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

4 br 4.5 acre secluded country property

MarkRating, 5 stars19 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.
Guest favourite
Home in Oshkosh
5 out of 5 average rating, 9 reviews

Anderson Casa

KariRating, 5 stars6 months ago
From the start, Mindy was friendly and helpful, and her communication was excellent. She asked if we would like suggestions about places or events in town, and provided great options. I can't say enough to express how beautiful her home is, inside and out. The original woodwork is in pristine condition, as is everything else. It was relaxing, clean and comfortable to just hang out inside. The back yard provided something for everyone. I particularly enjoyed lounging in the pool and sitting next to the little pond. Mindy provided a gracious welcome and her home was equally warm and inviting. We would love to return for longer stay next time in the Anderson casa!
Guest favourite
Home in Waukau
5 out of 5 average rating, 9 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!
Guest favourite
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 stars2 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 stars3 months ago
Our group has stayed here twice and love the facility
Guest favourite
Home in Green Bay
5 out of 5 average rating, 28 reviews

Spacious Green Bay Packer Home

MeganRating, 5 stars2 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.

Apartment rentals with a pool

Apartment 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!
Apartment 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.
Guest favourite
Apartment in Elkhart Lake
4.91 out of 5 average rating, 11 reviews

Lakefront Penthouse, Pvt Beach/Pools, Walk to Town

PatriciaRating, 5 stars3 months ago
This Penthouse is gorgeous! The photos do not exaggerate the beauty of the views, the spaciousness of the rooms and quality of the furnishings. It's so comfortable and peaceful. Luke is a great host and kindly guided us through the process since this was our first Airbnb experience. Elkhart Lake is a wonderful destination and a stay in the Penthouse will enhance your experience to make your trip truly memorable. We can't wait to return!
Guest favourite
Apartment in Elkhart Lake
5 out of 5 average rating, 11 reviews

Lakefront Condo, Private Beach/Pools, Walk to Town

StacyRating, 5 stars5 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 holiday rentals with a pool in Oshkosh

  • Total rentals

    40 properties

  • Nightly prices starting at

    £134 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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