
Holiday rentals in Oakville
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Top-rated holiday rentals in Oakville
Guests agree: these stays are highly rated for location, cleanliness and more.

Condo Style Basement in Oakville (Walk Up)
Looking for a cozy and comfortable place to stay during your next vacation or business trip? This spacious and stylish Airbnb accommodates up to 6 guests! Our beautiful space features everything you need to feel right at home! This condo style basement apartment is located in Oakville, one of Ontario’s most desirable neighbourhoods. 2 bedrooms with walk in closets 2 full bathrooms Sofa-come bed Contemporary chef kitchen (including utensils ) TV with Disney Plus and Netflix Dryer and washers

Sun-kissed 3BR family home in a quiet neighborhood
♡ The fastest internet w/ 1Gb download speed ♡ Fully Equipped Kitchen ♡ minutes drive to Sheridan college, Walmart, Oakville Place, lakeshore ♡ 7 min. drive to Trafalgar GO Station, 20 min. to Toronto premium outlets 25 min. to Pearson airport 30 min. to Toronto downtown ♡ Walking distance to convenient store, trails, food, bus stop, library. ♡ Free Parking ( 2 Spots) ♡ Automated Check in & Check Out ♡ Flexible Check in Check out - Message for Details ♡ A/C ♡ Laundry ❤ Book today!

Charming spacious townhome in Prime Oakville
Welcome to our spacious and inviting retreat! Nestled in a prime location in Oakville, this entire house offers a perfect blend of comfort and convenience. Unwind in the ample living spaces, and relish the privacy of having the entire house to yourself. With nearby attractions and a tranquil atmosphere, our Airbnb is your ideal home away from home. Explore the city by day which is 30 min drive, and return to the spacious serenity of your temporary abode by night. Your perfect getaway awaits

Bright, Spacious, Quiet 2 bedroom - Licensed
Quiet family neighborhood great for professionals, couples or family. Spacious and cozy home away from home. You control heat and cooling fan. Sound dampening so natural noises are minimized, not eliminated. 1 queen and 1 double bed. Two desks for computer work. Extra seating. Fast WiFi! Full kitchen. Bathroom with shower and bathtub. Close to highways, hospital, recreation centers, playgrounds, shopping, schools and college. All registered guests may be asked to provide ID upon request.

Modern Executive Townhome w/ Rooftop Hot Tub Oasis
Stylish contemporary townhome in Oakville! The perfect retreat for couples, families, and friends alike. Experience the rooftop terrace, complete with a Private Jacuzzi Hot Tub that provides the ultimate relaxation experience! It's the perfect spot to unwind after a long day of sightseeing or to enjoy an evening under the stars. You'll love the stunning and spacious living areas, fully equipped kitchen, and two comfortable bedrooms. Close to Three Major Highways in a Central Location!

Elegant Suite: Private Entrance & Full Amenities
This stylish and cozy 1-bedroom basement apartment is perfect for small families or couples. Enjoy complete privacy with a separate entrance in a quiet suburban neighborhood. Centrally located with easy access to major highways, this beautifully furnished space offers year-round comfort—warm and inviting in the winter, cool and refreshing in the summer. Equipped with all the essentials for a convenient and relaxing stay, this immaculate apartment is your ideal home away from home.

Cozy Basement Apartment in Oakville
Welcome to Your Cozy Oakville Basement Apartment! Newly built, this 2 bedroom apartment holds a open-concept living room that flows into the fully-equipped kitchen, offering a cozy space to relax along with backyard area. Guests have private access through a separate entrance and independent working area. Pond facing, located in a quite neighborhood in close proximity to restaurants and grocery stores. 10-15 mins from Oakville GO Station. 25-30 mins from YYZ Airport .

Private Boutique Style Smart Suite with Patio
A Charming private suite with a main-floor bedroom and a cozy basement living room featuring a TV and a mini kitchenette. Step out to your backyard oasis with a patio for morning coffee or evening wine. Perfect for a peaceful getaway in the modern city, this stylish retreat blends comfort, privacy, and convenience - just minutes from local cafes, shops, and Oakville's Downtown Area, as well as the GO station and a beautiful lakeshore. Steps away from a family-friendly park.

Cozy Modern Studio in Oakville | Free Parking
Welcome to your perfect retreat - an oasis for 1-2 guests seeking ultimate comfort. Enjoy seamless connectivity with WiFi, Netflix, and a luxurious Queen bed. Experience the essence of home in our inviting, modern basement studio. With a full kitchenette, in-unit laundry, and lots of storage. This modern unit is ideally situated in a serene, safe neighborhood in Oakville, steps from public transit, close to various amenities like restaurants, malls and trails

Waterfront Coach House Loft
This friendly, private open concept loft apartment is located on the top floor of a guest coach house located on a 2 acre waterfront estate. The loft apartment is a separate building from the main house. There is a maximum occupancy for the loft of 2 people, parties, get togethers and events are not permitted. Due to the tall spiral staircase, children are not permitted due to safety. Extra charges will apply if additional guests are present in the loft.

Elegant 2BR townhouse condo in central Oakville
Enjoy your stay in this elegant, clean, and fully equipped two bedroom and two-bathroom condo townhouse. Centrally located in Oakville and within walking distance to shops, restaurants, and parks. Beautiful upscale building in a quiet and safe neighborhood with large terrace overlooking a mature tree lined street. Abundant walking trails nearby for you to explore and enjoy. Easy access to highway 407, 403, QEW and Trafalgar GO Station.

Cozy Oakville Oasis | Modern & Peaceful Stay
Enjoy a peaceful stay in this stylish apartment near Saw Whet Golf Club and beautiful Bronte Creek Provincial Park. 3 min from the QEW, Bright, open-concept living space, full kitchen, private balcony, high-speed WiFi, and free parking. Just a short drive to Bronte Village with its waterfront trails, cafes, and shops. Ideal for couples, solo travelers, or business guests seeking comfort and convenience in Oakville.
Popular amenities for Oakville holiday rentals
Other great holiday rentals in Oakville

New European Vibe Room In The Basement!

009G Sunny room Good view private bath $1750/m

TG’s Luxurious House

Room#3 - Stylish - New - Shared Townhouse

Luxurious Private Bedroom En Suite

Private sun filled suite

Homey Hotel Suite

Single bedrooom with shared Kitchen bathroom
Quick stats about holiday rentals in Oakville
Total holiday rentals
Explore 870 holiday rentals in Oakville
Nightly prices starting at
Oakville holiday rentals start at € 9 per night before taxes and fees
Verified guest reviews
Over 18,900 verified reviews to help you choose
Family-friendly holiday rentals
430 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 200 rentals that welcome pets
Holiday rentals with a pool
40 properties feature pools
Rentals with dedicated workspaces
560 properties have a dedicated workspace
Wifi availability
860 of Oakville holiday rentals include wifi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Oakville rentals
4.7 Average rating
Oakville stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Budweiser Stage
- Exhibition Place
- Distillery District
- Sherkston Shores Beach Resort & Campground
- Port Credit
- Metro Toronto Convention Centre
- Clifton Hill
- The Danforth Music Hall
- Toronto Zoo
- Harbourfront Centre
- Financial District
- CF Toronto Eaton Centre
- Niagara Falls State Park
- BMO Field
- Trinity Bellwoods Park
- Massey Hall
- Casa Loma
- Whistle Bear Golf Club
- Dufferin Grove Park
- Legends on the Niagara Golf Course