Holiday rentals with a pool in Oshkosh

5 out of 5 average rating, 50 reviews

Home in Green Bay

4 BR home w/pool (lg groups) kid friendly

Welcome to our beautifully remodeled 4 bed 3.5 bath home. Lg brand new fully stocked kitchen{Heated} pool (10ftmaxdpth) & lg backyard w/ creek. Tons of outdoor space to enjoy & you'll even see some wildlife around property. This home offers plenty of space & privacy. The lower level has a pool table & other games. We are 2.3 miles from Austin Straubel Airport/Oneida Casino 3.3 miles to Lambeau Field, Resch Center, Titletown. There is tons of entertainment & dining a short drive in any direction.

4.79 out of 5 average rating, 34 reviews

Home in Montello

3bed lake house, private heated pool near WI Dells

Relax with the whole family at this peaceful pool lakeside home. If you enjoy kayaking, paddle boating, fishing/ice fishing or taking a dip in a pool then this place is for you! This home offers so many activities for the whole family to enjoy. Relax on the wrap around house deck with it’s own fireplace, grill, outdoor dinning or lounge area. Relax on the porch swing. Looking for a little more activity, head over to the pool deck, basketball court, or challenge your family to a yard game.

4.97 out of 5 average rating, 35 reviews

Cabin in Lodi

Modern cabin with pool and Hot Tub!

Forget your worries in this spacious and serene space. Secluded yet close to a big city (Maddison and Wisconsin Dells) and lots of entertainment! 20 min away from 2 ski resorts, an amazing winery and distillery, spas, restaurants, casino! 3 mile away from lake Wisconsin. Hiking trailers, 24 hour ferry service across the lake and more. This luxurious villa combines comfort and style, you won't want to leave it, but the area is full of enviting places to go to, so plan for a few extra days!

5 out of 5 average rating, 9 reviews

Home in Green Bay

JAmbers 1113 Shadow Ln w/Heated POOL

This brand new home (completed August 2024) boasts 6 bedrooms and 3 bathrooms with ample gathering space, an enormous backyard patio that wraps around the side of the house (partially covered) and enters into the party garage. Six spacious bedrooms all with luxurious king or queen beds & two queen premium pull out couches can accommodate your group for any event/weekend stay. Fast internet provided by Spectrum. Please message for special rates on Packer Home Games & other Special Events

5 out of 5 average rating, 3 reviews

Cottage in Wild Rose

Water's Edge Cottage @ Evergreen Campsites&Resort

Welcome to Waters Edge where you will feel right at home in this bright contemporary home! Our spacious home and the best deck in the resort will be sure to delight your family and friends. This pet free cottage features 2 bedrooms and 1 spacious bathroom perfect for your family getaway in any season. During the summer months you will be able to use all the resort's amenities and during the winter cozy up next to the fireplace after spending the day at the local ski and tubing hill.

Apartment in Elkhart Lake

5 out of 5 average rating, 14 reviews

Lakefront Condo, Private Beach/Pools, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, pools (indoor & outdoor), hot tub, water sports rentals, Tiki Bar, and easy access to hiking, golfing, and town. Fall brings vibrant foliage, trail hiking, and golf on scenic courses. Winter offers cross-country skiing, snowshoeing, ice skating, sledding and trail hiking, while spring delights with blooming wildflowers, birdwatching, and farmers markets. Experience nature’s magic any season!

4.92 out of 5 average rating, 13 reviews

Home in Ashwaubenon

Cozy & Modern Home in Green Bay

You will be close to everything you need when staying at this 4 bedroom, 2 bathroom retreat. This home is located in Ashwaubenon, 3 miles from Austin Straubel Airport, Lambeau Field, Resch Center and Titletown District. On top of that, it is also located a short distance from popular bars, restaurants and shopping centers. This home includes a heated garage in winter months and a heated pool in summer months. The lower level is equip with a game room including a foosball table.

4.95 out of 5 average rating, 19 reviews

Cabin in Montello

The Rabbit Retreat #1

Relax at Kilby Lake Campground in our beautiful log cabin, the Rabbit Retreat. This camping cabin is a perfect transition to camping; rustic enough to immerse yourself in the outdoors without the hassle of sleeping on the ground in a balmy tent! Share in our nature-centric campground and wander through the tranquil woods. If you desire more action, head to the playground, play a game of cornhole, paddle around the lake, or lounge in our heated pool that is open seasonally.

4.86 out of 5 average rating, 231 reviews

Home in Allouez

Amazing Six Bedroom Green Bay Vacation Home!!

