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

Guest suite in Naramata

5 out of 5 average rating, 15 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

Tiny home in Penticton

4.95 out of 5 average rating, 139 reviews

'Suite Skaha Retreat' Modern Pool House (licensed)

This self contained, modern, renovated 'pool house' is a city inspected, licensed (#00112755) suite that offers a private setting, beautiful landscaping, including a real palm tree,🌴 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.

Top guest favourite

Apartment in West Kelowna

4.97 out of 5 average rating, 77 reviews

“The Flock” @ Copper Sky

Enjoy a relaxation getaway in the heart of the Okanagan! The Flock @ Copper Sky offers high end amenities for you and your family to make the best of their vacation. Take a dip in the pool, work out in the gym, shoot some hoops, or try your hand at pickleball. Copper Sky has it all! We are proud to be located on Westbank First Nation! Book your vacation worry free! The Flock is exempt from BC's Short Term Rental ban. Refunds will be provided in the event of wildfire restrictions! BL#20240540

Guest favourite

Apartment in West Kelowna

4.96 out of 5 average rating, 109 reviews

Central Okanagan Condo - Lake View Hot Tub-Gym

Your semi-rural area REQUIRES A VEHICLE! There's lots to see and do! Enjoy LAKE & MOUNTAIN VIEWS plus **FREE** AMENITIES like..... * POOL * HOT TUB * GYM * PUTTING GREEN * BASKETBALL * TENNIS * BADMINTON * FOOSBALL * PICKLEBALL * PING PONG You'll be staying at Copper Sky resort-style condos located smack dab in the centre of the Okanagan Valley. A vehicle is a MUST so you can really enjoy the Okanagan; just like the locals! Your hosts, Robert and Sandi, WELCOME YOU !

Guest favourite

Apartment in Kelowna

4.91 out of 5 average rating, 125 reviews

Downtown Lakeside Resort Getaway!

No Cleaning Fee. Easy self check in. Well appointed, this 2 bed/2 full bath downtown oasis sleeps 6 comfortably If you are looking for markets, family fun activities, more than 30 wineries, concerts, plays and more, you've come to the right place! Discovery Bay is Kelowna's luxury resort in the heart of Downtown. Steps from breweries, wineries,shopping and amazing restaurants, you may not need your vehicle at all 1 hr drive from Big White and Silverstar at a fraction of their room price

Top guest favourite

Guest suite in Naramata

5 out of 5 average rating, 35 reviews

Naramata Dreaming - Poolside Panoramic Escape

Sounds like a perfect getaway! The Naramata Dreaming - View Suite With a Pool offers a sleek, modern vibe with direct deck access to a heated plunge pool and lounge chairs—ideal for soaking in those stunning views. Our second suite -Naramata Dreaming - Large View Deck Suite steps it up with cozy conversation couches, a dining table, and a BBQ for a relaxed outdoor experience. Both suites scream stylish comfort, but the pool access in the first one sounds like a dream. No children under 11

Top guest favourite

Guest house in Penticton

5 out of 5 average rating, 15 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

Guest suite in Kelowna

4.93 out of 5 average rating, 357 reviews

That Modern 70s Suite - Poolside Retreat

* LEGALLY LICENCED BY THE CITY OF KELOWNA- license number listed* Your reservation won't be cancelled due to the new legislations starting in May 2024 Welcome to the Garden Suite -This is a perfect getaway spot to the Okanagan! This is not your Grandma's house! Updated and modern 70's style suite - this space will take you back a few eras Enjoy a refreshing dip in the pool and a chilled glass of something local in Summer. Private garden entrance studio suite with private bath.

Guest favourite

Guest suite in Peachland

4.94 out of 5 average rating, 68 reviews

Fairhaven Suite-Pool & lakeview

Spectacular lakeview, 1100 sqft suite and huge 800 sqft private deck! Perfect for up to 5 adults (5th person additional charge). ⁕primary bedroom with ensuite bath ⁕open concept living/dining/kitchen area ⁕second sitting room (with sofa bed) ⁕second bedroom with queen bed and second bathroom ⁕WIFI ⁕washer/dryer ⁕propane BBQ for your private use. The seasonal pool with deck & pergola is shared with other guests. *Pool is heated and open May 16-September 28, 2025*

Superhost

Apartment in West Kelowna

4.8 out of 5 average rating, 201 reviews

Amazing Cove Lakefront Resort Full Condo !!

Beautiful Lakefront / Poolside Resort ***Fully licensed with the City of West Kelowna and the new STR regulations, see registration number below*** Guests have access to all amenities including: Swimming Pool (With Bar) / Kids Pool / Water Slide / Gym / Putting Green / Lake & Beachfront / Hot Tubs / Underground Garage / and Restaurant Located next to the Cove is Gellatly Tree Nut Farm - a popular walking path and heritage site - we recommend checking it out 😊

Top guest favourite

Guest suite in West Kelowna

4.94 out of 5 average rating, 234 reviews

Wine Trail: clean & bright w private beach (#9656)

Large, clean, & bright suite with private entrance, king-sized bed, and granny-style kitchen. Located on the WK wine trail between Quail's Gate & The Hatch. A quick 5-minute drive to over 8 additional award-winning wineries (including the stunning Mission Hills winery), multiple hiking trails, and the Gellatly Bay lake front area (boat launch, walking path, sandy beach). A short 7-minute drive to the bridge to go to downtown Kelowna. Private beach available.

Guest favourite

Home in Summerland

4.98 out of 5 average rating, 51 reviews

Stunning Lakeview Vineyard with Private Pool

This rare gem boasts a stunning lake view, its own vineyard, a private pool & hot tub, nestled in between rolling hills on a quiet country road - the quintessential Okanagan experience. Whether you are here for a wine getaway with friends, family outings, or group yoga getaways, this home is perfectly laid out and located for you to enjoy all the South Okanagan has to offer. Perfect for groups of up to 8 guests. District of Summerland business license #7391.