Holiday rentals with a pool in Chelan County

4.97 out of 5 average rating, 148 reviews

An outdoor area showcases a spacious pool surrounded by neatly manicured grass and stone pathways. A covered gazebo features seating along one side, while distant mountains and a shimmering lake form a scenic backdrop under a clear blue sky.

Home in Manson

Large Home with Pool, HotTub & Sweeping Lake Views

Cozy and Fun-Filled Vacation Retreat Welcome to this charming two-story home, perfect for families and groups seeking a blend of relaxation and entertainment! The upper level boasts three spacious bedrooms, two fully remolded bathrooms, a fully equipped kitchen, and a cozy living area, ideal for unwinding after a day of adventure. Head downstairs to the entertainment-packed basement, featuring a foosball table, an outdoor ping pong setup, and an additional bedroom outfitted with two bunk beds. Whether you’re binge-watching your favorite shows on the flatscreen smart TVs or diving into a game night on the game console, there’s something for everyone. Step outside to the expansive balcony for a serene evening under the stars or enjoy some friendly competition with yard games in the backyard. Dive into the seasonal pool, lounge in the sun, or take the excitement up a notch with a basketball match or a game of HORSE in the driveway. The hot tub off the patio offers year-round relaxation for your group. Just a short walk away, Willow Point Park provides easy lake access for more outdoor fun. With endless amenities and a prime location, this home is the ultimate destination for making lasting memories.

4.94 out of 5 average rating, 182 reviews

Winter Wanderlust *Walkable to Town* Mountain View

Beautiful mountain & golf course views! Spacious Top Floor, 2 bedrooms & 2 bathrooms, vaulted ceilings, well-equipped kitchen & comfortable living. Steps to pool,hot tub, tennis/pickleball/basketball court. Private patio with grill. Fab location -Walk to village, river & parks. Gas fireplace, A/C, Wi-Fi, & games. Leavenworth is a year-round vacation spot with something for everyone. Many outdoor activities including skiing,tubing,hiking & rafting, plus fun festivals,wineries,restaurants & more.

A modern living area features a tufted blue sofa with yellow accent pillows, positioned near a sleek coffee table. A dining table with white chairs is visible, along with a beautifully organized kitchen area in the background, showcasing minimalist décor and warm wooden flooring.

4.95 out of 5 average rating, 301 reviews

Romantic Boutique Getaway with Modern Remodel.

Top floor unit, no one above you! This newly remodeled private boutique-style condo with central AC is the perfect getaway for 1-4 guests. Located next to Lakeside Park, near the heart of Chelan. Includes free parking, fast WiFi, a community pool and sauna, and thoughtfully stocked kitchen and bathroom. Centrally located, just seconds from the lake, with quick access to vineyards, golf, fishing, water sports, hiking, shopping, and more! Need only 1 night? Send me a message for availability.

The image displays a scenic view of multi-level condominiums surrounded by lush greenery and landscaped gardens. Snow-capped mountains rise in the background under a clear blue sky, providing a tranquil and inviting backdrop for the property.

4.91 out of 5 average rating, 319 reviews

Alpenhaus Leavenworth

Why work from home when you can work from here. Xmas lights on next week. Enjoy the fresh air. Come and experience Leavenworth and the mountains. This spacious 1,300 s.f. condo sleeps 6. 2 bedrooms, 2 baths (master has it's own bath). Living room has a queen sleeper sofa. Second floor patio with fantastic views. Relax in one of the hot tubs or enjoy a swim in one of the pools (seasonal). Enjoy the fresh air and beautiful scenery. Only a short 15 minute walk to town. Leave the car behind.

The image depicts a serene outdoor view featuring a tranquil pond with a fountain surrounded by lush green lawns and trees. A swimming pool with deck chairs is visible in the foreground, set against a backdrop of rolling hills and a clear blue sky.

4.97 out of 5 average rating, 200 reviews

Park & Walk to town, 3 pools OPEN, Hot tubs, Views

Come & enjoy any season in Leavenworth You will feel right at home as soon as you enter our spacious, clean and up to date condo over looking the 14th fairway on the golf course, enjoy 2 pools + toddler pool, (Pools are open depending on winter weather) 3 hot tubs are open for guests use, views & an easy walk into the village of Leavenworth for strolling, shopping & dinner. The bonus is being able to park in carport and walk into front street, as parking can be a challenge on the busier days.

