Family-friendly holiday rentals in Medford

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

Pet friendly**Close to the I-5 interstate. Within walking distance to park! This guest house, is filled with natural light making it bright and inviting. Thoughtfully designed with guests in mind, you will have no trouble feeling comfortable with all the amenities you’ll need. *Fun fact**, the night stands in the main bedroom were made in the shop downstairs and designed by husband and I! *Airbnb is above working cabinet shop* Message me if you have any questions, I’ll respond within an hour!

Indoor spacesFamilyParking

4.94 out of 5 average rating, 654 reviews

4.96 out of 5 average rating, 182 reviews

A comfortable living room is furnished with two sofas and an armchair, arranged around a wooden coffee table. Soft pillows complement the seating. A lamp stands beside a wall, providing light, while artwork adorns the walls, adding a serene touch to the space.

Home in Phoenix

Phoenix Rising

Relax with the whole family at this peaceful home with a half acre backyard full of fruit and shade trees along with a gas BBQ. Games include board games, corn hole, outdoor Jenga. Several restaurants within walking distance. Wheelchair accessible park across the road at Blue Heron Park along Bear Creek Greenway. 3.8 mi. - Lithia & Driveway Fields 4.5 mi. - Rogue Regional Hospital 5.5 mi. - Medford Airport 5.9 mi. - Jackson County Expo 13 mi. - Shakespeare Festival 19 mi.- Mt Ashland ski area

FamilyKitchenParks

A covered cedar gazebo provides shaded seating, featuring a table and chairs set on a concrete patio. A gas grill is partially visible, and a playset is located in the grassy area nearby. The space is enclosed by a wooden fence.

4.94 out of 5 average rating, 510 reviews

🌟 🥂 Medford’s BEST 📣 🌟 💕Clean, Modern, Private💕

Simple and clean, with a hidden, private driveway in a safe and secure area of North East Medford. This home is only a few minutes from Rogue Valley International- Medford Airport, plenty of shopping, grocery stores, city transit & local hospitals. Take a short drive to explore Crater Lake, Oregon’s only National Park or head over to Ashland & experience the Oregon Shakespeare Festival. Mountains, lakes & rivers nearby & the Oregon Coast is only 2 hours away. There’s something for everyone here!

Indoor spacesFamilyLaundry

4.97 out of 5 average rating, 224 reviews

The exterior of the guest suite features a covered porch with white railings and a set of wooden steps leading to the entrance. Lush greenery surrounds the property, providing a natural setting in the hills of east Medford.

Guest suite in Medford

Angel Crest Casita Guest Suite - East Medford

Enchanting, large, private 1 bedroom guest suite with a view In Upper East Medford. Beautiful, open concept living /dining area has plenty of room to relax and unwind. This space also includes a semi private queen bed. There is a large luxurious shower, kitchenette, and other amenities (microwave, fridge, and coffee maker). Outside there is a large private covered deck with outside seating and a fire pit. Close to wineries, golf, restaurants, and great hiking. This is a non smoking property.

FamilyIndoor spacesCleanliness

4.93 out of 5 average rating, 463 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

FamilyKitchenAmenities

4.95 out of 5 average rating, 118 reviews

Manor Hill Haven | Hot Tub & Accessible Features

This single level 2-bedroom, 2-bathroom home is ideal for families, couples, or business travelers and has accessible features. Located in a residential only neighborhood, this property offers modern conveniences w/ comfort & style close to Medford medical plazas. - Handicap Accommodative & Wheelchair Accessible - EV Charger with access to a single-car garage for parking - Large Deck with mountain views - Hot Tub - .5 Mile to Golf Course - 1 Mile to Asante - 0.4 miles to Rogue Valley Manor

KitchenFamilyCheckout

4.96 out of 5 average rating, 152 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!)

