Holiday rentals with a pool in Southern Oregon

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Top-rated rentals with a pool in Southern Oregon

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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The tiny home is nestled among lush trees, showcasing a wooden deck with a railing. Large windows offer views of the surrounding greenery. The exterior features vibrant colors, contrasting with the natural landscape under a clear blue sky.
Tiny home in Rogue River
4.87 out of 5 average rating, 115 reviews

Tiny Groove with plunge pool and soaking tubs

A unique off grid experience awaits you at our eco-friendly solar powered tiny home on 6 secluded acres. The home site is perfectly cut into a groove in the hillside 200 feet above the valley below allowing for beautiful Mountain views and amazing privacy with no visible neighbors other than the variety of local wildlife. Enjoy the outdoor soaking tubs, wood fired sauna and a seasonal plunge pool. Just a short 5 minute drive to the lovely town of Rogue River and access to I-5. Pet friendly too!

Top Guest favourite
A modern living room is highlighted by a large flat-screen TV and a stylish fireplace. Expansive windows provide views of the outdoors, allowing natural light to fill the space. Comfortable seating arrangements create an inviting area for relaxation.
Home in Sisters
4.99 out of 5 average rating, 139 reviews

Cozy Mountain Escape: Amazing Views! Hot tub!

Relax in this calm, stylish newer home! The unobstructed mountain views are Jaw-dropping!! Walking distance to all that this amazing town has to offer. Enjoy the mountains and wildlife from the upper and lower decks after a day of exploring. Located in the desirable Pine Meadow Village neighborhood. Includes access to clubhouse, with a seasonal pool and a hot tub. You will take part of the mountain escape experience with you, wherever you go, and the memories you create will last a lifetime!

Guest favourite
A charming two-story home is framed by lush green grass and mature trees. The exterior features a classic design with a combination of large windows, a welcoming porch, and a tasteful blend of light and dark siding. The sky is bright with scattered clouds.
Home in Central Point
4.96 out of 5 average rating, 125 reviews

Beautiful Country Home next to Jacksonville!

The whole group will enjoy easy access to everything from this centrally located home! Enjoy a pool day with the family next to the serine pool. Or a fun day of wine tasting with Relik winery less than one mile away and Hummingbird less than 2 miles away! Or have a blast at a concert this summer at the Britt festival less than 2 miles away! Downtown Jacksonville is only a 3 minute drive! All queen beds have been upgraded to NEW Tempurpedic beds! King size bed is a Jennings (Very High Quality!)

Top Guest favourite
A comfortable seating area is showcased with a vibrant red sofa, accompanied by a white chair. Colorful woven textiles adorn the walls and floor, adding cultural richness. Soft lighting highlights the warm tones of the decor, creating an inviting space for relaxation.
Apartment in Ashland
4.94 out of 5 average rating, 274 reviews

Mexico Apartment at Wood Hamlet, by Downtown

The Wood Hamlet Mexico Apartment is a delightful space filled with color and culture. A short walk to town, 72-acre park & the theaters. Feel the welcoming warmth of the hand-crafted Mexican decor. Basement unit but with lots of windows and light. (4 beams at 6'1") Kitchen, with top of the line induction burner, fridge, microwave..., full bath, W/Dryer, work area... Wi-fi. Beautiful, garden with sitting areas & swimming pond. Parking. (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Top Guest favourite
A shared fire pit is surrounded by outdoor seating, providing a cozy gathering space. Warm light from the interior of the cabin and string lights create an inviting ambiance, while tall trees frame the backdrop, enhancing the peaceful setting.
Cabin in Grants Pass
4.96 out of 5 average rating, 327 reviews

Tiny Cabin in the Woods | Hot Tub & Alpaca Rescue

Enjoy the charm of staying in a Tiny forest cabin, surrounded by nature and stylishly decorated with thoughtful décor accents. This is a tiny cabin, but has all the essentials that you need for your stay. Great location on the outskirts of town (8 mins from Merlin & 15 mins from Grants Pass). The closest access to the river is only 10 mins away at Matson Park! After a day of exploring, enjoy your hot tub with a wooded view or stargaze by the shared fire pit. Perfect Couples little getaway!

Top Guest favourite
The open kitchen space features modern dark wood cabinetry and an expansive breakfast bar with ample countertop space. Light streams through large windows, illuminating the living area that includes a comfortable sectional sofa, fireplace, and a telescope positioned for scenic views of the outdoors.
Home in Klamath Falls
4.98 out of 5 average rating, 114 reviews

4BR W/ View, Crater Lake, Running Y Resort House

Take in the views at our "Dark Sky" Crater Lake Resort House. This family friendly home features 4 bedrooms and 2.5 bathrooms modernly designed and decorated to create a calm peaceful stay. This is not a condo or tiny chalet located at the Running Y Resort, it is a full on private custom home equipped with everything you will need to make you feel at home. With full access to all amenities at the Running Y Resort, a very short commute to Crater Lake National Park, you simply cant go wrong!

