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Kid-friendly holiday rentals in Ashland

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Ashland

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Villa in Grants Pass

4.86 out of 5 average rating, 161 reviews

Family Friendly Home! HotTub, Game Room, MiniGolf!

Welcome to our family friendly little home with all the fun add ons you could dream of. A Tiny home with tons to offer for the kids!! There's mini golf, a hot tub, a full arcade room, a playground, a jungle gym, and half court basketball court... Located on a pleasant street in a great part of town with a market just blocks away. just 3 minutes off the freeway. Two Bed room with queen size beds, and a sleeping loft for two kids. Come sit by the fire, watch the kids play in the yard, and relax.

Guest favourite

Home in Grants Pass

4.97 out of 5 average rating, 354 reviews

Charming Cottage, Walk To Downtown!

Newly remodeled 1910 cottage a few short blocks away from historic downtown! 1 bedroom and 1 loft both featuring brand new queen beds.The cottage is only two miles off of I-5 and within walking distance to some of the best restaurants, bars, and shops downtown has to offer. The living room features a 60in HDTV. The kitchen is equipped with dishes, glassware, pots and pans, a keurig and many other commodities . The Outdoor area includes a grill, picnic table as well as a fire pit. No pets.

Home in Medford

4.79 out of 5 average rating, 192 reviews

Common Area! Near Rogue X, 3 king beds 82" 4k tv

Huge grassy common area! Big 4k TVs. House is a large 3 bedroom in a nice neighborhood. Must be respectful of neighbors. No dogs left outside barking. There is an HOA at this house and disruptive behaviors are reported and fined. Guest pays all assessed fines! No outside music, no fireworks. This is a beautiful family oriented neighborhood backing up to a Huge common grassy area. There isn't any playground equipment but perfect for Frisbee, soccer, etc. Please treat it respectfully

Guest favourite

Home in Central Point

4.96 out of 5 average rating, 126 reviews

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

Kid friendly, Inviting & Comfortable, 3BR 2BA + office in a clean and safe neighborhood. All the comforts of home will meet you at our door in the peaceful town of Central Point, OR. Here you'll find excellent local restaurants, shops, and parks that will make your stay enjoyable. Less than a mile from Interstate 5, its a great location for travelers. A quick 15 minute drive to Jacksonville, 25 mins to either Ashland or Grants Pass, Central Point is an ideal spot for both work and play.

Guest favourite

Guest house in Ashland

4.99 out of 5 average rating, 542 reviews

Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

Guest favourite

Rental unit in Grants Pass

4.89 out of 5 average rating, 288 reviews

West Park Unit A

Located in the prime spot of the Riverside Park area, this 2-bedroom, 2-bathroom is newly built and designed to impress. The upscale and luxurious atmosphere will leave you feeling right at home. Only a 5-minute walk away from Riverside Park, Fairgrounds, Walking Bridge, and the Downtown Historical District, this location couldn't be any better. Despite its proximity to all these popular attractions, this spot remains quiet and private, making for a truly relaxing stay.

Guest favourite

Home in Gold Hill

5 out of 5 average rating, 141 reviews

Hygge Hideaway. A home for rest and adventure

In Scandinavia, "hygge" represents contentment & coziness. Settle into this sun-soaked, mountain-side, madrone forest & valley view home for relaxation on the deck, wine by the fire, & mineral baths. This solar powered home has easy access to outdoor adventures. Options include Laundry, Wood Stove (fire logs avail $), & fully equipped Kitchen. Whether you're looking for a getaway, family event, road stop, or retreat - you're welcome here. Pets require PRE-APPROVAL.

Guest favourite

Home in Medford

4.89 out of 5 average rating, 272 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.

Guest favourite

Guest suite in Grants Pass

4.79 out of 5 average rating, 146 reviews

Two room private suite on river, friendly hosts.

Our place has just been remodeled. It is close to public transport, the city center, and family-friendly activities. We are within walking distance of a store, and a great restaurant. You’ll love our place because of the outdoor spaces, the light, and sitting next to the Rogue River watching the rafters, boats, geese, Egrets, Herons, and eagles.. Our place is good for couples, solo adventurers, business travelers, and families (with kids).

Guest favourite

Home in Medford

4.95 out of 5 average rating, 109 reviews

Comfy Cozy Casa

Relax with the whole family at this comfy and clean family friendly home centrally located in a cute residential neighborhood. Only minutes away from major shopping, food, and entertainment. This location makes for an easy stop over along I-5 on an Oregon road trip. Hiking trails are not far from this location, many guests stay here to check out Crater Lake National Park, and even some of the mountain lakes not far away.

