Holiday rentals with a pool in Okanagan-Similkameen

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Top-rated rentals with a pool in Okanagan-Similkameen

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

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Top guest favourite

A serene outdoor space features a swimming pool with a basketball hoop, surrounded by comfortable lounge chairs. The vibrant sunset casts a warm glow over the water, offering expansive views of Okanagan Lake and the distant hills.

Guest suite in West Kelowna

Stunning Lakeview Hot Tub,Pool Sauna, Cold Plunge

Breathtaking lakeview mini-resort with spectacular views from almost every room, Enjoy a complete outdoor kitchen, heated pool with Waterslide( open May long weekend till September 30), traditional outdoor sauna, 6 person+ hot tub (open year around) , indoor infrared sauna, gym, air hockey, ping pong table, COLD PLUNGE foosball table, and trampoline. All bedrooms have king size beds. There are 3 full bathrooms and a laundry room with a washer and dryer. Our home is steps away from wineries.

4.99 out of 5 average rating, 103 reviews

Top guest favourite

Cottage in Osoyoos

Relax in Luxury at the Cottages

This luxurious, rancher style home features an open concept living space in one of the most convenient locations at the cottages! Enjoy your stay in a comfortable, spacious home with a large living space and large bedrooms. Smart TVs in every room with premium cable & Netflix included! Huge private patio to relax on and a sunroom to enjoy. Two paddle boards included! Beach wagon, beach chairs, beach tent. Less than 1 minute walk to the pool & park, 3 minutes to the beach. Double garage included

4.97 out of 5 average rating, 135 reviews

Top guest favourite

A serene outdoor setting features a large heated pool with lake views, surrounded by well-maintained greenery. A wooden table holds a bottle of sparkling wine, five glasses, and decorative candles, inviting relaxation. The mountains frame the background, adding to the peaceful ambiance.

Guest suite in West Kelowna

Bright, Airy Suite w/Pool, Lake & Vineyard Views

Imagine opening french doors to a large, quiet pool with stunning lake & vineyard views. Set your own pace from this newly-renovated lower-level, walk-out suite with two comfy bedrooms, one bath (shower), full kitchen, indoor & outdoor seating areas & in-suite laundry. Best for those seeking a calm setting with everything at their fingertips. Steps to your first winery, mins to the water. (Pool June - Sept) A home-away-from-home in the off-season with discounted weekly/monthly rates. Lic. #9159

5.0 out of 5 average rating, 100 reviews

Guest favourite

A scenic waterfront view is presented from a balcony featuring comfortable seating and a dining table. Trees with autumn foliage frame the serene lake, while mountains rise in the distance under a clear sky.

Apartment in West Kelowna

3 Bdrm Wine Country Luxury Waterfront Condo

Stunning views, beautiful grounds, this waterfront condo located along the Westside Wine trail, walking distance to world-class wineries and minutes to all the amenities. 3 bedrooms 2 full baths and fully equipped kitchen. Comes with an underground parking stall and elevator or stair access from the parkade up to the unit! Outdoor pool, hot tub, and private beach. Oh, did we mention the gym, cardio machines, & weights. please note Pool and Hot tub open May long weekend to Thanksgiving weekend.

4.85 out of 5 average rating, 115 reviews

Top guest favourite

Guest suite in Naramata

Naramata Vineyard . Heated Pool . Walk to Wineries

Welcome to your vineyard escape! Our bright, comfy 1,500 sq. ft. suite is tucked beneath the vines and just a lazy stroll from amazing local wineries. This property is not suitable for children under 12. You’ll have two queen bedrooms (one private, one semi), a full bathroom, and a spacious open area with a living room, dining area, and kitchenette. Sprawling patios, a BBQ, pool, and vineyard views. We’re right upstairs if you need anything—otherwise, it’s your little piece of paradise.

4.86 out of 5 average rating, 152 reviews

Guest favourite

Holiday home in Penticton

Hotel with Private Large Home

Master bedroom with two queens, bathroom & walk in closet Two bedrooms with single Queens each Main bathroom with tub Residential kitchen Dining room Living room 2 x 50 inch tv’s Deck with seating and bbq House sleeps 8 comfortably. Pub/liqour store right beside plus close to all shopping centres. Quiet area 1.5km from skaha beach. Bus stop next door. Business name: Apple Tree Inn House is separate from the Inn. Pool shared with property. Seasonal pool. Property number: 250-492–3029

4.83 out of 5 average rating, 100 reviews

Top guest favourite

An outdoor pool is illuminated in soft blue light, surrounded by trees that create a serene backdrop. The evening sky is visible, with hints of darkness mixed with distant city lights. Lounge chairs can be seen near the edge of the pool.

