
Pet-friendly holiday rentals in Oakville
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Oakville
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

Cottage On Lake Ontario Niagara
OPEN TIMESLOTS APRIL 6-12 APRIL 13-20 APRIL 23-25 APRIL 26-MAY 3 MAY 5-8 Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include: beautiful lake views and orchards.

Beautiful family Home near Downtown
A beautiful naturally bright, well-decorated, contemporary & open-concept home conveniently located in a peaceful & posh Oakville area. *Close to major highways QEW/403 & *Oakville GO Station. *A bus stop is right across its driveway. *The Beautiful view of Lake-Ontario, Shorewood-Promenade-Park, approx.1km; *Famous Kerr-Village, approx.1km & *Historic Downtown-Oakville, approx.2km are just at a walking distance. With multiple landmarks, upscale retail, exceptional dining, bars, cafes & etc.

Beautiful Renovated Beach Cottage Home
When you enter our immaculately clean Beach Cottage home you will feel like you are at a boutique hotel. Beautiful white linens and towels, WIFI, smart TV, Keurig coffee machine and more. Choose to have a BBQ with friends and family on one of our two decks as you watch the Sunset from Lake Ont. Take a stroll or a bike ride down the Beautiful boardwalk or visit the beautiful beach all located at the end of our yard. Whether you are here for business or pleasure there is something for everyone!

Hidden Cabin with hot tub
Immerse yourself in the woods. Experience the calmness and privacy of an off grid cabin in the woods, surrounded by nature and with a view of majestic horses. This cabin is perfect for a romantic getaway, or an escape with friends and family The large sliding glass door gives you the perfect view of a stunning morning sunrise with beautiful views of horses just steps away The Cabin consists of a main bedroom and also a full bathroom and kitchen to make your stay that much more comfortable

3Bd 2.5Bth House w/ Pool Table, Swing, Outdoor BBQ
Bring your friends and family to this family-friendly, centrally-located neighbourhood with lots of room for fun and find a home away from home during the travelling. Enjoy your stay in this licensed short-term accommodation for a modern, luxurious, and spacious three-bedroom and two-bathroom detached home with a huge backyard: watching a movie and cozying up by the fire, enjoying the company of friends and family seated around the dining table, or simply in between moving or renovations.

Modern 1 Bed Condo Mississauga
Welcome, new, stylish condo in the heart of Mississauga! This 1Bed/1Bath unit offers a cozy and convenient stay, perfect for both business and leisure travelers. Centrally located in Mississauga, you'll be close to public transport, shopping malls, restaurants, and major highways, making it easy to explore the city. The bedroom features a queen-sized bed. Smart TV and high-speed internet, perfect for relaxing or working remotely. Private Balcony to enjoy the city views. One parking spot.

Large Luxury Villa with Swim Spa! Near downtown!
Forget your worries in this spacious, serene and unique house! Large backyard with a Swim Spa to enjoy! Backyard filled with fire places! 6 Bedroom, 7 beds, 4 full baths, 4 offices, 3 family rooms, 9 TV, equipped kitchen, patio, board games, BBQ grill, fire place, Tesla charger. Quiet yet central from downtown Oakville, highways, groceries, shopping, bars, restaurants, cafe's and much more! Always professionally cleaned. For elderly guests a bedroom and full bath is on ground floor.

Toronto Island Wonderland View
Toronto Islands are a 10 minute ferry ride away from downtown Toronto. Switch from the hustle and bustle of the city to the tranquillity of one of Toronto's most coveted parks. Unique to any other metropolitan city, Toronto Island has limited vehicle access. This car free area boasts 6 kilometres of nature walks, children and pet friendly access to beaches, Centre island amusement park, artist exhibitions, restaurants and even a nude beach. A perfect getway for the hybrid vacationer.

Frenchman’s Pass - Cozy nook on the Hamilton brow
Welcome to your home away from home! This charming one-bedroom apartment is nestled on the beautiful Hamilton Mountain, steps away from the scenic brow. Located in one of the city's most upscale neighborhoods, it offers the perfect blend of tranquility and convenience. High-speed Wi-Fi, smart TV, private, on-site parking, private deck and all essentials for a relaxing stay. Situated centrally, you're just minutes from hospitals, shopping centers, restaurants, and public transit.

