Holiday rentals with a pool in Oshkosh

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

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 stars20 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 favourite
Home in Oshkosh
4.98 out of 5 average rating, 58 reviews

Hickory on the Lake- Modern home on the lake

SarahRating, 5 stars1 week ago
Beautiful home, great location, very clean. Will stay again!
Top guest favourite
Home in Waukau
5 out of 5 average rating, 10 reviews

Old Schoolhouse Stay

TravisRating, 5 stars7 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 stars1 month 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 favourite
Home in Menasha
5 out of 5 average rating, 8 reviews

Riverfront Oasis w/ hot tub and seasonal pool

MonicaRating, 5 stars9 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 reviews

Family 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 favourite
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.
Top guest favourite
Home in Ashwaubenon
4.97 out of 5 average rating, 93 reviews

Indoor Pool, 5 Bedrooms, 10 Min Walk to Lambeau

TrishaRating, 5 stars5 days ago
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

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

The Lake Street Kickback in Elkhart Lake!

AllysonRating, 5 stars4 months ago
This place was perfect for us! Itā€™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. Iā€™d book again!
Apartment in Elkhart Lake
4.15 out of 5 average rating, 13 reviews

Siebkens 1 bedroom condo

MichaelRating, 5 stars9 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.
Apartment in Mishicot
4.68 out of 5 average rating, 19 reviews

Lake Michigan and Door County Fun

Ginger LRating, 5 stars3 months ago
Very nice accommodations. We have stayed there every other Christmas for several years.
Top guest favourite
Apartment in Elkhart Lake
5 out of 5 average rating, 11 reviews

Lakefront Condo, Private Beach/Pools, Walk to Town

StacyRating, 5 stars7 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

    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

Destinations to explore

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Winnebago County
  5. Oshkosh
  6. Rentals with pools