Holiday rentals with a pool in Galena

4.92 out of 5 average rating, 101 reviews

Perfect Location! 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.

4.9 out of 5 average rating, 167 reviews

The Airy Aerie: Owners' Club access, golf nearby!

Welcome to the Airy Aerie: an avian themed townhome in the heart of the Galena Territory. Our space has been carefully curated to reflect the diversity of birds you will find in the natural surroundings of the area. There are two ensuite bedrooms and a full kitchen featuring granite countertops and stainless steel appliances. There is a loft space upstairs where a rollout twin bed can be set up. Our home can accommodate a maximum of 6 overnight guests (assuming 1 person on the twin rollout bed).

4.97 out of 5 average rating, 138 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.

4.97 out of 5 average rating, 145 reviews

Pools, Hot Tub, Fire tables, dog friendly

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

4.98 out of 5 average rating, 134 reviews

Villa in Galena

Semi-private Pool, King Bd, Near Spa, Golf, Trails

✓Near hiking trails & paved walking trails ✓Stonedrift Spa, 3 min drive ✓North Course & Driving Range, 2 min drive ✓Downtown Galena, 15 min drive ✓Semi-private outdoor pool, steps away ✓Well equipped kitchen w/modern appliances ✓Gas grill ✓Smart TV on each level w/Roku & YouTube TV ✓Computer desk ✓Fireplace w/supply of firewood ✓Queen sofa bed ✓2 Full baths ✓Owner's Club access ✓Indoor pool ✓Lake access ✓Chestnut Mountain (Ski & Zipline), 25 min drive ✓Guest favorites: "cleanliness & comfort"

4.94 out of 5 average rating, 150 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!

4.99 out of 5 average rating, 152 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).

4.98 out of 5 average rating, 160 reviews

Treehouse in Galena

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

4.95 out of 5 average rating, 243 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.

4.98 out of 5 average rating, 117 reviews

Cabin in Galena

Family Fun! Hot Tub•Fire Pit•Game Room•3 Kings!

Ultimate Family Escape in Galena Territory! Unwind, explore, and make memories at this chic, spacious cabin! Sip coffee on the deck as deer wander by, soak in the hot tub, and gather around the fire pit for s’mores. Stay cozy by the wood fireplace or challenge the family with arcade games, air hockey, pinball, and darts! Enjoy Owner’s Club access with a pool, fitness center & pickleball (8 amenity cards). Adventure awaits—book your perfect getaway today!

4.93 out of 5 average rating, 113 reviews

Peaceful 2Bedroom Townhome Sanctuary w/Soaking Tub

Welcome to Dear Galena, a modern Zen retreat on a corner-unit townhouse golf villa with a wooded view. It's the perfect getaway for couples, friends, family or just you! Situated within The Galena Territory and near Eagle Ridge South Golf Course, this townhouse has two bedrooms - each with a king size bed and two bathroom. A pull out sofa bed for additional guest and high-speed Wi-Fi for streaming and all of your work from home needs.