
Vacation rentals with a pool in Whitby
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Whitby

Total vacation rentals
Explore 20 vacation rentals in Whitby

Nightly prices starting at
Whitby vacation rentals start at G$6,271 GYD per night before taxes and fees

Verified guest reviews
Over 390 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Whitby vacation rentals include wi-fi access

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

4.7 Average rating
Whitby stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Whitby
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Bright Modern Central 2Bd2Ba Lakeview + Big Screen
Welcome to The Perch — our beloved pied-à-terre in the most vibrant city, Toronto. Comfort and design define this bright, creative, cozy, curated, and clean space. Enjoy our perch above it all! We have chosen everything within these walls based on how it makes us feel. The floors feel good on bare feet. The mattresses and pillows inspire sleep. Sheets and towels are luxuriously soft. The lighting is an ode to mood. Made with love, shared with love. See more @ ThePerchToronto on socials

Bluffs Private Suite | Pool | 25 Min to World Cup
Enjoy this beautiful, sun-filled private suite with a large pool and secluded fenced yard in a safe, upscale and serene forested neighbourhood where deer and other wildlife are often spotted. A short walk to public transit (TTC, GO Trains), shopping, restaurants, parks and scenic trails to the top of the Bluffs with breathtaking views of Lake Ontario. Hike down to the waterfront trail to Bluffers Park Beach and Marina. Fast Fibre Internet. Parking for multiple vehicles. EV charger (Tesla/J1772).

Treehouse on private, isolated forest (300 acres)
You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

Custom Luxury 2BR | Marble Pool | Games | Fire Pit
Welcome to our brand new, luxury modern suite located in a quiet, family-friendly neighbourhood. Mins to HWY401/DVP, TTC. Featuring: ✓ Luxury Finishes Throughout ✓ Heated Swimming Pool (seasonal April - Oct) ✓ Dedicated Workspace ✓ Washer/Dryer ✓ High-Speed WIFI ✓ Smart TV with Netflix, Prime & sound system ✓ Keyless Entry (24/7 Self Check-In) ✓ Outdoor BBQ, seating and fire table This upscale oasis is truly the perfect space for business travellers, young professionals & couples alike!

Modern Downtown Loft with Private Garden
Welcome to this modern and spacious (765 square feet / 71 square meters) one bedroom condo loft in the prestigious Verve Residences and Lofts located minutes away from Yonge & Bloor, Yorkville, the Village, Yonge & Dundas Square, the University of Toronto, two Subway lines and countless other Toronto landmarks, museums and restaurants. This condo loft features luxurious finishes & decor, a king size bed, as well as a rarely found private entrance and garden in the centre of the city.

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.

Stylish 1BR on Toronto’s Harbourfront
Discover the ultimate Toronto experience in our fabulous 1BR condo on Yonge Street, right in the heart of downtown. My husband Saeid and I are proud to host you in this vibrant space with unbeatable access to the Harbourfront, CN Tower, and all of Toronto’s top attractions. Enjoy stunning city views from our thoughtfully decorated condo, featuring a fully-equipped kitchen and a cozy bedroom. Plus, access to great amenities for your comfort. Your Toronto adventure begins here!

Canadiana Downtown Condo w/King Bed + Free Parking
We pride ourselves on delivering a 5 star hotel-like experience!! Condo offers FREE PARKING inside of the building. Whether you're in town for a concert, sporting event, business trip or just to catch some local touristic hotspots, you'll be within 8min walk of your destination. Condo is attached to Scotiabank Arena + Union. The condo has a King Bed and 2 Queens to comfortably accomodate your large group. Book now there's a surprise waiting inside!

FIFA: 4BR: 365 Days Open- Heated Pool & Hot Tub
A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

Casa Meya - Toronto Poolhouse Villa
Casa Meya : This exclusive modern and fully renovated Villa at 2024. Upper Floor : Beautiful Kitchen with brand new Bosch and LG appliances. An Island to host 4 guests plus a 6 seats Dining Table. 85" Samsung QLED TV to watch included Premium TV channels. Master Bedroom ( KING ) - 65" TV / 1st Bathroom 2nd Bedroom ( QUEEN ) - 42" TV / 2nd Bathroom Lower Floor : 3rd Bedroom ( QUEEN ) - 42" TV / 3rd Bathroom

Downtown Markham Unionville
Newer Condo, 2 bedroom entire unit, fully furnished with everything you need as if you were at home; steps to Historic Unionville, Cineplex with VIP Cinema,, Famous Ruth's Steak House, Good Catch Creole Seafood Place; Japanese Restaurant, Go-for-Tea Fusion, Historic Rouge Valley, Great Dining, Pubs, theatre, shopping Malls

Pool Now Open | Executive Suite | 3PM checkout
🏊 Pool NOW OPEN! Early check-in | Rare 3PM checkout. 600 sqft executive suite built for remote workers & business travellers. 1.5Gbps fiber, 24” monitor, office chair & private walkout entrance. King bed + sofa bed, private shower, full kitchen & gas fireplace. Total indoor privacy.
Popular amenities for Whitby rentals with a pool
House rentals with a pool

Walk-out Luxury basement with Gym & Theatre

Horse Farm Luxury Estate

Modern home away from home in Courtice

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Luxury 4BR Designer Retreat with Heated Wave Pool

Toronto Pool Retreat

The Ridge Roost - Uxbridge Township

Luxury Toronto Retreat -Pool, Lush Yard & Garden
Condo rentals with a pool

2 bed Near FIFA BMO/CN Tower/ Scotia/Free Parking

FIFA 2026| 15 Mins to BMO FIELD & Free Parking

“Modern 3BR Condo w/ Free Parking | 1 Min to 401”

Boho HighRise, Heart of City 2Bed2Bath w Pool/Gym

Cozy, Modern & Spacious Condo In Downtown Toronto!

47F Sub-Penthouse | Lake + Skyline | Private Patio

Welcome to Toronto. We hope you enjoy your stay!

Boutique 1BR Downtown | Pool•Hot Tub•Sauna•Parking
Other vacation rentals with a pool

Charming 2BR Condo in Riverdale

270° CN Tower View - Stunning 3BR - Free Parking

6ix Hideaway | Skyline Views | Pool•Hot Tub•BBQ

Beautiful High Rise View Condo W/Pool&Free Parking

The Princess Suite: Cozy Condo in Old Town Toronto

Waterfront community ideally for long stays

Stylish 1 BDRM/ GYM/WIFI/ Laundry

Luxe Cozy Downtown 1BR Condo w/Views&Free Parking
When is the best time to visit Whitby?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$15,051 GYD | G$21,740 GYD | G$22,785 GYD | G$16,096 GYD | G$18,813 GYD | G$22,785 GYD | G$31,774 GYD | G$37,836 GYD | G$16,096 GYD | G$17,141 GYD | G$16,723 GYD | G$16,305 GYD |
| 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 |
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Union Station
- BMO Field
- The Danforth Music Hall
- Downsview Park
- Harbourfront Centre
- Toronto Eaton Centre
- Exhibition Place
- Toronto Zoo
- Scarborough Town Center
- Nike Square One Shopping Centre
- Trinity Bellwoods Park
- Massey Hall
- Enercare Centre
- Casa Loma
- Yorkdale Shopping Centre
- York University
- Coca Cola Coliseum
- Sheppard–Yonge Station
- Dufferin Grove Park





