Vacation rentals with a pool in Galena

Townhouse in The Galena Territory

A welcoming living area features a vaulted ceiling and large windows that provide views of the outdoors. A brick fireplace adds warmth, while comfortable seating is arranged around a coffee table. Soft lighting enhances the cozy atmosphere, complemented by decorative plants and artwork.

4.91 out of 5 average rating, 191 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).

The exterior of the home is showcased, highlighting a multi-level structure surrounded by lush greenery. Large windows reflect warm indoor lighting, and a spacious deck is visible, featuring Adirondack chairs positioned near the lawn, offering ample space for relaxation and outdoor enjoyment.

4.96 out of 5 average rating, 106 reviews

Treehouse • Hot Tub + Firepit • Spacious Retreat

🌲7 minutes to Owner's Club 🌲10% Weekly Discount 🌲3 BRDM+3.5 BTH (all ensuite) 🌲Secluded + Spacious on 2-acre lot 🌲Hot tub! 🌲Smokeless firepit (wood provided)🪵 🌲Year-round community indoor pool & seasonal outdoor pool 🏊‍♂️ + zero entry kiddie pool 🌞 🌲Open concept main level 🌲Games & puzzles for all ages 🧩 🌲Axe throwing game 🎯 🌲Large connect 4 game & jenga 🌲New & fully equipped kitchen 🍽️ 🌲Kid & Dog friendly 👧🏼🐶 🌲Seasonal valley views 🌲Gym access 🌲High-speed internet

4.98 out of 5 average rating, 162 reviews

Wooded Villa with Resort Access, Fireplace, K Bed

⭐King bed with plush bedding in a peaceful, private setting ⭐Wood-burning fireplace — perfect for cozy evenings together ⭐2-minute drive to the North Golf Course, driving range, & Stonedrift Spa ⭐Wooded nature views & tranquil surroundings for a relaxing escape ⭐Just 12 minutes to downtown Galena — excellent shopping, dining, & sight-seeing ⭐Access to Owner’s Club amenities including indoor pool & fitness center ⭐15 miles to Chestnut Mountain Skiing ⭐2 Full bathrooms & newer full size sofa bed

4.86 out of 5 average rating, 118 reviews

Cute Galena Townhouse - Close to Resort and Spa

Location, location, location!! Forget about your worries in this nicely updated townhome. Close to everything Galena has to offer! ~0.5 mile away: -Eagle Ridge Resort -Stonedrift Spa -North Golf Course -East Golf Course -tennis courts ~1.5 miles away: -South Golf Course -Owners Club with indoor/outdoor pools, basketball court, gaming lounge ~2.0 miles away: -Thunder Bay Falls ~3.5 miles away: -The General Golf Course ~7 miles away: -Downtown Galena ~13 miles away: -Chestnut Mountain

Cabin in The Galena Territory

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, 124 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, 181 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 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!

Cabin in The Galena Territory

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, 162 reviews

*Hot tub-Fire-3 king beds-Game room*Winter fun!*

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.

4.97 out of 5 average rating, 115 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.

A comfortable living area is featured with two spacious sofas and a round coffee table. A wall-mounted television is positioned above a stylish fireplace, with large windows showcasing views of grassy landscapes. Soft textiles and decorative art add a welcoming touch.

4.96 out of 5 average rating, 100 reviews

*King Bed*, *Fire Pit Table* & *Stunning Views*

Welcome to The Golf View, where relaxation and fun collide! This 1-bedroom, 2-bath abode is perfect for a romantic getaway or a golfing adventure with pals. Whip up a culinary masterpiece in the fully-equipped kitchen, chill out with some vintage tunes on the mezzanine loft, or binge-watch your favorite shows on the 50" Smart TV. Outside, unwind on the deck or get cozy around the fire pit table for some unforgettable nights. Book your stay now and get ready for a hole-in-one experience!

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, 198 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

Villa in The Galena Territory

An aerial view of the living room is displayed, showcasing a dark leather sectional couch positioned around a textured area rug. A wooden coffee table is centered in the space, while a flat-screen television is positioned next to a large stone feature wall. Natural light fills the room through large windows.

4.88 out of 5 average rating, 144 reviews

Spring Creek Sanctuary-2BR-Owners’ Club Access

Welcome to Spring Creek Sanctuary! This 2BR/2BA condo in Galena Territory offers comfort and nature. Relax by the wood-burning fireplace, cook in the modern kitchen, or unwind on the private deck with wooded views. Enjoy Owners’ Club amenities—pools, fitness, game room, tennis—plus nearby golf, trails, and Lake Galena. Just 15 minutes to historic downtown Galena, shopping, dining, and wineries!

An outdoor deck features comfortable seating arrangements, including wicker chairs and a coffee table. Large windows in the background allow natural light to fill the adjacent indoor area while showcasing the surrounding greenery.

