Family-friendly vacation rentals in Jacksonville

A modern kitchen features a spacious island with seating for four, complemented by stylish wooden stools. Light-colored cabinets and countertops enhance the airy feel, while a sleek stainless steel refrigerator and oven are visible in the background. Natural light enters from a large window.

5.0 out of 5 average rating, 221 reviews

Refined, Serene Home in Jacksonville

Professionally decorated in a Mid-Century Modern style. Sleep soundly on Hungarian down pillows and BeautyRest Black mattresses made up with soft 600 thread-count Italian linens. Beautifully tiled bathroom offering Turkish towels, bathrobes, and luxe sundries. Living room and full kitchen with gas stove and quartz counter tops. Step outside to a private yard with outdoor eating area and cozy fire pit. Other amenities include three flat-screen Smart TV's, cable, WIFI, washer and dryer and so much more. Come and enjoy! You'll have this complete private cottage to yourself with private (and ample) parking. Come and go as you please in complete privacy. Self Check-in Available I'm available, if needed. I typically give a complete walk through of the property. For busy travelers, special arrangements can be made to stock the kitchen with additional supplies such as eggs, juice, special drinks. Our goal is to provide you with wonderful service. Let us know how we may help you have a terrific stay. The house is set in a laid-back neighborhood with a mix of shopping and dining within walking distance to Jacksonville's historic core. Ashland and Oregon Shakespeare Festival are a 15 minute drive away. 9% City Guest Tax will be applied to nightly rate & any additional charges. Tax is billed at arrival and must be paid via cash or check before departure. Airbnb is not allowed to collect this tax in advance.

Indoor spacesFamilyLayout

4.99 out of 5 average rating, 349 reviews

Spa Like Stay at the Britt Bungalow in J’Ville

The Britt Bungalow is an Award Winning boutique style stay in the historical heart of Jacksonville Oregon created and designed by the owner and host. Enjoy a spa like private stay w/ 2 bed, 2 bath cottage with 17' ceilings, fresh flower’s throughout, #1 rated Dreamcloud mattress in primary, living room with a fireplace and an abundance of natural light throughout. You will want for nothing during your stay. Just 2 blocks to the trolly, all the best restaurants, boutiques, & the Britt Pavilion.

FamilyKitchenRiver

4.93 out of 5 average rating, 467 reviews

Guesthouse in Medford

The Greenwood Villa w/wood fire hot tub

The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

KitchenFamilyHot tub

4.96 out of 5 average rating, 155 reviews

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

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!)

FamilyIndoor spacesBeach

Treehouse in Jacksonville

A cozy studio is nestled among tall pine trees, illuminated softly by warm outdoor lights. The clear night sky is filled with stars, adding a serene backdrop to the natural surroundings. A pathway leads to the entrance, inviting exploration of the tranquil setting.

Tree Top Studio

Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is very private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.

KitchenIndoor spacesCleanliness

4.97 out of 5 average rating, 321 reviews

5.0 out of 5 average rating, 105 reviews

Farm stay in Grants Pass

Cozy Wild West Covered Wagon next to River

Reconnect with nature in the breathtaking Applegate Valley while enjoying the comfort of our cozy covered wagon. Take a step back in time and create memories as our ancestors did on the Oregon trail in covered wagons. Escape the hustle and bustle of everyday life & unwind in our Paradise on the Applegate River. Enjoy the many nature trails that meander throughout the 11 acres on our farm. Say hello to all of the cute furry animals grazing on our pasture. Your adventure awaits!!

Indoor spacesKitchenSleep quality

Guesthouse in Jacksonville

La Petite Maison + Spa

Welcome to La Petite Maison! Come take it easy at our unique and tranquil home away from home. Located in the heart of the Applegate with nearby wineries and exquisite views of the mountains. Our guest house is equipped with 1 master bedroom, full kitchen/bath, dining and living room with and private SPA on your very own deck! Only a 10 minute drive from the historic town of Jacksonville. At La Petite Maison you will have the peace and quiet of the country, and all that you may need.

