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Holiday rentals with a pool in Jo Daviess County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Jo Daviess County rentals with a pool

House rentals with a pool

Top Guest favourite
Home in Galena
4.96 out of 5 average rating, 282 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

DianeRating, 5 stars1 week ago
Stayed here for a sisters weekend- and it was great for 6 sisters between the ages of 60-75. Two bedrooms on main floor and 2 downstairs worked great for us. Things were a little dated- but hey- so are we. We had a couple of issues that needed attn and James was most attentive and took care of them immediately. I would recommend. Great value for 6 women with varying needs! Especially loved the hot tub in the natural surroundings!!!
Guest favourite
Home in Galena
4.89 out of 5 average rating, 127 reviews

Cozy Retreat | Hot Tub | Firepit | Dog-friendly

LindaRating, 5 stars2 weeks ago
Brian and Jonny were very responsive and communicative from beginning to end. It was a last minute trip and we were lucky to find a pet friendly place during the start of the summer season. The house was clean, cozy and close to walking trails. Although we did not take advantage of the outdoor grill or hot tub (they have a wood burning fireplace for the winter), we enjoyed the screened in porch and open concept layout of the house, as pictured in the profile. The house is situated between two other houses blocked somewhat by the trees. I would describe as semi-private where we could see their back patio/hot tub/fire pit and vice versa. But whatever your personal comfort level, you can’t beat the proximity to trails, Owners Club, and easy access to Hwy 20 to Galena! We enjoyed our stay and exploring!
Guest favourite
Home in Galena
4.89 out of 5 average rating, 121 reviews

Modern Home w/Amazing Views, Hot Tub, Game Room

RobinRating, 5 stars2 months ago
We had such a great time! We took the whole family (10 people) and there was plenty of room. The basement was great for keeping the kids entertained. They were wore out from playing video games, air hockey, basketball, and hot rubbing. The area has beautiful views, and feels very private even though there are houses close buy - which we prefer just in case we would need help. We all wished we could have stayed longer! We highly recommend and will definitely be back!
Guest favourite
Home in Galena
4.94 out of 5 average rating, 66 reviews

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

LindsayRating, 5 stars1 day ago
Always a great time in Galena. This space was perfect for a small group, and had a lovely view.
Guest favourite
Home in Galena
5 out of 5 average rating, 5 reviews

Playful Pines Retreat *hot tub* *arcade*

NancyRating, 5 stars1 month ago
This home was beautiful with a peaceful location. It looks just like the pictures and even better. The community indoor pool and other facilities you get with this home was awesome. I had so much fun with the games at the house too- even at my age! :) I’ll definitely be back with my family!
Top Guest favourite
Home in Galena
4.92 out of 5 average rating, 160 reviews

DunPuttin Place

EmilyRating, 5 stars1 week ago
Stayed here for a girl’s trip! The home is lovely. The game room downstairs was a blast. The deck in back was perfect for drinks and conversation at night and calm morning coffee in the morning! Todd is quick to respond if anything is needed. Would definitely go back
Guest favourite
Home in Galena
4.82 out of 5 average rating, 295 reviews

Galena Retreat - Eagle Ridge Territories

RayRating, 5 stars1 week ago
Even better than advertised. Sandy was wonderful and so was the home. We were very pleased with our stay and her communication. The house is in a nice, quiet neighborhood, close to the strip, around golf courses, wineries, great food, fishing, historical places, and kayaking. Thanks again Sandy, we will be talking to you soon I’m sure.
Guest favourite
Home in Galena
4.97 out of 5 average rating, 31 reviews

Charming Galena Getaway

CatherineRating, 5 stars2 months ago
This house was more than just a home base for our time in Galena - it was like an attraction itself. There were so many fun things to do in the home (piano, mini golf putting, PacMan, mini bowling, darts, games, puzzles, jetted tub…) that even in chilly/rainy weather, we were not bored. Additionally, it was super clean and comfortable, spacious with plenty of room for our belongings, and equipped with all that we needed. The outdoor spaces (balcony, screened room, and backyard) and dark sky community (so many stars!) added to the fun. The nearby clubhouse had a wonderful pool with 3’6” depths and up, perfect for kids. It was a wonderful, relaxing stay!

