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Holiday rentals with a pool in Okanagan-Similkameen

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Top-rated rentals with a pool in Okanagan-Similkameen

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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
5 out of 5 average rating, 79 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, 125 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
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 out of 5 average rating, 34 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.

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, 153 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 Kelowna
4.96 out of 5 average rating, 125 reviews

Waterfront Oasis with Pool, Hot Tub, Pet Friendly

Charming Kelowna Waterfront Retreat: Your Ideal Escape! Set along scenic Mission Creek, framed by majestic willows, enjoy true waterfront access; launch a kayak from the backyard and reach Okanagan Lake in under 100 metres by kayak. Inside, enjoy soaring vaulted ceilings, a cozy fireplace, and serene willow views. Relax in the hot tub, swim in the pool, or stroll to nearby beaches and the Greenway. Perfect for families, couples, and professionals, with exclusive use of all amenities. BL4094880

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
4.85 out of 5 average rating, 107 reviews

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.

Top guest favourite
Guest suite in Naramata
4.85 out of 5 average rating, 144 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.

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
5 out of 5 average rating, 24 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".

Top guest favourite
A charming outdoor area is illuminated by warm string lights, casting a gentle glow over the space. Surrounding trees and flowering plants add a natural ambiance against the twilight sky, with the cozy silhouette of the caboose visible nearby.
Train in Oliver, BC V0H 1T5 Canada
4.99 out of 5 average rating, 114 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
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
4.91 out of 5 average rating, 447 reviews

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

Top guest favourite
Guest suite in Peachland
4.88 out of 5 average rating, 295 reviews

Poolside Retreat, private and tranquil mini resort

Welcome to our spacious, bright walk-out suite with high ceilings, situated on the lower level of our house, where we reside in a quiet Peachland setting, adjacent to farmland. Enjoy our seasonal pool, outdoor games area, badminton, and peaceful nights with no highway noise. In summer, soak up the sun; in winter, curl up by the cozy fireplace, watch a favourite movie on Netflix or Amazon or play a board game. Great for mature adults and families.

Guest favourite
Guest house in Oliver
4.96 out of 5 average rating, 27 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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