Holiday rentals with a pool in Galena

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.

4.93 out of 5 average rating, 214 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. )

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.

4.96 out of 5 average rating, 116 reviews

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.

The exterior of a spacious home is displayed, featuring a wraparound deck and large windows that allow ample natural light. Outdoor seating options, including blue chairs and a stone fire pit, are positioned on a grassy area surrounded by mature trees.

4.94 out of 5 average rating, 168 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!

A cozy living area features a stone fireplace as the focal point, surrounded by large windows that provide views of the woods. A comfortable armchair and modern lamp are positioned nearby, while a TV and a stack of firewood add to the inviting ambiance.

4.98 out of 5 average rating, 145 reviews

*Winter Fun* *Hot tub-Fire-3 king beds-Game room*

Relax, unwind, & explore at this winter 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 winter adventure!

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.

4.96 out of 5 average rating, 110 reviews

Secluded Treehouse, w/great views, close to Hwy 20

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.

Treehouse in The Galena Territory

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.

4.98 out of 5 average rating, 187 reviews

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

A charming exterior view of the house is showcased, featuring a welcoming front porch with white railings and two rocking chairs. Lush greenery surrounds the home, and a stone pathway leads to the entrance. Sunlight filters through the trees, casting gentle shadows on the lawn.

4.95 out of 5 average rating, 152 reviews

Family-Friendly Wooded Retreat- 3 Ensuite Bedrooms

Loved by guests for its cleanliness, location, and value, this spacious 3BR, 3.5BA home is perfect for families, families traveling together, or groups of friends. This Galena Territories retreat is steps away from the Owners Club, Marina, and championship golf courses. After a day exploring, unwind in two comfortable living areas and enjoy private en-suite baths in every bedroom. Surrounded by wooded views, this home offers ample space to relax, recharge, and reconnect with nature.

A spacious living area features soft seating arranged around a circular glass coffee table. A large window allows natural light to fill the room, with a view of the outdoors visible. A stone fireplace and wall-mounted television enhance the cozy atmosphere.

4.94 out of 5 average rating, 176 reviews

The Beauty on Belden: Owners' Club access & more!

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.

Townhouse in The Galena Territory

The open-concept living area showcases a cozy couch accented by a decorative rug. A mounted television is positioned on a wooden feature wall. A dining table is visible in the background, accompanied by modern kitchen amenities and large windows that allow natural light to illuminate the space.

4.96 out of 5 average rating, 113 reviews

Hook Wine And Sinker - Golf, Shop, Pools, & Relax

Relax with the whole family at this peaceful getaway. A beautifully renovated, 3 bedroom / 3 bathroom townhome located within The Galena Territory in Galena, Illinois. This home is a perfect, peaceful getaway that sleeps up to eight (8) people comfortably. Whole home Golf Lake Self Check in WiFi Coffee Oven Dishwasher Grill BBQ accessories Washer/Dryer Free parking Board games Exercise equipment Pool table Deck Outdoor dining Child friendly Pack 'n play Pickleball set

Holiday home in The Galena Territory

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.

4.96 out of 5 average rating, 127 reviews

Fall Escape | Hot Tub, Fire Pit & Galena 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.

A round dining table is set outdoors with four yellow plates, each topped with a drink garnished with olives and celery. A bottle of cocktail mix rests beside the glasses, surrounded by textured placemats. Lush greenery provides a natural backdrop.

4.92 out of 5 average rating, 109 reviews

Perfect Location! Owner Club Access, Steps to Pool

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!

Townhouse in The Galena Territory

A modern soaking tub is centered against a natural wood accent wall. A wooden bath tray rests across the tub, holding a glass of red wine and a book. Soft blue water adds a serene touch to the inviting space.

4.92 out of 5 average rating, 125 reviews

2 Bedroom Townhouse w/Soaking Tub + Rain Shower

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.

Popular amenities for Galena rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An open living space features a modern kitchen with stainless steel appliances and a spacious island. A staircase with wooden railings leads to a second-level area illuminated by large windows. The dining area includes a long table and comfortable chairs, creating an inviting atmosphere.

4.92 out of 5 average rating, 64 reviews

Cozy retreat in Galena Territory

A spacious living area is highlighted by a large sectional sofa in warm tones. Natural light pours in through skylights, illuminating wooden floors. A dining table with multiple chairs is visible, alongside a well-equipped kitchen in the background, creating an inviting and open atmosphere.

4.9 out of 5 average rating, 138 reviews

Cozy Retreat | Hot Tub | Firepit | Dog-friendly

An open living area showcases a bright red sofa with decorative pillows, positioned next to a glass-top coffee table. The wooden staircase leads to an upper level with a railing, while large windows invite natural light and offer views of the surrounding greenery.

4.81 out of 5 average rating, 72 reviews

House 3bd/3bth- indoor pool -close to chestnut mnt

The modern home is set against a backdrop of trees, with a flat grassy area in the foreground. The structure features large windows and a prominent stone chimney, offering ample outdoor seating on the deck. The natural surroundings create a peaceful atmosphere.

4.89 out of 5 average rating, 125 reviews

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

A comfortable sleeping area is presented with a queen bed featuring warm-toned pillows and a navy throw blanket. The backdrop is adorned with a nature-inspired birch tree wallpaper, and bedside tables hold soft-lit lamps, creating a serene atmosphere.

4.96 out of 5 average rating, 93 reviews

Treehouse: Hot Tub + Fireplace • Secluded Getaway!

