Vacation rentals with a pool in Jefferson County

Chalet in Crooked River Ranch

A red timber-framed chalet is showcased, featuring a covered patio with picnic tables and chairs. The surrounding landscape includes landscaped areas and distant hills under a clear blue sky, creating an open and spacious environment.

4.87 out of 5 average rating, 52 reviews

Classic Timber Framed Chalet

Our Classic Timber Framed Chalet the perfect place to call your home away from home. A main floor master bedroom with king bed & separate sleeping loft are perfect for families or groups. The full kitchen makes the Chalet the complete package for your next vacation rental. Pet Friendly (Pet fee required, max 2 pets) And the views! Take in the expansive views across the 14th hole of the CRR Golf Course and marvel at the towering canyon walls & mountains in the background from your private deck.

5 out of 5 average rating, 6 reviews

A cozy cabin is framed by surrounding greenery, showcasing a wraparound deck. Large windows reflect the colors of the sunset, enhancing the rustic wooden architecture. The tranquil landscape includes scattered trees and shrubs, contributing to the serene atmosphere of the setting.

Cabin in Terrebonne

The Rim House, Timeless & Serene

High desert beauty is on full display, no matter the season. Deer, rabbits, quail cross just outside your windows, eagles soar overhead, and yipping coyote echo across the canyon at night. This gem of a getaway is not new to visitors to Terrebonne and Crooked River Ranch. It’s been a guest favorite for over ten years- in March 2025 we purchased the home and are pleased to continue sharing it's unique qualities and location… and to live up to former host Michelle’s high standards of hospitality!

4.98 out of 5 average rating, 898 reviews

The lookout tower is framed by green trees, featuring multiple wooden decks and a spacious entryway. Steps lead up to the main entrance, and large windows provide glimpses of the interior overlooking the natural landscape.

Home in Terrebonne

Cozy Three Story Lookout Tower

Thank you for your interest in The Cozy Lookout Tower! Our unique vacation home is really a destination location rather than just a place to stay while you explore the area. Many of our guests are repeat guests that use our home as a place to recharge, relax, cook, read, talk, play games and connect with that special someone. There are some lovely hikes in the area, we encourage you to bring your dog and enjoy the beautiful surroundings by taking some hikes then returning for a soak in the tub!

4.98 out of 5 average rating, 283 reviews

A spacious deck offers unobstructed views of the canyon and distant mountains during sunset. Comfortable outdoor seating is arranged around a central table, inviting relaxation while taking in the serene landscape. Warm hues light up the sky, creating a tranquil atmosphere.

Home in Terrebonne

Pointe of Blessing with hot tub and canyon views

Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South.

A seasonal swimming pool is surrounded by a spacious deck, with steps leading into the clear, inviting water. Dense pine trees provide a natural backdrop, and sport courts for activities are visible in the distance across a manicured lawn.

4.8 out of 5 average rating, 15 reviews

Creekside Studio Cabin at Lake Creek Lodge

Cabin 7 at Lake Creek Lodge is the coziest of them all, with a fireplace literally at the foot of your queen bed. Located just downstream from the main Lodge in a wooded area that is perfect for watching the wildlife, this cabin has a kitchenette and private bath with everything you'll need for a comfy stay. Bring your pooch to hike the Metolius Basin trails, fly fish our private pond, swim in our seasonal pool and enjoy fun evenings in Lake Creek Lodge's restaurant and bar.

4.96 out of 5 average rating, 456 reviews

An expansive deck overlooks the Deschutes River canyon, featuring a hot tub and several outdoor seating areas. The rugged landscape is characterized by rocky cliffs and sparse vegetation, leading to a serene view of the river winding through the canyon.

Home in Terrebonne

Canyon House, Crooked River Ranch

Canyon House sits on the edge of the Deschutes River canyon and has a beautiful and scenic view of 11 mountains and peaks. Your home is a 2 bedroom and 2 bath 1450 sf manufactured home. It is attached to ours and Donna and I live on site family. Your privacy is my first rule and quiet is my second. Yet, you may see me watering plants or checking on the Spa. We are open for a 1 night minimum. Checkout time is strict to allow for cleaning and sanitizing on same day check ins.

A seasonal swimming pool is surrounded by a concrete deck, with a railing along one side. Lush green grass and tall trees are visible in the background, while a tennis court is situated outside the pool area.

Cabin in Crooked River Ranch

Two Bedroom Creekside Cabin at Lake Creek Lodge

These cabins are a favorite amongst our guests that come back year after year. Located adjacent to Lake Creek, perfect for watching the wildlife, these cabins have a living room full kitchen, 2 bedrooms (1 queen bed & 2 twin beds) and a private bath with everything you'll need for a comfy stay. Bring your pooch to hike the Metolius Basin trails, fly fish our private pond, swim in our seasonal pool & enjoy fun evenings in Lake Creek Lodge's restaurant and bar (seasonal).

Guest favorite

A row of rustic cabins is set against a natural backdrop, showcasing wooden exteriors and inviting porches. Each cabin features a distinct entrance, with picnic tables arranged on the deck. A gravel path leads through the surrounding shrubbery, offering a sense of tranquility.

