Vacation rentals with a pool in Caledon

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Cozy Fall HotTub Getaway - Headwaters Retreat

Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

The Penty: Luxurious Penthouse with Pool, Hot Tub

Welcome to our modern & luxurious corner penthouse! Stylishly designed with lush greenery and upscale touches, this bright space offers comfort, elegance, and a relaxed tropical vibe. Take in stunning panoramic city views and unwind with premium amenities including an outdoor pool, hot tub, and steam room sauna. Just a 15-min drive to downtown. Public transit at the doorstep. 10-min drive to Rogers Stadium. Perfect for discerning guests seeking an elevated stay in Toronto’s vibrant urban core

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

Hydropool Spa HotTub/Bowling Alley/Patio/BBQ/Games

**Hydro spa hot tubs are open! **Fully licensed Airbnb - no hassle during your stay! **Stunning Interior decor, guests'' unique experience **Unmatched amenities in town! you must check out the amenities' pictures **Corner unit with stunning city views ** Location! Heart of Kitchener, centrally located to grocery stores, hip restaurants/bars, cute local shops, parks & happening city life ** 3 mins walk GO Station. 126 Weber St. W **Across Goo-gle Head office w/ LRT rail at doorsteps

Upscale Spa Getaway w/ Private Sauna

Welcome to our most Dramatic, Romantic Spa Getaway Suite! Reconnect with your loved one in our incredible professionally designed to play with all your senses PH suite, this escape will melt away all your woes and leave you feeling refreshed and relaxed! Cozy up to any of 3 fire elements and cleanse your soul in your own private in suite infrared Sauna! Cook up a gourmet meal in our fully equipped kitchen and brand new Weber BBQ! Catch some rays in our pool and hot tub, NOW OPEN!

Luxury Oasis!! Heated Pool☆Sauna ☆Hot tub☆4Patios

Featured in Forbes "5 Charming Towns In Ontario" A cottage which has more to offer than a resort. Be it Summer or Winter! Indulge in the longest waterfront view you've ever seen from a cottage, nestled atop a hill. With an array of luxurious amenities, including heated pool, sauna, hot tub, gym, outdoor kitchen, fire pit, and multiple patios, this retreat exceeds all expectations. 4 family rooms, offices, a chef's kitchen, 10-person dining area, your every need is catered to.

The Captain's Cottage at Willow Pond

You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

The Fox's Retreat - A Cozy Cabin for Two

Escape to this open concept cabin in Flamborough, Ontairo. Get to Flamborough Downs Casino and Racetrack, McMaster University, African Lion Safari, Valens and Christie's Conversation Areas, Westfield Heritage Village, and Dundas Waterfalls and multiple Golf Courses in under 15 minutes. Modern amenities provide all the comforts necessary for a relaxing stay, quiet remote work, or a unique space to get wedding ready.