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.

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Top guest favourite
Apartment in Oakville
4.91 out of 5 average rating, 100 reviews

LUXURY CONDO, GREAT DECOR, WHEELCHAIR FRIENDLY!!!

NEW GORGEOUS LUXURY CONDO WHEELCHAIR ACCESIBLE. *** NEW BED in 2nd!*** PRIME BEDROOM has a queen size memory foam mattress & a desk. SECOND BEDROOM has a brand new bed with double mattress medium/firm and a working desk, now accessible to guests. 2 FULL BATHROOMS: The en-suite has has a step up shower and a Bidet. SECOND: Has a tub & shower, very spacious. *OPEN CONCEPT LIV. AREA. *OPEN BALCONY. TASTEFULLY FURNISHED, SOFT AND CLEAN COLORS HARDWOOD FLOORS THROUGHOUT EXTRA WIDE HALLS AND DOORS

Guest favourite
Home in Oakville
4.88 out of 5 average rating, 26 reviews

Cozy Spacious 2 bedrooms

Welcome to our cozy retreat in the heart of Oakville, a perfect blend of comfort and convenience! Ideal for business trips,city adventures, or family visits, our space caters to all your needs for a refreshing stay. Conveniently close to Toronto Pearson Intl Airport and within 20 minutes to Square One Shopping Centre, Celebration Square, and the Coronation Park, our location ensures both accessibility and peace. Explore the city effortlessly with readily available public transportation options.

Guest favourite
Flat in Oakville
4.95 out of 5 average rating, 109 reviews

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

Guest favourite
Townhouse in Oakville
4.93 out of 5 average rating, 75 reviews

Luxury Urban Town home

Discover urban sophistication at our modern townhome, ideally located for both comfort and convenience. Thoughtfully designed with stylish decor and all the amenities you need, you'll find grocery stores just a short walk away and easy access to highways 401 and 403 for effortless travel. - Superstore, Walmart, LCBO: 10-minute walk - Oakville Trafalgar Memorial Hospital: 10-minute drive - Oakville GO Station: 12-minute drive - Toronto Premium Outlets: 14-minute drive Book your stay today!

Top guest favourite
Flat in Oakville
4.98 out of 5 average rating, 131 reviews

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.

Guest favourite
Home in West Oakville
4.9 out of 5 average rating, 110 reviews

Luxury Villa! Swim Spa! 6 Bedroom 3 Family Rooms

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.

Superhost
Apartment in Oakville
4.87 out of 5 average rating, 63 reviews

Modern & Spacious Condo (Two Bed, Two Bath)

Welcome to our highly rated and 5-star reviewed property. This is a spacious (>900 sq ft) and modern 2-bedroom, 2-bathroom condo, perfectly nestled in the picturesque town of Oakville, Ontario. Ideal for families, couples, or small groups, this condo promises a comfortable and unforgettable stay. Don't miss the opportunity to experience the best of Oakville and Toronto from the comfort of this stylish condo. Book your stay and create lasting memories! We look forward to hosting you.

Superhost
Flat in Oakville
4.8 out of 5 average rating, 71 reviews

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.

Guest favourite
Flat in Oakville
4.98 out of 5 average rating, 83 reviews

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 .

Guest favourite
Guest suite in Oakville
5 out of 5 average rating, 7 reviews

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.

Top guest favourite
Loft in Lorne Park
4.96 out of 5 average rating, 1,063 reviews

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.

Superhost
Flat in Oakville
4.57 out of 5 average rating, 14 reviews

Luxurious Upper Oakville Condo

This comfortable, fresh and newly furnished one bedroom executive suite is perfect for both long-term stays and short getaways. Located in Oakville, Ontario's largest town, this prime location offers the best of both worlds. Conveniently situated between Toronto and Niagara Falls, you'll enjoy the best of both worlds. Easy access to major city hubs and a variety of outdoor attractions, making it ideal for sightseeing, exploration and adventure.

Popular amenities for Oakville holiday rentals

Quick stats about holiday rentals in Oakville

  • Total rentals

    870 properties

  • Nightly prices starting at

    ₹888 before taxes and fees

  • Total number of reviews

    19K reviews

  • Family-friendly rentals

    430 properties are a good fit for families

  • Pet-friendly rentals

    200 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Destinations to explore