Home in Kelowna

Wine Trail Retreat.

Unwind at this welcoming family home. The suite was lovingly built with repurposed cabinetry, worry free flooring, comfort minded details throughout the space giving a charming feel. Kids welcome. Enjoy walks in the woods, lake and city views. The suite is located on a hillside with attractions in every direction. Enjoy the quiet street, wide open spaces and warm sunrises. Although wineries, shops and restaurants are only five minutes away, the area feels peaceful and secluded.

4.98 out of 5 average rating, 103 reviews

Top guest favourite

A modern outdoor area features a solar-heated infinity pool surrounded by lounging chairs. A shaded seating area with comfortable furniture and elegant drapes is visible. Scenic views of the surrounding landscape are complemented by greenery in the background.

Guest house in Penticton

Wine with a View

We are delighted to share with you our little piece of heaven. Spectacular views of Okanagan Lake and rolling vineyards from your own balcony. Tastefully decorated with modern furniture, art work and luxurious bedding. Little extras include fireplace, king size bed, AC and plush robes. Shared outdoor solar heated infinity pool available seasonally. Located between Penticton and Naramata close to the KVR bike trail. Complimentary bottle of wine on arrival. Enjoy your "Wine with a View".

5.0 out of 5 average rating, 35 reviews

Top guest favourite

Train in Oliver

Runaway Express Coach

Our little caboose seems to have escaped the Kettle Valley Rail Line; offering a slice of peaceful, mountain retreat. The passengers whistle with pleasure as they rest in the queen size luxury bed. Tucked away amongst the rocks, pines and burbling creek; the cute woodstove brings it together as a cozy place for dreaming. In the past two years the railroad tycoons staying here have always rated us 5 stars on cleanliness. Includes business ready wifi speeds of 350 mbps.

4.99 out of 5 average rating, 133 reviews

Top guest favourite

Home in Kelowna

Waterfront Oasis with Pool, Hot Tub, Pet Friendly

Waterfront Retreat on Mission Creek with Pool & Hot Tub. Launch a kayak from the backyard and reach Okanagan Lake in under 100 metres. Relax beneath majestic willow trees, unwind in the handcrafted hot tub, cool off in the pool, or gather around the firepit. Inside, enjoy vaulted ceilings, a cozy fireplace, and a fully equipped kitchen. Family- and pet-friendly, minutes from beaches, the Greenway, wineries, golf courses and downtown Kelowna. BL409488.

4.97 out of 5 average rating, 144 reviews

Top guest favourite

A cozy balcony area is depicted, featuring a comfortable seating arrangement around a fire table. In the background, the horizon reveals a colorful sunset over the water, with the reflections mirrored in the calm water's surface. Lush trees provide a serene setting.

Apartment in Kelowna

Downtown Lakefront Condo - Amazing Views BN82776

Business License Valid Through 2026 Indoor and outdoor pools 2 bedroom (2nd bedroom converted from a den) 1 bathroom with standing shower Updated kitchen with stainless steel appliances and granite countertops 2 balconies facing east and west Wifi & Telus TV with Crave & HBO + Chromecast Laptop friendly working space with monitor Washer and dryer Coffee + Espresso Machine 1 underground parking space Central location in Kelowna's downtown waterfront

4.92 out of 5 average rating, 488 reviews

Top guest favourite

A private pool area features a turquoise-blue swimming pool surrounded by a spacious concrete deck. Comfortable seating is provided with blue lounge chairs and a cozy outdoor sofa set. Lush greenery and colorful flowers enhance the garden-like atmosphere.

Home in Westbank

Beautiful suite with pool (open till Oct 1st)

Hi there My husband Darrel and I live with our four kiddos, 2 energetic boys aged 11 and 9, and our beautiful girls aged 4 and 1, with our sheltie on a beautiful and quite street in West Kelowna. My husband is Canadian and has lived in Kelowna for over 20 years so can help you with directions, fun activities to do and much more. I am from the Netherlands (can speak Dutch) and have been in Canada 14 years now. Absolutely love it!

4.92 out of 5 average rating, 129 reviews