Indoor spacesKitchenWalkability

4.87 out of 5 average rating, 260 reviews

Big Pool, Great Room, Spa, Work Crews or Families

Perfect for Work Teams or Families to build lasting memories. Private home in Beautiful Scenic Medford Foothills! Close to everything, but out of town. Nearby dining and groceries. Quick drive to Ski Ashland, Crater Lake, Water Ski Lakes, Fishing Lakes, and Roxy Ann Winery. Hiking at Roxy Ann and Table Rocks. Vaulted Great Room, huge modular couch, 65" and 75" TVs, Redzone, Pool Table, Ping Pong, Coffee & Wine Bar, Golden Tee. Year-Round Hot Tub, Seasonal Swimming Pool (mid May-End of Sept.)

FamilyIndoor spacesCleanliness

4.99 out of 5 average rating, 178 reviews

The Cutie Little Local

The Cutie Little Local is a clean, stylish and centrally located new build. A comfortable bed, a full kitchen with new appliances, and extra special little touches, will make your stay easy and enjoyable. Whether your main destination is Medford, or perhaps you plan to visit nearby cities like historic Jacksonville or Ashland, the CLL is a great point of access for all. Numerous restaurants, hiking trails and wineries are nearby allowing an eventful trip to the beautiful Southern Oregon.

KitchenFamilySolo travel

The exterior of the charming home features a light grey facade with white trim, complemented by a welcoming porch. Wooden planters are mounted under two windows, and a neatly landscaped path leads to the front door, framed by seasonal foliage.

4.89 out of 5 average rating, 467 reviews

Southern Oregon Gem (EV Charger)

Welcome to our charming little home in Medford, Oregon. a delightful haven designed for comfort, cleanliness, and efficiency. Nestled near the city center, this inviting space offers a perfect blend of coziness and functionality for a memorable stay. The thoughtful layout maximizes every inch of space, creating a welcoming atmosphere for solo travelers, couples, or small groups. The color palette is soothing, creating a serene ambiance that promotes relaxation.

FamilyIndoor spacesEV charging

4.95 out of 5 average rating, 127 reviews

A well-lit hallway features warm wooden flooring and white walls. Natural light filters in through windows, illuminating the space. Doorways lead to adjacent rooms, creating an inviting transition within the home. The overall design conveys a sense of openness and flow.

Guest suite in Medford

Secluded suite in town

Light and modern space with garden access and private porches. Quiet neighborhood near the hospitals, golf course, and close to the freeway. Only 20 minutes to Ashland's Shakespeare Festival or Jacksonville's Britt Festival. Separate heating and cooling unit as well as a Cal-King Casper mattress (new Feb 2024) for your comfort. Small kitchenette stocked with the basics. LGBTQ+ friendly space.

FamilyIndoor spacesAccuracy

The exterior of a chic home is displayed, featuring white siding and a welcoming porch supported by wooden pillars. A neatly landscaped yard is visible, bordered by shrubs and rocks, with a garage on one side. Daylight enhances the inviting appearance of the property.

4.99 out of 5 average rating, 162 reviews

Designer Home w/ Chef’s Kitchen

Stunning designer home with a true chef’s kitchen, perfect for families, couples, remote workers, wedding parties, and four-legged friends. Thoughtful high-end finishes throughout, sleeps 7 comfortably with lightning-fast WiFi. Close to gorgeous Rogue Valley wineries, Britt trails and outdoor adventures. Less than 10 minutes from historical downtown Jacksonville and The Britt Festival!

KitchenIndoor spacesAmenities

Popular amenities for Medford family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Superhost

The living area features a cozy arrangement of seating, including a dark leather couch and a light-colored armchair. A large television is mounted above a white fireplace, complemented by a coffee table. Natural light enters through a window adorned with light curtains.

4.9 out of 5 average rating, 276 reviews

Hot Tub huge yard 5 kings fiber wi-fi 4k huge tv

KitchenFamilyWi-Fi

Guesthouse in Central Point

Hot Tub • Near Jacksonville & Wineries - King Bed

KitchenFamilyAccess

4.93 out of 5 average rating, 196 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

Indoor spacesKitchenComfort

4.94 out of 5 average rating, 880 reviews

4.98 out of 5 average rating, 119 reviews

A modern, single-story home sits beneath a bright sky, surrounded by tall trees. The structure features a covered wooden deck at the entrance, with large glass doors that open to an expansive outdoor space, creating a seamless transition between indoors and outdoors.

