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Holiday rentals with a pool in Jackson County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Jackson County

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

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Guest favourite

4.88 out of 5 average rating, 26 reviews

Expansive 5b6ba Countryside Home

Come enjoy your home-away-from-home with a private forest on a serene 2.12 acres. This home is perfectly designed for guests to spend quality time with family, friends, or colleagues in large, open concept common spaces and then discreetly escape to recharge into your own space/bedroom. The kitchen is professional grade and fully stocked to help you impress others with your cooking techniques OR to hire a professional. Each bedroom has with a private bathroom and towels of the highest quality.

4.63 out of 5 average rating, 16 reviews

Modern Home - Sauna, Steam Shower & Chef's Kitchen

Escape to this 4,000 sqft retreat, perfect for family gatherings or groups. Unwind with a private hot tub, sauna, steam shower, and two fireplaces. Indulge Your Inner Chef: Prepare culinary delights in the gourmet chef's kitchen, then challenge your friends to a foosball or poker game. The GTA Awaits: Enjoy full access to all GTA amenities, a pool & recreation complex, lake & marina, and over 25 miles of scenic trails. Downtown Galena & Chestnut Mountain Ski Resort are both 10 minutes away.

Guest favourite

4.96 out of 5 average rating, 96 reviews

Secluded Treehouse w/amazing views & private trail

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.

5 out of 5 average rating, 4 reviews

Spacious/hot tub/games/firepit

Bring the family to this great place with lots of room for fun. Spacious home features living areas along w/downstairs game room. 2 fireplaces, outdoor hot tub, firepit or barbeque grill. Six bedrooms, each w/TV & bath. 5 bedrooms furnished w/kings & 6th bdrm w/2 queens. Wireless internet. Fully furnished kitchen. Screened porch. Owners Club guests can enjoy amenities (swimming pools, tennis, exercise room, bball). Lake Galena/Marina/Shenandoah Riding Center/golf all nearby.

Top Guest favourite

Cabin in Elizabeth

5 out of 5 average rating, 15 reviews

Cedar Cove Cabin, Private Beach near Galena

Cedar Cove Cabin, nestled amongst the woods and a newly structured pond you’ll wake up feeling like you’re in the north woods! A luxury cabin amongst a wooded retreat on 50 acres, pond to swim and fish, beautiful surroundings , trails, and so much more! Welcome to your perfect vacation home! As you drive down the lane to our Cedar Cove Cabin you will instantly feel that you are leaving your busy, hectic daily life and you have entered a place of serene getaway.

Guest favourite

5 out of 5 average rating, 69 reviews

Stunning 5 bdm home on The General in Galena Terr!

No MGMT Fees! Enjoy all that Galena Territory and Jo Daviess County has to offer! Nearly 5k sq ft with 5 bdrm/5.5 baths and located on the number one handicap hole on The General golf course with views of holes 12, 13, 14, 15 and 16! A one-of-a-kind location on over 2 acres of land. About 20 min from Downtown and Chestnut Mtn! Minutes from golf, hiking, horseback riding, boat rentals, fishing, indoor/outdoor pool, fitness center and game room at the Owner's Club!

10 Golenrod

Stunning 5R/5.5BA BIG Retreat in The Galena Territory! Pool Table! Firetable! This stunning 5 bedroom/5 ensuite FULL bath Galena Territory resort home has a large screen porch and deck. This home is designed to accommodate ten guests in beds. Two additional guests are allowed, but there is no sofa sleeper. NEW!! We now have a large fire table on the back deck. Enjoy gathering around a warming fire without the inconvenience of wood. We provide propane. Have fun!

Guest favourite

Holiday home in Galena

4.96 out of 5 average rating, 104 reviews

Modern,hot tub firepit,nature horse view,amenities

4 Bedrooms, 4.5 Bathrooms, Outdoor Hot Tub, New Construction, 3000 sq ft, Sleeps 10 in beds. Modern newer construction 4 bedroom home with gorgeous furnishings in the Shenandoah Valley. Just 7 minutes from the GTA Owners Club and 15 minutes to downtown Galena. This home is NOT pet friendly. Total price per night - No added 3rd party fees.

Apartment in Galena

4.76 out of 5 average rating, 38 reviews

WorldMark Galena One-Bedroom Condo - Sleeps 4

There is no cleaning fee and guests are not expected to clean anything upon departure! You can leave the condo as-is when checking out :) The resort requires a valid ID and credit/debit card for check in. There is a $250 refundable deposit required. Please provide the full name you would like to use for the reservation when booking.

Apartment in Galena

Studio Deluxe Suite @ Club Galena Resort

You'll have a great time at this comfortable place to stay. You’ll come upon the brick and timber edifice of this resort along a quiet, tree-lined road. The lodge-like design offers peaceful accommodations draped in style and comfort. Second only to Chicago as the most-visited destination in Illinois, Galena is a vacation dream.

