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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home

4.92 out of 5 average rating, 91 reviews

Winter Sports/Fireplace/Owner Club Access, Dog Friendly!

Cozy Tranquility on Walnut, Galena IL Entire Home Vacation Rental, 1 Bed, 2 Bath, 4 Person Occupancy This adorable, recently remodeled and refurnished, 1 bedroom/2 full bath townhome is ready to welcome and embrace you any time of the year! Situated with seasonal views of the North Golf Course, and just a short distance from the driving range makes it a great choice for golfers... it's charm and central location make it an ideal choice for everyone! The lower floor offers a fully equipped kitchen, dining area, and living room lounge with large Smart TV (featuring Roku, Hulu, Disney+, ESPN+) and rustic wood burning fireplace. Exit the sliding door and enjoy nature at its finest. The back deck has a gas grill, and table and chair set to savor some alfresco dining or dark sky star gazing. On the upper level, as you pass the landing area, you will find the bedroom with heavenly king sized bed and private full bath. A second Smart TV (with the same options as the lower level TV) is featured in the bedroom as well. As a fabulous bonus, our guests will have access to a second pool reserved for the exclusive use of guests of this town home group. If your dog will be accompanying you, please let us know. We kindly ask that he/she be kenneled any time left alone in the townhome. There is a one time charge of $75 for your pet's stay. Guest Access Our guests have full complimentary access to the Galena Territory Owners' Club and all the amenities it offers such as indoor and outdoor pools, fitness center/workout facility, large game room, gym, tennis, basketball, pickle ball courts and more. The Area Galena IL has hundreds of unique gift and clothing shops, antique stores, art galleries and artist studios. It boasts a rich performing arts community, live music, gourmet delights, as well as a multitude of museums, wineries, historical sites and tours. There are opportunities to enjoy the outdoors golfing, skiing, playing tennis, boating, fishing, zip-lining, hiking, horseback riding, hot-air ballooning and much more. Getting Around A car is necessary to see all that Galena and the surrounding area has to offer! Taxi, Uber and Lyft services are available.

Guest favorite

Home

4.96 out of 5 average rating, 140 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!

Superhost

Home

4.87 out of 5 average rating, 116 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

4.98 out of 5 average rating, 164 reviews

Adorable Settlement home, views of lake/waterfall

Views of the waterfall and lake Galena in the fall, winter and spring. This home was just fully remodeled. All new furniture, flooring,cabinets and bathrooms. You will have access to 6 proxy cards to enter into the Owners Club. Parking is on site, WI-FI, all smart TV's to login into your NetFlix acct. Each of the bedrooms has their own private bathroom. The kitchen is stocked with mostly everything you need. Towels, linens, throw blankets, coffee, creamer provided. Toilet paper, paper towels too

Guest favorite

Home

4.8 out of 5 average rating, 25 reviews

House 4bd/3bth-fire pit-screen porch-outdoor pool

Less than 5 minutes from Golf Club and Guest Club. Less than 10 minutes from Marina and Shenandoah Riding Center!!! Relax with the whole family at this peaceful place to stay. Enjoy the backyard fire pit and the indoor fireplace. Make a meal in the well appointed kitchen. Enjoy a glass of wine in the spacious screened in porch, while others are playing pool in the basement. Go enjoy the indoor pool(year round) and outdoor pool(during summer). 25 minutes to Chestnut Mountain Ski Resort.

Guest favorite

Home

4.94 out of 5 average rating, 36 reviews

Three Kings and A Little Bling

WELCOME HOME! Your own 3 bedroom townhome with 3 luxuriously furnished king size beds, each with attached/adjacent baths - and every room with A Little Bling! Everything is fresh & clean - the way we like it when we travel! Personal touches like E&O soaps & shower gel. Kitchen, grill, 2 comfy living areas and 2 woodsy decks. A short walk to Eagle Ridge Resort with golf, lake, restaurant, bar, & Spa. Also, all amenitiesThe Galena Territory has to offer within a short driving/walking distance.

Guest favorite

Home

4.82 out of 5 average rating, 293 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

Townhouse

5 out of 5 average rating, 16 reviews

Perfect Getaway: Newly Renovated

Take it easy at this unique and tranquil getaway. Relax with a few friends at this peaceful place to stay. Located in the Galena Territories, this rental provides something for everyone. During the summer months you can access trails, golfing, an indoor and outdoor pool and so much more. During the winter months you are close to one of the finest ski resorts around. In Fall, access breath-taking views of trees as they change color. All year round there is something to look forward to!

Superhost

Cabin

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 favorite

Home

4.91 out of 5 average rating, 111 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!!

Guest favorite

Home

4.91 out of 5 average rating, 152 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 favorite

Home

4.97 out of 5 average rating, 38 reviews

Cliffside Cottage, Breathtaking Views near Galena

Cliffside Cottage, a secluded wooded retreat located on 50 acres with breathtaking views, a pond to swim, fish, wooded trails, and so much more! A perfect destination to get away from it all while being in close vicinity to so many amenities. The cottage, conveniently located just off Highway 20. Only a 15 minute drive from Eagle Ridge/Galena Territory, and only 20 minutes from Chestnut mountain and historic downtown Galena that offers museums, boutiques & restaurants!