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Vacation rentals with a pool in Lake Galena

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lake Galena

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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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, 106 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.

Top guest favorite

4.93 out of 5 average rating, 209 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 sparkling swimming pool is surrounded by numerous lounge chairs, each positioned under blue shaded canopies. A colorful water slide is visible next to the pool, and decorative flower planters enhance the welcoming space.

Townhouse in Galena

4.97 out of 5 average rating, 150 reviews

Fall Colors! Game Room! Close to all amenities!

Many amenities just steps from our home! Including pickleball, a spa and golf. Escape to our bright modern townhome in Galena. Enjoy 3 levels of space for the whole family. Experience outdoor fun at local attractions, enjoy the pools at The Owners Club. Unwind with movies in the game room or relax to records in the living room. This retreat offers the perfect blend of comfort and convenience. Book your stay and create cherished memories. Pet friendly if you would like to bring your fur baby.

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

4.95 out of 5 average rating, 106 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.

Top guest favorite

A cozy living area is featured with a warm fireplace and a mounted television above it. Two side tables are positioned beside the fireplace, enhancing comfort. Natural light enters through the windows adorned with wooden blinds, creating an inviting space for relaxation.

Villa in Galena

4.98 out of 5 average rating, 143 reviews

King bed, Wood Fireplace, Near Spa, Golf, Trails

✓Peaceful, nature views ✓Serene, wooded backdrop ✓Semi-private outdoor pool, steps away ✓Well equipped kitchen w/modern appliances ✓Gas grill on deck ✓Smart TV on each level ✓Computer desk ✓Fireplace w/supply of firewood ✓King sized bed ✓2 Full baths ✓Near hiking trails & paved walking trails ✓Stonedrift Spa, 3 min drive ✓North Course & Driving Range, 2 min drive ✓Downtown Galena, 15 min drive ✓Owner's Club access ✓Indoor pool ✓Lake access ✓Chestnut Mountain (Ski & Zipline), 25 min drive

Top guest favorite

An indoor swimming pool area features a large, inviting pool surrounded by a tan tiled deck. Lounge chairs line one side, while a colorful beach ball floats on the water. Exposed beams and large windows allow natural light to illuminate the space.

Townhouse in Galena

4.98 out of 5 average rating, 119 reviews

Farmhouse Chic|Fireplace|View|Peloton|Near Town

Are you searching for a serene and idyllic countryside escape in a winter wonderland? Look no further. Our elegantly appointed farmhouse-inspired townhome is located in the picturesque Galena Territory, boasting an array of amenities such as indoor/outdoor swimming pools, a fitness center, game room, tennis courts, 20+ miles of hiking trails, a private lake and more. Surrounded by verdant hills, the home offers a peaceful retreat while being only 20 min from Chestnut Mountain Ski Resort.

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

4.98 out of 5 average rating, 171 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

Top guest favorite

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, 146 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.

4.95 out of 5 average rating, 251 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.

Top guest favorite

Townhouse in Galena

4.95 out of 5 average rating, 100 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

Top guest favorite

Vacation home in Galena

4.97 out of 5 average rating, 107 reviews

The Gathering Place- Modern, Spacious, 6 bedrooms

The Gathering Place is a modern, spacious 6 bedroom/6 bathroom home that accommodates up to 14 people. We are family friendly and pet friendly. - 7 seat hot tub - Pool Table -Arcade games - Lightning fast Wi-Fi - 8 Smart TV's - Fully Stocked Kitchen + Coffee Bar -Yard games - Laundry - Downstairs Bar - Upstairs and Downstairs Fireplaces - < 5 minutes to owners club facility - Right across from East Golf Course - Walking trail near property - Dedicated workspace

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

4.96 out of 5 average rating, 116 reviews

Hot Tub Retreat|Summer Nights · Fall Colors Await

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations with great services and amenities

Popular amenities for Lake Galena rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

A spacious outdoor area is showcased with a hot tub situated beneath a wooden deck. The hot tub is surrounded by a stone patio and features steps leading up to it. Natural stone walls provide a rustic backdrop, enhancing the tranquil environment.

4.97 out of 5 average rating, 292 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

A spacious living area features vaulted wooden ceilings and rich hardwood flooring. A large flat-screen television is mounted above a modern electric fireplace. Comfortable seating includes a leather sofa and two chairs. A decorative area rug enhances the inviting atmosphere of the room.

5 out of 5 average rating, 4 reviews

Getaway on Wheatstrand!

