary skills with the well appointed kitchen. Don't overpack, your in-unit washer and dryer will keep your clothes clean.

Top Guest favourite
The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.
Home in The Beaches
4.99 out of 5 average rating, 182 reviews

FIFA: 4BR: 365 Days Open- Heated Pool & Hot Tub

A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

Guest favourite
An outdoor hot tub is nestled beneath a wooden pergola, featuring jets and seating. In the background, a swimming pool is visible, surrounded by greenery and blue skies, evoking a relaxing atmosphere.
Cottage in Niagara-on-the-Lake
4.89 out of 5 average rating, 338 reviews

Modern Farmhouse XL Hot Tub NOTL 15Mins- Falls

Indulge in the rejuvenating health benefits of a mid-week retreat at our Outdoor Spa. Immerse yourself in the refreshing autumn ambiance, relishing the crisp cool air, snug days, and enchanting evenings amidst the fragrant scents of fall in our picturesque outdoor setting. Discover the myriad ways to savor the essence of fall at our spa. Unwind with an overnight stay at our Modern Farm House in charming Niagara-on-the-Lake.

Popular amenities for Oakville rentals with a pool

When is the best time to visit Oakville?

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Avg. price$186 NZD$227 NZD$229 NZD$252 NZD$291 NZD$289 NZD$431 NZD$276 NZD$264 NZD$248 NZD$255 NZD$250 NZD
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Destinations to explore

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