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Family-friendly holiday rentals in Jo Daviess County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Jo Daviess County

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

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Guest favourite

Townhouse in Galena

4.87 out of 5 average rating, 169 reviews

Galena Territories 3 level Townhome Sleeps nine

Beautiful vacation home in Galena Territories. Located in central resort core, close to all 4 golf courses, owners club, hiking trails and main lodge. Only 15 minutes drive from historic Galena IL. Three level townhome, large screen TV in living room and family room all bedrooms have HDTV. Upper level BR w/en-suite bathroom. Two BR’s are full sized showers/tubs. All linens/toiletries/coffee/condiments provided. Wood burning fireplace with wood provided. Free access to all owners club facilities.

Guest favourite

Home in APPLE RIVER

4.92 out of 5 average rating, 79 reviews

The Ho Hum East on Apple Canyon Lake

The Ho Hum East is a beautiful lake house with private dock on pristine Apple Canyon Lake! The house is named in honor of my grandparents who ran the Ho Hum Motel in Denison, Iowa :) A place to unwind, de-stress, and have some family fun! The house features all brand new mattresses in 3 bedrooms plus flex space; master bedroom with queen bed, guest bedroom with 1 queen and 1 twin, loft bedroom with 2 queens, pull out couch in living room, and 2 couches in the loft that pull out into twin beds.

Guest favourite

Home in Galena

4.99 out of 5 average rating, 191 reviews

The Downtown House - 1820s home steps from Main St

Just steps from Main Street in downtown Galena, this beautifully rehabbed 1820s vacation rental home sleeps up to 7 people. The kitchen is fully stocked with pots & pans, dishes, toaster, standard coffee maker (coffee/cream provided) and more! There is a washer/dryer with detergent for own your personal use. Don't worry about washing the sheets and towels. That's my job :) Enjoy high speed WiFi, board games, stereo system and streaming-ready/smart TV. My home has 1 reserved parking spot.

Cabin in Galena

4.88 out of 5 average rating, 126 reviews

Serenity Cabins - A rustic, yet upscale cabin!

Welcome to Serenity Cabins. Whether your stay here is for a vacation, anniversary, family get together, romantic get away, or spiritual retreat, you'll find your stay to be welcoming, relaxing, memorable, full of charm and you'll love the luxurious modern amenities while feeling the rustic atmosphere. You can fall asleep with the sounds of nature and the whispers of the winds. Go for quiet walks as you surround yourself by nature's natural beauty or unwind in front of the fireplace.

Guest favourite

Home in Galena

5 out of 5 average rating, 35 reviews

3 Greenwood Trail The Galena Territory

"Adorable" cabin in the woods! This cabin has 2 bedrooms (both Queen) and 2 full baths. There are twin beds in the loft, so it is perfect getaway for 2 couples with children or a small family. It also has internet with a smart tv, a fireplace and a deck with a gas grill. This unit is a short 1.8 miles to the Owners' Club where you will have access to the Indoor, Outdoor, and Kiddie Pools, Game Room, Fitness Center, Indoor/ Outdoor Basketball Courts, etc. Sleeps 6. Max. Occupancy 6.

Guest favourite

Home in Galena

4.92 out of 5 average rating, 154 reviews

DunPuttin Place

Nestled on a secluded hillside that overlooks miles of Galena Territory's wildlife preserve, DunPuttin Place offers its guests total privacy, yet the convenience of being only minutes from the area's many popular amenities. DunPuttin Place is not just another carbon copy resort rental. It is a unique private home that has many features seldom found in vacation rentals. It has been tastefully designed and decorated to comfortably accommodate up to 12 guests of all ages.

Guest favourite

Home in Galena

4.92 out of 5 average rating, 117 reviews

Boulder Creek

Strategically placed on the edge of tall woods this home takes advantage of it's beautiful surroundings by featuring floor to ceiling windows so our guests can enjoy nature from both the outside and the inside. Often you will see deer, wild turkey, fox, and birds of all colors! The home features 4 bedrooms and 3.5 baths, bright great room, full length deck with grill, large family room, pool table, games for the little ones and access to the Owners' Club amenities.

Guest favourite

Loft in Galena

4.87 out of 5 average rating, 740 reviews

The Brick Apartment Main Street Galena

My apartment is located right on Galena's historic main street also known as the Helluvahalfmile. There are great views, restaurants and dining, family-friendly activities, and nightlife. You’ll love my place because of it's location, the ambiance, people and the Galena main street life. You are right above my restaurant, which serves coffee, breakfast and lunch!

