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Family-friendly holiday rentals in Jefferson County

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Jefferson County family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Home in Madras
5 out of 5 average rating, 3 reviews

Lake Simtustus Resort-B10 Tiny Home

JakeRating, 5 stars49 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!
Top guest favourite
Home in Terrebonne
4.98 out of 5 average rating, 878 reviews

Cozy Three Story Lookout Tower

NickolettRating, 5 stars1 week ago
Such a fantastic place to stay. Expected it to be a bit more rustic since it was a converted fire lookout. But the kitchen and bathrooms were great. Instant hot water, great water pressure, and comfy beds. Hot tub after hiking Smith Rock was a delight. Patti was really responsive, friendly and helpful. We'll definitely be back and enjoy it again. Oh and we saw the lunar blood moon eclipse when we were there! Very memorable time with friends.
Superhost
Home in Madras
5 out of 5 average rating, 4 reviews

Lake Simtustus Resort- B11 Tiny Home

BrittanyRating, 5 stars35 months ago
This place was a great find after struggling to find any good hotel accommodations nearby. Amazing views, very relaxing.
Top guest favourite
Home in Terrebonne
4.96 out of 5 average rating, 446 reviews

Canyon House, Crooked River Ranch

AmandaRating, 5 starstoday
5 stars isn’t enough! We had the most peaceful and magical stay at the Canyon House. The view took our breath away—sunsets and sunrises over the canyon were absolutely stunning. We loved soaking in the hot tub, dancing under the stars by the campfire, and enjoying the quiet beauty of nature all around us. The space was clean, cozy, and just what we needed for some much-needed rest and recovery. We also made a few tiny spider friends who kept us company—no trouble at all, just part of the charm of being so close to nature. Jeff was a responsive and thoughtful host, and everything about the experience felt welcoming and easy. We’re so grateful for our time here. Highly recommend this spot to anyone needing a reset, a romantic getaway, or just a little magic. —BikeDreamRider & LatePizza
Superhost
Home in Madras
4.75 out of 5 average rating, 4 reviews

Lake Simtustus-B14 Tiny Home

AmiyaRating, 5 stars39 months ago
super clean and friendly staff!
Superhost
Home in Madras
4.83 out of 5 average rating, 6 reviews

Lake Simtustus-B12 Tiny Home

AdityaRating, 5 stars37 months ago
Amazing place run by amazing people. My girlfriend and I loved the place and its vibe! We would definitely return!
Superhost
Home in Madras
4.8 out of 5 average rating, 5 reviews

Lake Centered Resort-B13 Tiny Home

ChristopherRating, 5 stars37 months ago
If you’re looking for an off grid spot, this is it. Quiet and tranquil. Definitely will be back.

Family- and pet-friendly home rentals

Superhost
Home in Madras
5 out of 5 average rating, 3 reviews

Lake Simtustus Resort-B10 Tiny Home

JakeRating, 5 stars49 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!
Guest favourite
Campsite in Camp Sherman
4.9 out of 5 average rating, 10 reviews

The Property - A Unique Campsite at Camp Sherman

ToniRating, 5 stars8 months ago
Marks property was absolutely amazing!! Our family had the most magical stay! The river is beyond beautiful!!! He has so much there to make your stay easy ! I recommend this property to everyone! Camp Sherman is a dream!
Top guest favourite
Home in Terrebonne
4.98 out of 5 average rating, 878 reviews

Cozy Three Story Lookout Tower

NickolettRating, 5 stars1 week ago
Such a fantastic place to stay. Expected it to be a bit more rustic since it was a converted fire lookout. But the kitchen and bathrooms were great. Instant hot water, great water pressure, and comfy beds. Hot tub after hiking Smith Rock was a delight. Patti was really responsive, friendly and helpful. We'll definitely be back and enjoy it again. Oh and we saw the lunar blood moon eclipse when we were there! Very memorable time with friends.
Guest favourite
Cottage in Terrebonne
4.9 out of 5 average rating, 293 reviews

Quiet central Oregon desert retreat with a view!