4.94 out of 5 average rating, 111 reviews

Classic Cozy Cabin with Awe-inspiring Views

Come enjoy rustic relaxation in our Classic Cozy Cabin. It's 208sq ft of cozy comfort in the breathtaking Crooked River Gorge. The private cabin is equipped with a private bathroom, kitchenette, wifi, cable TV, private deck, and just enough leg room to rest, relax and unwind after a day of adventure in beautiful Central Oregon! And the cabin is pet friendly! (Pet fee required, max 2 pets). It's a great place to kick off your boots and stay awhile!

Guest favorite

A row of rustic cabins is set against a backdrop of hills, with a gravel path leading to a communal deck area. Each cabin features a welcoming porch and warm wooden finishes. Surrounding shrubbery adds to the natural scenery.

Cabin in Crooked River Ranch

4.87 out of 5 average rating, 79 reviews

Classic Cozy Cabin with Awe-inspiring Views

Come enjoy rustic relaxation in our Classic Cozy Cabin. It's 208sq ft of cozy comfort in the breathtaking Crooked River Gorge. The private cabin is equipped with a private bathroom, kitchenette, wifi, cable TV, private deck, and just enough leg room to reset, relax and unwind after a day of adventure in beautiful Central Oregon! And the cabin is pet friendly! (Pet Fee Required, 2 pets max) It's a great place to kick off your boots and stay awhile!

The outdoor heated swimming pool is surrounded by a spacious deck, showcasing clear water. In the background, tall pine trees create a peaceful setting, with sport courts visible for tennis and other games.

Three Bedroom Creekside Cabin at Lake Creek Lodge

Original to the 1920’s, this cabin type is situated on the south side of the Main Lodge with a beautiful view of Lake Creek. This cabin type has 3 bedrooms (with either 2 queen beds & 2 twin beds or 1 queen bed & 4 twin beds subject to availability), 2 baths, a fully appointed kitchen. Many have fireplaces or woodstoves in the living area but are subject to availability. Enjoy all of the amenities at Lake Creek Lodge while staying with us!

A heated outdoor pool is visible, surrounded by a spacious patio and lush greenery. Tall pine trees frame the scene, with tennis courts clearly seen in the background. The pool's clear water invites relaxation and leisure in a natural setting.

5 out of 5 average rating, 3 reviews

Luxury Cabin - 3 Bedroom / 2 Bath

Envision opulent comfort & rustic charm rolled into a pretty pine-paneled package. Our luxury cabins are designed to bring the outside in with huge windows & exquisite natural touches throughout. Dreamy, right? Every luxury cabin features: • Three Bedrooms • Fireplace or Woodstove • Full Kitchen with High-end Appliances • Huge Decks, Outdoor Seating & Propane BBQs • Large Windows with Expansive Views • Luxury Cabins 9 & 20 are Pet Friendly

A serene outdoor pool is surrounded by a concrete deck, with steps leading into the water. Lush green trees create a natural backdrop, while a tennis court is visible in the distance, offering additional recreational space.

A space thats all yours, with room for everyone

Two Bedroom Lodge Cabin at Lake Creek Lodge

Located conveniently close to the Main Lodge on the Lake Creek Lodge campus, and nestled in a forested area, this cabin type features 2 bedrooms with either 2 queens & 2 bathrooms or 1 queen bed, 2 twin beds and 1 bathroom (subject to availability), a full kitchen and a nice large wrap around deck that is perfect for a family or friend gathering. Enjoy all of the amenities at Lake Creek Lodge while staying with us!

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Popular amenities for Jefferson County rentals with a pool

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Air conditioning

House rentals with a pool

The tiny home’s exterior is made of natural wood panels, featuring large windows that offer views of the surrounding landscape. A shaded deck with seating is visible, while a hot tub is situated on the side. Steps lead down to a gravel pathway, surrounded by trees.

5 out of 5 average rating, 3 reviews

Lake Simtustus Resort-B10 Tiny Home

JakeRating, 5 stars52 months ago

Amazing views of the lake. Tiny houses have everything you’d want for a quiet getaway (hot tub, grill, comfy beds) and nothing you don’t (tv). Very friendly staff! Perfect couples or family getaway!

A spacious deck is featured with a shaded area, furnished with a round table and four blue dining chairs. A comfortable couch sits adjacent on the deck, surrounded by wooden railings and framed by natural landscaping.

5 out of 5 average rating, 4 reviews

Lake Simtustus Resort- B11 Tiny Home

BrittanyRating, 5 stars37 months ago

This place was a great find after struggling to find any good hotel accommodations nearby. Amazing views, very relaxing.

A cozy seating area is positioned near a large glass door, offering scenic views of the lake and surrounding greenery. Natural light brightens the space, highlighting the soft gray couch and decorative throw blanket placed nearby.

4.67 out of 5 average rating, 3 reviews

Lake Simtustus Resort- Crown Point Tiny Home C 14

TiffanyRating, 5 stars23 months ago

Tiny home for sure…. If you active and going to be out of the house then this is prefect. 3 rooms in one…. For a vacation this was great. Amazing views of the lake and stars. Birds fly by. We spend so much time in the tiny yard…. a beautiful table is prefect for meals. BBQ ready and waiting for help make dinner. I wish there was a little more shade but otherwise it’s was great. No service, WiFi can be spotty during the hot periods of the day. Plan accordingly…. Shower pressure is meh… but hot water was good. Would come back again. Price was worth it.

A modern tiny home, framed by greenery, is shown with a hot tub on a grassy area. A shaded deck is visible, featuring a table and chairs, while large sliding doors provide access to the interior space.