Vacation rentals with a pool in Jackson County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Jackson County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

Ranch in Elizabeth

4.59 out of 5 average rating, 29 reviews

The Cabin at The Ranch, Galena, aka The Love Shack

Newly renovated, private romantic cabin with high end appliances, granite kitchen and bath counters, knotty alder doors. Located on 500 acre working cattle ranch and commercial wine grape vineyard. Wildlife abounds: Bald Eagles, coyote, bobcat, deer, pheasant, raccoon, and turkey. Close to The General golf course. Hayride and vineyard tour available. Use the amenities of GTA Owner’s Club. See adjacent Sister property The Lodge at The Ranch, airbnb.com/h/thelodgeattheranch, for groups up to 12.

Superhost

Home in Galena

4.87 out of 5 average rating, 23 reviews

Expansive 5b6ba Countryside Home

Come enjoy your home-away-from-home with a private forest on a serene 2.12 acres. This home is perfectly designed for guests to spend quality time with family, friends, or colleagues in large, open concept common spaces and then discreetly escape to recharge into your own space/bedroom. The kitchen is professional grade and fully stocked to help you impress others with your cooking techniques OR to hire a professional. Each bedroom has with a private bathroom and towels of the highest quality.

Superhost

Home in Galena

4.57 out of 5 average rating, 7 reviews

Modern Home - Sauna, Steam Shower & Chef's Kitchen

Escape to this 4,000 sqft retreat, perfect for family gatherings or groups. Unwind with a private hot tub, sauna, steam shower, and two fireplaces. Indulge Your Inner Chef: Prepare culinary delights in the gourmet chef's kitchen, then challenge your friends to a foosball or poker game. The GTA Awaits: Enjoy full access to all GTA amenities, a pool & recreation complex, lake & marina, and over 25 miles of scenic trails. Downtown Galena & Chestnut Mountain Ski Resort are both 10 minutes away.

Guest favorite

Home in Galena

4.96 out of 5 average rating, 83 reviews

Secluded Treehouse close to Hwy 20 to access

Enjoy the many charms of this one of a kind Tuscan style treehouse with different levels showcasing spectacular views. This home has every amenity and personal touch of home to make your stay relaxing and memorable. Conveniently located approximately 1 mile off Highway 20 in the Galena Territory, backing up to hole 13 on The General Golf Course. Set back off the main road you will enjoy privacy without sacrificing convenience and access to the many amenities offered during your stay.

Guest favorite

Cabin in Elizabeth

5 out of 5 average rating, 9 reviews

Cedar Cove Cabin, Private Beach near Galena

Cedar Cove Cabin, nestled amongst the woods and a newly structured pond you’ll wake up feeling like you’re in the north woods! A luxury cabin amongst a wooded retreat on 50 acres, pond to swim and fish, beautiful surroundings , trails, and so much more! Welcome to your perfect vacation home! As you drive down the lane to our Cedar Cove Cabin you will instantly feel that you are leaving your busy, hectic daily life and you have entered a place of serene getaway.

Guest favorite

Home in Galena

5 out of 5 average rating, 54 reviews

Stunning 5 bdm home on The General in Galena Terr!

No MGMT Fees! Enjoy all that Galena Territory and Jo Daviess County has to offer! Nearly 5k sq ft with 5 bdrm/5.5 baths and located on the number one handicap hole on The General golf course with views of holes 12, 13, 14, 15 and 16! A one-of-a-kind location on over 2 acres of land. About 20 min from Downtown and Chestnut Mtn! Minutes from golf, hiking, horseback riding, boat rentals, fishing, indoor/outdoor pool, fitness center and game room at the Owner's Club!

Superhost

Home in Galena

4.71 out of 5 average rating, 31 reviews

Cozy home nestled into the trees

Cozy 1 bedroom home located in the Galena Territory. Wooded background, screened porch. Access to resort amenities, outdoor pool, indoor pool, basketball court, tennis courts, horseback riding, golf, game room, exercise room, snack bar, hiking, walking trails, marina for boat rental and fishing. Only 6 miles from downtown historic Galena for shopping, restaurants, Trolly tours, ghost tours, wine tasting, and so much more!

Guest favorite

Vacation home in Galena

4.99 out of 5 average rating, 73 reviews

Modern,hot tub firepit,nature horse view,amenities

4 Bedrooms, 4.5 Bathrooms, Outdoor Hot Tub, New Construction, 3000 sq ft, Sleeps 10 in beds. Modern newer construction 4 bedroom home with gorgeous furnishings in the Shenandoah Valley. Just 7 minutes from the GTA Owners Club and 15 minutes to downtown Galena. This home is NOT pet friendly. Total price per night - No added 3rd party fees.

Superhost

Serviced apartment in Galena

4.91 out of 5 average rating, 46 reviews

Studio Unit @ Galena Condo Resort

Studio Unit at a resort condo development in beautiful, Galena,Illinois ❤ Free Parking. Free Internet ❤ ★ If reserving a FRIDAY OR SATURDAY there is a 2 night minimum unless request is made last minute (3 days before check in)★ ★24 hour reception★ ★Calendars updated daily★ ★Multiple Units/Room Sizes Available★