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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Top guest favorite

A tranquil vacation home is set in a lush green landscape. The house features a screened-in porch and multiple balconies, surrounded by a wooden fence. Mature trees provide shade, and the inviting lawn enhances the serene outdoor environment.

Home in Galena

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. )

4.93 out of 5 average rating, 222 reviews

Guest favorite

The lake house is situated on a sloping hillside, surrounded by trees. A stone pathway leads down to the water's edge, where a private dock can be seen. The calm lake reflects the blue sky and scattered clouds, creating a serene setting.

Home in Apple River

The Ho Hum East on Apple Canyon Lake

The Ho Hum East is a beautiful lake house with private dock on pristine Apple Canyon Lake! The house is named in honor of my grandparents who ran the Ho Hum Motel in Denison, Iowa :) A place to unwind, de-stress, and have some family fun! The house features all brand new mattresses in 3 bedrooms plus flex space; master bedroom with queen bed, guest bedroom with 1 queen and 1 twin, loft bedroom with 2 queens, pull out couch in living room, and 2 couches in the loft that pull out into twin beds.

4.93 out of 5 average rating, 103 reviews

Top guest favorite

A custom log cabin is framed by lush greenery and manicured landscaping. The warm wooden exterior features multiple gabled roofs and large windows. A stone pathway leads through the vibrant garden, creating an inviting approach to the entrance.

Cabin in Galena

Private, Galena Log Cabin

This custom log cabin is the perfect getaway for friends & family seeking the solitude of the Galena Territory and fine dining and shops just 10 minutes away on Galena's Main Street. Each of the 3-levels offers an owner's suite with bath. Cozy up to 2 fireplaces, grill on the deck, or make 'smores at the firepit. The cabin has high speed, fiber internet and the lower-level walkout features a 55” flat screen TV. Guests can access swimming pools & pool tables at the Owner's Club 7 minutes away.

4.96 out of 5 average rating, 139 reviews

Top guest favorite

A well-maintained cabin is set amid lush greenery, featuring a stone accent facade. The exterior includes a two-car garage with a vibrant teal door, and a welcoming porch with blue chairs inviting relaxation. Spacious lawns surround the cabin, enhancing the natural setting.

Cabin in Galena

Fast Wi-Fi | EV Charger | Fireplace | Hot Tub

Unwind in our comfortable Galena Territory cabin with 3 bedrooms, 3 full baths and sofa sleeper. EV Charging outlet in garage. Strong Eero boosted Wi-Fi; Roku streaming on every floor. Stone wood burning fireplace. Three-season room with scenic sunrise and wooded views. Lower-level walkout to patio with hot tub, fire pit and beautiful stargazing. Minutes away from the Lake Galena Marina, golf, tennis, pool, and fitness center. 15 mins from Chestnut Mountain and historic downtown Galena.

4.98 out of 5 average rating, 129 reviews

Top guest favorite

A spacious living area features vaulted wood ceilings and a stone fireplace, creating a warm focal point. Cozy seating arrangements include plush sofas and armchairs, accompanied by decorative blankets. Large windows allow natural light to flood the space, showcasing wooded views outside.

Cabin in Galena

Family Fall! Hot Tub•Fire In/Out•Game Room•3 Kings

Relax, unwind, & explore at this Fall Retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful winter getaway. Sip morning coffee as snow falls through the trees, then unwind in the hot tub or by the fireplace. Roast marshmallows around the fire or enjoy arcade games, air hockey, darts, and more indoors. Stay active with access to the owner's club—indoor pool, fitness center, and pickleball (8 amenity cards included). Perfect for relaxation and fall/winter adventure!

4.97 out of 5 average rating, 199 reviews

Top guest favorite

A warm living area features a brick fireplace with a mounted television above it. Large skylights and windows allow natural light to fill the space. A coffee table stands at the center, adorned with decorative items, complemented by comfortable seating and a vibrant area rug.

Home in Galena

Secluded Treehouse w/great views from every room!

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.

4.97 out of 5 average rating, 133 reviews

Top guest favorite

The living area features mid-century modern furniture with vibrant green and orange chairs surrounding a coffee table. A gas fireplace is centered under a unique light fixture, and large windows allow views of the surrounding woods. A dining area is visible in the background.

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

4.99 out of 5 average rating, 241 reviews

Guest favorite

Home in Galena

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.

4.94 out of 5 average rating, 282 reviews

Top guest favorite

An outdoor seating area is arranged around a central fire pit on a spacious deck. Comfortable chairs with decorative pillows face the fire, surrounded by a plaid rug. Lush green hills are visible in the background, enhancing the tranquil outdoor setting.

Home in Galena

Golden Meadows Escape: A Luxurious Country Retreat

"This home is flawless! From the serene, private location to the abundant amenities, our trip was perfect. My kids especially loved the theater room and gaming console." – Sadie Golden Meadows Escape offers the perfect blend of tranquility and entertainment, with easy access to everything Galena has to offer. This beautifully designed home rests on a spacious 2+ acre lot, ensuring endless peace and family fun. "A taste of luxury with all the charm of the countryside" – Matt

4.98 out of 5 average rating, 101 reviews

Top guest favorite

A spacious home is situated on a gently sloping landscape, framed by mature trees. The exterior features a combination of stone and wood elements, with a welcoming front porch and large windows that enhance natural light. A paved driveway leads up to the property.

Home in Galena

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!

5.0 out of 5 average rating, 104 reviews

Top guest favorite

A spacious dining area features a large wooden table surrounded by black chairs. A living space is visible in the background with comfortable seating, large windows, and a sleek gas fireplace. Natural light fills the room, highlighting the open and airy layout.

Vacation home in Galena

Summer in Galena | Hot Tub, Fire Pit & Views

Welcome to Shenandoah Ridge—our thoughtfully designed 4-bedroom, 4.5-bath vacation rental tucked into the woods of The Galena Territory. Spacious, peaceful, and full of cozy touches to help you unwind. Whether you’re here for a family getaway, group trip, remote work retreat, or just time in nature, you’ll find everything you need to feel at home. Just 7 minutes to the Owners Club and 15 minutes to downtown Galena—close to the action, but still calm and quiet.

4.96 out of 5 average rating, 167 reviews

Top guest favorite

Home in Galena

5 Min to Owners Club | Hot Tub & Bunkhouse

Escape to the idyllic charm of our 5-bedroom Cottage, tucked in the beautiful Galena territories. Prime location within minutes of the Owners Club (free access) & Eagle Ridge Resort where you can enjoy all of their public amenities. From the inviting warmth of the interiors to the large, covered deck overlooking the open backyard and the hot tub on the patio, every feature of our rental promises a unique and unforgettable escape.

5.0 out of 5 average rating, 101 reviews