4.98 out of 5 average rating, 179 reviews

Covered Hot Tub • 2 Fire Tables • Huge Deck •

Relax at Rolling Hills Retreat, featuring a covered private hot tub, two fire tables, a huge upper deck, and a screened-in porch—perfect for outdoor living year-round. Enjoy Owner’s Club access with indoor/outdoor pools, pickleball, fitness center, marina, hiking & more. Every bedroom has a private bath for comfort and privacy. Dog-friendly, peaceful wooded setting just minutes from Galena.

Popular amenities for Galena rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A charming house is nestled among trees, with a gravel driveway leading to the entrance. The natural landscape features various shades of green, and the sky above is partly cloudy. The design of the house includes multiple windows and a welcoming front entry.

4.98 out of 5 average rating, 105 reviews

*Ski*Screened In Hot Tub*Owners Club*Dogs Ok*

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.

4.93 out of 5 average rating, 70 reviews

Cozy retreat in Galena Territory

The exterior of the tree house is softly illuminated at night, showcasing large windows that reveal the warmth inside. A red-lit sauna entrance is visible on the side, while a cozy fire pit is situated nearby, inviting relaxation in the serene outdoor setting.

4.87 out of 5 average rating, 30 reviews

The Tree House

A modern living room features a comfortable seating arrangement with a light gray sofa and armchair. A large window allows natural light to fill the space, while a flat-screen TV is mounted above a cozy fireplace. Built-in shelves are neatly arranged with books and decorative items.

4.98 out of 5 average rating, 92 reviews

Inviting & Bright | Firepit Sauna Hot Tub & Games!

A welcoming living room features a cozy seating area with a plush sofa and a coffee table. The stone fireplace is complemented by a sleek television mounted above. Large windows provide ample natural light and views of the surrounding greenery.

4.99 out of 5 average rating, 77 reviews

Country Chic + Comfort|Fireplace|Perfect Getaway

4.92 out of 5 average rating, 172 reviews

DunPuttin Place

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.

4.88 out of 5 average rating, 60 reviews

Comfy, end unit, on Golf Course!

A spacious game room features a traditional billiard table set against a warm wood-paneled wall. Decorative elements include a dartboard and a wooden rack for cues. Natural light filters in from a nearby door, enhancing the inviting atmosphere of the space.

4.88 out of 5 average rating, 111 reviews

Tranquil Home Away From Home

Condo rentals with a pool

A peaceful outdoor deck features two chairs and a round table, overlooking Lake Galena. Bare trees frame the view, while the water reflects the clear sky, creating a serene atmosphere for relaxation.

4.93 out of 5 average rating, 14 reviews

The Cozy Lake Stay You've been Craving - Fireplace

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.

4.81 out of 5 average rating, 16 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, 4 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.

4.92 out of 5 average rating, 12 reviews

Long Bay Point Unit C5

The resort's brick and timber façade is framed by lush greenery and a spacious lawn. Large windows are visible, hinting at comfortable accommodations within. The sun casts a warm glow over the building, highlighting its lodge-like design amidst a serene, tree-lined setting.

4.82 out of 5 average rating, 11 reviews

Tranquil Retreat: Cozy Studio @ Wyndham Galena

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.

4.83 out of 5 average rating, 29 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, 11 reviews

Lakeside Comfort: Snowy Views & Fireside Nights! C

Other vacation rentals with a pool

Cabin in The Galena Territory

4.99 out of 5 average rating, 76 reviews

Epic View. Huge Hot Tub. King Beds. Amenities.

A spacious living area features a circular wooden dining table surrounded by four black stools. A comfortable brown sofa faces a modern stone fireplace, with a large television mounted above. Natural light floods in through sliding glass doors that lead to a wooded view.

4.98 out of 5 average rating, 54 reviews

Long Bay Point Getaway

Cottage in The Galena Territory

A charming two-story cottage features blue siding and a decorative front door, framed by small windows on either side. A front pathway, bordered by greenery, leads to the entrance, while a lamp post stands nearby, illuminating the welcoming exterior.

4.98 out of 5 average rating, 65 reviews

Storybook Countryside Cottage

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.

5 out of 5 average rating, 85 reviews

Stunning 5 bdm home on The General in Galena Terr!

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.

4.9 out of 5 average rating, 29 reviews

The Cottage on Lake Galena

Townhouse in The Galena Territory

An arcade room is displayed featuring a foosball table and arcade machines. The floor is made of light wood, creating a bright environment. Wall decorations and a framed artwork are visible, providing a playful atmosphere for entertainment.

4.82 out of 5 average rating, 76 reviews

Getaway - Indoor Pool, Arcade, Hiking, Skiing

5 out of 5 average rating, 11 reviews

The Drey: A Winter Getaway In the Treetop Canopy

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.