
Holiday rentals with a pool in Oshkosh
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Top-rated rentals with a pool in Oshkosh
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Popular amenities for Oshkosh rentals with a pool
House rentals with a pool

Retreat! Delightful stay with a pool.
I stayed at Tina's rental during a visit to the Oshkosh airshow. As promised, it was very convenient to get to from the airport and it was in a very peaceful location. This rental comes with use of a very inviting pool and fire pit. There was another rental party in the house on the property (next to the pool), but there is enough space and privacy that I didn't feel like we were on top of each other. I also want to share how clean and organized the space was when I arrived. I'm very picky about staying in rentals, but I was pleasantly surprised how tidy it was and how it was just as promised on the website. I really appreciated how incredibly responsive Tina was to all my messages. Tina also sent me a youtube video which gave me a tour of the space and an explanation of all the switches. As someone who has no experience with campers, this was super helpful. I highly recommend this rental to anyone looking for a comfortable stay and a great host. Thank you Tina

Hickory on the Lake- Modern home on the lake
Beautiful home, great location, very clean. Will stay again!

Old Schoolhouse Stay
Our stay at the Old Schoolhouse was great! The house was clean and well organized and had all the things we needed. The grounds were beautiful and we had a great time swimming in the pool, relaxing in the hot tub, and gathering at nights around the fire pit. Communication from Heather was fast and she thoroughly answered my questions. We had a great time at the Old Schoolhouse and would absolutely stay there again! Thank you, Heather!

Your Home Away From Home!
This was our third time staying at this house and it was still easy, convenient, and with everything we needed. The location is great for accessing some of the local ski resorts, and there were enough bedrooms and space to accommodate three families and a gaggle of kids. The whole process was easy and Brittney was responsive and helpful the whole time. Looking forward to returning next year!

Riverfront Oasis w/ hot tub and seasonal pool
Beautiful home and property for a quiet family get away. Lots of fun amenities for the kids to enjoy, and a safe, private, fenced in back yard. Very responsive owners with any questions we had. Would love to rent again.

Family Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!
Our group has stayed here twice and love the facility

Riverfront Appleton Home with Pool & Boat Dock!
We love the place plenty of room for cooking for family. Nice open floor plan loved everything about the place.

Indoor Pool, 5 Bedrooms, 10 Min Walk to Lambeau
Great place, plenty of room to accommodate 7 adults and 3 kids. Massive kitchen and counter space! Great having the downstairs common space for when kids napped or went to bed earlier than adults. Pool was clean and a nice added bonus! Great location of the Green Bay Area, everything we wanted to do was within a 5-20 minute drive. Host was attentive and answered questions before and during our stay.
Apartment rentals with a pool

The Lake Street Kickback in Elkhart Lake!
This place was perfect for us! Itās located in a homey, small town with several fun restaurants and shops. The condo was clean, functional, and cozy. The check in/out process was very easy, and the host was very responsive. Iād book again!

Siebkens 1 bedroom condo
A true gem in the heart of sweet little Elkhart Lake. What a great find! I will be back. Thank you Andrew for the great hosting and place to stay.

Lake Michigan and Door County Fun
Very nice accommodations. We have stayed there every other Christmas for several years.

Lakefront Condo, Private Beach/Pools, Walk to Town
We had two families that stayed together, all adults. We had a blast at the Tiki Bar and beach. The water was crystal clear! We didn't hit the pool because we couldn't pull ourselves away from the beach. We walked downtown and walked through a Porsche car show on the way. We hit a local Brewhouse for a beer then a swanky little restaurant for some Martini's. Everything was so close and the weather was amazing! Make sure to hit the Speak Easy right next to the condo. We stumbled upon so many cool things! We also rented SUP boards and paddle boats one afternoon. The rentals is quick and right there at the beach. We will definitely go back!
Quick stats about holiday rentals with a pool in Oshkosh
Total rentals
40 properties
Nightly prices starting at
Ā£116 before taxes and fees
Total number of reviews
250 reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
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- Lambeau Field
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- The Golf Courses of Lawsonia
- The Bull at Pinehurst Farms Golf Course
- Trout Springs Winery
- Oneida Golf Club
- West Bend Country Club
- Pollock Community Water Park
- Green Bay Country Club Sports Center
- Bay Beach Amusement Park
- Sunburst
- Pine Hills Country Club