Vacation rentals with a pool in Oshkosh

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Popular amenities for Oshkosh rentals with a pool

House rentals with a pool

Home in Rosendale
4.77 out of 5 average rating, 13 reviews

Retreat! 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
Home in Fond du Lac
4.9 out of 5 average rating, 10 reviews

4 br 4.5 acre secluded country property

MarkRating, 5 stars21 months ago
We had six senior men and there three adult age children who flew into the local airport for the EAA Air Adventure. This home was large with plenty of beds and couches for everyone and ten minutes from Fond Du Lac County Airport (FLD) and 30 minutes from Wittman Regional Airport (OSH). This turned out to be am ideal location to get away from the busy crowds and recharge after each long day. Most days we cooked breakfast at the home, but there are options close by. This was all detailed in the owners guest book. Lunches were at the airshow and dinners were usually eaten out. The owner even welcomed us with some local brew and pizzas in the fridge as he knew we would be tired after long day of traveling from the east coast. We enjoyed the home and would book again.
Top guest favorite
Home in Waukau
5 out of 5 average rating, 10 reviews

Old 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!
Guest favorite
Home in Menasha
5 out of 5 average rating, 8 reviews

Riverfront 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 Oshkosh
4.82 out of 5 average rating, 11 reviews

Close to EAA, pool, tennis/pickelball, pets ok

AmyRating, 5 stars4 months ago
Beautiful house! Very comfortable and has everything you need and more.
Top guest favorite
Home in Green Bay
5 out of 5 average rating, 28 reviews

Spacious Green Bay Packer Home

MeganRating, 5 stars4 months ago
Katie’s home is exactly what it says it is. The home is so spacious and cozy. I would absolutely recommend anyone stay here.
Guest favorite
Home in Appleton
4.93 out of 5 average rating, 30 reviews

Riverfront 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 reviews

Resort 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.

Quick stats about vacation rentals with a pool in Oshkosh

  • Total rentals

    40 properties

  • Nightly prices starting at

    $170 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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