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Holiday rentals with a pool in Okanagan-Similkameen

Find and book unique homes with a pool on Airbnb

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
4.99 out of 5 average rating, 98 reviews

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.

Top Guest favourite
Cottage in Osoyoos
4.97 out of 5 average rating, 131 reviews

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

Top Guest favourite
A vibrant palm tree is positioned beside a spacious swimming pool, reflecting the clear blue sky above. Lush greenery lines the perimeter of the pool area, with mountains visible in the background, creating a serene outdoor environment for relaxation.
Tiny home in Penticton
4.95 out of 5 average rating, 158 reviews

'Suite Skaha Retreat' Modern Pool House (licensed)

This self contained, modern, renovated 'pool house' is a city inspected, licensed suite that offers a private setting, beautiful landscaping, pool and many sitting areas to enjoy the property. Located steps from Skaha Lake, below Skaha Bluffs Provincial Park and walking distance to Painted Rock Winery. Enjoy our kayaks and SUPs as well as a shed to lock your bikes/gear. Here's your opportunity to enjoy the Okanagan lifestyle and all it has to offer. City Lic#00112755, BC Permit #H210316582

Top Guest favourite
Home in West Kelowna
5 out of 5 average rating, 18 reviews

Villa Royale with Pool and Hot Tub

Discover your perfect West Kelowna escape—a modern retreat with a sparkling pool, hot tub, and sweeping views. Designed for both relaxation and entertaining, this home boasts an open-concept layout, a gourmet kitchen with a pizza oven and BBQ, and a chic dining space. Challenge friends at the poker table or simply lounge poolside in total comfort. With its blend of contemporary elegance and unique charm, this upscale getaway sets the stage for unforgettable gatherings and serene moments alike.

Top Guest favourite
Guest suite in Naramata
4.85 out of 5 average rating, 148 reviews

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.

Top Guest favourite
Cabin in Osoyoos
5 out of 5 average rating, 19 reviews

Osoyoos Lake View | 2BR Hot Tub Retreat

🌅 Your Private Mountain Retreat with Breathtaking Views Wake up to pastel sunrises over Osoyoos Lake, slip into your private hot tub as a billion stars appear overhead, and drift off knowing you have 3 gated acres of complete privacy. This is the mountain escape couples and families dream about—peaceful, romantic, and just minutes from everything Osoyoos and wine country have to offer. You're tucked away in the mountains—far enough to feel truly secluded, yet just 20 minutes from Osoyoos.

Top Guest favourite
An indoor pool area features a turquoise pool surrounded by a smooth tile deck. Two rattan chairs are positioned nearby, complementing lush greenery that adds a serene touch. Sunlight streams through large glass block windows, illuminating the space and providing views into an adjacent cozy bedroom.
Guest suite in West Kelowna
5 out of 5 average rating, 64 reviews

Suite with private indoor pool and sauna

After a day of wine tasting and hiking, relax in your private infrared sauna, then cool off with a swim in the pool surrounded by tropical plants. Enjoy stunning views of Okanagan Lake and mountains from your private patio nestled among the pines. Downtown Kelowna is just a 10-minute drive away for local shopping and dining. When you're ready for rest, fall asleep to the peaceful sounds of nature on this quiet side street. Note: construction next door, noise may occur between 7am and 8pm

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.
Guesthouse in Penticton
5 out of 5 average rating, 32 reviews

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".

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 West Kelowna
4.92 out of 5 average rating, 120 reviews

Beautiful suite with pool (open till Oct 1st)

Hi there My husband Darrel and I live with our four kiddos, 2 energetic boys aged 10 and 8, our beautiful little daughters who are 4 years old and 1 month and with our sheltie and kitty 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 10 years now. Absolutely love it!

Top Guest favourite
Train in Oliver, BC V0H 1T5 Canada
4.99 out of 5 average rating, 125 reviews

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.

Top Guest favourite
Home in Kelowna
4.96 out of 5 average rating, 142 reviews

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.

Top Guest favourite
Guesthouse in Oliver
4.95 out of 5 average rating, 41 reviews

Cozy Stay in Wine Country

Welcome to your relaxing retreat in the heart of Canada’s wine country! SoOak Cottage is Nestled in Oliver, this cozy stay offers the perfect blend of comfort and adventure. Steps from award-winning wineries and two world-class golf courses, it’s ideal for couples. Enjoy a private hot tub, fire pit, and access to a shared pool and Putting Green. Whether you’re sipping local wine or teeing off in the sun, your perfect getaway starts here.

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