Holiday rentals with a pool 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, 118 reviews

Secluded Treehouse: Hot Tub • Fire pit • Games

🌲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

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, 114 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, 133 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 outdoor deck features a spacious hot tub surrounded by a wooden railing. Nearby, two wooden benches and a table provide additional seating. Sunlight filters through the surrounding greenery, casting a natural warmth on the deck.

4.96 out of 5 average rating, 113 reviews

Lake Views | Hot Tub | Nature Retreat | Movie Room

Looking for nature? Come immerse yourself in nature at this private oasis. • 3 bed/3.5 bath (7 adults comfortably w/max 8 guests) • 12 mins to downtown Galena • Outdoor hot tub • Grill & dining space on upper deck • Seasonal views of Lake Galena • Lounge/Movie room with pool table, electric fireplace & smart TV • Full Kitchen w/fridge, oven, microwave, dishwasher, keurig coffee machine, air fryer, instant pot, & crockpot • Upstairs family room with smart TV, fireplace, & board games

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.

4.97 out of 5 average rating, 144 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, 118 reviews

Secluded Treehouse, w/great views, new luxury bath

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, 106 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.

4.99 out of 5 average rating, 218 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

An electric fireplace is positioned below a large flat-screen TV mounted on a stone mantel, which adds texture to the living space. A comfortable armchair is shown with a patterned upholstery, and natural light filters through nearby windows, illuminating the inviting decor.

4.97 out of 5 average rating, 203 reviews

Newly Renovated. Gorgeous Retreat!

Newly Renovated. Gorgeous Retreat w/seasonal waterfall view! *This home has Large flat screen TV's in Living Room and Both BDRMS. All new kitchen cabinets, Side by Side Refrigerator with Ice Maker, Electric Stove, Microwave, and includes Dishwasher, Keurig Coffee pot, Regular 12 c coffee pot. New Flooring through out, and new Furniture.. Relax by the electric fireplace indoor or the backyard firepit. NO SMOKING IN UNIT New windows coming in the near future. Minimum 2 night stay

Townhouse in The Galena Territory

The villa is a three-level structure, featuring a wood siding exterior and multiple windows allowing natural light. A spacious deck extends from the upper level, surrounded by green grass and mature trees, contributing to a peaceful outdoor setting.

4.92 out of 5 average rating, 118 reviews

Sunny Farmstead: Owners' Club access, golf nearby!

Welcome to Farmstead: a quiet and comfortable villa nestled within the heart of the Galena Territory. This home features 3 KING beds, a wood burning fireplace, bumper pool table, child bunk beds, dart board, and a closet full of games. Property is 10min from downtown Galena. Booking Sunny Farmstead also gives you access to the Owners' Club (4 minute drive) which features indoor and outdoor heated pools, basketball courts, game room, tennis courts and more.

4.98 out of 5 average rating, 112 reviews

Spacious, King Beds, Pool steps away, Near Golf

🔹2 King beds 🔹2 Full baths 🔹Cozy fireplace + firewood 🔹Modern, fully equipped kitchen 🔹Private deck with grill & seating for 4 🔹Peaceful wooded end-unit 🔹Steps to semi-private pool 🔹Full club amenities, including fitness center 🔹3 Smart TVs 🔹Computer workspace 🔹Paved walking trails nearby 🔹Lake access 🔹2 min to golf, driving range & spa 🔹12 min to downtown Galena 🔹15 miles to Chestnut Mountain, zipline & ski

4.88 out of 5 average rating, 104 reviews

Hot Tub | Fireplace | Screened Porch | Pool Access

Escape to this cozy 2-bedroom + loft retreat in The Galena Territory—perfect for relaxing, reconnecting, and enjoying everything Galena has to offer. ✨ HIGHLIGHTS • Private hot tub + outdoor fire tables • Screened-in porch surrounded by nature • Wood-burning fireplace • Access to Owner’s Club (pool, fitness center & more) • Smart TVs + fast WiFi • 12pm check-in & check-out • 11 minutes to downtown Galena

Popular amenities for Galena rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 75 reviews

Cozy retreat in Galena Territory

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.