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, 134 reviews

Cozy Retreat | Hot Tub | Firepit | Dog-friendly

The living room features a spacious layout with large windows providing views of the outdoors. A comfortable brown sofa is positioned around a coffee table, and a stone fireplace serves as a focal point. Rustic decor elements are incorporated throughout the space.

4.92 out of 5 average rating, 76 reviews

Galena Getaway Retreat | 3BD/3BA | Hot Tub + Games

Top guest favorite

An indoor pool area is presented with a spacious swimming pool, surrounded by large windows allowing natural light to fill the space. Comfortable lounge chairs are arranged along the poolside, with towels neatly placed on the side. The ceiling showcases exposed wooden beams, adding a warm touch to the atmosphere.

4.97 out of 5 average rating, 157 reviews

Pools, Hot Tub, Fire tables, dog friendly

Top guest favorite

A modern, two-story house is set against a lush green landscape, featuring dark exterior siding and a pitched roof. A welcoming entrance is framed by two white chairs on a front porch, with trees and a bright blue sky in the background.

5 out of 5 average rating, 6 reviews

Modern Home in Galena Territory

An open-concept living and dining area is showcased, featuring a stone fireplace and large windows that invite natural light. A dining table with wooden chairs is set with dinnerware, while a breakfast bar with stools complements the adjacent kitchen. Cozy furnishings enhance the inviting space.

4.97 out of 5 average rating, 31 reviews

*Secluded Hot Tub*, *Fire Pit* & Grand Fireplace

Top guest favorite

The exterior of the home features a combination of natural stone and wood accents under a pitched roof. Lush greenery surrounds the entrance, where a welcoming front door is framed by large windows, allowing natural light to fill the space.

4.98 out of 5 average rating, 40 reviews

*Dogs Ok*Golf*Hot Tub* Firepit*Owners Club*

Condo 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.

Condo in Galena

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.

Condo in Jo Daviess County

4.91 out of 5 average rating, 11 reviews

Lake Links Loft in Galena, Illinois

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.

Condo in Jo Daviess County

4.89 out of 5 average rating, 9 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.

Condo in Galena

4.6 out of 5 average rating, 5 reviews

Tranquil Retreat: Cozy Studio @ Wyndham Galena

An aerial view showcases a welcoming living room with a sectional sofa positioned near a stone fireplace. A patterned area rug contrasts with the wood flooring. Large windows allow natural light to fill the space, complemented by decorative elements like throw pillows and a coffee table.

Condo in Galena

5 out of 5 average rating, 19 reviews

Fall Golf Bliss at Lucky Bunker – Swing Into Gal

Condo in Galena

4.93 out of 5 average rating, 14 reviews

Come Vibe @ Valleywood! 2BR Modern TH - Owner's Cl

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.

Condo in The Galena Territory

5 out of 5 average rating, 8 reviews

Summer Lake Views! King Bed, Screened Porch, Pool

The exterior of a lodge-like building showcases a blend of stone and timber construction. A striking central entrance is framed by large windows and a welcoming porch. Surrounding greenery enhances the peaceful atmosphere, while the sky features calming clouds overhead.

Condo in Galena

Galena, 1 bedroom condo, fireplace!

Other vacation rentals with a pool

A bright and inviting living area features large windows that provide ample natural light and views of the surrounding trees. A stone fireplace serves as a focal point, while comfortable seating and accent cushions add to the space's warmth.

4.9 out of 5 average rating, 84 reviews

Quiet & Peaceful

Townhouse in Galena

4.94 out of 5 average rating, 90 reviews

2BR 2BA + 3rd BR loft lakefront townhome sleeps 6!

Top guest favorite

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.

Cottage in Galena

5 out of 5 average rating, 34 reviews

Charming & Peaceful, Cozy Galena Retreat!

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.

4.91 out of 5 average rating, 53 reviews

Cozy retreat in Galena Territory

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

4.99 out of 5 average rating, 76 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.

Cabin in Galena

4.93 out of 5 average rating, 70 reviews

The MacRae Cabin

Top guest favorite

An outdoor deck features a spacious hot tub surrounded by a wooden railing. Nearby, two wooden benches and a table provide additional seating. Sunlight filters through the surrounding greenery, casting a natural warmth on the deck.

4.97 out of 5 average rating, 92 reviews

Hot Tub, Movie Lounge, Deck w/Forest Vibe

The spacious living area features a large sectional sofa adorned with decorative pillows. A light-colored coffee table sits in front, while a dining area is visible in the background, creating a seamless flow. Two framed art pieces are mounted on the wall, adding warmth to the modern decor.

Vacation home in Galena

4.81 out of 5 average rating, 88 reviews

Modern & bright home with resort amenities

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