Vacation rentals with a pool in Jo Daviess County

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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

Home in Galena

4.97 out of 5 average rating, 101 reviews

Major reno, photos coming! 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

4.92 out of 5 average rating, 185 reviews

Galena Getaway

Peaceful, pet-friendly ($50 fee per reservation) vacation home in the Galena Territory. 3 bedrooms, 3 bathrooms, two living rooms, 2 wood fireplaces, screened in porch, upper level porch, deck, firepit, access to owner's club (pool, exercise room and game room), marina and 24 miles of hiking trails. Sleeps up to ten people. (Please ensure your guest count is accurate when you make your reservation. The guest count can be updated if needed. Inaccurate reservations will be charged accordingly. )

Guest favorite

Home in Galena

4.97 out of 5 average rating, 125 reviews

Galena Territory Sun-Drenched TreeHouse w/ Views

Enjoy your respite in this 4000 sq ft, 3 bed/3 bath, sun-filled home. Perched on a hill in the Territory, the home is nestled among Oak trees w/ expansive views. Perfect for families, couples, friends, bird watchers and nature lovers alike. The private location is mere minutes from the Owners Club, Eagle Ridge, Stonedrift Spa, Golf, Shenandoah Riding Ctr, Marina, walking trails and only 15 minutes to Downtown Galena and Chestnut Mountain Ski Slopes. 3 levels of living and room to spread out!

Guest favorite

Home in Galena

4.89 out of 5 average rating, 106 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

4.93 out of 5 average rating, 108 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

Townhouse in Galena

4.99 out of 5 average rating, 100 reviews

Are you seeking a stylish and tranquil escape in the countryside? Our fully renovated and modernized townhome is the epitome of luxury and comfort, ensuring a memorable stay. Situated in the picturesque, resort-like Galena Territory, surrounded by lush hills, and with access to a plethora of amenities (e.g., pools, tennis/pickleball courts, gym, game room), our home offers a peaceful retreat while being conveniently close to downtown, golfing, wineries, dining, shopping, and ski (Chestnut).

Guest favorite

Home in Galena

4.82 out of 5 average rating, 277 reviews

Galena Retreat - Eagle Ridge Territories

The perfect place to relax and unwind in a wooded setting far away from the hustle of daily life. Short drive to downtown Galena for shopping and dining. Short drive to skiing and you can walk to the resort for dining and adult beverages. Indoor and outdoor swimming pool at the owners club along with other activities. 1 bedroom w/one queen, 1 bedroom w/two single beds, 2 full bathrooms, Kitchen, Living Room Dinning area, Screened Summer room, Fully equipped Kitchen, Cable TV and wifi.

Guest favorite

Home in Galena

4.95 out of 5 average rating, 203 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

Welcome to the Toasted Marshmallow; your cozy escape from reality. Enjoy the peace and quiet of this charming three bedroom, two bath home in The Galena Territories. Kitchen is fully equipped to meet your needs. Enjoy the additional lower level family room w/ 2nd fireplace so your group may spread out. Deck with ample room for dining outside and enjoying your coffee or wine. Home includes six access passes to the GTA Owner's Club and pools. Strong Wi-Fi for remote work, if needed.

Guest favorite

Home in Galena

4.97 out of 5 average rating, 174 reviews

Newly Renovated. Gorgeous Retreat!

Newly Renovated. Gorgeous Retreat w/seasonal waterfall view! *This home has Large flat screen TV's in Living Room and Both BDRMS. All new kitchen cabinets, Side by Side Refrigerator with Ice Maker, Electric Stove, Microwave, and includes Dishwasher, Keurig Coffee pot, Regular 12 c coffee pot. New Flooring through out, and new Furniture.. Relax by the electric fireplace indoor or the backyard firepit. NO SMOKING IN UNIT New windows coming in the near future. Minimum 2 night stay

Guest favorite

Home in Galena

4.93 out of 5 average rating, 122 reviews

The Beauty on Belden: minutes from amenities!

Our 3 bedroom, 3 bathroom retreat located in the Galena Territory is the perfect choice for your getaway with access to the Owners' Club. Each bedroom has its own private bathroom. The four seasons room is perfect for relaxing. The home has a spacious back deck for cookouts and entertaining. The house is a 3 minute drive from the Owners' Club and minutes away from 4 golf courses, Shenandoah Riding Center and Marina. 10 minutes to downtown Galena, 15 min to Chestnut Mountain.

Guest favorite

Townhouse in Galena

4.96 out of 5 average rating, 125 reviews

Vista View Golf Villa in lovely Galena

Relax and enjoy the countryside of the galena territory in this cozy golf view townhouse with all the comforts of home. Located within the Eagle Ridge Resort community with 4 highly rated golf courses , a beautiful lake, indoor/ outdoor pool, horseback riding , and a short 15 minute drive to the quaint historic town of Galena for strolling along Main St. for unique shopping , delicious dining choices and spirits , art, kayaking along the river , and beautiful architecture .

Guest favorite

Home in Galena

4.9 out of 5 average rating, 103 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!!