Oakville holiday rentals

Holiday Rentals in Oakville

2025 available vacation rental offers

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Oakville holiday rentals: compare the best deals

2 Bedroom 1 Bathroom Prime Location in Mississauga - Oakville
8.5Very good 81 reviews
Oakville
2 2
HK$2398/nighttotal: HK$64746 (27 )

2 Bedroom 1 Bathroom Prime Location in Mississauga

apartment - Mississauga
This apartment is conveniently located in central Mississauga, just a short drive from both the Mississauga Convention Center and Toronto Pearson International Airport. It has consistently received high ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The two-bedroom flat is compact, measuring just 4 square metres, but is well-equipped for a comfortable stay. Guests can enjoy a range of amenities including a swimming pool, fitness centre, sauna, and outdoor barbecue area, providing plenty of opportunities for relaxation and recreation.
2bd Best Value And Prime Location - Oakville
8.8Very good 53 reviews
Oakville
1 2
HK$2424/nighttotal: HK$72720 (30 )

2bd Best Value And Prime Location

apartment - Toronto
This two-bedroom apartment is situated in Mississauga, just a short distance from the Mississauga Convention Center and Toronto Pearson International Airport. The property has received very good ratings for cleanliness and user experience, along with an excellent location rating.
The apartment spans 84 square metres and comfortably accommodates up to four guests. It comes equipped with a range of amenities, including a fully equipped kitchen, a private balcony, a swimming pool, a sauna, a fitness centre, and secure parking.
Apartment In Home - Oakville
9.6Excellent 57 reviews
Oakville
2 1
HK$800/nighttotal: HK$24000 (30 )

Apartment In Home

apartment - Toronto
This apartment is located in a quiet neighbourhood just a short five-minute walk from Lake Ontario, making it a peaceful retreat while still being within easy reach of downtown Toronto (30 minutes) and Niagara Falls (45 minutes). The apartment has consistently received excellent ratings for its cleanliness, location, and overall user experience.
The apartment is a one-bedroom, one-bathroom flat with a capacity of two guests, offering a private and independent space. Guests can enjoy a fully equipped kitchen, a private garden, parking, and a range of amenities including a TV, Wi-Fi, and laundry facilities.
Spacious Townhouse In Family Area - Oakville
9.9Excellent 14 reviews
Oakville
3 3
HK$1452/nighttotal: HK$43560 (30 )

Spacious Townhouse In Family Area

house - Toronto
House listing for up to 10 people with an excellent rating of 99% based on 14 reviews. You will be based in Toronto.
Facilities and services include air conditioning, an iron and a kitchen. Enjoy free parking with this accommodation in Toronto!
Luxury 3 Bedroom House @Dundas/trafalgar, Oakville - Oakville
9.0Excellent 39 reviews
Oakville
4 3
HK$2133/nighttotal: HK$149310 (70 )

Luxury 3 Bedroom House @Dundas/trafalgar, Oakville

apartment - Milton
This brand new house is situated in Oakville, just a short drive from Milton, offering easy access to the town's attractions and amenities. The property enjoys excellent user, location and cleanliness ratings, making it an ideal choice for travellers. This three-bedroom home features a spacious living area, a modern kitchen and two bathrooms, providing ample space for families or groups of friends. The house also benefits from a garden, parking, air conditioning, high-speed internet, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
Entire End Unit Townhouse With Finished Basement. - Oakville
Oakville
3 3
HK$1429/nighttotal: HK$42870 (30 )

Entire End Unit Townhouse With Finished Basement.

house - Toronto
This three-bedroom townhouse is located in West Oakville, a short walk from the Plaza and a Starbucks, offering easy access to shops, restaurants, and cafes. The neighbourhood is popular with both locals and visitors, and is known for its friendly atmosphere and convenient location.
The property is fully furnished and equipped, with a spacious kitchen, three bedrooms, and a finished basement, comfortably accommodating up to six guests. Amenities include a private garden, air conditioning, parking, and bi-weekly housekeeping, ensuring a comfortable and enjoyable stay.
Modern 1 Br Walk Out Condo - Oakville
9.6Excellent 32 reviews
Oakville
2 1
HK$720/nighttotal: HK$87120 (121 )