4.97 out of 5 average rating, 207 reviews

The exterior of a spacious two-story lodge is highlighted, featuring a large swim spa on a patio. Surrounding the spa, multiple lounge chairs and an umbrella provide seating options. The lodge is set against a backdrop of lush trees and mountain scenery, with a gravel driveway leading up to the structure.

Cabin in Leavenworth

12 ft Swim Spa Pool * Pets * Ping-Pong * By River

💌 Pls read our glowing reviews for more details! 👯‍♀️This home is setup perfectly for multi-generational family vacas w/infants through grandparents 🛌7beds + crib - sleeps 12 🏊🏻‍♂️12x8 foot swim spa that doubles as a large hot tub or small pool 🏓Ping-Pong, foosball, arcades, TV's, Fiber Internet, games/toys, large yard, stocked kitchen, baby-friendly w/gate, high chairs, crib 📍25 MIN TO LEAVENWORTH 📍10 MIN TO LAKE WENATCHEE 🔑Moonrise Mountain Lodge Poss Pines Vacation Rentals

A private balcony is shown with a clear view of the tranquil water, where several boats are anchored. The surrounding landscape features gentle hills under a blue sky, creating a serene waterfront scene.

4.92 out of 5 average rating, 134 reviews

Waterfront Studio Condo on Lake Chelan

You can't beat this WATERFRONT location with great amenities, and private condo-living a short walk to downtown Chelan! Features include: - Large sandy beach, grassy areas, beautiful landscaping, picnic areas - Year-round heated adult hot tub. - Seasonal: heated pool, charcoal BBQ's, picnic tables, lawn furniture, cabana - Onsite coin-operated laundry, children's playground, large dock, pickle ball court, and free parking City of Chelan Short Term Rental License: #STR-0004

Guest suite in Leavenworth

A charming entryway is framed by lush greenery and colorful flowers. The path of stone pavers leads to a welcoming wooden door, with large windows offering glimpses into the interior. A spacious porch showcases outdoor seating amidst comfortable landscaping.

4.94 out of 5 average rating, 189 reviews

Leavenworth Country Stay

STR #000065 Spring is Here! We are all enjoying the warmer weather and the wildflowers are about to burst-they may have by time you read this! This is a great time to get out walking and soon hiking in the higher country. The birds are so busy, singing and settling down to nesting time. Don't forget Bird Fest in May! Town is still quiet now in early Spring, so it's a great time to visit Leavenworth before schools let out and the many visitors arrive.

4.92 out of 5 average rating, 155 reviews

Apartment in Manson

Stunning views, Luxury on Lake Chelan - Pool, Spas

Located in the quaint and peaceful town of Manson, Marina's Edge features dazzling views of Lake Chelan and surrounding Cascade peaks. Relax in the spacious pool or one of the hot tubs while you soak in the stunning natural beauty. Walking distance to downtown Manson, local brewery, award winning wineries, and restaurants. Across the street for Manson Bay's public swimming area, and boat dock. Luxury all the way! This unit is on the third floor.

A bright bedroom features a spacious bed adorned with a light quilt, complemented by two bedside lamps. Large windows with horizontal blinds allow natural light to fill the space, offering views of the surrounding area.

4.92 out of 5 average rating, 101 reviews

Lake Access Condo with Indoor Pool & Hot Tub

Winter at Lake Chelan awaits. This cozy 1-bedroom condo is steps from the water and close to wineries, winter events, and snow-covered mountain views. Enjoy a fireplace, full kitchen, queen bed, bunks, and a balcony with partial lake views. After a day exploring Chelan, unwind in the indoor pool and hot tub — a perfect winter retreat for couples or small families. City permit number:STR-0248

Superhost

A spacious living area features a dark sectional sofa with accent pillows, paired with a round glass coffee table. Natural light pours in from large windows, showcasing access to a private balcony with views. Decorative artwork adorns the walls, adding visual interest.

4.76 out of 5 average rating, 170 reviews

Top floor 2BR condo w pool & hot tub open all year

Most desirable top floor, lakefront condo at Chelan Resort Suites. Conveniently located next to Lakeside Park & Beach where you can enjoy water activities and sunbathing by day or take a walk or short drive to various local wineries, golf courses, restaurants, shops, Slide Waters and more! At night, soak up the beautiful sunset & gorgeous views of Lake Chelan from your private patio.

A view from the balcony showcases the surrounding mountains and lush greenery. A cozy basket chair is visible on the left, while a coffee cup rests on the railing, hinting at a peaceful morning in a picturesque alpine setting.