Holiday rentals with outdoor seating in Galena

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, 126 reviews

Treehouse! 3BR Ensuites•Secluded• 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

Outdoor spacesLocationView

4.99 out of 5 average rating, 135 reviews

* 10 min Walk to Main Street*Stocked kitchen*

Take a step back in time in this 1840s era home! Newly renovated with an eye to maintaining it's vintage charm, this house fits right into Galena's historic character. Grab your morning coffee on the side porch swing. Take the 10 min walk to Main Street for shopping and lunch. Relax in the light filled living room or fully stocked kitchen. Or, enjoy front porch rockers. Be sure to keep an eye out for some historic surprises in the house. NOTE: There are a lot of stairs to the side porch entry.

ValueOutdoor spacesParking

4.96 out of 5 average rating, 135 reviews

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 Galena

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.

Outdoor spacesLocationPool

A tri-level house with a muted gray exterior features multiple large windows. A front porch with railings is visible, inviting relaxation. Surrounding greenery and a neatly maintained yard contribute to the peaceful setting. The sloped roof adds character to the home.

4.9 out of 5 average rating, 113 reviews

Cozy Wooded Tri-Level In Galena Territory

Relax with friends or the whole family at this wooded and peaceful place to stay in the Galena Territory.Cozy Tri-Level with 3 comfortable bedrooms and 3 baths. Tvs in 2 bedrooms as well as large tvs in the living room and downstairs rec room.Fireplace in living room area.Sit outside and enjoy the scenery on the front porch or back screened patio.Only 6 miles to Downtown Galena .Guests are welcome at Lake Galena,the Owners Club,Restaurants,Pools and Trails.Six Free passes are included.

Outdoor spacesLocationBiking

4.98 out of 5 average rating, 124 reviews

An inviting firepit area features two black Adirondack chairs positioned around a circular stone firepit. The A-frame cabin is seen in the background, softly illuminated by decorative lights, surrounded by trees at dusk.

Cabin in Elizabeth

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

Outdoor spacesLocationCondition

4.99 out of 5 average rating, 167 reviews

A rustic cabin is presented, featuring a sloped metal roof and wooden exterior. Snow covers the ground, while a stone pathway leads to the porch. Two rocking chairs are positioned on the deck, inviting relaxation amid the natural surroundings.

Cabin in Hazel Green

Romantic one bedroom cabin with indoor fireplace

Relax and unwind at this getaway on a private 8 acres. Quaint decor yet newly updated amenities in this cabin only 7 miles away from the historic and charming Galena, Illinois. Convenient access to renowned fine dining and shopping in Galena and Dubuque and surrounding tri-state area, casinos, river life with boating and fishing, museums, cafes, vineyards/wineries, located on ATV/UTV trails and much more. You will find a guidebook in the cabin outlining these attractions and many more.

Outdoor spacesLocationTV

4.94 out of 5 average rating, 209 reviews

Cabin in Galena

Family Fun! Xbox-Hot tub-Firepit-Games in/outdoor!

Enjoy the ultimate summer retreat at our stylish 4-bedroom cabin in Galena Territory! New furniture and Xbox just added! Sip your morning coffee on the deck, explore nearby trails or relax in the hot tub. Challenge family and friends to arcade games, air hockey, darts, and board games. With 8 amenity cards, access the Owner’s Club for swimming, fitness, and indoor pickleball—rackets and balls provided! Whether you seek adventure or relaxation, this cabin is your perfect summer getaway!

ValueOutdoor spacesQuiet

4.99 out of 5 average rating, 233 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

LocationOutdoor spacesTV

Place to stay in East Dubuque

An open interior space features a spacious bed with neutral bedding and a cozy throw. A modern kitchenette, equipped with essential appliances, is visible. A jetted tub sits beside a decorative wall, while large windows offer views of the water and bring in natural light.

4.97 out of 5 average rating, 324 reviews

Custom Floating Suite-HOT TUB!

Enjoy a stay directly on the backwaters of the Mississippi River. This custom cabin is floating right on the water, and you won't find anything like it! Grab your loved one or friend and surround yourself in nature, while soaking in the hot tub on the floating patio, or in the beautiful tub inside. Relax in the king size bed thats in front of one of the two fireplaces. The cabin has everything you need, including a small kitchen. This floating oasis is located at Millennium Marina.