Home in Grants Pass

Rogue Reefs

Indoor spacesKitchenHot tub

4.98 out of 5 average rating, 836 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!

FamilyKitchenWi-Fi

4.97 out of 5 average rating, 177 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

KitchenFamilyGetting around

Guesthouse in Jacksonville

La Petite Maison + Spa

KitchenFamilyPets

4.96 out of 5 average rating, 178 reviews

Superhost

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.

Guest suite in Jacksonville

The Birdhouse Retreat| Views & Hot Tub

FamilyIndoor spacesBarbecue

4.83 out of 5 average rating, 279 reviews

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 248 reviews

The classic cottage is framed by green foliage, showcasing a welcoming entryway with a black door and a symmetrical window. A bench is positioned on the porch, complemented by flower pots on either side. The gravel path leads to the entrance, surrounded by trees.

Cottage in Jacksonville

Cottage on River Farm -Applegate Wine Trail

FamilyKitchenOutdoor spaces

4.9 out of 5 average rating, 405 reviews

The exterior of a modern guesthouse is highlighted, featuring a black front door with arched glass panels and decorative sidelights. Flanked by neatly trimmed evergreen shrubs, the house presents a clean, inviting entrance, with subtle architectural details accentuated by a light fixture above.

Cottage in Medford

Stunning Private Orchard Property

Indoor spacesFamilyCheck-in

A cozy room is presented with a queen bed draped in a light green coverlet. A wooden desk and chair are positioned near a window adorned with cream curtains, while an area rug adds warmth to the hardwood floor. Decorative accents include wall art and a classic wooden dresser.

4.91 out of 5 average rating, 227 reviews

Historic Upstairs Apartment

FamilyIndoor spacesQuiet

A bright bedroom features a spacious bed adorned with neutral bedding. A wooden desk and lamp are positioned nearby, with framed photographs decorating the walls. Natural light filters through a window draped with sheer curtains, while a small potted plant adds a touch of greenery.

4.96 out of 5 average rating, 250 reviews

Clean, comfy, pet friendly & fully stocked

FamilyIndoor spacesLayout

4.92 out of 5 average rating, 106 reviews

Guest suite in Medford

New, spacious, quiet, private, comfy studio

KitchenFamilyWi-Fi

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

Indoor spacesFamilyHiking

4.93 out of 5 average rating, 1209 reviews

4.93 out of 5 average rating, 242 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

FamilyKitchenQuiet

5.0 out of 5 average rating, 110 reviews

Luxury Guest House in Charming Old East Medford

Indoor spacesKitchenCheck-in

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 102 reviews

Home in Jacksonville

Luxury Mountain-Top Retreat | Sleeps 14

FamilyIndoor spacesHospitality

Guest suite in Grants Pass

An inviting swimming pool is set in a landscaped area, surrounded by palm trees and a wooden fence. The pool features a unique shape with a brick border and a small, rounded seating area nearby. Sun loungers are positioned adjacent to the water.

Cool Blue Waters-Guest Suite

KitchenIndoor spacesLocation

4.93 out of 5 average rating, 115 reviews

4.91 out of 5 average rating, 191 reviews

A fenced front yard is displayed, featuring a porch with two blue chairs and a small table. String lights are hung above, adding a warm touch. The entrance to the cottage is framed by two black shutters, leading into a bright and welcoming space.

Cottage in Central Point

Farm Cottage 1/2 Mile Outside Jacksonville

KitchenFamilyAmenities

4.95 out of 5 average rating, 164 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

FamilyIndoor spacesAccuracy

4.97 out of 5 average rating, 191 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

KitchenFamilyBarbecue

Guesthouse in Grants Pass

A cozy cottage exterior is framed by well-maintained grass and landscaping. A wooden bench is positioned on the porch, while a circular patio features a small table and blue chairs, inviting relaxation in the outdoor space.

Sweet Vintage Cottage steps from Rogue River

FamilyKitchenCheck-in

4.94 out of 5 average rating, 470 reviews

4.9 out of 5 average rating, 472 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

FamilyKitchenBackyard