FamilyKitchenHot tub

4.96 out of 5 average rating, 183 reviews

Guesthouse in Jacksonville

An inviting outdoor patio area is surrounded by greenery, featuring a round table with a floral tablecloth and two green chairs. A large red umbrella provides shade. The cottage's door is framed by a vibrant window box filled with flowers, contributing to a charming ambiance.

Cozy Jacksonville Cottage

This cozy, rustic one bedroom cottage (325 sq. ft.) is just a 15 min. walk from downtown Jacksonville (3/4 mile) and 30 min. from Ashland. It has private parking, on the property. The owner is happy w/ pets in the cottage, but needs to know in advance that a pet is coming (maximum 35lbs) too. There isn't a full kitchen but it has a kitchenette with sink, fridge, microwave, hot plate and coffee maker, so cooking basics won't be a problem. Relax in the outside patio in the summer.

Indoor spacesFamilyPets

4.93 out of 5 average rating, 1217 reviews

Farm stay in Jacksonville

Red Barn in Wine Country

Luxury barn with a rustic feel on "Red Barn Farm" in Southern Oregon Wine Country. Our five-acre micro-farm is situated on the Applegate River exactly between Crater Lake & the Redwood forest. Our lush Applegate valley is a region of 19 artisan wineries. Walk to Red Lily Vineyard tasting room. This farmstay has a river swimming hole, friendly chickens, mini-goats & sheep, and a fire pit to spend dreamy evenings under the stars. Visit Wine Country Farm Stay dot com for more info!

Indoor spacesFamilyPets

4.91 out of 5 average rating, 112 reviews

Guest suite in Jacksonville

A covered porch features a blend of seating options, including four chairs around a small table and a reclined chair. A grill is positioned nearby, and the area is surrounded by lush greenery, creating a peaceful outdoor space.

Claudia's Retreat Sanctuary

Retreat here on my 6 acres of madrone forest with pastoral views, 2 meditation labyrinths- yet only 3 miles to the quaint, historic town of Jacksonville, Oregon, home of Britt Festival, 35 minutes to Ashland and 1.5 hours to Mt. Shasta or Crater Lake. This guest suite in the lower level of my house. Walk the spiral labyrinths. Book a Sacred Sound bath session with Tibetan and crystal bowls & Paiste gongs for $70 during your stay. Massage chair available too. Simply divine!

FamilyIndoor spacesOutdoor spaces

4.84 out of 5 average rating, 308 reviews

4.95 out of 5 average rating, 147 reviews

B.F. Dowell House | Walk to Britt & Downtown

Experience one of Jacksonville’s most iconic historic homes. The beautifully restored 1861 B.F. Dowell House blends original stained glass, marble fireplaces, soaring ceilings, and exposed brick with modern comfort. Located on a large corner lot across from the market and steps from downtown, Britt Festival, restaurants, and tasting rooms. Features private baths for every bedroom, an adjustable Tempur-Pedic bed, clawfoot tub, full kitchen, porch, patio, garden, and lawn.

FamilyKitchenShared spaces

A historic home with a welcoming front porch is surrounded by lush greenery. White flowers bloom in the garden, adding a natural touch to the setting. The sturdy stone base supports the structure, while a dark roof contrasts with the light-colored exterior.

4.99 out of 5 average rating, 127 reviews

Historic 1875 Kitchen House

Easy walking distance to Britt concert venue, trails, and downtown. The base rate is for the entire first floor and includes one bedroom with en suite bathroom with a large clawfoot tub. Upstairs attic space can also be rented for an additional fee, which includes 3 beds and a full bathroom. Declare 3 guests if 2 people need their own suites. Air conditioning upstairs and downstairs keeps you feeling cool in summer. Heating keeps you comfy and warm in winter.