Modern 1 Br Walk Out Condo

apartment - Toronto
This modern one-bedroom flat is situated in Oakville, a town just west of Toronto, close to the intersection of Dundas and Trafalgar, and within easy reach of Oakville Hospital, Walmart and Canadian Tire. The property has received excellent ratings for its cleanliness, location and overall user experience.
The flat has a contemporary design and is fully furnished, comfortably accommodating two guests. It includes a range of amenities such as a fully equipped kitchen, in-unit laundry, a private patio, a Smart TV with Chromecast and air conditioning.
Cozy 2 Bedroom Basement Unit Parking Wifi Netflix - Oakville
9.4Excellent 13 reviews
Oakville
2 2
HK$754/nighttotal: HK$91234 (121 )

Cozy 2 Bedroom Basement Unit Parking Wifi Netflix

apartment - Milton
This two-bedroom basement flat is conveniently located in the heart of Milton, close to shops, restaurants, and amenities. The property has received excellent ratings for location, cleanliness, and overall experience.
The self-contained flat comfortably accommodates two guests and features a fully equipped kitchen with a fridge, freezer, and microwave. You'll also enjoy air conditioning, a garden, parking, and the convenience of internet access.
Cozy Private Guest Suite With Separate Entrance - Oakville
9.5Excellent 21 reviews
Oakville
1 1
HK$393/nighttotal: HK$13755 (35 )

Cozy Private Guest Suite With Separate Entrance

- Hamilton
This lower-level flat is conveniently located in Hamilton, within easy reach of grocery stores, restaurants, and pubs, and just a short drive from the highway and public transport. It has received excellent ratings for location, cleanliness, and overall user experience.
The self-catering apartment is suitable for one guest and includes a private bathroom. It is equipped with a full kitchen, air conditioning, and parking, and is attached to the owner’s house.
Dreamliving - Oakville
9.5Excellent 8 reviews
Oakville
3 3
HK$1729/nighttotal: HK$51870 (30 )

Dreamliving

bungalow - Toronto
This charming bungalow is located in a peaceful residential area of Toronto, just a short distance from the city's major attractions. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
The bungalow offers three bedrooms and two bathrooms, comfortably accommodating up to five guests. Guests can enjoy a fully equipped kitchen with modern appliances, air conditioning, and secure parking, ensuring a comfortable and convenient stay.
New 2bd Furnished Townhome Location - Oakville
9.8Excellent 10 reviews
Oakville
4 2
HK$1199/nighttotal: HK$83930 (70 )

New 2bd Furnished Townhome Location

house - Toronto
This 2-bedroom house is situated in a central Toronto neighbourhood, within easy walking distance of major attractions and public transport. The property has consistently received excellent ratings for location, cleanliness and overall experience.
The house comfortably accommodates up to 4 guests and features a fully equipped kitchen, in-suite laundry, cable TV, unlimited Wi-Fi, and underground parking. Guests can enjoy a private garden and benefit from the convenience of air conditioning.
Two Bed/two Bath Apartment- Oakville - Oakville
9.7Excellent 22 reviews
Oakville
2 2
HK$1248/nighttotal: HK$37440 (30 )

Two Bed/two Bath Apartment- Oakville

apartment - Toronto
This apartment is situated in Oakville, a peaceful suburb just west of Toronto, offering easy access to the city's attractions. It has consistently received excellent ratings for location, cleanliness and user experience.
The property is a comfortable and well-equipped home, perfect for up to four guests. Amenities include a fully equipped kitchen, a garden, parking, and air conditioning.