Condo rentals with a pool

Superhost
Condo in Galena
4.92 out of 5 average rating, 13 reviews

Enjoy the SUN & Beautiful Lake Galena Views - Walk

KerryRating, 5 stars9 months ago
We just returned from a 3-night stay at this incredible Airbnb, and I can't recommend it enough! Our group of four had an absolute blast – it truly exceeded all our expectations. First and foremost, the cleanliness was top-notch. You could tell the hosts take pride in maintaining a space that makes guests feel welcome and comfortable from the moment they step inside. The amenities were thoughtfully curated – we didn't want for a single thing during our stay. From the kitchen to the bedrooms to the living areas, every detail was considered to create a home-away-from-home atmosphere. But what really made our stay special was the peaceful surroundings. The quiet, relaxing environment was the perfect antidote to our busy lives. We left feeling refreshed and rejuvenated. If you're looking for a stress-free, comfortable getaway... look no further. We can't wait to come back and create more amazing memories.
Condo in Jo Daviess County
4.83 out of 5 average rating, 6 reviews

Lake Links Loft in Galena, Illinois

DavidRating, 5 stars5 months ago
Our family had a fantastic job at Dan's place. The location is great - close enough to the Eagle Ridge Inn and Owners Club, but very private location with a beautiful view of the lake. The unit had everything we need and was much larger than the pictures made it seem. Galena had great shopping and restaurants. Galena Territory Owners Club indoor pool was perfect for the kids. I'd recommend staying here anytime we make it back to Galena Territory!
Superhost
Condo in Jo Daviess County
4.8 out of 5 average rating, 5 reviews

Long Bay Point Unit C5

AlyxRating, 5 stars7 months ago
My husband and I stayed here for 4 nights. It's a 10 min drive from downtown Galena in a quiet wooded area with paved trails that you can take to the nearby amenities. The place was clean, quiet, and the bathtub was amazing! The gym and indoor/outdoor pool are very nice but about 1.5 miles from the condo which wasn't stated anywhere (or at least not anywhere we saw) and was a little disappointing but overall wasn't a huge deal. The restaurant is a short walk through the trails or you can drive to it. It's right next door. Also, the initial message you get after booking with the rules and asking to email them out of the app was a little daunting and not normal for Airbnb bookings. It just had a less "homey" experience that you expect from Airbnb. It made me slightly nervous but after everything I would certainly stay here again.
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.
Guest favourite
Condo in Galena
5 out of 5 average rating, 17 reviews

Access to Pools and Lake Galena Marina #Dog Friend

SeanRating, 5 stars2 months ago
The place was exactly as described and what we expected. Far enough out of town to not be busy but close enough for a quick drive into town.
Superhost
Condo in Galena
4.79 out of 5 average rating, 24 reviews

Long Bay Point Unit C11 The Galena Territory

JenniferRating, 5 stars7 months ago
Super cute condo! The area was nice, about a 10-15 minute drive to downtown Galena, so it was nice being away from the crowds.
Guest favourite
Condo in Galena
5 out of 5 average rating, 11 reviews

Come Vibe @ Valleywood! 2BR Modern TH - Marina and

ConnorRating, 5 stars1 month ago
Nice quiet condo near golf within the Galena Territory. The unit was easy to find, very clean and has updated furniture/decor. Highly recommend if you are looking for a quiet retreat!
Superhost
Condo in The Galena Territory
5 out of 5 average rating, 6 reviews

Summer Lake Views! King Bed, Screened Porch, Pool

JanetRating, 5 stars1 week ago
We had great time staying in this beautiful condo! Very peaceful and comfortable. Had everything we needed and more except usb ports. Am looking forward to returning with a few friends for a women’s getaway!

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