Holiday rentals with a pool 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

'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.

Beautiful, Private Home with Pool and Hot tub

Private Vacation Haven, Resort Style Home Just steps away from Osoyoos Golf Course, Fairwinds Guest Suite is a brand new walk out featuring two luxurious queen bedrooms, each with it's own private ensuite. This beautiful vacation home boasts a pool, hot tub, full kitchen, living room, gym and walkout patio with bbq. Perfect choice for: -Golf Adventures -Wine Tours -Beach & Boat Lovers -Ladies Retreats -Romantic Getaways -Adventure Activities Owners live upstairs in a fully separate space.

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".

Paradise on the River Cabin Retreat -Seasonal Pool

Plenty of space to explore, enjoy, and relax. You can raft down the river, enjoy the pool, trampoline, barbeque, have a campfire, play games. Golfing is located across the street. Close to the Trans Canada Trail. Covid safe, special cleaning procedures in place, social distancing, no contact check-in process. If you'd like to book a longer stay there is a weekly special 15 % off, monthly special 40% off. 11 acres of amazing views, and fresh air make this truly a paradise by the river.

Lakeshore Villas Resort - Lake Front Condo

The lake front condo is a 3 bedroom / 2 bathroom 1380 sq. ft home located on the quieter side of Osoyoos lake. With sweeping views of the lake from the two large balconies with Weber BBQ, dining, and lounge seating. Condo is located across the street from the beach, and outdoor heated pool, hot tub, and gym. The Pool is open from May long weekend to Thanksgiving. Posted rates from October through March are based on 1 or 2 guests, additional cost for more guests. Snowbirds Welcome

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.

3BR Cottage on Osoyoos Lake w/ Pool + Hot Tub.

Enjoy a relaxing stay at one of the best locations at The Cottages just steps away from Osoyoos Lake! Drink your morning coffee and evening wine in the beautiful sunroom or spread out in the open concept kitchen and living area. Take full advantage of the nearby private beach, clubhouse, pool, hot tubs and gym. Located 15 mins outside of Osoyoos and just minutes to some of Canada's best wineries surrounding nearby Oliver, you're sure to make lasting memories.

The Wine Country Villa with Pool and 3 Acres

Hello, and welcome to our beautiful Oliver villa, private pool. The villa is located on 3 acres of privacy, all to yourself, and close to many wineries and orchards. You’ll love my place because of the pool, the vineyard views, the outdoors space and the mountain views. My place is good for golfers, wine-o's, athletes in training, people wanting to get away from it all, couples, families with kids and will consider pets. Let us know how we can help.

Serenity Home In Osoyoos

Enjoy the cottage life in beautiful Okanagan wine country. This peaceful home and the surrounding vicinity will have everything you ever wanted in lake gateway. The Osoyoos Cottages offers a beautiful private lake w/ volleyball courts, a pool/playground that kids will love and a gym for all your workouts. Or take a step-back and enjoy your lazy days on the dual deck set-up at the Serenity Home. We welcome you and your family to come stay in our home!

Osoyoos lakefront paradise

Bring the whole family to this great place with lots of room for fun. 1383 sq. ft. top floor elevator access condo. Stunning lake and mountain views, three bedrooms, two bathrooms, two patios, in suite laundry, 10' ceilings, A/C, Internet, Optic Apple TV, BBQ, fully furnished, fully equipped, Pool (May to Oct), Hot tub (May to Oct), Gym, steps to lake and private dock, boat slips available to rent. AVAILABLE FOR SNOWBIRDS FOR WINTER 2025/2026.

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.