Holiday rentals with a pool in Dubuque

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 aerial view captures a serene landscape with lush greenery and hills in the background. The townhome neighborhood is highlighted, surrounded by trees and well-maintained lawns, with a glimpse of a red barn in the distance. The scene conveys a peaceful natural setting.

4.98 out of 5 average rating, 165 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

Cabin in The Galena Territory

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.

4.98 out of 5 average rating, 167 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!

The living area features a comfortable sofa and a rustic coffee table atop a circular rug. A stone fireplace serves as a focal point, complemented by a vibrant artwork of a rooster above it. Natural light floods in through large windows, providing views of the outdoor patio.

4.98 out of 5 average rating, 131 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.

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.

4.95 out of 5 average rating, 103 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.

4.99 out of 5 average rating, 203 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

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.

4.95 out of 5 average rating, 120 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.

4.97 out of 5 average rating, 143 reviews

Hot Tub & Fire Pit | Galena Spring Escape

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.

4.91 out of 5 average rating, 112 reviews

Quiet Yet Close/Steps to Pool/Paths, Pet Free Home

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!

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, 132 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.

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, 146 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!

Popular amenities for Dubuque rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living room features a cozy seating area with a light grey sofa and a wooden coffee table. Large windows provide wooded views, and a large clock adorns the wall above a stone fireplace, where a warm fire can be seen flickering.

4.98 out of 5 average rating, 83 reviews

Private 3BR/2BA Home in the Trees | Stonecrest

The exterior of a charming blue vacation rental showcases a welcoming front porch with seating. A stone pathway leads through landscaped areas with plants, approached by a warm sunset sky. The structure features multiple windows, allowing natural light to illuminate the inviting entryway.

4.97 out of 5 average rating, 110 reviews

Hot tub | 3BD|3BA en-suites | Resort Amenities

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, 107 reviews

*Screened In Hot Tub*Owners Club*Dog Friendly*

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

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, 71 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, 31 reviews

The Tree House

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

5 out of 5 average rating, 11 reviews

The Drey: A Winter Getaway In the Treetop Canopy

Condo rentals with a pool

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.

4.82 out of 5 average rating, 17 reviews

Lake Links Loft in Galena, Illinois

The exterior of the lodge features a combination of wooden and stone elements, framed by well-kept grass and mature trees. Balconies are visible on the upper levels, while the entrance highlights large windows and a distinctive gabled roof, creating a welcoming appearance.

4.75 out of 5 average rating, 32 reviews

Galena, IL, Studio 2

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

5 out of 5 average rating, 4 reviews

Amazing Golf Views! Close 2 Driving Range! Pools!

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.

4.75 out of 5 average rating, 12 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.

4.8 out of 5 average rating, 30 reviews

Long Bay Point Unit C11 The Galena Territory

Other holiday rentals with a pool

Home in Apple Canyon Lake

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.

4.93 out of 5 average rating, 94 reviews

The Ho Hum East on Apple Canyon Lake

Cabin in The Galena Territory

4.99 out of 5 average rating, 78 reviews

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

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, 122 reviews

The Gathering Place- Modern, Spacious, 6 bedrooms

5 out of 5 average rating, 27 reviews

Secluded retreat, great Outdoor spaces, Hot tub

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

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, 30 reviews

The Cottage on Lake Galena

A spacious living area features a large sectional sofa and an armchair, arranged around a sleek electric fireplace. A flat-screen TV is mounted on the wall above a decorative clock. Natural light filters in through large windows, complementing the modern decor.

5 out of 5 average rating, 28 reviews

Perfect Getaway: Newly Renovated

The exterior of the house is seen from a grassy area, showcasing a modern design with large windows and a steeply pitched roof. A paved driveway leads to a garage on the left. Lush green trees frame the scene, adding a natural touch.