Best Oakville holiday rentals with a pool

Among the 2025 accommodations in Oakville, here are the 8 best rentals with a pool

Heartful Family Retreats In A Reverie Suite - Oakville
10Excellent 4 reviews
Oakville
4 1
HK$3187/nighttotal: HK$223090 (70 )

Heartful Family Retreats In A Reverie Suite

- Toronto
This 2-bedroom suite is located in Oakville, a short drive from downtown Toronto, Lake Ontario, and Bronte Harbour Marina, offering a peaceful escape from the city buzz. The property boasts excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The open-plan living, dining, and kitchen area provides ample space for up to 5 guests to relax and socialise. Enjoy the private oasis with a BBQ, gas fire pit, heated saltwater pool, and waterfall, perfect for al fresco dining and relaxing after a day exploring Toronto.
Cozy Guest Suite - Oakville
9.9Excellent 17 reviews
Oakville
2 1
HK$640/nighttotal: HK$19200 (30 )

Cozy Guest Suite

studio - Hamilton
This cosy basement flat is located in a quiet residential neighbourhood in Hamilton, just a short distance from the Go station, a grocery store, and the bus station. The property has received excellent ratings for location, cleanliness, and user experience.
The flat has a private bathroom and can accommodate up to two guests. It comes equipped with a microwave, kettle, and a small fridge, making it ideal for a short stay.
Spacious Executive Studio Apartment With Pool - Oakville
9.9Excellent 14 reviews
Oakville
2 1
HK$730/nighttotal: HK$21900 (30 )

Spacious Executive Studio Apartment With Pool

studio - Milton
This ground-floor studio apartment is located in Milton, a short walk from the charming downtown area and its shops and restaurants. The studio has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has one bedroom and one bathroom, comfortably accommodating two guests. It features a modern kitchen, a spacious bathroom with a walk-in shower, and access to a shared swimming pool.
Ultra Luxurious 2.5 Bedroom 2 Full Bathroom 1 Parking Condo Near Sq1 Striking Views - Oakville
8.9Very good 9 reviews
Oakville
4 3
HK$3888/nighttotal: HK$54432 (14 )

Ultra Luxurious 2.5 Bedroom 2 Full Bathroom 1 Parking Condo Near Sq1 Striking Views

apartment - Toronto
This apartment is situated in Mississauga, just 19 miles from Casa Loma in Toronto, offering a convenient location near Square One shopping mall and its various restaurants, shops, and entertainment options. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The three-bedroom apartment spans 93 square metres, comfortably accommodating up to seven guests. It includes a range of amenities and activities, from a fully equipped kitchen and a fitness centre to a swimming pool, sauna, spa, and tennis court, providing something for everyone.
Luxury Private Suite In Oakville + Pool - Oakville
9.3Excellent 14 reviews
Oakville
2 1
HK$932/nighttotal: HK$112772 (121 )

Luxury Private Suite In Oakville + Pool

B&B - Toronto
This one-bedroom apartment is located in the uptown core of Oakville, just a short walk from a plaza with shops and restaurants, and close to the Oakville Uptown Transit Station. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is modern, with an open-plan layout and a converted den that can be used as a second bedroom, comfortably accommodating up to three guests. You'll have access to a swimming pool, gym, and free underground parking, as well as a garden for relaxing.
Lovely 2 Bedroom Condo - Oakville
Oakville
4 1
HK$2767/nighttotal: HK$193690 (70 )

Lovely 2 Bedroom Condo

apartment - Toronto
This apartment is located in Oakville, a town just west of Toronto, a 10-minute walk from the bustling downtown area with its many restaurants. You can easily reach Toronto by car or public transport, making this a convenient base for exploring the city. This two-bedroom flat offers ample space for four guests and includes two bathrooms. The apartment is equipped with modern amenities such as a fully equipped kitchen, comfortable furniture, laundry facilities, and a swimming pool, fitness centre, and parking.
Rare Property In Luxurious Toronto Area & Lake - Oakville
Oakville
3 3
HK$3267/nighttotal: HK$98010 (30 )

Rare Property In Luxurious Toronto Area & Lake

- Toronto
City Centre Lodge ( Downtown) - Oakville
9.0Excellent 1 review
Oakville
4 2
HK$1491/nighttotal: HK$20874 (14 )

City Centre Lodge ( Downtown)

apartment - Toronto
This two-bedroom flat in Mississauga is just a short 15-mile drive from Toronto's BMO Field and Budweiser Stage, making it an ideal base for exploring the city. The property has received excellent ratings for its location, cleanliness and overall experience.
The 75 square metre flat comfortably accommodates four guests and features a fully equipped kitchen with a dishwasher, a washing machine, free parking and Wi-Fi, plus a balcony for enjoying the fresh air.

