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Vacation rentals with a pool in Dubuque

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Dubuque

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

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An indoor swimming pool is surrounded by a spacious deck with multiple lounge chairs. Natural light filters through large windows, while wooden beams create an airy atmosphere. The pool area is tranquil, showcasing clear blue water and colorful beach balls scattered throughout.

Townhouse in The Galena Territory

4.9 out of 5 average rating, 179 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).

Home in The Galena Territory

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. )

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.

Home in The Galena Territory

4.98 out of 5 average rating, 160 reviews

Pools, Hot Tub, Fire tables, dog friendly

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

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 The Galena Territory

4.95 out of 5 average rating, 108 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

Villa in The Galena Territory

4.98 out of 5 average rating, 146 reviews

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

✓ Peaceful, nature views ✓ Serene, wooded backdrop ✓ Lovely Fall colors ✓ 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 The Galena Territory

4.98 out of 5 average rating, 120 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.

Home in The Galena Territory

4.96 out of 5 average rating, 106 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.

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 The Galena Territory

4.98 out of 5 average rating, 175 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

An outdoor fire pit is surrounded by several black Adirondack chairs, set among fallen leaves. The cabin is visible in the background, illuminated by warm lights, creating a cozy ambiance. Tall trees frame the scene, providing a sense of seclusion.

Cabin in The Galena Territory

4.99 out of 5 average rating, 134 reviews

*Fall Fun* *Hot tub-Fire-3 king beds-Game room*

Relax, unwind, & explore at this fall retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful fall 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 pit 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 fall adventure!

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.

Home in The Galena Territory

4.95 out of 5 average rating, 147 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.

Home in The Galena Territory

4.95 out of 5 average rating, 252 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 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.

Home in The Galena Territory

4.92 out of 5 average rating, 107 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!

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Dubuque rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

Home in The Galena Territory

5 out of 5 average rating, 5 reviews

Getaway on Wheatstrand!

Home in Apple Canyon Lake

4.93 out of 5 average rating, 88 reviews

The Ho Hum East on Apple Canyon Lake

Top guest favorite

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.

Home in The Galena Territory

4.98 out of 5 average rating, 47 reviews

Long Bay Point Getaway

Top guest favorite

Home in The Galena Territory

4.95 out of 5 average rating, 87 reviews

Treehouse!• Hot Tub • Fire Pit • Games • Spacious

Top guest favorite

An outdoor seating area is arranged around a central fire pit on a spacious deck. Comfortable chairs with decorative pillows face the fire, surrounded by a plaid rug. Lush green hills are visible in the background, enhancing the tranquil outdoor setting.

Home in The Galena Territory

4.98 out of 5 average rating, 60 reviews

Golden Meadows Escape: A Luxurious Country Retreat

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.

Home in The Galena Territory

4.83 out of 5 average rating, 304 reviews

Galena Retreat - Eagle Ridge Territories

Top guest favorite

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.

Home in The Galena Territory

4.98 out of 5 average rating, 42 reviews

Charming Galena Getaway

Top guest favorite

Home in Elizabeth

4.96 out of 5 average rating, 50 reviews

Cliffside Cottage, Breathtaking Views near Galena

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 The Galena Territory

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 The Galena Territory

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 The Galena Territory

4.89 out of 5 average rating, 9 reviews

Long Bay Point Unit C5

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.

Condo in The Galena Territory

5 out of 5 average rating, 3 reviews

Golfer's Valleywood Getaway

Top guest favorite

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 The Galena Territory

5 out of 5 average rating, 19 reviews

Fall Golf Bliss at Lucky Bunker – Swing Into Gal

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.

Condo in The Galena Territory

4.81 out of 5 average rating, 26 reviews

Long Bay Point Unit C11 The Galena Territory

Condo in The Galena Territory

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, 9 reviews

Fall into Lake Views! King Bed, Screened Porch & F

Other vacation rentals with a pool

Top guest favorite

Cabin in The Galena Territory

4.97 out of 5 average rating, 74 reviews

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

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 The Galena Territory

5 out of 5 average rating, 36 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.

Home in The Galena Territory

4.91 out of 5 average rating, 55 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 The Galena Territory

4.99 out of 5 average rating, 79 reviews

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

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.

Home in The Galena Territory

4.83 out of 5 average rating, 59 reviews

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

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.

Cottage in The Galena Territory

4.98 out of 5 average rating, 52 reviews

Storybook Countryside Cottage

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.

Home in The Galena Territory

4.91 out of 5 average rating, 79 reviews

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

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.

Cottage in The Galena Territory

4.86 out of 5 average rating, 22 reviews

The Cottage on Lake Galena

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