Vacation rentals with a pool in Caledon

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Top-rated rentals with a pool in Caledon

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Barrie

4.92 out of 5 average rating, 90 reviews

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Our luxury home rental is located in one of the best neighborhoods in Barrie. Secluded neighborhood surrounded by forest. 5 min to HWY 400 8 min to Downtown Barrie 11 min to Snow Valley Ski resort 40 min to Blue Mountain & Wasaga Beach 25 min to Friday Harbor Resort Free WiFi-Cable & Parking Perfect home for families and large groups. Newly renovated home, with beautiful large outside area and swimming pool. Accommodates up to 9 guests. Pool open May 31 (Solar heated) Pool closes Sept.7

Superhost

Home in Aldershot

4.85 out of 5 average rating, 40 reviews

Four seasons Pool Retreat

6 bedrooms, 4 washrooms, pool, large, kitchen and family room. Mins from lake, restaurants, shopping, bars, cafes and so much more. Central, yet quiet neighbourhood. Relax and Enjoy our indoor pool available year long. Fully equipped kitchen and family room perfect for a large family. Comfortably sleep in our high-end mattresses in a thought-through decorated home. Hosting has been my passion. Super host 6 years in a row we plan to offer you the same comfort we have provided guests over years

Top guest favorite

Home in Niagara Falls

4.98 out of 5 average rating, 66 reviews

whole house with Hot tub. 5 min walk(attractions)

About this property -Require atleast 3 good reviews before acceptance - Heated underground pool with lights - 9 Person hot tub with lights and waterfalls - 2 Car parking (up to 4 cars) - 3 Cozy bedrooms (2 bedrooms with Qled T.VS) - 70 Inch smart T.V in living room with brackets to move T.V. - 2 smart T.VS in 2 of the 3 bedrooms - Fully equipped kitchen with water and ice maker fridge - 6 Minutes walk to all attractions - Complementary coffe and tea - Living room couch turns into a bed

Superhost

Cottage in Niagara-on-the-Lake

4.73 out of 5 average rating, 121 reviews

Niagara on the Lake Cottage Vine Ridge Resort

Family friendly resort getaway/romantic weekend in the heart of wine region. Located off Niagara Parkway near bike/walking trail. 10kms from historic Notl, 13kms from Niagara Falls/US border, near grocery stores, wineries & golf. Amenities on site for your enjoyment at no additional fee such as pools,kids club,multi-sport court,horseshoe pit,playground, and more. Larger pool with children splash pad (opens July Long Weekend) Heated salt water pool(opens May 17th) Rogers High Speed Internet

Top guest favorite

Apartment in Innisfil

4.97 out of 5 average rating, 39 reviews

Trendy 1 Bdrm w/Pool & Hot Tub View

Surround yourself with style in this standout & brand new space. Friday Harbour's Newest Addition. This 1 Bedroom 1 Bath unit with fantastic pool & hot tub views into the beautifully landscaped courtyard. Enjoy strolling the Promenade Boardwalk filled with Restaurants, shops, grocery, LCBO, Starbucks & more. Enjoy the views of the large marina landscaped with boats & jet ski's. The beach is serene and peaceful w/plenty of water activities to enjoy from paddle boards, kayaks, canoes & swimming.

Superhost

Condo in Innisfil

5 out of 5 average rating, 4 reviews

Luxurious 2-Bed, 2-Bath Furnished - 5 Star Resort

Spectacular view of marine and lake view! Abundant natural light. Opening to a spacious atmosphere. 1,010.00 sf, luxurious living space. 2 bedrooms equipped, 2 upgraded bathrooms. Fully furnished, all brand new furniture. Hot top available all season. Kitchen includes Island, microwave oven, toaster, kettle (all new). Dining table seats four. 65 inch Sony smart TV. Washer & dryer. Over 15 days+ require to pay utilities. Underground parking. Wifi included. long term rental available.

Superhost

Bungalow in Burlington

4.75 out of 5 average rating, 118 reviews

Sleeps 12 ADULT private hot tub pool Walk to Lake

Max 12 ADULTS* - Price varies with # of guests*. (Add correct # for price accuracy.) - Cottage Vibe, Cozy, secluded - POOL June to October - HOT TUB open all year - Ping pong/pool table - AC/furnace. NEW! - BBQ + fuel - Private entrance - Short walk to the lake - Towels: Provided (guests bring beach towels). *ADULTS ONLY. Unfenced pool = RISK to toddlers/non-swimmers. **No parties, events, unregistered guests. ** Pool & Hot Tub close @ 10:30 PM NALOXONE kit avail.

Superhost

Cabin in Niagara-on-the-Lake

4.85 out of 5 average rating, 33 reviews

Wine Country Cottage

Relax with the whole family at this peaceful place. Our PREMIUM lot would give you everything, like farm and big pool views, large deck with full sunshine in the morning, close to big pool, small salted pool, tennis court and children playground. One master bedroom, two trailer style bunkbeds bedrooms and one double sofa bed of 466 square feet are waiting for you and your lovely family. Enjoy your natural fresh air at our beautiful and comfortable resort in Niagara-on-the-lake. Thank you.

Guest favorite

Home in Niagara-on-the-Lake

4.9 out of 5 average rating, 77 reviews

Wine country Cottage 15 min drive to old Town NOTL

Welcome to our modern, spacious vacation rental, featuring a stylish interior and a private backyard pool, all situated in a safe and quiet neighborhood. Conveniently located just 15 minutes drive from the world-famous Niagara Falls and the charming downtown area of Niagara-on-the-Lake—one of Canada’s prettiest towns. Enjoy great wineries, restaurants, golf courses, and outlet shopping nearby, as well as a post office, grocery and hardware stores, and a park with a children’s playground.

Guest favorite

Home in Utopia

4.86 out of 5 average rating, 43 reviews

Serene Escape: A Nature Getaway

Escape to our secluded woodland oasis, where privacy and tranquility reign supreme. Our tastefully furnished cottage boasts modern chic décor with all-new furniture, making it the ultimate nature lover's retreat. Discover nearby attractions, including the sands of Wasaga Beach, just 30 minutes away, or hit the slopes at Snow Valley Ski Resort, only 15 minutes drive. Enjoy complete relaxation, surrounded by trees and birds, and take a dip in the pool, available from June to September.

Top guest favorite

Condo in Innisfil

5 out of 5 average rating, 9 reviews

Perfect Comfort 2 Bed ~ BBQ ~ Parking ~ Resort

A sun-drenched patio and corner unit, our space is professionally designed and located in the heart of Friday Harbour close to all attractions. Our place features: → Free secured parking for 1 car → Keyless 24HR self check-in → Over 800 ft² of space → Building features hot tub and pool → 2 stylish and separated bedrooms with comfy mattresses → Close to all Resort features - beach, harbour, golf, restaurants Only an hour north of Toronto, and 20 minutes from Barrie. Come and enjoy!

Guest favorite

Apartment in Niagara Falls

4.88 out of 5 average rating, 117 reviews

Niagara Falls Retreat: Walk to the Wonders

Welcome to my spacious lower apartment, perfectly situated within walking distance of the magnificent Niagara Falls! With three bedrooms and three bathrooms, the apartment comfortably sleeps up to six guests. Each bed features premium quality mattresses, hotel-grade linens, cozy duvets, and plush pillows—guaranteeing a restful night’s sleep. We’ve taken care of the details. Enjoy the convenience of a fully equipped kitchen, a spacious living area, and a dedicated laundry room.