Best family friendly Oakville holiday rentals

Among the 2025 accommodations in Oakville, here are the 8 best family friendly rentals

South Oakville Custom 5 Bed 4500 Sq Ft Luxury - Oakville
9.8Excellent 24 reviews
Oakville
4 5
HK$3697/nighttotal: HK$51758 (14 )

South Oakville Custom 5 Bed 4500 Sq Ft Luxury

apartment - Toronto
This modern house is located in a quiet neighbourhood in South Oakville, just a short drive from the bustling city centre of Toronto. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The house offers spacious accommodation for up to 10 guests, with five bedrooms and four bathrooms. Guests can enjoy a range of amenities including a fully equipped kitchen, a private garden, a fitness centre, and parking for four cars.
Boutique 3Br+Study Townhouse - Oakville - Oakville
10Excellent 3 reviews
Oakville
3 3
HK$3383/nighttotal: HK$101490 (30 )

Boutique 3Br+Study Townhouse - Oakville

apartment - Milton
This three-bedroom townhouse is situated in Oakville, a short drive from Milton, offering easy access to both towns and the wider Toronto area. It's conveniently located just 15 miles from the Mississauga Convention Center, 21 miles from BMO Field, and 21 miles from Budweiser Stage, making it a great base for exploring the region. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The spacious 186 square metre townhouse comfortably accommodates up to six guests. Enjoy a relaxing stay with modern amenities such as free Wi-Fi, air conditioning, a private garden, and a balcony, as well as free parking on-site.
Family Bungalow In South Burlington Close To Lake, Bronte/appleby Go/w 3 Parking - Oakville
10Excellent 14 reviews
Oakville
4 3
HK$3906/nighttotal: HK$54684 (14 )

Family Bungalow In South Burlington Close To Lake, Bronte/appleby Go/w 3 Parking

bungalow - Hamilton
This family-friendly house is located in Burlington, just a short distance from Lake Ontario and Paletta Lakefront Park, making it an ideal base for exploring Hamilton and its surrounding areas. It has received excellent user ratings, suggesting a comfortable and enjoyable stay for guests.
The house spans 102 square metres and comfortably accommodates up to 7 guests across 3 bedrooms. It features a fully equipped kitchen, a private water park, a tennis court, a garden, and a terrace, providing ample space for relaxation and entertainment.
Gorgeous Basement Apartment Awaits - Oakville
10Excellent 2 reviews
Oakville
1 2
HK$1553/nighttotal: HK$46590 (30 )

Gorgeous Basement Apartment Awaits

apartment - Toronto
This two-bedroom house is situated in Clarkson-Lorne Park, a short distance from Benares Historic House and within a 5km radius of attractions like Scooter's Roller Palace and Bradley Museum. This property has received excellent user ratings, making it a popular choice for travellers.
The 139 square metre house can accommodate up to three guests and offers a range of amenities including a fully equipped kitchen, a private garden, a fitness centre and a spa. Guests can also enjoy a fireplace, a terrace or balcony and free Wi-Fi access.
Renovated 2 Bedroom Condo In Glenn Abbey Oakville - Oakville
8.8Very good 17 reviews
Oakville
2 2
HK$1378/nighttotal: HK$37206 (27 )

Renovated 2 Bedroom Condo In Glenn Abbey Oakville

apartment - Toronto
This ground floor flat is conveniently located near walking trails, a park, a grocery store, and restaurants, making it ideal for exploring the city. The property has received very good user ratings and excellent ratings for location and cleanliness.
This two-bedroom, one-bathroom flat offers 74 square metres of space and can comfortably accommodate up to four guests. It features a modern kitchen with a fridge and dishwasher, a spacious living area with a wood-burning fireplace, a private terrace, a garden, a fitness centre, a tennis court, and parking.
Warm Family Home With Executive Kitchen & Backyard - Oakville
10Excellent 3 reviews
Oakville
4 4
HK$5491/nighttotal: HK$76874 (14 )