A cozy living area features a stone fireplace adorned with festive decorations and a lush tree, while a hot tub bubbles on a patio overlooking green scenery. An outdoor fire pit, surrounded by comfortable seating, invites evenings under the stars. A game room showcases a pool table and arcade games.

5 out of 5 average rating, 39 reviews

Luxury Stay- Sauna, Hot Tub, Fire Pit, Arcade!

The living room features large windows that allow natural light to fill the space, surrounded by tasteful seating options including a light-colored sofa and a brown armchair. A stone fireplace serves as a focal point, with a television mounted above. Decorative plants and a rug add warmth.

4.91 out of 5 average rating, 53 reviews

Comfy, end unit, on Golf Course!

A two-story home is set within a green landscape, featuring a dark exterior with light trim. A covered porch offers seating and welcomes guests. The sloping lawn leads to a manicured pathway, while trees provide a natural backdrop. A screened area is visible on the right.

4.83 out of 5 average rating, 307 reviews

Galena Retreat - Eagle Ridge Territories

Apartment rentals with a pool

This charming lodge features a blend of stone and wood siding, set amidst lush green landscaping. Multiple balconies extend from the rooms, framing views of the surrounding nature. The sky transitions into soft pastel shades of pink during sunset, adding to the serene ambiance.

Galena Resort Studio

A bright living space is showcased, featuring large windows that invite natural light. A stone fireplace is positioned against the wall, complemented by a wooden mantel with artwork above. A television stands on a stand nearby, and a cozy seating area is arranged for relaxation.

4.85 out of 5 average rating, 13 reviews

Lake Links Loft in Galena, Illinois

A comfortable living area features a dark leather sofa adorned with decorative pillows. A light-colored coffee table with a woven basket sits centrally. Two lamps provide soft lighting, while a staircase is visible in the background, leading to the upper level.

5 out of 5 average rating, 3 reviews

Golfer's Valleywood Getaway

An entryway is shown, featuring a covered structure with a wooden floor and gently sloping roof. Snow is visible on the ground and rooftops, while shrubs and bare trees surround the area, indicating a serene and wintry atmosphere.

4.91 out of 5 average rating, 11 reviews

Long Bay Point Unit C5

The resort features a rustic exterior with stone and wood accents, set against a backdrop of blue skies. Lush green grass and landscaping frame the entrance, which includes a prominent stone fireplace. Balconies extend from the upper levels, enhancing the building's welcoming appeal.

4.9 out of 5 average rating, 29 reviews

Galena, IL, 2 Bedroom #1

The exterior of the Long Bay Point Condo is shown, featuring a blend of warm wood tones and natural landscaping. A welcoming entrance with a covered porch leads into the property, surrounded by large windows that reflect the building's spacious design. A mature tree provides shade.

4.81 out of 5 average rating, 27 reviews

Long Bay Point Unit C11 The Galena Territory

A screened-in porch features white furnishings with blue and green striped cushions, providing ample seating. A small wooden table is positioned in front of the couch. Large windows overlook lush trees, allowing natural light to brighten the space.

5 out of 5 average rating, 10 reviews

Holiday Lights & Lake Views! Cozy King Bed, Firepl

A spacious resort building is framed by lush green grass and towering trees. The structure features a stone and wood facade, highlighted by a prominent entrance with large windows. Balconies extend from the upper level, adding to the welcoming outdoor ambiance.

4.82 out of 5 average rating, 17 reviews

Galena, IL, 1 Bedroom #1

Other holiday rentals with a pool

Cottage in The Galena Territory

A charming cottage features a steeply pitched roof and two dormer windows, allowing natural light to brighten the space. A welcoming front door adorned with a wreath invites guests, while lush greenery and well-maintained landscaping create a serene setting against a clear blue sky.

5 out of 5 average rating, 40 reviews

Charming & Peaceful, Cozy Galena Retreat!

Holiday home in The Galena Territory

A spacious 7-seat hot tub is situated on the back patio, surrounded by lush greenery. The bubbling water and soft glow of market lights create a serene atmosphere, providing a perfect spot for relaxation amidst nature.

4.97 out of 5 average rating, 112 reviews

The Gathering Place- Modern, Spacious, 6 bedrooms

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.

4.99 out of 5 average rating, 89 reviews

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

A welcoming cabin exterior is framed by lush greenery, featuring a central entrance with a covered porch. The gentle slope of the pathway guides visitors toward the door. Large windows allow for natural light, while surrounding landscaping adds a touch of nature.

4.92 out of 5 average rating, 77 reviews

The MacRae Cabin

Cottage in The Galena Territory

A spacious outdoor porch features log pillars and stone accents, offering seating with a wooden rocking chair and a small table. The view showcases the tranquil lake, surrounded by lush greenery and distant hills under a clear blue sky.

4.86 out of 5 average rating, 22 reviews

The Cottage on Lake Galena

A spacious living area features a stone fireplace with a warm fire, surrounded by large windows that offer views of the landscape. Plush seating options include an armchair and ottoman, while rustic decor adds a touch of charm to the inviting space.

5 out of 5 average rating, 4 reviews

Romantic Galena Escape. Epic View. Hot Tub. Luxe.

Townhouse in The Galena Territory

A bright living room features large arched windows that provide natural light and views of the outdoors. A gray sofa and a red accent chair are arranged around a modern coffee table. A wall-mounted Smart TV is positioned above a sleek fireplace, creating a cozy focal point.

4.9 out of 5 average rating, 92 reviews

Cozy villa near downtown Galena!

A welcoming sign is positioned near a large tree, directing guests to a modern home. The house features a sloped roof and is partly surrounded by lush greenery. A winding driveway leads up to the residence, set against a backdrop of rolling hills.