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Holiday rentals in Whitby

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Top-rated holiday rentals in Whitby

Guests agree: these stays are highly rated for location, cleanliness and more.

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Home in Bowmanville

4.77 out of 5 average rating, 162 reviews

Lavish Bowmanville Vacation Home (Short/Long Term)

Gorgeous 3,200 sqft. Fully furnished upscale urban home located in Bowmanville. The open floor plan encompasses 4 spacious bedrooms, 3.5 luxurious bathrooms. This home has a pristine, stylish gourmet kitchen. The convenience of your own off-street parking. The neighborhood is near many shops, restaurants, parks and trails minutes away. An exceptional residence to spend your Vacation with your loved ones! Appropriate for out of area workers. For the perfect home in Bowmanville search no further!

Guest favourite

Guest house in Uxbridge

4.95 out of 5 average rating, 116 reviews

Private Guesthouse in Nature minutes to Trails

Relax and unwind at this peaceful and private guesthouse situated on 25 acres of forest. We are family friendly and invite you to roam the land and visit our resident ducks! If you are feeling more adventurous, enjoy a hike on our private onsite trail or on one of the many local trails within walking distance in the Trail Capital of Canada! Later we'll get the Woodstove lit for you (Dec - Feb). Catch up on your fav programs with Roku TV. Enjoy the therapeutic rainfall shower guests rave about!

Guest favourite

Home in Trinity Bellwoods

4.91 out of 5 average rating, 327 reviews

Garden Home @ Trinity Bellwoods Park

City of Toronto Lic. # STR-2009-HSDPBL Come and enjoy the Trinity Bellwoods area and our tree covered deck! Inside, enjoy our modern 2 bed renovation with a studio-style layout. All mod cons. Check In 3pm/Out 11AM. Chill on the patio for your morning coffee or evening cocktails and BBQ. Permits for street parking are available-inquire. NOTE: The stairs are narrow to the lower level, where the bathroom, laundry & 2nd bedroom are located. The bedroom has a 6 foot - 1 inch ceiling height only.

Guest favourite

Farm stay in Campbellcroft

4.99 out of 5 average rating, 170 reviews

Ganaraska Forest Getaway

Reconnect with nature at this unforgettable escape. Come and explore the Ganaraska Forest, Farm Life and Relaxation. Go mountain biking, hiking or head to Rice Lake and go fishing and boating. Enjoy living on a horse farm in the rolling hills of Northumberland County. Tour Prince Edward County for a Wine Tour. Enjoy Historic Port Hope. Go to the Cobourg Beach. Minutes from Canadian Tire Motorsport. Room to park your trailers. In the Winter ski Brimacombe or Snow Shoe on our private trails.

Guest favourite

Rental unit in Brooklin

4.91 out of 5 average rating, 240 reviews

Cozy luxury 2-bedrooms private en-suite in Whitby

Unwind in this gorgeous, modern 2 bdrms Legal /separate apartment with keyless entry. Guest can enjoyed the spacious and beautiful oasis away from home. Access to microwave, fridge, toaster, coffee maker and blender. Ignite TV premier PKG, Netflix, Air Fryer, fully functional kitchen, free 500 mbps Wifi, work desk. Close to 401, baby cot, fresh fruits. Minutes walk to the bus stop, restaurants and playground. Theatre within 10 mins , parking on premises. IT’S AN APARTMENT NOT WHOLE HOUSE

Guest favourite

Apartment in Downtown Toronto

4.88 out of 5 average rating, 140 reviews

Modern & Spacious Condo in Downtown+1 Free Parking

Welcome to your 1-bedroom modern downtown cozy retreat on a high floor! This brand new high-end skyrise is situated in the heart of Toronto's vibrant Waterfront Communities-The Island neighborhood. Here’s what you’ll enjoy: → one (1) free parking spot! → Approximately 650 sq ft / 60m² of space → High-speed WIFI → Private balcony with a great city view! → Transit score of 96! → Bike score of 96! (Rentable Bixi bikes located nearby!) → Fully equipped kitchen with a complete set of cookware

Guest favourite

Home in Bowmanville

4.9 out of 5 average rating, 125 reviews

Luxury Waterfront Bowmanville getaway home!