Top Guest favourite
A spacious outdoor area features a crystal-clear swimming pool adjacent to a stone hot tub. Surrounding greenery and colorful flowers enhance the serene setting. Seating options are available nearby, with steps leading elegantly from the house to the poolside.
Home in Ashland
4.96 out of 5 average rating, 124 reviews

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

Top Guest favourite
The exterior view of the modern house showcases a single-story structure with a prominent terracotta roof. Large glass panel doors provide a glimpse of the inviting interior. The surrounding landscape features mature trees and a landscaped pathway leading to the entrance.
Home in Eugene
4.94 out of 5 average rating, 124 reviews

Modern home - Billiards, Pingpong, Sauna & Views!

Enjoy panoramic sunset views over Eugene when you stay at this modern Skyline property. This luxurious newly-remodeled 3-bedroom house has a private sauna, game room, and is centrally located, 5 minutes from the University of Oregon and Matthew Knigh Arena and 10 minutes from Autzen Stadium. It is 5 minute walk to Hendricks Park and steps away from the famous Pre's Rock! This home is ideal for travelers, reunions, bridal groups, graduations, office retreats and romantic staycations!

Guest favourite
Four orange Adirondack chairs are arranged on a grassy area, facing a wide, open view of a distant mountain landscape. A clear blue sky scattered with white clouds creates a serene backdrop, while leafy branches frame the scene.
Guest suite in Jacksonville
4.85 out of 5 average rating, 253 reviews

Scenic and relaxing roadtrip stop-over!

This is a scenic stop between PDX and SF and its own destination. One guest says " Her home has a magic of its own." Simple, elegant, and a great base for wine-tasters, paraglider, or roadtrippers. If a house surrounded by nature, vineyards, paraglider pilots, creativity and occasional other travelers sounds interesting, you'll love it here. As a local tourism coordinator, I can direct you to the top attractions. Note: this is a self-contained unit but attached to the main house!

Guest favourite
An inviting bedroom features a spacious bed with light-colored bedding, positioned beneath a sloped wooden ceiling. Large windows provide natural light and a view of the surrounding greenery. A decorative wooden dresser and a small table add functional charm to the room.
Guest suite in Gold Hill
4.91 out of 5 average rating, 222 reviews

Octagon Studio / Beautiful Rogue River property

Park-like setting; Rogue River premier property. Use the Octagon Studio to enjoy the luxuries of the property or as a home base for the many amenities in the Rogue Valley. Relax by the pool or soak in the hot tub, lounge on the rivers beach, watch the river go by from the floating dock(seasonal) swing between two large pine trees, have an evening fire in the fire pit, catch trout for a morning breakfast, watch the abundant wildlife. Relaxing, romantic, fun, resort quality....enjoy

Top Guest favourite
A modern studio features a spacious bed with crisp white linens, a wooden accent wall, and an electric fireplace below a wall-mounted television. A unique wood table sits atop an area rug, with plants adding a touch of greenery to the warm atmosphere.
Condo in Bend
4.97 out of 5 average rating, 273 reviews

Sunriver Studio with Pool and Hot Tub

This stylish studio in the heart of Sunriver is newly remodeled with a King bed. Seasonal pool and year round Hot Tub! Just a short walk to a brand new food truck lot with 7 trucks, indoor and outdoor seating and a bar. Fast WiFi, a new Samsung 50” tv signed into Netflix, Hulu, HBO Max and more. 25 minutes to Mt. Bachelor. 25 minutes to downtown Bend. Parking is just a few feet from your door. This super clean condo is perfect for all of your central Oregon adventures.

Guest favourite
An indoor pool area features a spacious swimming pool with clear water. A wooden structure showcasing a bunk bed can be seen above the pool. Natural light floods the space, reflecting off the water's surface, while wooden accents provide a warm touch to the environment.
Guesthouse in Junction City
4.89 out of 5 average rating, 320 reviews

Pool house with hot tub and extras (year round)

Bring the whole family or use it as a private get away. Bedroom has a bunk bed that sleeps up to 3 people. The queen bed by the hot tub and pool sleeps 2 (privacy curtains). There is 1 couch and 1 futon. In addition to the pool and kitchen, there is an indoor fire pit, ping pong and foos ball, outdoor deck, yard (games bocci and croquet). One room with toilet/sink and one with shower/dressing area. VCR/DVD on two TVs, internet on 3rd.

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