LocationOutdoor spacesTV

The charming two-story miner's cottage features a welcoming front porch adorned with historic American flags. Lush greenery surrounds colorful flower beds, enhancing the outdoor space. The stone and white clapboard exterior reflects classic architectural elements within the Galena National Historic District.

4.96 out of 5 average rating, 603 reviews

Beautiful Miner's Cottage in a Garden

This 1840's miner's cottage in the heart of Galena is only 3 blocks from beautiful, historic and fun Downtown Galena Main Street, but is far enough to have quiet times in the quarter acre yard of perennial gardens as well the expansive 2 story front porch, and 3rd porch off the kitchen, with gas grill. The house sits on a corner lot in the Galena National Historic District. The bathroom and kitchen are newly remodeled and the entire house is designer decorated. Beautiful!

LocationValueBack garden

A spacious living area features a contemporary black sofa set, complemented by a sleek area rug. Exposed brick walls and wooden beams create a cozy atmosphere. A well-equipped kitchen is visible in the background, enhancing the open layout. Natural light floods in from large windows.

4.96 out of 5 average rating, 107 reviews

Suite Victory #3 On Main St w/Reserved Parking

Suite Victory #3- Beautifully renovated apartment on Main St. right where you want to be with Reserved Parking. Dining, entertainment, and shopping just outside your door. Open floor plan with beautiful views of downtown Main Street. King bed. Double sink vanity and large walk-in shower. Kitchen has island, quartz countertops, and new appliances. Stackable washer and dryer within the unit. Above Charlie’s Place Eatery on Main Street. MAX 2 PEOPLE. NO DOGS ALLOWED.

LocationValueCleanliness

A spacious living area is highlighted by large windows allowing natural light to fill the room. A round dining table with orange chairs complements a cozy seating arrangement near the fireplace, featuring a stylish couch and armchairs. Decorative elements enhance the contemporary aesthetic.

4.99 out of 5 average rating, 152 reviews

Ulysses Suites, Suite 201

Ulysses Suites has just been completed inside the historic J. G. Schmohl building in the heart of downtown Galena, located at 213 to 217 S. Main Street. The location is walking distance to all the best restaurants and shops. We have 7 suites and a beautiful lobby that are modern and luxurious, with lots of historical character and texture as a nod to its previous existence as the Grant Hotel from 1895 to 1933. Suite 201 is located on the 2nd floor.

ValueLocationSleep quality

Popular amenities for outdoor seating rentals in Galena

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

The charming craftsman-style house features a welcoming front porch with brick accents and a porch swing. A well-manicured garden with vibrant foliage adds a touch of color, while tall trees provide a natural backdrop. The entrance is framed by large windows, enhancing natural light.

4.95 out of 5 average rating, 200 reviews

Galena home close to Main St with parking and deck

ValueOutdoor spacesNearby

A living area is showcased with hardwood flooring, featuring a spacious sofa and two patterned armchairs. A coffee table is positioned centrally, surrounded by two end tables. Natural light is welcomed through large windows, complemented by decorative wall art.

5 out of 5 average rating, 211 reviews

The Downtown House - 1820s home steps from Main St

ValueOutdoor spacesSleep quality

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, 219 reviews

Galena Getaway

LocationOutdoor spacesCondition

Superhost

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.

4.8 out of 5 average rating, 107 reviews

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

Outdoor spacesLocationFamily

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, 207 reviews

*Covered Hot Tub * 2 Fire Tables * Massive Deck*

ValueOutdoor spacesSleep quality

A modern kitchen features a large island with a marble countertop, complemented by dark wooden stools. Cabinets with a sleek gray finish line the walls, and patterned tiles add visual interest. Large windows allow natural light to brighten the space.

4.95 out of 5 average rating, 186 reviews

Historic Downtown 1852 Home - Newly Renovated

LocationValueView

This historic brick home features multiple windows reflecting a classic architectural style. A stone garage, designed with modern doors, complements the house. Lush greenery surrounds the property, enhancing its natural appeal. A paved driveway leads to the garage, showcasing an inviting approach to the entrance.

