Vacation rentals with a pool in Jo Daviess County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Jo Daviess County

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

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Guest favorite

Cabin in Galena

4.96 out of 5 average rating, 114 reviews

Winter Getaway! <-Hot tub- Fire place-Game room->

Escape to our cozy luxe cabin in Galena Territory, the perfect retreat for winter! Start your mornings sipping coffee by the gas fireplace, then warm up each evening in the hot tub! Enjoy friendly competition with arcade games, board games, air hockey, and darts. With 10 amenity cards, you can access the owner’s club for swimming and exercise including indoor pickle ball-rackets and balls at the house! Experience relaxation and adventure in this tranquil haven—your unforgettable getaway awaits!

Superhost

Home in Galena

4.87 out of 5 average rating, 115 reviews

Sweet Escape~Galena Territory~Hot Tub~Pool Table

Beautiful 6 bedroom, 5.5 bath home with a screened-in hot tub, pool table & fire-pit table in the gorgeous Galena Territory - perfect for enjoying Galena! The home boasts 4 en suite bedrooms, 3 king beds, 3 queen beds, and 1 twin bed. Bedrooms have a 32" smart TV. The large kitchen has a table that seats 6 and 3 island bar stools. The dining room seats 8. There are 2 refrigerators. There is a deck and screened-in porch, a living room and family room with a 65" flat-screen TV & DVD player.

Guest favorite

Home in Galena

4.97 out of 5 average rating, 126 reviews

Newly Remodeled! Hot tub, views, 6BR/6BA

Welcome to The Double Eagle! Experience Galena and the Territory while you relax in this 6 bedroom/6 bath home overlooking the fairway. This well-stocked and spacious three story home easily accommodates multiple families or large groups and has many outdoor spaces to enjoy! Sip your morning coffee in the 3-season room with cozy sectional, make the most of your afternoon playing pool or foosball in the game room, and finish the day by grilling out on the back deck and relaxing in the hot tub.

Guest favorite

Home in Galena

4.96 out of 5 average rating, 113 reviews

Holiday Hot Tub Escape-Open for December!

Step into Rolling Hills Retreat, a sanctuary from the everyday bustle! Our dog-friendly rental offers breathtaking views and numerous amenities for your pleasure and relaxation. Enjoy a swim in the indoor or outdoor pool, and discover a variety of amenities that promise an unforgettable stay. *Pickle Ball *Basketball *Pool Tables *Hiking Trails *Workout Room *Tennis Courts *Brand new (June 2024) Marina with boat rental (additional charge) *Ping Pong tables *Arcade *Scenic Waterfall *Kayaking

Guest favorite

Townhouse in Galena

4.97 out of 5 average rating, 116 reviews

Pickleball & Game Room! Close to all amenities

Many amenities just steps from our home! Including pickleball, a spa and golf. Escape to our bright modern townhome in Galena. Enjoy 3 levels of space for the whole family. Experience outdoor fun at local attractions, enjoy the pools at The Owners Club. Unwind with movies in the game room or relax to records in the living room. This retreat offers the perfect blend of comfort and convenience. Book your stay and create cherished memories. Pet friendly if you would like to bring your fur baby.

Guest favorite

Villa in Galena

4.98 out of 5 average rating, 108 reviews

King Bed, Woodburning Fireplace, Indoor Pool

THANKSGIVING now available after last minute cancellation! ◆ Peaceful, nature views ◆ Indoor pool, year round access ◆ Well equipped kitchen ◆ Smart TV on each level w/Roku & YouTube TV ◆ Woodburning fireplace w/supply of firewood ◆ Computer desk ◆ Queen sofa bed ◆ Gas grill ◆ Fitness center ◆ Paved walking trails nearby ◆ North Course & driving range conveniently up the road ◆ Stonedrift Spa, 3 min. drive ◆ Downtown Galena, approx. 15 min drive ◆ Chestnut Mountain Ski , approx. 25 min drive

Guest favorite

Home in Galena

4.94 out of 5 average rating, 125 reviews

Awesome Lodge in Galena Territory

Bring the whole family to our Galena home for fun, games, and making memories! Located 1.3 miles from the Owner's Club in The Galena Territory, enjoy many amenities and everything Galena has to offer! 15 mins to downtown! 3 bedrooms and 3 full bathrooms, the house is equipped with great Wi-Fi and 8 key cards to access Territory amenities! There is tons of space to spread out across 3 floors . Enjoy the game room, hot tub, three seasons room, deck, and outdoor space in this awesome home!

Guest favorite

4.91 out of 5 average rating, 110 reviews

Modern Home w/Amazing Views, Hot Tub, Game Room

Modern home on the hill with great views overlooking the valley. Main level features a dining room, living room w/fireplace & sitting area for reading time. Nice size deck off the main w/gas grill & seating. Good size kitchen! ML also has King bedroom/full bath. Upper Level has 2 bdrms/full bath. Lower level has bar area, foosball, air hockey, bdrm/bath, walkout to deck & HOT TUB! Outside features a firepit and play area for the kids. Great place for families to enjoy!!