Amazing one-of-a-kind home is built for entertaining and full of amenities. You'll love the huge indoor pool that is heated year-round! Very spacious layout. Home has hosted celebrities & Packers Hall of Fame Players. Amenities include a full arcade, outdoor sauna, theatre room, large open kitchen and living room, high-end massage chair, poker table, and more! Six-minute drive to Lambeau, five-minute drive to the airport, very close to everything. 5,200 Sq Feet

4.97 out of 5 average rating, 33 reviews

Home in Plymouth

Private Home 4 BR+2Ba, Heated Pool by Road America

Family friendly, private home in Plymouth, WI. Approx. 4 miles to Road America. A beautiful Two-Story, 4 bedroom, 2 bath home with outdoor heated private pool, hot tub, gas grill and an outdoor pavilion available June - Labor Day. Close to Plymouth Dirt Track, Golf Courses, grocery stores, various local events, bars, restaurants, and child-friendly places within walking distance. NO PETS allowed on property. *For Long Stays over 7 days, please contact us.

4.97 out of 5 average rating, 63 reviews

Guest house in Freedom

A Sweet Suite in Freedom! Country Comfort!

Visiting friends or family in Freedom? Why bother them for an air mattress when you can stay right in town!? Going to a Packer Game and looking for a comfy place to stay with a super short drive? Found it! Ask about using the game room, golf simulator, or pool while you're here too! There's not a FULL kitchen!! Just one burner, and a flat griddle. There's also a microwave and small refrigerator/freezer, but overall, it's a suite. We think you'll LOVE it!

4.96 out of 5 average rating, 25 reviews

Home in Wisconsin

Sunny Days Await | Private Pool & Hot Tub Retreat

Looking for a relaxing summer escape? Whether you're here to explore or soak in the hot tub, you've found the perfect place to call home! ➤ Best for large groups and families ➤ Jacuzzi Spa w TV ➤ Outdoor smoker/grill combo ➤ Private Pool ➤ Dedicated Workspace | Fast wifi ➤ Outdoor Lounging & Bar with mini fridge ➤ Fully finished basement w/ 75" TV & bar! ➤ 2 Cozy indoor gas fireplaces (+ 3 outdoor) ➤ Fully Equipped Kitchen ➤ Local cafe & food mins away

Holiday rentals for every style

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A space that's all yours, with room for everyone

Popular amenities for Oshkosh rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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 stars23 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

4.88 out of 5 average rating, 8 reviews

Home in Newton

Country Cottage Indoor Pool HOT TUB NFL Draft ava

CassandraRating, 5 stars10 months ago

Great stay! My group loved it and had a blast. House was Beautiful & Host was GREAT, was very understanding and helpful. DEFINITELY recommend and would love another stay sometime.

5 out of 5 average rating, 10 reviews

Home in Waukau

Old Schoolhouse Stay

TravisRating, 5 stars10 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 Oshkosh

4.82 out of 5 average rating, 11 reviews

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

AmyRating, 5 stars6 months ago

Beautiful house! Very comfortable and has everything you need and more.

Home in Oshkosh

5 out of 5 average rating, 3 reviews

3 Bedroom, 2 Bath House, Available during EAA only

NadègeRating, 5 stars35 months ago

Ron and Jean were very quick at answering all our questions before and during our stay and very helpful. Their house was all we could wish for and as per the description. The little extra touches they had prepared for us made our stay even more personal! Very convenient also with a range of stores a few minutes drive... And open very late for shopping after the evening at Airventure! I definitely recommend (and would happily come back here myself!) for another Airventure...

4.94 out of 5 average rating, 33 reviews

Home in Appleton

Riverfront Appleton Home with Pool & Boat Dock!

LelaRating, 5 stars4 weeks ago

We loved this place so much! Beautiful home to stay at! Definitely our dream home! ❤️

Home in Menasha

5 out of 5 average rating, 18 reviews

Resort in the city

TikiRating, 5 stars10 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 Oshkosh

5 out of 5 average rating, 16 reviews

5 BR Oshkosh Home: 7 ml to EAA/1 ml to Hwy 41

BeaRating, 5 stars10 months ago

April’s place was perfect for our big group! We were in town for a wedding and this had everything we needed along with being close to the venue. I would definitely recommend her place to anyone staying in the area and would also stay here again. We all felt right at home, had everything we needed in the home and plenty of space for us all. Thank you again!

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Apartment rentals with a pool

Apartment in Elkhart Lake

Private Beach, Pools & Full-Kitchen

SaraRating, 5 stars3 weeks ago

Cute little airbnb in a private vacation rental community, but everyone is so close that it’s not very private. i wish i would’ve known beforehand that most businesses and some of the amenities such as the hot tub were still closed for the year… i think the price is steep for the off season since half the amenities weren’t available, but still had a nice retreat.