4.83 out of 5 average rating, 41 reviews

The Tree House

A spacious home is situated on a gently sloping landscape, framed by mature trees. The exterior features a combination of stone and wood elements, with a welcoming front porch and large windows that enhance natural light. A paved driveway leads up to the property.

5 out of 5 average rating, 94 reviews

Stunning 5 bdm home on The General in Galena Terr!

A modern living room features a comfortable seating arrangement with a light gray sofa and armchair. A large window allows natural light to fill the space, while a flat-screen TV is mounted above a cozy fireplace. Built-in shelves are neatly arranged with books and decorative items.

4.98 out of 5 average rating, 102 reviews

Inviting & Bright | Firepit Sauna Hot Tub & Games!

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.

4.94 out of 5 average rating, 164 reviews

Galena Territory - Pets - Fireplace - Pool Access

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.

4.98 out of 5 average rating, 83 reviews

Golden Meadows Escape: A Luxurious Country Retreat

5 out of 5 average rating, 56 reviews

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

A cozy house is nestled among trees, featuring a gray facade and large windows. In the foreground, bright yellow daffodils blossom, contrasting with the earthy tones of the surrounding landscape. A path leads to the entry steps, enhancing accessibility to the home.

5 out of 5 average rating, 11 reviews

The Drey: A Private Retreat in the Treetop Canopy

Apartment rentals with a pool

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.

4.82 out of 5 average rating, 17 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.

4.92 out of 5 average rating, 13 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.

4.78 out of 5 average rating, 18 reviews

Tranquil Retreat: Cozy Studio @ Wyndham Galena

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.

4.82 out of 5 average rating, 33 reviews

Long Bay Point Unit C11 The Galena Territory

5 out of 5 average rating, 14 reviews

Lakeside Comfort: Sunny Days & Relaxing Nights! C

A rustic resort building features dark wooden siding and large stone accents. The entrance is framed by a pitched roof and large windows, while green lawns and trees are visible in the foreground, enhancing the natural setting.

4.93 out of 5 average rating, 28 reviews

Galena, IL, 1 Bedroom S #1

The exterior of a lodge-style resort is depicted, featuring a mix of stone and timber elements. Large windows and balconies invite natural light, while an expansive green lawn and trees create a peaceful setting. A stone pathway leads towards the entrance.

4.84 out of 5 average rating, 19 reviews

Tranquil Retreat: Cozy 1BR Suite @ Wyndham Galena

Other holiday rentals with a pool

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, 55 reviews

Long Bay Point Getaway

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, 66 reviews

Storybook Countryside Cottage

A spacious yard features a circular stone fire pit surrounded by four metal chairs. The house stands in the background, showcasing a classic architecture with a hipped roof and a front porch. Green grass and trees provide a natural setting under a clear blue sky.

4.99 out of 5 average rating, 67 reviews

Spring savings*hot tub*dog friendly*5 stars*arcade

Cabin in The Galena Territory

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.

4.93 out of 5 average rating, 82 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.

4.92 out of 5 average rating, 36 reviews

The Cottage on Lake Galena

A spacious hot tub sits on a covered deck, surrounded by outdoor lighting and natural scenery. Nearby, a pair of hammocks provide relaxation options, while a staircase leads to additional levels. The tranquil view of trees and open fields enhances the peaceful setting.

4.96 out of 5 average rating, 53 reviews

Galena Spring Escape! Hot Tub, 6 Ensuite BRs +Fun!

The exterior of a modern cabin is framed by lush green foliage. The structure features a prominent a-frame design with large glass windows and a spacious balcony. The surrounding lawn is well-maintained, showcasing the home's integration into the natural landscape.

4.97 out of 5 average rating, 67 reviews

*Golf*Firepit*Hot Tub*Owners Club*Dog Friendly*