4.96 out of 5 average rating, 257 reviews

1842 Bavarian Brew House

LocationOutdoor spacesView

An outdoor deck is shown featuring comfortable furniture and a fire pit table. The expansive, grassy area extends toward a picturesque golf course, framed by trees and distant buildings under a blue sky with scattered clouds.

4.96 out of 5 average rating, 113 reviews

King Suite • Jetted Tub • Fire pit • Golf Views

Outdoor spacesValueBack garden

Apartment rentals with outdoor seating

4.91 out of 5 average rating, 423 reviews

A cozy living room features exposed brick walls, a comfortable sectional sofa, and a round coffee table. A flat-screen TV is mounted above a wooden console, while natural light enters through the window with wooden blinds. Decorative wall art enhances the space.

Flat in Downtown Dubuque

Drake House: Fleur de Lis with Private Hot Tub

LocationValueHot tub

4.85 out of 5 average rating, 239 reviews

A cozy bedroom is presented with a spacious bed dressed in white linens and accented by a blue decorative pillow. A bedside table with a lamp provides soft lighting. Dark curtains frame the window, enhancing the restful ambiance.

Flat in Dubuque

Historic oasis next to spa in downtown Dubuque

LocationValueCondition

4.91 out of 5 average rating, 79 reviews

An entrance to the property is shown, featuring a wooden door framed by large glass panels. Green bushes and flower pots with blooming plants are situated on either side of the stone path, which leads to the door. A striped awning provides shelter above.

Flat in Elizabeth

Derinda house B&B private apartment.

Outdoor spacesValueView

A spacious bedroom is presented with a large, upholstered king size bed layered with a white quilt. A pair of bedside lamps, a decorative bench, and an armchair with floral accents are featured, complemented by soft wall colors and warm natural light from the nearby window.

4.96 out of 5 average rating, 77 reviews

Suites at 414 - Suite 2

LocationValueSleep quality

4.93 out of 5 average rating, 138 reviews

A cozy sleeping area features a spacious bed with blue and white bedding. Natural light enters through the dark window treatments, illuminating the wooden dresser and nightstand. Coordinating wall art adds subtle character to the serene gray walls.

Flat in Dubuque

Tom's place

ValueLocationCondition

A comfortable living area features a dark leather sofa positioned in front of a rustic wooden table. A vase with dried flowers adds a touch of decor. In the background, a spacious bed is visible, set against a soft blue wall.

4.88 out of 5 average rating, 383 reviews

Fever River View Master Suite

ValueOutdoor spacesBiking

Superhost

A single-story residence is displayed with a welcoming front porch and a light brown exterior. A pathway leads to the entrance, flanked by neatly trimmed bushes. The roof features a gentle slope, with nearby trees providing partial shade.

Flat in Dubuque

4.88 out of 5 average rating, 159 reviews

Check It Out! Great Location Large Priv w/Parking

ValueLocationAmenities

A comfortable seating area features a patterned chair positioned beside a stone fireplace. Warm light flickers from the fire, while a wall-mounted window allows natural light to brighten the space. Decorative items, including a framed floral print, are displayed above the fireplace.

5 out of 5 average rating, 29 reviews

Comfortable and Cozy 2bdrm!

LocationPetsCleanliness

Apartment rentals with outdoor seating

4.93 out of 5 average rating, 14 reviews

Apartment in Galena

The Cozy Lake Stay You've been Craving - Fireplace

Outdoor spacesLocationFamily

Apartment in The Galena Territory

4.86 out of 5 average rating, 22 reviews

2 King Beds | Game Area + Foosball | Pool Access

LocationOutdoor spacesIndoor spaces

Apartment in Jo Daviess County

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.

4.83 out of 5 average rating, 18 reviews

Lake Links Loft in Galena, IL

LocationOutdoor spacesWalkability

4.9 out of 5 average rating, 190 reviews

The kitchen features a spacious island with four industrial-style bar stools. Modern pendant lights hang above, illuminating the dark cabinetry and white subway tile backsplash. A stainless steel refrigerator and microwave are visible, contributing to the contemporary design.

Apartment in Dubuque

Modern Loft Overlooking Downtown

Outdoor spacesLocationView