Vacation 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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Scarborough

4.97 out of 5 average rating, 37 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 favorite

Guest suite in Scarborough

4.95 out of 5 average rating, 91 reviews

Cozy 2 Bedroom Guest Unit - Firepit - Game Room

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 favorite

Home in Scarborough

4.93 out of 5 average rating, 112 reviews

Entire house with Pool, ravine, and nature trail

Enjoy your stay in this artsy, minimalistic 2 story home. The entire house is yours! This house has 3 bedrooms, each with a queen bed, night stand, closet space, and USB charging ports. One room has a desk/workspace. It also has 2 full bathrooms, open concept kitchen/living/dining rooms, and laundry and one parking spot on the driveway. We offer high speed WIFI, and a wall mounted, 55" flat screen, 4K, Roku Smart TV. In addition, we have a Keurig machine with complimentary coffee and tea.

Guest favorite

Home in Uxbridge

5 out of 5 average rating, 29 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

Welcome to Redwood Haven, your lavish Uxbridge retreat! 2 bedrooms await, comfortably accommodating 4 guests. Be captivated by breathtaking views, immerse yourself in luxury, taking a dip in the inviting heated pool (shared by our guests of the attached East and West units). Embark on thrilling equestrian adventures for an extra touch of excitement. With ample parking, heating, and AC, ensuring the ultimate comfort throughout your stay. Unleash unforgettable memories in this enchanting haven.

Superhost

Home in Ajax

4.83 out of 5 average rating, 12 reviews

Entire Modern Home | Spacious | Near Lake & Park

Welcome to our spacious home in the GTA (Ajax), the ideal retreat for family getaways and local adventures. ENTIRE HOUSE* (3+1 BR + 2 Baths) ** Cozy Living Space: The living area is perfect for relaxation. ** Fully-Equipped Kitchen: stocked with cookware. ** Outdoor Patio: Step outside to a patio, ideal for sipping morning coffee. ** Convenient Location: Located near groceries and shopping. ** Public transit is also easily accessible. Perfect walk score to waterfront lake for fresh air.

Superhost

Home in Oshawa

4.71 out of 5 average rating, 14 reviews

[30%+OFF] PS4 + BBQ: 5 Br, 3 Bath - 2 Units in 1!

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. Book now for a cozy stay! IMPORTANT: Outdoor Backyard is unavailable during quiet hours 11 PM to 7 AM daily. Zero tolerance for parties, loud noises. Quiet, family-friendly neighborhood.

Guest favorite

Home in Port Perry

4.93 out of 5 average rating, 214 reviews

Home away from home with a hot tub and pool

This spacious home is a short walk to downtown Port Perry. Enjoy your time around the pool or hot tub, relaxing by the outdoor fireplace, lounging at the bar or just spending your time under a large covered deck ( rain or sunshine, uv ray protection). Port Perry offers shopping, fun at the lake (fishing and boating), skiing, hiking, local brewery, many restaurant choices and easy access to the Blue Heron casino. Check local web site for the many events going on around town.

Guest favorite

Home in Whitby

4.9 out of 5 average rating, 10 reviews

A Quite 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 from September 2024 this year

Superhost

Home in Pickering

4.81 out of 5 average rating, 36 reviews

Toronto Vacation with Heated 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

Home in Ajax

4.82 out of 5 average rating, 11 reviews

Luxurious house with private Pool

Enjoy Luxury Living in detached bungalow with 3 bedroom 1.5 washroom. Sitting on a Massive 50 Ft. Wide Lot with Fully Interlocked Resort Style Backyard Featuring Huge private Pool(closed mid September- end of May)along with Deck Prime Neighborhood of Ajax, 1.5km from Serene Ajax Lakefront 800 Mts from grocery store, convinience stores and restaurants 500 mts from Lush Parks and 4.5 km from Ajax Go Station

Guest favorite

Guest suite in Uxbridge

4.96 out of 5 average rating, 190 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

Guest favorite

Home in Scarborough

4.88 out of 5 average rating, 16 reviews

Private Pool Lakeview House

Enjoy a memorable visit when you stay in this unique place. Absolutely stunning waterfront cozy home near the Toronto bluffs beach. This is a gorgeous place in a classy neighbourhood with everything you need. Private pool and spacious yard with extraordinary views. Walking distance to the beach, Go transit, restaurants, grocery, pharmacy and more. You'll love it!

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oshawa rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favorite

Home in Port Perry

5 out of 5 average rating, 6 reviews

Horse Farm Luxury Estate

Home in Whitby

New place to stay

Modern Specious house with pool

Home in Pickering

New place to stay

weekend get away close to home

Guest favorite

Home in Uxbridge

4.86 out of 5 average rating, 86 reviews

The Ridge Roost - Uxbridge Township

Home in Bowmanville

4.27 out of 5 average rating, 11 reviews

2 Bedroom Modern Apartment

Show all

Quick stats about vacation rentals with a pool in Oshawa

Total rentals
10 properties
Total number of reviews
190 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Oshawa Centre, Tribute Communities Centre, and NEB's Fun World

Vacation rentals with a pool in Oshawa

Top-rated rentals with a pool in Oshawa

Home in Scarborough

Guest suite in Scarborough

Home in Scarborough

Home in Uxbridge

Home in Ajax

Home in Oshawa

Home in Port Perry

Home in Whitby

Home in Pickering

Home in Ajax

Guest suite in Uxbridge

Home in Scarborough

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Oshawa rentals with a pool

House rentals with a pool

Home in Port Perry

Home in Whitby

Home in Pickering

Home in Uxbridge

Home in Bowmanville

Quick stats about vacation rentals with a pool in Oshawa

Total rentals

Total number of reviews

Family-friendly rentals

Wifi availability

Popular amenities

Local attractions

Destinations to explore