ArnavRating, 5 stars2 months ago
One of the best Airbnbs we have been to: Location-great private place, near Redmond ; which has a lot of restaurants. If you like privacy and want a place away from city hustle this is it . Very remote ! Property - amazing property ! Clean spacious and it’s an accessible home ! One of the bedroom and bath is built such that it’s easy for someone in wheelchair. The kitchen was very well stocked ; great quality of utensils ; we loved to cook there. The bedroom linen was very comfortable and they had ample spare linen! They had a great collection of books and games for couple and families ! We really liked their thoughtful gesture of warnings that the decks could be icy- both front and back decks. There were comforts all over the house which made it very cozy. The decor of the house is so warm and it has beautiful pictures of Oregon and horses all over the house.
Guest favourite
Farm stay in Prineville
4.93 out of 5 average rating, 388 reviews

Cozy ranch bunkhouse in Ochocos at Wine Down Ranch

AndyRating, 5 stars2 months ago
We felt at home in the bunkhouse and on the ranch. Hosts are friendly, helpful, and approachable. The setting is really stunning, and we loved hiking up the road into the National Forest. The dogs on the property were friendly and companionable, and the horses were a special treat. Plus there is so much stunning landscape within a short drive. We hope to be back!
Top guest favourite
Home in Terrebonne
4.96 out of 5 average rating, 446 reviews

Canyon House, Crooked River Ranch

AmandaRating, 5 starstoday
5 stars isn’t enough! We had the most peaceful and magical stay at the Canyon House. The view took our breath away—sunsets and sunrises over the canyon were absolutely stunning. We loved soaking in the hot tub, dancing under the stars by the campfire, and enjoying the quiet beauty of nature all around us. The space was clean, cozy, and just what we needed for some much-needed rest and recovery. We also made a few tiny spider friends who kept us company—no trouble at all, just part of the charm of being so close to nature. Jeff was a responsive and thoughtful host, and everything about the experience felt welcoming and easy. We’re so grateful for our time here. Highly recommend this spot to anyone needing a reset, a romantic getaway, or just a little magic. —BikeDreamRider & LatePizza
Superhost
Home in Madras
4.75 out of 5 average rating, 4 reviews

Lake Simtustus-B14 Tiny Home

AmiyaRating, 5 stars39 months ago
super clean and friendly staff!
Superhost
Home in Madras
4.83 out of 5 average rating, 6 reviews

Lake Simtustus-B12 Tiny Home

AdityaRating, 5 stars37 months ago
Amazing place run by amazing people. My girlfriend and I loved the place and its vibe! We would definitely return!

Family-friendly home rentals with a pool

Superhost
Home in Madras
5 out of 5 average rating, 3 reviews

Lake Simtustus Resort-B10 Tiny Home

JakeRating, 5 stars49 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!
Top guest favourite
Home in Terrebonne
4.98 out of 5 average rating, 878 reviews

Cozy Three Story Lookout Tower

NickolettRating, 5 stars1 week ago
Such a fantastic place to stay. Expected it to be a bit more rustic since it was a converted fire lookout. But the kitchen and bathrooms were great. Instant hot water, great water pressure, and comfy beds. Hot tub after hiking Smith Rock was a delight. Patti was really responsive, friendly and helpful. We'll definitely be back and enjoy it again. Oh and we saw the lunar blood moon eclipse when we were there! Very memorable time with friends.
Superhost
Home in Madras
5 out of 5 average rating, 4 reviews

Lake Simtustus Resort- B11 Tiny Home

BrittanyRating, 5 stars35 months ago
This place was a great find after struggling to find any good hotel accommodations nearby. Amazing views, very relaxing.
Top guest favourite
Home in Terrebonne
4.96 out of 5 average rating, 446 reviews

Canyon House, Crooked River Ranch

AmandaRating, 5 starstoday
5 stars isn’t enough! We had the most peaceful and magical stay at the Canyon House. The view took our breath away—sunsets and sunrises over the canyon were absolutely stunning. We loved soaking in the hot tub, dancing under the stars by the campfire, and enjoying the quiet beauty of nature all around us. The space was clean, cozy, and just what we needed for some much-needed rest and recovery. We also made a few tiny spider friends who kept us company—no trouble at all, just part of the charm of being so close to nature. Jeff was a responsive and thoughtful host, and everything about the experience felt welcoming and easy. We’re so grateful for our time here. Highly recommend this spot to anyone needing a reset, a romantic getaway, or just a little magic. —BikeDreamRider & LatePizza
Superhost
Home in Madras
4.75 out of 5 average rating, 4 reviews

Lake Simtustus-B14 Tiny Home

AmiyaRating, 5 stars39 months ago
super clean and friendly staff!
Superhost
Home in Madras
4.83 out of 5 average rating, 6 reviews

Lake Simtustus-B12 Tiny Home

AdityaRating, 5 stars37 months ago
Amazing place run by amazing people. My girlfriend and I loved the place and its vibe! We would definitely return!
Superhost
Home in Madras
4.8 out of 5 average rating, 5 reviews

Lake Centered Resort-B13 Tiny Home

ChristopherRating, 5 stars37 months ago
If you’re looking for an off grid spot, this is it. Quiet and tranquil. Definitely will be back.

Destinations to explore