Holiday rentals with a pool in Oshawa

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Oshawa

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

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Guest favourite

Home in Port Perry

5 out of 5 average rating, 7 reviews

Horse Farm Luxury Estate

Unwind in this serene, stylish retreat nestled within a stunning 100-acre horse farm.Property boasts a park-like ambiance and is situated on a secluded section behind a gate. Guests can enjoy picturesque views of horses grazing in the distance. The house features a spacious event/lounge room, perfect for gatherings. The fully renovated basement offers a pool table, multiple TVs, and a bar for your entertainment. The entire house is equipped with a 'Sonos' sound system for an audio experience.

Top guest favourite

Home in Scarborough

4.98 out of 5 average rating, 51 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Surrounded By Nature,This East-End Toronto Gem Features A Heated 4Ft Deep Pool(Open May-Oct),Pergola w/Ample Seating+BBQ On An Over-Sized Deck.The HGTV Inspired Renos Will Make Your Stay Extra Special.A True Get-Away Where Lasting Memories Will Be Made! ✔ 5-7 Min to PanAM Centre, Toronto Zoo, Rouge Beach &Train Station ✔ 10 Min To Pickering Casino ✔ 35 Min to CNtower ✔ 35 Min To YYZ airport ✔ 5 Min Walk to TTC bus stop ✔ 5 Min To Groceries ✔ 5 Min To Highland Creek Village ✔ 10 Min To The Guild

Guest favourite

Home in Scarborough

4.95 out of 5 average rating, 107 reviews

Modern Custom Home w/ Pool, Games & Parking

Welcome to our brand new, luxury modrn unit located in a quiet, family-friendly neighborhood only min from HWY401,407,DVP, TTC & countless amenities! Newly & lovingly modern space with luxury finishes throughout. Enjoy comfortable living quarters, brand new kitchen appliances, bright rooms, large windows, a dedicated workspace, in-unit washer/dryer, free WIFI, Netflix, Prime & free parking. This upscale oasis is truly the perfect space for business travelers, young professionals & couples alike!

Guest favourite

Guest suite in Uxbridge

4.78 out of 5 average rating, 9 reviews

Hilltop Getaway|Scenic Views| Pool | Back toTrails

Escape to this stunning hilltop 2-bedroom Airbnb, nestled on 22 acres of beautiful woodland just 2 minutes from Lake Ridge Ski Resort.Enjoy breathtaking panoramic views of the mountains from your private retreat, perfect for those seeking both relaxation and adventure This cozy unit is ideal for hikers, with direct access to Glen Major Forest and scenic trails right at your doorstep There is no living room, you will have 2 bed rms, 1 washroom and a kitchen This unit is a portion of main cottage

Guest favourite

Guest suite in Scarborough

4.89 out of 5 average rating, 94 reviews

Prestigious Bluffs Private Guest Suite

Beautiful, private, sun-filled guest suite with a large private yard and pool in a safe, upscale, tranquil, forested neighbourhood. Deer and other wildlife. Short walk to public transport (TTC, GO Trains), shopping, restaurants, parks and trails to the top of the Bluffs with breathtaking views of Lake Ontario and also down to the waterfront trail to nearby Bluffers Park Beach and Marina. Parking for 6 vehicles and boat trailer. Fast Fibre Internet. EV Charger (Tesla/J1772). No parties or events.

Guest favourite

Home in Hampton

5 out of 5 average rating, 8 reviews

Enniskillen Vacation Home Retreat!

Located in a sought after community, this attractive modern home is situated on 3/4 acre surrounded by farmland and estate homes. Explore the area with tons to do! Conveniently 5min from 407, an hour east of Toronto, 10min from Canadian Tire Motorsport Park, 5min from Cedar Park (waterpark) 20min to Brimacombe Ski Hill & Ganaraska Forest, with many ATV, snowmobile, mountain biking and walking trails close. “Pack your bags and get ready for a memorable, stress-free stay at our retreat”

Superhost

Bungalow in Whitby

4.87 out of 5 average rating, 15 reviews

2 BHK home 5 min from Go Train

7 min walk from Whitby train and Lake, this is a 2 BR house that offers accommodation with a 2 private parkings The self contained apartment is located in a brightly lit lower floor features, a separate entrance, a living room, and a fully equipped kitchen & laundry room. Guests can enjoy sun bathing in the garden or a barbque grill with your family. The backyard is shared however the guests have a private entrance. The pool is closed until June 2025 For monthly discounts contact us

Superhost

Home in Oshawa

4.82 out of 5 average rating, 34 reviews

Private Pool + BBQ + PS4: 5 Bedooms, 3 Bathrooms!

Welcome to our spacious 5 bedroom / 3 bathroom bungalow with 3 queen beds, 2 king beds, 2 kitchens, 2 dining areas, and 2 cozy living rooms. With 3 bathrooms and plenty of space, it's ideal for families or groups. Conveniently located near shopping, HWY 401, and just a 45-minute drive to Toronto. IMPORTANT: Outdoor Backyard is unavailable during quiet hours 11 PM to 7 AM daily. Zero tolerance for parties, loud noises. Quiet, family-friendly neighborhood.

Superhost

Home in Pickering

4.84 out of 5 average rating, 50 reviews

Toronto Vacation Pool/Park/Zoo/Casino

Welcome to our newly renovated 4-bedroom home. This spacious and stylish accommodation offers both a living room and a family room for your comfort and convenience. Dive into relaxation with access to our private heated pool. We take pride in upholding high cleanliness standers to ensure your stay is comfortable and enjoyable. Whether you’re here for a family getaway or a group retreat, our home provides the perfect blend of comfort and convenience.

Superhost

Campervan/Motorhome in Haydon

4.78 out of 5 average rating, 45 reviews

The Happy Camper @ Cedar Park Resort

No trailer? No problem! Camping at this family fun waterpark is for trailers only. Accomodation in a pop up camper with all amenities to make for a comfortable 'glamping' experience. 1 queen and 1 double bed with upgraded mattresses. additional children can sleep on the dinette which converts to a single bed. Bring your own bedding. kitchen is all inclusive except kitchen cloths. must bring your own pillows and blankets and sheets

Superhost

Apartment in Scarborough

4.94 out of 5 average rating, 47 reviews

Luxury High Rise Living | Parking, Gym, Pool, View

Experience upscale high-rise living in this stylish 2-bedroom, 2-bath condo in Scarborough. Enjoy breathtaking forest views from your private balcony and modern open-concept design. Just steps from Scarborough Town Centre and the TTC, with easy access to Highway 401. ✔ Panoramic forest views ✔ Modern open-concept living ✔ Access to gym, indoor pool, and secure parking ✔ Steps to Scarborough Town Centre & TTC ✔ Easy access to Highway 401

Guest favourite

Guest suite in Uxbridge

4.96 out of 5 average rating, 209 reviews

Mackenzie Cottage

Historic Log home in a country oasis. Nestled in the forest with a large pool just outside the back door, and quick access to some of the most beautiful and exciting trails in southern Ontario. Inside, surround yourself with the warmth of a log cabin circa 1815, as well as the soaring ceilings of the newer post and beam structure. Visit us on Insta @allbrightlane