Warm Family Home With Executive Kitchen & Backyard

apartment - Toronto
This four-bedroom flat is located between Oakville's bustling downtown and the tranquil Bronte neighbourhood, offering a blend of urban excitement and peaceful retreat. The property has consistently received excellent ratings for location, cleanliness, and user experience.
This spacious home comfortably accommodates up to eight guests and features a well-equipped kitchen with modern appliances, a private patio and garden, and a nursery with a crib and single bed for families with young children. Enjoy the convenience of air conditioning, high-speed internet, and parking, ideal for exploring the city and surrounding areas.
Bbq-ping Pong-king Bed-2 Workspaces-2 Car Garage - Oakville
9.9Excellent 32 reviews
Oakville
4 3
HK$3141/nighttotal: HK$43974 (14 )

Bbq-ping Pong-king Bed-2 Workspaces-2 Car Garage

house - Toronto
This luxurious townhouse is located in the family-friendly Joshua Creek neighbourhood in Oakville, just a short drive from major highways and attractions like Bronte GO station, Lake Ontario and downtown Oakville. The property has received excellent ratings for location, cleanliness and user experience.
The spacious three-bedroom townhouse can accommodate up to nine guests and features a dedicated office room and two workspaces. Guests can enjoy high-speed internet, two smart TVs with unlimited Netflix, a fully equipped kitchen, a ping pong table, a backyard with outdoor dining furniture, a BBQ, two garage parking spaces and two driveway parking spaces.
Central 4 Bed Room Home By Go Station And Sq One! - Oakville
9.7Excellent 29 reviews
Oakville
4 4
HK$3675/nighttotal: HK$51450 (14 )

Central 4 Bed Room Home By Go Station And Sq One!

house - Toronto
This centrally located Mississauga home is just 7.5 miles from the Mississauga Convention Center and 16 miles from Toronto's BMO Field, making it a convenient base for exploring both Mississauga and Toronto. The property has consistently received excellent reviews for its cleanliness, location, and overall user experience.
This four-bedroom property spans 279 square metres and offers a spacious living area with two living rooms, a fully equipped kitchen, and two bathrooms. Guests can enjoy modern conveniences including air conditioning, a dishwasher, a coffee machine, a hair dryer, and free Wi-Fi, as well as a private garden and complimentary parking.

Frequently asked questions for the vacation rentals in Oakville

Destinations nearby

Best pet friendly Oakville holiday rentals

Among the 2025 accommodations in Oakville, here are the 8 best pet friendly rentals

Townhouse In Oakville - Oakville
10Excellent 5 reviews
Oakville
4 3
HK$1891/nighttotal: HK$132370 (70 )

Townhouse In Oakville

house - Toronto
This three-bedroom townhouse is situated in Oakville, a suburb of Toronto, just a short drive from the city centre and close to the QEW highway. The property has received excellent ratings for its cleanliness, location and overall experience, making it a great choice for travellers.
The spacious property can comfortably accommodate up to six guests and features a private garden and parking. Guests can enjoy modern amenities such as a fully equipped kitchen, air conditioning and high-speed internet, as well as a convenient location close to Bronte Park and a local plaza with amenities.
Fully Furnished, Beautiful & Cozy, Entire House - Oakville
10Excellent 21 reviews
Oakville
2 3
HK$2096/nighttotal: HK$253616 (121 )

Fully Furnished, Beautiful & Cozy, Entire House

apartment - Toronto
This three-bedroom apartment is situated in a peaceful residential neighbourhood, a short drive from Toronto's major attractions like the CN Tower and the Distillery District. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property offers ample space for up to six guests, with three bathrooms and a fully equipped kitchen. Guests can enjoy the convenience of a private garden, a modern fireplace, and a dedicated play area in the basement, along with parking facilities.
Brand New 2 Bdr + 2wsh Condo W/parking In Oakville - Oakville
9.5Excellent 46 reviews
Oakville
2 2
HK$1123/nighttotal: HK$135883 (121 )