Apartment in Galena

4.88 out of 5 average rating, 8 reviews

Galena 1 Bdrm Condo Resort

Large 1 Bedroom condo at a resort condo development in beautiful, Galena,Illinois ❤ Free Parking. Free Internet ❤ ★ If reserving a FRIDAY OR SATURDAY there is a 2 night minimum unless request is made last minute (3 days before check in)★ ★24 hour reception★ ★Calendars updated daily★ ★Multiple Units/Room Sizes Available★

Top Guest favourite

5 out of 5 average rating, 71 reviews

Secluded Country Dream with all the fun!

You'll make lasting memories in our newly appointed stylish retreat located in The Galena Territories! Whether you come to Galena to shop, ski, golf or just soak up the sun, Owl's Stay has all the essentials needed to relax, have fun, and spread out with your loved ones.

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Popular amenities for Jackson County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

4.67 out of 5 average rating, 15 reviews

Summer is ON at Haven! Dog Friendly, Outdoor Hot T

WendiRating, 5 stars12 months ago

My husband and I with our 4 kids and 2 inlaws had plenty of space to move around and still have private sleeping quarters. we would recommend this home to anyone wanting to visit this area. Also had easy and great communication with host. wendi

Top Guest favourite

Home in Elizabeth

4.96 out of 5 average rating, 45 reviews

Cliffside Cottage, Breathtaking Views near Galena

DianaRating, 5 stars1 day ago

Danesa was a fantastic host and was easy to communicate with and quick to respond. The Cliffside Cottage was everything the listing said it would be and more. Not only was the house gorgeous, but the layout was so well thought out and gave our party of 9 plenty of space to enjoy without being on top of each other. The highlight of the house was the screened in porch. It was truly such a peaceful place to sit and listen to the birds or to watch the rain come down without any pesty bugs or mosquitos. We could have spent hours and hours sitting there enjoying the incredible views while enjoying each others company. Other highlights included the well stocked kitchen (truly everything you could need and more), the location (close enough to enjoy Galena, but far enough away to feel as if you are the only ones around for miles) and the outdoor space which was perfect for fires and stargazing. We truly loved this house and would love to come back one day to experience it in a different season.

5200 Sq Ft Home, Outdoor Hot Tub, Pool Table, Fire

RossRating, 5 stars58 months ago

This was a great place to spend the weekend. We had 6 couple stay here and it comfortably for us all. The girls spend the days hiking with goats and in the close vineyard, while the guys spent the weekend golfing. The house is in a great location and was a great place to come back to and relax for the evening. The hot tub is also a lot bigger than the pictures make it look. Linda was also very quick to respond to any questions we had which was greatly appreciated. We will definitely be back!

Liberty Living - charming & cozy

KristyRating, 5 stars1 month ago

The house felt like a home. Very easy to get to, well kept up on the outside and inside, very clean, had everything we needed and more. Simple directions to check in and out. Tracy was easy to get a hold of and responded right way from the booking all the way til the end of the stay! Highly recommend staying here and will return again next time!

New place to stay

Comfortable retreat w/sounds of nature!

New place to stay

Galena Getaway

Condo rentals with a pool

Condo in Galena

4.33 out of 5 average rating, 6 reviews

Galena, IL, Studio # 1

AaronRating, 5 stars54 months ago

Just stayed here with a friend for 2 nights. It was close to downtown Galena. The room was very clean and had everything we needed. We were happy that the pool was open (by appointment) We look forward to returning!

Condo in Galena

4.75 out of 5 average rating, 32 reviews

Galena, IL, Studio 2

MariaRating, 5 stars24 months ago

Great place to stay very close to downtown Galena.

Condo in Galena

4.6 out of 5 average rating, 5 reviews

Tranquil Retreat: Cozy Studio @ Wyndham Galena

DinaRating, 5 stars21 months ago

This place was absolutely B.E.A.U.T.F.U.L! The staff were super sweet and friendly. So many things to do at Galena. Also, there was a table with “to do activities” That was very helpful. I would 100% come back. Thank you all staff for being such a good host.

Condo in Galena

4.38 out of 5 average rating, 8 reviews

Galena, IL, Studio Z # 1

JohnRating, 5 stars46 months ago

Great location. Very quiet and beautiful. Used the pool and hot tub.

Condo in Galena

4.81 out of 5 average rating, 16 reviews

Galena, IL, 1 Bedroom #1

KeithRating, 5 stars22 months ago

Jan was great!! The place messed up our room but she did her best to make it right. We appreciate her attention and her desire to fix the situation.

Condo in Galena

4.44 out of 5 average rating, 16 reviews

Galena, IL, Studio Z # 2

SteveRating, 5 stars32 months ago

Great place to stay while visiting Galena especially if you plan on golfing at Eagle Ridge!

Condo in Galena

5 out of 5 average rating, 3 reviews

Galena, IL, 1 Bedroom Z #1

DanRating, 5 stars53 months ago

A great place to stay that was about 20 minutes to chestnut and 15 minutes to Galena. Fireplace makes for a nice touch when it’s snowy and cold outside

Condo in Galena

Galena, IL, 1 Bedroom S #2

AshleyRating, 5 stars33 months ago

It was exactly as advertised. Was perfect.

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