Erin Cabin Getaway and Bunkie
Take it easy at this unique and tranquil getaway. Located steps from Calerin Golf Course (350 m) and includes many amenities, such as: a BBQ, patio w/ dining area, private hot tub, acres of groomed trails, games galore, pool table, fire pit, comfy queen bed w/ separate heated bunkie with a second queen bed and more! Optional pull out available, please inquire within (fee may apply). 2 km or 5 mins, from the picturesque town of Erin. Lots of restaurants, shops, and plenty to do!

Waterfront Hillside Villa
Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.

Spacious 3-Bedroom Apartment|Perfect for Families
Luxury 3-Bedroom Retreat | Prime Location | Free Parking Newly renovated, this private 3-bedroom apartment offers modern comfort and convenience. Features 100% cotton luxury bedding, full kitchen with espresso machine, 2 full bathrooms, Smart TV, WiFi, and keyless entry. Steps from shops, dining, and transit. 10-20 min to Downtown, <10 min to Pearson Airport & malls. Includes 2 FREE parking spots. Book your stay today!
Popular amenities for Oakville pet-friendly home rentals
Pet-friendly house rentals

Studio Apartment

Luxury 4BR Oasis Year Round Heated Pool & Hot Tub

Langford House

Comfy Oasis In Historic Downtown Neighborhood

" The Heart of the Village" Main Street, Jordan

Niagara Wine Country Art House | Hot Tub | 2 ppl

2BR+2Bath! 2queen beds! Luxury Private Quiet Clean

Private Suite. Milton New Modern Basement Suite
Pet-friendly home rentals with a pool

2BR by Union, Scotia Bank Arena CN Tower + Parking

Beautiful Penthouse with Breathtaking View

*5BR 4Bath Family GetAway near Lake & Harbor*

The Farmer's Cottage

Canadiana Downtown Condo w/King Bed + Free Parking

Humber Bay Family Friendly condo w Terrace&Parking

Beautiful Lake View Studio Condo + 1 free Parking

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍
Private, pet-friendly home rentals

Central Location Beautiful Full Townhome

Modern Loft with Immersive Theatre Experience

Everest Luxury In Oakville

King Bed, Queen Bed, Free Parking, Gym, WiFi

Luxury & Modern 2 Bedroom w/Parking

2026 FIFA |40 Mins to BMO Field |Oakville GO Train

Entire Lower Level Home 3500 Sq Walk Out

Luxury Suite ~ Cozy Winter Escape
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $152 SGD | $162 SGD | $162 SGD | $172 SGD | $185 SGD | $190 SGD | $209 SGD | $221 SGD | $190 SGD | $165 SGD | $156 SGD | $167 SGD |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Quick stats about holiday rentals that are pet-friendly in Oakville

Total holiday rentals
Explore 210 holiday rentals in Oakville

Nightly prices starting at
Oakville holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 4,170 verified reviews to help you choose

Family-friendly holiday rentals
160 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wifi availability
200 of Oakville holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Oakville rentals

4.7 Average rating
Oakville stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Pocono Mountains Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Pittsburgh Holiday rentals
- Erie Canal Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Rentals with a hot tub Oakville
- Flat rentals Oakville
- House rentals Oakville
- Rentals with beach access Oakville
- Rentals with lake access Oakville
- Fitness-friendly rentals Oakville
- Townhouse rentals Oakville
- Rentals with outdoor seating Oakville
- Rentals with a washing machine and dryer Oakville
- Rentals with a fireplace Oakville
- Family-friendly rentals Oakville
- Private suite rentals Oakville
- Apartment rentals Oakville
- Rentals with breakfast Oakville
- Rentals with a firepit Oakville
- Rentals with an EV charger Oakville
- Rentals with a patio Oakville
- Rentals with pools Oakville
- Waterfront rentals Oakville
- Pet-friendly rentals Halton
- Pet-friendly rentals Ontario
- Pet-friendly rentals Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Distillery District
- Harbourfront Centre
- Nike Square One Shopping Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Niagara Falls State Park
- Massey Hall
- Wilfrid Laurier University
- Casa Loma
- Downsview Park
- Horseshoe Falls
- Dufferin Grove Park
- Casino Niagara