Brand New 2 Bdr + 2wsh Condo W/parking In Oakville

apartment - Milton
This two-bedroom apartment is situated in Oakville, just a short distance from Milton, close to the intersection of Dundas and Trafalgar and easily accessible from major highways. The property enjoys excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The flat is well-equipped for guests, comfortably accommodating up to six people. Guests can enjoy free high-speed internet, underground parking, and access to Netflix, along with a fully equipped kitchen, a garden, a gym, and air conditioning.
Furnished 3000 Sqft 4 Bedrooms Home In Oakville - Oakville
10Excellent 6 reviews
Oakville
2 1
HK$1267/nighttotal: HK$153307 (121 )

Furnished 3000 Sqft 4 Bedrooms Home In Oakville

house - Milton
This spacious townhome is conveniently located in Milton, close to local amenities and attractions. The property has consistently received excellent ratings for cleanliness, location and user experience.
The three-bedroom townhouse comfortably accommodates up to eight guests. It features modern design, a fully equipped kitchen, a private garden, parking, air conditioning, and internet access, making it ideal for families or groups.
Basement Apartment - The Preserve Area - Oakville
9.8Excellent 13 reviews
Oakville
4 1
HK$853/nighttotal: HK$11942 (14 )

Basement Apartment - The Preserve Area

apartment - Milton
This newly built basement flat is located in The Preserve area of Milton, close to major attractions and amenities. It has received excellent ratings for location, cleanliness, and overall user experience.
The flat is modern and spacious, with high ceilings and large windows, accommodating up to four guests. It comes equipped with a fully fitted kitchen, air conditioning, parking, and internet access, ensuring a comfortable and convenient stay.
Fully Furnished 4 Br Luxury Townhome - Oakville
8.9Very good 9 reviews
Oakville
3 4
HK$2256/nighttotal: HK$67680 (30 )

Fully Furnished 4 Br Luxury Townhome

house - Milton
This Milton property is ideally located for exploring the town's attractions, with easy access to [mention specific landmarks and their distances]. The house has received excellent ratings for cleanliness, location, and overall guest experience.
The four-bedroom, two-bathroom house comfortably accommodates up to eight guests. The kitchen is fully equipped with a fridge, microwave oven, and dishwasher, while modern amenities like Wi-Fi, cable TV with 1000+ channels and video on demand, ensure a comfortable and enjoyable stay.
L'éspace Essentielle De L'artist! - Oakville
9.3Excellent 28 reviews
Oakville
2 1
HK$848/nighttotal: HK$25440 (30 )

L'éspace Essentielle De L'artist!

apartment - Toronto
This renovated one-bedroom flat is situated in Oakville, a short walk from Kerr Village and downtown Oakville, offering easy access to shops, restaurants and attractions. The property has received excellent ratings for its location, cleanliness and overall experience.
The apartment features a comfortable living area and a cosy bedroom, accommodating up to two guests. It comes equipped with a fully equipped kitchen, laundry facilities, a balcony with a barbecue and free parking, making it ideal for a relaxing and enjoyable stay.
Adorable Apt In Burlington - Oakville
Oakville
2 1
HK$440/nighttotal: HK$53240 (121 )

Adorable Apt In Burlington

apartment - Hamilton
This one-bedroom flat is located in Burlington, just a short distance from Lake Ontario and a number of family-friendly attractions like Paletta Lakefront Park and Amazing Adventures Playland. The area offers a peaceful and scenic setting with easy access to both the waterfront and local amenities.
The 58 square metre flat comfortably sleeps two guests and is equipped with a fully fitted kitchen, a washing machine and a spa bath. Guests can enjoy free Wi-Fi, a Smart TV, and the convenience of parking, making this a great option for a relaxing and comfortable stay.