Vacation rentals with a pool in Dubuque

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, 101 reviews

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

Leave your worries behind at our 3-bed, 3-bath vacation rental in The Galena Territory. Our updated home offers a fully equipped kitchen, screened-in porch for enjoying your morning coffee, a furnished deck with a grill, and access to amenities such as a fitness center and indoor/outdoor pools. Explore all Galena has to offer! Stroll historic Galena, visit Ulysses S. Grant's Home, hike the various trails in the territory, or race down to the banks of the Mississippi at Chestnut Mountain Resort!

4.85 out of 5 average rating, 98 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

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, 112 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.

An open living area is featured, showcasing a cozy sofa adorned with decorative pillows. A patterned chair with the word 'home' is positioned next to a small wooden table, which holds a few items. The area is brightened by natural light from sliding glass doors.

4.98 out of 5 average rating, 150 reviews

Wooded Golf Villa • King Bd • Pool • Near Spa, Ski

Escape to this quiet and peaceful golf villa nestled in a beautiful wooded setting with a seasonal view of Hole #11 on the North Course. Located just 12 minutes from downtown Galena, it offers the perfect blend of relaxation and convenience. Walk to the semi-private outdoor pool, and enjoy close access to the golf course, driving range, spa, and hiking. In winter, cozy up by the fireplace or venture outdoors for some winter sports. Enjoy full access to the Owner's Club with an indoor pool.

4.98 out of 5 average rating, 141 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, 108 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, 183 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, 150 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.

4.94 out of 5 average rating, 254 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.

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.

4.95 out of 5 average rating, 173 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.

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, 108 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, 124 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

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.

4.97 out of 5 average rating, 68 reviews

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

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, 60 reviews

Cozy retreat in Galena Territory

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, 90 reviews

Serene Treehouse Retreat! Hot Tub & Scenic Views

An aerial view of Tower House reveals a spacious home surrounded by lush greenery. The private saltwater pool and ample patio space are visible, with seating areas and a fire pit integrated into the outdoor landscape. Scenic hills form the backdrop.

4.89 out of 5 average rating, 70 reviews

Private Galena Escape w/ Heated Pool and Views

An outdoor fire pit area features several chairs arranged around a stone fire pit, set against a backdrop of grassy fields. The interior living space showcases high ceilings, a stone fireplace, and a cozy seating area with a sectional couch. An outdoor hot tub is surrounded by greenery, while an indoor game area features a pool table next to arcade games.

5 out of 5 average rating, 39 reviews

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

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, 306 reviews

Galena Retreat - Eagle Ridge Territories

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.

4.98 out of 5 average rating, 44 reviews

Charming Galena Getaway

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.

4.97 out of 5 average rating, 89 reviews

*King Bed*, *Fire Pit Table* & *Golf Course Views*

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

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

Superhost

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'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, 8 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.

5 out of 5 average rating, 19 reviews

Fall Golf Bliss at Lucky Bunker - Swing Into Galen

Superhost

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, 26 reviews

Long Bay Point Unit C11 The Galena Territory

Other vacation rentals with a pool

An aerial view of a spacious cabin is displayed, showcasing large glass windows and a broad deck. A cozy fire pit with colorful chairs surrounds the outdoor area, and string lights are visible, enhancing the serene atmosphere amidst lush greenery.

4.98 out of 5 average rating, 80 reviews

5KING Bed 5 Bath~Upscale~Views~Pets~Luxe Amenities

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, 84 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, 56 reviews

Storybook Countryside Cottage

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, 74 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

Townhouse in The Galena Territory

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, 22 reviews

Perfect Getaway: Newly Renovated

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.

4.91 out of 5 average rating, 90 reviews

Cozy villa near downtown Galena!

A welcoming living area features a dark marble fireplace with a mounted TV above. Two comfortable chairs are positioned nearby, complemented by a coffee table. Natural light enters through the large windows, while decorative plants add a touch of greenery to the space.