Home in Medford

4.84 out of 5 average rating, 231 reviews

Trailer parking, king bed, great for guests/pets!

Great location-directly across from North Medford High School. Newly renovated house inside and out! We created this house with comfort in mind-cozy pillow-top beds, super fast wi-fi, and 2 tv’s with Netflix, Disney and Hulu apps, new couch, granite countertops with a great table to enjoy a meal or a cup of coffee!

Guest favourite

Guest house in Ashland

4.99 out of 5 average rating, 141 reviews

Courtside Cottage - WalkScore 93 - Dog Friendly

The same cottage you've known and loved. Now we manage it ourselves. A sampling of previous reviews are in the photos. Named one of the Top Ten Traveler's Accommodations in Ashland by The Oregonian. Dogs always welcome. Please read all of the house rules and particulars regarding parking. Thanks!

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Flats

Convenient locations with everyday essentials

Popular amenities for Ashland family-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Guest favourite

Home in Grants Pass

4.97 out of 5 average rating, 243 reviews

Home with gated driveway near Downtown & River

Guest favourite

Home in Grants Pass

4.96 out of 5 average rating, 293 reviews

Mid Century Modern

Home in Grants Pass

4.83 out of 5 average rating, 104 reviews

Full House: Fenced Backyard, Wi-Fi, Dogs Allowed!

Guest favourite

Home in Central Point

4.9 out of 5 average rating, 113 reviews

Lovely Central Point Home w/EV Charger

Guest favourite

Home in Talent

4.81 out of 5 average rating, 125 reviews

First class Home in Fine Neighborhood

Guest favourite

Home in Ashland

4.91 out of 5 average rating, 124 reviews

The Madrone House, mountain views.

Guest favourite

Home in Medford

4.98 out of 5 average rating, 101 reviews

Howell House-The Perfect Getaway

Guest favourite

Home in Grants Pass

4.89 out of 5 average rating, 310 reviews

Home Away From Home in Grants Pass, OR

Family-friendly apartment rentals

Rental unit in Medford

4.77 out of 5 average rating, 247 reviews

Classic & Cozy | W/D & Parking | close to DT

Guest favourite

Rental unit in Ashland

4.89 out of 5 average rating, 752 reviews

Clean, Stylish Apt w/kitchen. block from Downtown

Guest favourite

Rental unit in Medford

4.96 out of 5 average rating, 378 reviews

Suite Comice (Sanitized daily)

Guest favourite

Rental unit in Grants Pass

4.82 out of 5 average rating, 204 reviews

Great location to I-5 and city! King bed!

Guest favourite

Rental unit in Grants Pass

4.99 out of 5 average rating, 169 reviews

Light and Bright! Entire 2 Bedroom Apt!

Guest favourite

Rental unit in Medford

4.99 out of 5 average rating, 251 reviews

Suite Madrona

Guest favourite

Rental unit in Grants Pass

4.93 out of 5 average rating, 114 reviews

Brand New Stylish MCM Studio

Guest favourite

Rental unit in Ashland

4.95 out of 5 average rating, 630 reviews

Swank House -Downtown Suite- Pet Friendly

Family-friendly apartment rentals

Guest favourite

Apartment in Rogue River

4.9 out of 5 average rating, 124 reviews

The Executive Suite

Guest favourite

Apartment in Phoenix

4.99 out of 5 average rating, 69 reviews

Phoenix OR Duplex-Full House Rental (1,100 Sq Ft)

Guest favourite

Apartment in Ashland

5 out of 5 average rating, 6 reviews

Plaza North Penthouse

Guest favourite

Apartment in Jacksonville

4.93 out of 5 average rating, 15 reviews

Selah House!

Guest favourite

Apartment in Ashland

4.78 out of 5 average rating, 36 reviews

Spacious Modern Condo Walk Downtown & OSF

Apartment in Grants Pass

4.17 out of 5 average rating, 6 reviews

Modern, retro updated bungalow

Guest favourite

Apartment in Rogue River

4.92 out of 5 average rating, 66 reviews

Black Pearl

Guest favourite

Apartment in Ashland

4.92 out of 5 average rating, 13 reviews

Plaza North Suite 202 Sonoma

Quick stats about holiday rentals that are kid-friendly in Ashland

Total rentals
30 properties
Nightly prices starting at
£61 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore