Vacation rentals with a pool in Dubuque

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, 163 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 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.

4.98 out of 5 average rating, 102 reviews

Fast Wi-Fi | EV Charger | Fireplace | Hot Tub

Unwind in our comfortable Galena Territory cabin with 3 bedrooms, 3 full baths and sofa sleeper. EV Charging outlet in garage. Strong Eero boosted Wi-Fi; Roku streaming on every floor. Stone wood burning fireplace. Three-season room with scenic sunrise and wooded views. Lower-level walkout to patio with hot tub, fire pit and beautiful stargazing. Minutes away from the Lake Galena Marina, golf, tennis, pool, and fitness center. 15 mins from Chestnut Mountain and historic downtown Galena.

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.

Townhouse in The Galena Territory

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, 102 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, 199 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, 155 reviews

Galena Territory - Pets - Fireplace - Pool Access

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 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, 182 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, 111 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!

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!

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, 82 reviews

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

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*

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, 70 reviews

Cozy retreat in Galena Territory

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, 146 reviews

Cozy Retreat | Hot Tub | Firepit | Dog-friendly

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

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!

5 out of 5 average rating, 11 reviews

The Drey: A Winter Getaway In the Treetop Canopy

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, IL

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

The open-concept living area features a spacious sectional sofa positioned in front of a modern fireplace. Large windows allow natural light to fill the space, while a dining area with a wooden table and chairs is visible in the background. Tasteful decor enhances the minimalist aesthetic.

4.91 out of 5 average rating, 22 reviews

Early check-in/Late check-out (JAN-MARCH)

Cabin in The Galena Territory

4.99 out of 5 average rating, 77 reviews

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

Cottage in The Galena Territory

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.

5 out of 5 average rating, 42 reviews

Charming & Peaceful, Cozy Galena Retreat!

An open living area showcases a bright red sofa with decorative pillows, positioned next to a glass-top coffee table. The wooden staircase leads to an upper level with a railing, while large windows invite natural light and offer views of the surrounding greenery.

4.82 out of 5 average rating, 87 reviews

House 3bd/3bth- indoor pool -close to chestnut mnt

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

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, 28 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.

4.9 out of 5 average rating, 29 reviews

The Cottage on Lake Galena