Experience the ultimate in refinement and relaxation on the north shore of beautiful Lake Ontario. Luxurious waterfront 5000 sq ft modern house with an incredible 180 degree view of Lake Ontario. Just 5 minutes walks to Port Darlington Marina & beach. This brand-new house with modern high-end furnishings and decor in the prestigious Lakebreeze community is something you don't want to miss. Enjoy sunrise and sunsets directly from the house. All this is only 40 minutes away from Toronto!

Guest favourite

Home in Port Perry

4.94 out of 5 average rating, 211 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.

Cottage in Bowmanville

4.86 out of 5 average rating, 129 reviews

Waterfront Beach House Oasis - All Season Hot Tub!

Welcome to the one of a kind beach house - Paradise just outside of the City! Our waterfront 4 bedroom property features unobstructed lake views, a view of an infinite horizon featuring breathtaking sunsets, kayaks, a fire pit, BBQ, and an all-season hot tub. Whether it’s staying in and enjoying a movie, relaxing on our private beach, or exploring the nearby Darlington conservation areas, our home will provide you with everything you need for the perfect urban getaway!

Guest favourite

Guest suite in Uxbridge

4.89 out of 5 average rating, 109 reviews

Beautiful&Spacious 2bdrm in the Heart of Uxbridge

Brand new rental newly renovated. 2 Bedroom, 1 bathroom, large living/dining area, cozy fireplace in master bedroom and a dedicated work space in the second bedroom. Sleeps 4; perfect for families and small groups. Private washer and dryer access, secluded outdoor patio and secured parking for up to 3 vehicles. Pet friendly. Walking distance to local restaurants, shops, movies, bowling, arena and so much more! Surrounded by biking and walking trails and local cideries.

Guest favourite

Home in The Beaches

4.99 out of 5 average rating, 111 reviews

Vacation Getaway:Heated Pool-Hottub Open 365 Days

Welcome to the Toronto Beach and to this century old home, right on the beach with a private pool and spa that is open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails (bring your own equipment) and lots of walking to be had. We decorate for for holidays, and the house has a real wood burning fireplace.

Guest favourite

Guest suite in Leslieville

4.92 out of 5 average rating, 489 reviews

Great 1 bdrm suite in Leslieville

Hotel style lower level unit with separate entrance and parking in the heart of Leslieville. NY times travel calls Leslieville Toronto's hippest place to dine, drink, shop and live. Short transit to the Beaches and both Distillery & Financial dist. We have a sweet golden retriever named Coco. She loves people and attention so if you happen to run into her in the yard while coming or going from the unit don’t be afraid but she will definitely want to say hi!

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Popular amenities for Whitby holiday rentals

Free parking on premises

Air conditioning

Stay near Whitby's top sights

Durham College9 locals recommend

Oshawa Centre81 locals recommend

Deer Creek Golf Club7 locals recommend

Sky Zone Trampoline Park55 locals recommend

Trent University Durham GTA4 locals recommend

Casino Ajax31 locals recommend

Other great holiday rentals in Whitby

Guest favourite

Treehouse in Port Perry

4.98 out of 5 average rating, 548 reviews

Treehouse on private, isolated forest (300 acres)

Guest favourite

Rental unit in Downtown Toronto

4.86 out of 5 average rating, 37 reviews

Stylish Condo Heart of Downtown

Campervan/Motorhome in Blackstock

4.82 out of 5 average rating, 112 reviews

Unique Glamping RV on 100 acres 1 hr from Toronto

Guest favourite

Apartment in Downtown Toronto

4.91 out of 5 average rating, 35 reviews

Chic 1-BR Condo | Parking included |Downtown Core

Apartment in Downtown Toronto

4.84 out of 5 average rating, 62 reviews

Heart of downtown deluxe condo close to CN Tower

Guest favourite

Home in Scarborough

4.93 out of 5 average rating, 54 reviews

- Hot Tub - Modern Getaway Home - 4Bd/3Wr

Guest favourite

Rental unit in Downtown Toronto

4.94 out of 5 average rating, 32 reviews

Stylish Condo Near CN Tower

Guest favourite

Home in Ajax

4.87 out of 5 average rating, 61 reviews

Cottage getaway in the city, for large gatherings.

Quick stats about holiday rentals in Whitby

Total rentals
1.1K properties
Total number of reviews
21K reviews
Family-friendly rentals
410 properties are a good fit for families
Pet-friendly rentals
190 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
660 properties have a dedicated workspace

Destinations to explore