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
4.99 out of 5 average rating, 100 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.

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Top Guest favourite
Cottage in Osoyoos
4.97 out of 5 average rating, 134 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

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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, 161 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

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Top Guest favourite
An open living space features a cozy light grey armchair and a circular marble-top coffee table. A kitchen island with wood accents sits adjacent to modern appliances. The dining area is highlighted by a long table with wooden stools, and a comfortable bed is visible in the background.
Guest suite in Naramata
5.0 out of 5 average rating, 46 reviews

The Dutch Touch

This stylish Studio Suite has a unique vibe. A well thought out space for you to relax and enjoy all that Naramata has to offer. You will be walking distance from Therapy (the vineyards that is) and several other local wineries. And for a slightly longer walk head to the beach or the Village of Naramata. And at the end of the day you can watch the sunset from the Island as you prepare a bite in the well equipped kitchenette. There is a memory foam King Size mattress for a good nights rest.

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Top Guest favourite
Guest suite in Naramata
4.85 out of 5 average rating, 151 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.

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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
5.0 out of 5 average rating, 34 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".

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Guest favourite
Home in West Kelowna
4.86 out of 5 average rating, 43 reviews

Pool, Hot Tub, Private Vineyard & Lake Views

Welcome to SUNVIEW! Quintessentially Kelowna B&B! Enjoy some of the most stunning lake and vineyard views from our 20’ crystal clear seasonal above ground pool, or our year-round 8 person Jacuzzi hot tub, or our spacious patio, or one of our many bedrooms. No matter which window you look out of at SUNVIEW you are sure to either see a luscious vineyard or that calming Okanagan Lake water. Minutes to some of Okanagan’s most notable wineries or a short drive to Downtown Kelowna.

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Top Guest favourite
Train in Oliver
4.99 out of 5 average rating, 129 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.

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Top Guest favourite
Home in Kelowna
4.97 out of 5 average rating, 144 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.

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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
4.92 out of 5 average rating, 123 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 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!

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Guest favourite
A well-maintained pool area is displayed, featuring clear blue water surrounded by a spacious deck. Lush greenery and flowering plants add color to the landscape, while a stunning view of the lake and distant mountains is visible in the background.
Home in Westbank
4.84 out of 5 average rating, 153 reviews

Sunny Mediterranean Influence

The perfect vacation home. Wineries, parks, beaches, views, pool, garden, grocery and liquor stores are all within a short walk or drive. Spacious layout and plenty of parking space. Property is just over an hour away from beautiful Big White Ski Hill in Kelowna and Apex Ski Hill in Penticton. And about 20 minutes away from Telemark Nordic Cross Country Skiing and Snowshoe trails right in West Kelowna. West Kelowna BL# - 8748

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Guest favourite
A serene rooftop infinity pool is highlighted, with water extending toward a scenic view of Okanagan Lake. A lounge area with stylish seating is visible nearby, creating a tranquil atmosphere for relaxation under the clear blue sky.
Hotel room in Kelowna
4.89 out of 5 average rating, 253 reviews

The Royal Kelowna® Boutique Hotel - 2Bedroom Suite

This 1170 sq ft (approx.) luxury suite in downtown Kelowna backs directly on to Okanagan Lake. The suite includes a gourmet kitchen, dining area, living room, gas fireplace, and in-suite laundry. Relax in the rooftop infinity pool and hot tub with sweeping lake views of the valley below — the perfect ending to a day of exploration around the vibrant Okanagan Valley. Nightly parking charge of $24 for a single space.

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