Vacation rentals with a pool in Dubuque

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, 134 reviews

Treehouse! 3BR Ensuites• Spacious•Hot Tub•Fire Pit

🌲7 minutes to Owner's Club 🌲10% Weekly Discount 🌲3 BRDM+3.5 BTH (all ensuite) 🌲Secluded + Spacious on 2-acre lot 🌲Hot tub! 🌲Smokeless firepit (wood provided)🪵 🌲Year-round community indoor pool & seasonal outdoor pool 🏊‍♂️ + zero entry kiddie pool 🌞 🌲Open concept main level 🌲Games & puzzles for all ages 🧩 🌲Axe throwing game 🎯 🌲Large connect 4 game & jenga 🌲New & fully equipped kitchen 🍽️ 🌲Kid & Dog friendly 👧🏼🐶 🌲Seasonal valley views 🌲Gym access 🌲High-speed internet

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, 221 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. )

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, 138 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 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, 128 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.

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, 132 reviews

Secluded Treehouse w/great views from every room!

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.

4.99 out of 5 average rating, 236 reviews

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 Galena

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

Superhost

A spacious living room features a stone fireplace as a focal point, surrounded by large windows offering natural light. A comfortable sofa is complemented by two leather chairs. A dark coffee table sits in the center with decorative items, creating a cozy gathering space.

4.82 out of 5 average rating, 119 reviews

Log Home/Firepit/Game Room/Hot tub

Relax with the whole family at this peaceful log home. Located in the Galena Territory. 3 bedroom (2 kings) (2Twins located in lower level family room), 3 baths w/futon and sofa sleeper in loft area, sleeps up to 10. Hot tub, pool table, ping pong/air hockey, arcade game, main level family room with wood fireplace and lower level family room. Very Spacious and quiet, wooded surrounding, firepit. Access to the resort amenities which is a short drive away as well as downtown Galena.

4.98 out of 5 average rating, 185 reviews

Cute & Cozy King Suite Villa ~ Steps to Pool

⭐ Bright, open villa with king suite ⭐ Fully equipped kitchen & wooded views ⭐ Private deck with gas grill overlooking woods ⭐ Dedicated loft workspace perfect for remote work ⭐ Full bath on each level for maximum convenience ⭐ Steps to semi-private neighborhood outdoor pool ⭐ Indoor pool & fitness center access ⭐ Lake access & paved walking trails ⭐ 2 min to golf, driving range & spa ⭐ 12 min to Downtown Galena ⭐ 15 miles to Chestnut Mountain Resort (skiing, zipline & river views)

Guest favorite

4.94 out of 5 average rating, 280 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 cozy living area features a stone fireplace as the focal point, surrounded by large windows that provide views of the woods. A comfortable armchair and modern lamp are positioned nearby, while a TV and a stack of firewood add to the inviting ambiance.

4.97 out of 5 average rating, 196 reviews

Family Fall! Hot Tub•Fire In/Out•Game Room•3 Kings

Ultimate Family Escape in Galena Territory! Unwind, explore, and make memories at this chic, spacious cabin! Sip coffee on the deck as deer wander by, soak in the hot tub, and gather around the fire pit for s’mores. Relax on the screen porch or challenge the family with arcade games, air hockey, pinball, and darts! Enjoy Owner’s Club access with a pool, fitness center & pickleball. Adventure awaits—book your perfect getaway today! Family fun!-Hot tub-Fire pit-3 king beds-Game room

Guest favorite

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.

4.89 out of 5 average rating, 124 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!