
Vacation rentals with a pool in Oshkosh
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Top-rated rentals with a pool in Oshkosh
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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House rentals with a pool

Home in Rosendale
4.77 out of 5 average rating, 13 reviewsRetreat! Delightful stay with a pool.
RaquelleRating, 5 stars21 months ago
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
Top guest favorite

Home in Waukau
5 out of 5 average rating, 10 reviewsOld Schoolhouse Stay
TravisRating, 5 stars8 months ago
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!

Home in Poynette
4.81 out of 5 average rating, 47 reviewsYour Home Away From Home!
MoiraRating, 5 stars2 months ago
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!
Guest favorite

Home in Menasha
5 out of 5 average rating, 8 reviewsRiverfront Oasis w/ hot tub and seasonal pool
MonicaRating, 5 stars10 months ago
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.

Home in Kiel
4.92 out of 5 average rating, 12 reviewsFamily Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!
FrancescoRating, 5 stars5 months ago
Our group has stayed here twice and love the facility
Guest favorite

Home in Appleton
4.93 out of 5 average rating, 30 reviewsRiverfront Appleton Home with Pool & Boat Dock!
LindaRating, 5 stars3 months ago
We love the place plenty of room for cooking for family. Nice open floor plan loved everything about the place.

Home in Menasha
5 out of 5 average rating, 18 reviewsResort in the city
TikiRating, 5 stars8 months ago
My family and I travel to Oshkosh in July every year for the EAA Air show. This year staying in Menasha at Chad's place was our best stay by far. The location of the residence was only about 10 miles from Oshkosh which made it an easy back and forth commute to the Airport each day. Upon arrival the home was much more than we expected. It was show-room cleaned throughout the entire home with pool cleaned and monitored each day, extremely spacious, warm and home-like, cozy, room for activities including game room with fireplace and table tennis set-up for play. The outdoor surrounding was very peaceful and quiet with beautiful trees and a lovely park across the street with beautiful rose gardens and play areas for fun. Chad checked in on us to ensure that things were going well and offered to provide suggestions of places to eat for late hours after the Air Show events. Chad was extremely helpful to us even after we ended our stay. My Mom left her phone and Chad mailed it directly to us.

Home in Fond du Lac
4.8 out of 5 average rating, 103 reviewsLuxury house with lots of space and a huge yard!
JamesRating, 5 stars8 months ago
Nice house, kids enjoyed the playground and pool. Clothes dryer did not work and the screen door coming in from the garage was not working very well. Kitchen and dinning room were great. We enjoyed the hot tub.
Quick stats about vacation rentals with a pool in Oshkosh
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ624 before taxes and fees
Total number of reviews
260 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
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- Trout Springs Winery