Home in Galena

4.88 out of 5 average rating, 64 reviews

Cozy 2 bedroom home with fireplace

2 bedroom, 1.5 bath with deck and grill, sofa sleeper, close to amenities in the resort. Enjoy the indoor/outdoor pool, horseback riding, marina for boat rentals and fishing, walking/hiking trails, tennis courts, basketball court, fitness room and game room. Only 6 miles from downtown Galena for antique shopping, fine dining, trolley and wine tours.

Guest favourite

Flat in Galena

4.94 out of 5 average rating, 113 reviews

Main Street Apartment - Free Parking!

This spacious open floor plan apartment on the quiet south end of Main Street has all the comforts of home. Enjoy a large selection of dining options just outside your door! The entire 1200 sq. ft. 2nd floor apartment is yours alone with separate entrances on both Main Street and at the back of the building with FREE DEDICATED PARKING area.

Loft in Bellevue

4.75 out of 5 average rating, 216 reviews

Riverview Loft Guesthouse

Quaint and cozy little haven located in a small community with panoramic view of the Mississippi River from your balcony. This small but charming property has a private entrance and everything you need to be comfortable including kitchen essentials. Close to shopping, parks, public pool, scenic hiking trails and fishing.

Guest favourite

Guest house in Stockton

4.99 out of 5 average rating, 351 reviews

Highview Country Escape - Cozy Cabin with a view

Quiet secluded setting, with spectacular view, on one of the highest hilltops in Illinois! Morning sunrises are exceptional. Evening sunsets are breathtaking. Starry nights are amazing. Our rental is fully independent and has everything that you need for your getaway. Please see all photos

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Popular amenities for Jo Daviess County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Galena

4.78 out of 5 average rating, 18 reviews

HUGE ALL En Suite 6 BR home~Outdoor Hot Tub, Pool

Guest favourite

Home in Galena

4.82 out of 5 average rating, 78 reviews

Fire Pit - Hot Tub - Pool Table - OH MY! Best 5 BR

Cabin in Galena

4.65 out of 5 average rating, 118 reviews

Private 4BR Log Cabin - Jacuzzi, Nature, Lake

Guest favourite

Home in Galena

4.72 out of 5 average rating, 57 reviews

Fabulous Home Away From Home

Home in Saint Donatus

5 out of 5 average rating, 9 reviews

Luxemburg Beauty- The Gehlen House Inn

Apartment in Galena

4.81 out of 5 average rating, 16 reviews

Galena, IL, 1 Bedroom #1

Home in Galena

4.9 out of 5 average rating, 10 reviews

~Make Memories @ Fore Augusta+ New Fire Pit, Outdo

Home in Galena

4.71 out of 5 average rating, 24 reviews

All En Suite 6 BR-Hot Tub! Fire Pit! Whiskey Room!

Family- and pet-friendly home rentals

Villa in East Dubuque

4.75 out of 5 average rating, 84 reviews

Merry Mansion

Home in Bellevue

4.78 out of 5 average rating, 95 reviews

Mississippi River house has everything you need

Cabin in Elizabeth

4.84 out of 5 average rating, 75 reviews

Homestead Hideaway Seven Sisters Suite

Townhouse in Galena

4.69 out of 5 average rating, 26 reviews

25 Oak Glen Drive The Galena Territory

Home in Galena

5 out of 5 average rating, 3 reviews

111 W. Glen Hollow Rd Galena Territory

Home in Galena

4.78 out of 5 average rating, 23 reviews

Fido Friendly! Awesome Resort Core Location! Hot

Home in Galena

4.95 out of 5 average rating, 22 reviews

*4BR Talisman Lodge* w/Outdoor Hot Tub* Pool Table

Guest favourite

Home in Galena

4.97 out of 5 average rating, 30 reviews

Minutes to Galena. Bird Cottage @ Sorriso Vineyard

Family-friendly home rentals with a pool

Home in Galena

4.71 out of 5 average rating, 31 reviews

Cozy home nestled into the trees

Home in Galena

4.55 out of 5 average rating, 38 reviews

Galena Territory overlooking sublime valley

Home in Galena

5 out of 5 average rating, 3 reviews

Redtail Retreat, Galena Territory

Guest favourite

Home in Galena

4.95 out of 5 average rating, 38 reviews

3bd/3.5ba, Bright & Spacious, Fab Screened Porch, Fireplace

Guest favourite

Home in Galena

4.96 out of 5 average rating, 108 reviews

Galena Territory Home with full resort amenities**

Home in Galena

4.56 out of 5 average rating, 9 reviews

57 Oak Glen The Galena Territory

Villa in Galena

4.67 out of 5 average rating, 15 reviews

Cozy spot on Creekwood! Fireplace, Outdoor Gas Fir

Home in Galena

4.9 out of 5 average rating, 10 reviews

14 Southridge Drive The Galena Territory

Destinations to explore