Indoor spacesFamilySleep quality

Popular amenities for Jacksonville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guesthouse in Central Point

Hot Tub • Near Jacksonville & Wineries - King Bed

Indoor spacesFamilyView

4.94 out of 5 average rating, 202 reviews

Guesthouse in Central Point

A light-filled kitchen area features modern cabinetry, a central island with seating, and stainless steel appliances. Mirrored panels and a small potted plant add depth to the space. An area rug with intricate patterns enhances the warm atmosphere, while a ceiling fan provides air circulation.

BEE WELL Organic Spa Garden Studio w/ Hot Tub

FamilyKitchenBackyard

4.94 out of 5 average rating, 887 reviews

Guest suite in Jacksonville

A hot tub filled with clear water is positioned on a private deck, offering panoramic views of surrounding mountains and lush forest. Sunlight reflects off the water's surface, enhancing the tranquil setting, with a glimpse of a river in the distance.

The Birdhouse Retreat| Views & Hot Tub

KitchenIndoor spacesSleep quality

4.83 out of 5 average rating, 287 reviews

4.97 out of 5 average rating, 182 reviews

An A-frame home is nestled among tall trees, featuring a wraparound deck illuminated by string lights. The natural wood structure contrasts with the surrounding greenery as the sky transitions into twilight, creating a serene ambiance.

Cabin in Grants Pass

The Epic A - Charming 1960s A-Frame w/Hot tub

Indoor spacesKitchenLocation

4.98 out of 5 average rating, 841 reviews

The exterior of the yurt is highlighted by warm light emanating from the windows, creating a welcoming ambiance in the evening. A wooden deck leads to the entrance, while a nearby chair rests under a small tree. Soft landscaping and a hammock are visible in the background.

Yurt in Grants Pass

Sunset View Yurt of Applegate Valley with HOT TUB!

KitchenIndoor spacesHospitality

4.95 out of 5 average rating, 123 reviews

Home in Medford

Manor Hill Haven | Hot Tub & Accessible Features

Indoor spacesFamilyHot tub

4.93 out of 5 average rating, 485 reviews

An outdoor hot tub is illuminated under warm string lights, set within a wooden gazebo. The surrounding area features wooden fencing and lush greenery, creating a serene environment. A soft blue glow from the water contrasts with the warm evening sky, enhancing the tranquil ambiance.

Cottage in Jacksonville

Romantic Retreat w/ Hot Tub & Starlit Massage Room

KitchenIndoor spacesHospitality

Guesthouse in Grants Pass

A spacious chalet is nestled among lush greenery, showcasing its wooden exterior and large windows. The outdoor seating area with a comfortable sofa arrangement is highlighted on the deck, surrounded by well-maintained landscaping, creating a welcoming outdoor retreat.

Chalet in the Woods

FamilyKitchenCleanliness

4.97 out of 5 average rating, 248 reviews

Family- and pet-friendly home rentals

Camper/RV in Jacksonville

Lux Glamping | Private Airstream Retreat Getaway

FamilyKitchenRiver

5.0 out of 5 average rating, 144 reviews

The exterior of the Plymale Cottage is displayed, featuring a classic white façade with a pitched roof. A well-maintained front yard is bordered by a white picket fence, complemented by several leafy trees, contributing to a welcoming atmosphere.

4.87 out of 5 average rating, 296 reviews

Plymale Cottage Bed & Biscotti - 2BR, Kitchen, AC

KitchenIndoor spacesParking

Farm stay in Jacksonville

The exterior of the modern two-story cottage features a large outdoor deck with steps leading to a landscaped yard. A circular fire pit surrounded by wooden chairs offers a cozy gathering space, while the fenced yard provides privacy and a serene environment.

Cozy Family Ranch Cottage! Near Vineyards & Lake!

FamilyIndoor spacesHeating

4.98 out of 5 average rating, 153 reviews

Guesthouse in Central Point

A spacious living room area is highlighted by a brown leather sectional sofa accompanied by two decorative pillows. A light wood coffee table sits in the center, situated on a warm-toned wooden floor. Open doorways lead to other rooms, enhancing the airy feel.

The Hygge Stay in the Heart of Southern Oregon

FamilyIndoor spacesSolo travel

4.94 out of 5 average rating, 657 reviews

4.93 out of 5 average rating, 249 reviews

A well-equipped kitchen features stainless steel appliances, including a large refrigerator and an oven. A spacious countertop with seating for four is illuminated by pendant lighting. Natural light floods in through the window, and a glass door leads to the backyard.

Home in Central Point

Ideal & quiet location, 3BR+office, perfectly cozy

KitchenIndoor spacesValue

Guesthouse in Jacksonville

A rural cottage is set in a peaceful environment, surrounded by trees and green grass. The fenced yard offers a spacious area for outdoor activities. A small table with chairs is visible, enhancing the outdoor seating option. The sky is partly cloudy, creating a bright atmosphere.

Starthistle Cottage in Applegate wine country

Indoor spacesFamilyComfort

4.99 out of 5 average rating, 221 reviews

4.97 out of 5 average rating, 516 reviews

The inviting living area showcases a stone fireplace as a focal point, complemented by a wooden mantel. Sunlight filters through large windows, illuminating a seating area with a comfortable chaise lounge and a wooden table. A rich area rug adds warmth to the hardwood floor.

Cottage in Ashland

Victorian Garden Carriage House

KitchenFamilyLayout

4.97 out of 5 average rating, 299 reviews

A wooden deck extends along the riverbank, framed by lush green trees. Two chairs provide seating for relaxation, while flower pots add a touch of color. The tranquil water reflects the surrounding nature, creating a serene atmosphere ideal for enjoying the outdoors.

Home in Gold Hill

Rogue River Retreat

Indoor spacesKitchenGetting around

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 168 reviews

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

The Aloha House - Hot Tub - Pool

FamilyKitchenValue

4.9 out of 5 average rating, 477 reviews

A custom in-ground pool is surrounded by a spacious patio and lush greenery, offering a serene outdoor setting. A wooden fence provides privacy, and a tree offers shade beside the pool area. Sunlight reflects off the water, enhancing the tranquil atmosphere.

Home in Grants Pass

Quiet neighborhood 3 BR w/ pool

KitchenIndoor spacesValue

4.87 out of 5 average rating, 262 reviews

Home in Medford

Crew Work, personal Space, Swim, Hot Tub, Big TVs

FamilyIndoor spacesLong stay

4.95 out of 5 average rating, 243 reviews

A wooden outdoor seating area is positioned on a concrete patio, featuring two chairs and a loveseat with white cushions. A table sits in the center, surrounded by blooming purple flowers and green vegetation. Large glass doors lead into the interior space.

Apartment in Grants Pass

1940s Vintage apartment steps from the Rogue River

FamilyKitchenValue

4.97 out of 5 average rating, 195 reviews

A spacious indoor pool is surrounded by wooden beams and natural stone accents. Sunlight filters through large windows, reflecting off the clear water. Lush greenery and unique decor elements, including a whimsical sun motif, enhance the serene environment.

Home in Cave Junction

Private Country Paradise

KitchenFamilyValue

Superhost

Tiny home in Rogue River

Tiny Groove with plunge pool and soaking tubs

Indoor spacesKitchenCleanliness

4.86 out of 5 average rating, 132 reviews

4.88 out of 5 average rating, 302 reviews

A serene pond surrounded by vibrant autumn foliage reflects hues of red, yellow, and green. The trees frame the water's edge, creating a peaceful natural setting highlighted by scattered leaves floating on the surface.

Apartment in Ashland

The Carriage House, Winner 2025 Best of Ashland!

Indoor spacesFamilyBackyard