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 stars19 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
Guest favorite
Home in Waukau
5 out of 5 average rating, 10 reviews

Old Schoolhouse Stay

TravisRating, 5 stars6 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 reviews

Your Home Away From Home!

MoiraRating, 5 stars2 weeks 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 reviews

Riverfront Oasis w/ hot tub and seasonal pool

MonicaRating, 5 stars8 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 stars3 months ago
Beautiful house! Very comfortable and has everything you need and more.
Home in Kiel
4.92 out of 5 average rating, 12 reviews

Family Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!

FrancescoRating, 5 stars4 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 reviews

Riverfront Appleton Home with Pool & Boat Dock!

LindaRating, 5 stars2 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 stars7 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.

Condo rentals with a pool

Condo in Elkhart Lake
5 out of 5 average rating, 3 reviews

The Lake Street Kickback in Elkhart Lake!

AllysonRating, 5 stars3 months ago
This place was perfect for us! It’s 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. I’d book again!
Condo in Elkhart Lake
4.15 out of 5 average rating, 13 reviews

Siebkens 1 bedroom condo

MichaelRating, 5 stars8 months ago
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.
Condo in Mishicot
4.68 out of 5 average rating, 19 reviews

Lake Michigan and Door County Fun

Ginger LRating, 5 stars2 months ago
Very nice accommodations. We have stayed there every other Christmas for several years.
Guest favorite
Condo in Elkhart Lake
5 out of 5 average rating, 11 reviews

Lakefront Condo, Private Beach/Pools, Walk to Town

StacyRating, 5 stars6 months ago
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 vacation rentals with a pool in Oshkosh

  • Total rentals

    40 properties

  • Nightly prices starting at

    $150 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

Destinations to explore