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.

4.9 out of 5 average rating, 187 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).

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. )

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, 170 reviews

*Holiday Getaway! Fireplace, Hot Tub, Fire Tables*

Step into Rolling Hills Retreat, a sanctuary from the everyday bustle! Our dog-friendly rental offers breathtaking views and numerous amenities for your pleasure and relaxation. Enjoy a swim in the indoor or outdoor pool, and discover a variety of amenities that promise an unforgettable stay. *Pickle Ball *Basketball *Pool Tables *Hiking Trails *Workout Room *Tennis Courts *Brand new (June 2024) Marina with boat rental (additional charge) *Ping Pong tables *Arcade *Scenic Waterfall *Kayaking

The inviting main living area features a high wooden ceiling with exposed beams, a stone fireplace at the center, and ample seating options. Natural light floods in from large windows, illuminating cozy furnishings and warm earth tones throughout the space.

4.95 out of 5 average rating, 172 reviews

Winter Fun! Hot tub-Fires in/outdoor-Game room!

Escape to our cozy luxe cabin in Galena Territory, the perfect retreat for fall! Start your mornings sipping coffee by the gas fireplace, then warm up each evening in the hot tub! Enjoy friendly competition with arcade games, board games, air hockey, and darts. With 8 amenity cards, you can access the owner’s club for swimming and exercise including indoor pickle ball-rackets and balls at the house! Experience relaxation and adventure in this tranquil haven—your unforgettable getaway awaits!

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, 117 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.

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, 188 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 gravel fire pit area is positioned in the foreground, surrounded by a circular stone border. The spacious yard is framed by trees, providing a natural setting. In the background, a cozy wooden house with a deck is partially visible, blending harmoniously into the landscape.

4.95 out of 5 average rating, 257 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.

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, 128 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!

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, 126 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 Dubuque rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 104 reviews

Hot tub | 3BD|3BA en-suites | Resort 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, 50 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.

4.92 out of 5 average rating, 64 reviews

Cozy retreat in Galena Territory

A hot tub filled with bubbling water is situated in a serene outdoor setting, surrounded by lush trees. The warm light of the setting sun filters through the branches, creating a calming atmosphere for relaxation.

4.51 out of 5 average rating, 47 reviews

6BR Galena Territory Amenities | Private Hot Tub

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, 94 reviews

Treehouse • Hot Tub + Fireplace • Secluded Getaway

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, 78 reviews

Stunning 5 bdm home on The General in Galena Terr!

A heated saltwater pool reflects the evening sky, surrounded by lounge chairs. The dark exterior of the house features large windows, showcasing interior spaces filled with warm light. Umbrellas provide shade over the seating area, complementing the beautifully landscaped surroundings.

4.89 out of 5 average rating, 73 reviews

Hilltop 4Bed Ski Getaway | HotTub, Sauna & Sunsets

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.

4.98 out of 5 average rating, 45 reviews

Luxury on the Green

Apartment 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

Enjoy the SUN & Beautiful Lake Galena Views - Walk

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

Other holiday rentals with a pool

A brightly lit neon sign for 'Log Cabin' is positioned in front of a lively street scene, showcasing quaint storefronts and a bustling atmosphere during twilight. In the lower segment, a foosball table is visible within a well-lit game room, featuring arcade machines and hardwood flooring.

4.88 out of 5 average rating, 32 reviews

Townhome - Indoor Pool, Arcade, Hiking, Skiing

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

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, 59 reviews

Storybook Countryside Cottage

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, 23 reviews

Perfect Getaway: Newly Renovated

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

4.82 out of 5 average rating, 11 reviews

Home in Galena

Chic 3BR w/ Pond, Hot Tub & Nature Views

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.

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.