Holiday rentals in Olalla

The Second Breakfast Hideaway

Second Breakfast Hideaway is your own little slice of Middle-earth. This cozy, halfling-inspired retreat offers a charming escape with its round door, rustic details & cozy, nature-filled surroundings. Whether you’re an Hobbitier at heart or just seeking peace, this enchanting whimsical hideaway is the place for you. It’s the perfect spot enjoy a second breakfast or curl up by the fire. Located just minutes from local attractions, it's the ideal place to unwind and embrace your inner halfling.

Blush Bliss – Herrera Vineyard Estate Home

Enjoy an amazing vacation at a picturesque countryside retreat. It’s the perfect place for outdoor enthusiasts and wine lovers to reconnect with nature. Relax on the patio while admiring the gorgeous view of the mountains, relax in the sunroom, and access fantastic wineries, cideries, & a distillery a short drive away. The property is shared with a second vacation home, separated by a large courtyard to ensure each guest's privacy. For package rental options, go to: airbnb.ca/h/hererrapackage

Beautiful Skaha Lake View Studio

Welcome to your perfect getaway in the heart of the Okanagan Valley This new, stylish studio offers a spectacular unobstructed 180-degree view of Skaha Lake, surrounding mountains, and vineyard. The large studio is modern in design and decor, has a king sized bed, sitting area, well equipped kitchenette.and a large private outdoor living space. Whether you're enjoying your morning coffee or unwinding with a glass of local wine on your patio in the evening, this view will leave you in awe.

Cawston Farm Stay

Unwind in a private suite for two adults, surrounded by orchards, vineyards, and friendly animals. Enjoy modern comforts with rustic charm. Close to cafés, restaurants, grocery stores, and shops—plus top wine and cider tastings, live music, and outdoor adventures in the Similkameen Valley. Traveling with children? Let us know—child accommodations may be available upon request. Unfortunately, we are not able to accomodate pets. As an operating farm with livestock, it is too much of a risk.

Pincushion Cottage

Our charming rural cottage is tucked into the mountainside, surrounded by the natural beauty of sage and mountain flowers, with spectacular views in all directions. The Pincushion Mountain hiking trail leading to Keremeos Columns Provincial Park is literally out the front door. Minutes away from the fruit stands, wineries, and cideries of the Similkameen Valley wine region, the cottage is fully equipped for you to enjoy cooking up your own tasty dishes from fresh local organic ingredients.

Juccuzi & Stars 2 Bed Home on 1/2 Acre Okanagan

Take it easy at this unique and tranquil getaway on 1/2 acre!! Jacuzzi in the stars. Majestic Mountains surrounding Vineyards and Fruit Stands. 7 Lakes all within an HR drive. Essentials Provided. Best Rates for the area. Peachland Zipline, Loco landing Penticton Watersport Rentals at most lakes. Famous spotted lake is Cool and fishing on the dock is popular at yellow lake, also known for ice fishing in cold winter months. Fun for All! The Home has installed filter for drinking & cooking

Similkameen Sunset Suite

Brand-new 2-bedroom suite on a peaceful riverfront orchard with beautiful mountain views. Enjoy nearby walking trails, great river swimming spots, and easy access to local lakes, wineries, fruit stands, and more. You’re also just a short drive from both Apex and Mount Baldy ski hills. The suite includes a heat pump and AC for year-round comfort. It’s still new and kept simple - minimal décor, but fully equipped with TV and Wi-Fi. Clean, comfortable, and perfect for a relaxing stay.

B & B Minute's walk to Lake

Escape to our peaceful garden retreat, only a minute’s walk from Skaha Lake. Perfect for a weekend getaway or short stay, it offers comfort, privacy, and a quiet connection to nature. Relax in the garden, explore local attractions, and enjoy the beauty of the Okanagan—all just moments away. Start your stay with a little treat! We provide complimentary muffins upon arrival as a warm welcome to help make your stay even more enjoyable. Municipal License - NOT REQUIRED

The Emerald Dome

Disconnect from the hustle and bustle of life and reconnect with nature in this peaceful dome located in Kaleden, BC. The dome is on 10 acres and borders 350 acres of crownland to explore. Includes a hangout area with a fire pit, patio table and chairs, solar lights, and an outdoor cooking area. There are lights and a charging station in the dome. **This is a rustic off-grid glamping experience. It has an outhouse, outdoor heated shower, and no cell or wifi service.

Scandinavian Escape

When palm springs meets a peaceful lush secluded forest - welcome to our Scandinavian escape. This private hotel style suite has its own separate entrance, patio and is the perfect spot to enjoy the beauty and serenity of nature while only being 12 minutes from Osoyoos & 30 minutes from Mt. Baldie ski resort. Step back in time with the mid century decor but enjoy the luxury of a rainfall walk in shower, workspace and mini kitchen to prep any meal.

Whole 2BD House – Spectacular Orchard Overlook!

Perched on a private hillside overlooking a valley of orchards, vineyards, and pastoral properties, this two-story home offers breathtaking views through expansive windows. The design blends rustic charm with modern comfort, featuring natural wood finishes, open-concept spaces, and wraparound deck and patio areas. Inside, enjoy a cozy living area with a wood-burning fireplace, a modern kitchen, and serene bedrooms for a restful retreat.

Owl Studio Guesthouse at Farmersdotter Organics

Owl Tiny Studio Guesthouse at Farmersdotter Organics (See also Osprey Tiny Studio Guest House). One of two architecturally designed studio guest houses Owl and sister unit Osprey are situated front and centre at Farmersdotter Organics, a certified organic garlic farm ideally located in the heart of the Similkameen Valley wine region and Canada's organic farming capital.