Vacation rentals with a pool in Oshkosh

4.97 out of 5 average rating, 60 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.

5 out of 5 average rating, 6 reviews

Home in Green Bay

NewPool|HotTub|TheaterRoom|Sleeps 15|HeatedGarage!

Score big at this Green Bay getaway! Splash in the pool, soak in the hot tub, or relax under the gazebo swing. Inside, enjoy billiards, arcade games, foosball, shuffleboard, cornhole, and plenty of board games. Movie night is a hit in the theater room complete with a popcorn machine. Gather in the furnished heated garage with TV & games. A fully stocked kitchen and coffee bar keep everyone ready for fun. Minutes from Lambeau, it’s game day central and the ultimate spot for family or group fun!

5 out of 5 average rating, 3 reviews

A cozy living area features a pair of sofas with decorative pillows, arranged around a round wooden coffee table. A light fixture and patterned area rug add character, while a doorway leads towards the kitchen, providing a glimpse of the open layout.

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 friendly 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.

The outdoor area features a spacious pool surrounded by multiple lounge chairs and umbrellas. Lush greenery and landscaped gardens enhance the inviting atmosphere. The house in the background complements the serene setting, providing a relaxed environment for gatherings and leisure activities.

4.95 out of 5 average rating, 39 reviews

Sunny Days Await | Seasonal 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 Seasonal Pool (closed until May 1st) ➤ 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

An aerial view captures the expansive waters of Elkhart Lake, with shimmering reflections of sunlight. The shoreline is lined with lush greenery and a sandy beach, complemented by a few boats gently floating on the surface. Nearby, various residential structures can be seen nestled among the trees.

5 out of 5 average rating, 22 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!

A spacious studio condo is showcased with two queen beds, a cozy sitting area, and a fully equipped kitchenette. A flat-screen TV is mounted on the wall, while a high-top table for two is featured in the background, providing a functional living space.

5 out of 5 average rating, 19 reviews

The Lake Street Kickback in Elkhart Lake!

Welcome to The Lake Street Kickback! This privately owned studio condo is located at The Shore Club of Wisconsin & has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach, Tiki bar, on site restaurant, indoor pool & game room. A unique blend of updates, convenience, comfort & relaxation. Just steps away from local favorites including village restaurants, bars, farmers market, shops & neighboring resorts like Osthoff and Siebkens Resorts.

4.9 out of 5 average rating, 30 reviews

The exterior of a luxurious log cabin is framed by lush landscaping, featuring a spacious patio with seating around a heated pool. The large stone structure is complemented by expansive windows, showcasing the inviting atmosphere of the residence.

Home in Suamico

Grand on Longtail | Lazy River · Lake · Luxe Stay

🌊 Welcome to The Grand on Longtail — one of Wisconsin Getaways’ most iconic escapes. 💦 Float your cares away in the lazy river-style heated pool, unwind in the sauna, or soak under the stars in the hot tub. 🎮 Game room, kayaks, paddleboards, theater room & more. 🛏 Sleeps large groups in luxury across multiple suites. 🔥 Fire pit, lakefront deck, private dock access. 📍 Just 15 mins to Lambeau. Book The Grand on Longtail and experience lakeside luxury like never before.

4.95 out of 5 average rating, 20 reviews

A rustic log cabin is surrounded by greenery, featuring wooden walls and a peaked roof. A picnic table and flower planter are positioned in front of the cabin. A neighboring RV is visible in the background, integrating outdoor living with nature.

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.

4.64 out of 5 average rating, 69 reviews

An aerial view presents a spacious outdoor area featuring a large swimming pool surrounded by a sun deck with lounge chairs. The multi-tiered landscape includes lush greenery and decorative shrubs, while the house is visible in the background with expansive windows and a covered patio.

Home in Wrightstown

**NEW** Waterfront Vacation DREAM HOUSE

**NEW** Incredible one-of-a-kind waterfront dream home was built for entertaining and full of amenities. Boat access, dock equip with boat lift and two jet ski lifts, boat house and breathtaking views. House features huge pool, full basketball court, theater room with six reclining massage chairs, arcade, gym, in ground fire pit, spacious interior layout and two fireplaces. Centrally located right between Green Bay and Appleton. 15 minute Uber to Lambeau Field.

The exterior showcases a contemporary two-story structure with a dark facade and large windows. A welcoming entrance is highlighted by a distinctive overhang. The well-maintained yard features a combination of concrete pathways and lush greenery, surrounded by mature trees and neighboring homes.

4.96 out of 5 average rating, 82 reviews

Hickory on the LakeWaterfront Luxury on Winnebago

✨ Welcome to Hickory on the Lake 🌊🏡 – A beautifully renovated 3-bedroom, 3-bath retreat on Lake Winnebago. ☀️ Four-Seasons Room – Enjoy stunning sunrises & sunsets with your morning coffee ☕ or evening cocktail 🍹. 🌳 Quiet, Family-Friendly Neighborhood – Relax in peace while staying close to Oshkosh attractions 🎨🚴‍♂️. 📍 Lakeside Luxury – Immerse yourself in comfort and create unforgettable memories against the breathtaking backdrop of Lake Winnebago 🌅✨.

4.97 out of 5 average rating, 77 reviews

An aerial view captures a spacious property featuring a rectangular pool surrounded by lounge chairs. Manicured grass and trees provide greenery, while nearby homes and a winding road are visible in the background.

Guesthouse 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!

4.98 out of 5 average rating, 43 reviews

The exterior of a two-story home is portrayed, featuring a welcoming front porch with potted plants. Lush green grass lines the pathway leading to the stairs. The facade combines traditional elements with modern updates, reflecting a craftsman style. A clear sky with scattered clouds adds to the scene.

Home in Plymouth

Holiday Home for 8ppl w/ Hot Tub in Plymouth, WI

Family friendly, private home in Plymouth, WI. Approx. 4 miles to Road America. A beautiful Two-Story, 4 bedroom, 2 bath home with an outdoor hot tub. Close to 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. HOLIDAY DECORATIONS for NOV-DEC 2025 BOOKINGS! Ready to host families in town for the holidays! Book today!

Popular amenities for Oshkosh rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 16 reviews

A view from atop a waterslide into a pool, showcasing a spacious backyard. In the distance, shaded by trees, are several structures including a camper, a playground, and a storage shed. A clear blue sky enhances the serene landscape.

Home in Rosendale

Retreat! Delightful stay with a pool.

5 out of 5 average rating, 12 reviews

Two yellow Adirondack chairs are positioned on a wooden dock overlooking a calm river, reflecting the warm hues of the sunset. The water stretches out smoothly, with trees lining the opposite shore and a soft glow from the sun creating a serene atmosphere.

Home in Doty Island

Riverfront Oasis w/ hot tub and seasonal pool

5 out of 5 average rating, 13 reviews

The exterior of the historic schoolhouse is framed by lush greenery, highlighting the entrance adorned with a decorative arch. Multiple decks provide outdoor space for relaxation, while flower pots add a touch of color. Well-maintained gardens complement the inviting facade.

Home in Waukau

Old Schoolhouse Stay

The exterior of a charming single-story home is visible, featuring a well-maintained lawn with neatly trimmed hedges. A stone pathway leads to the entrance, which is flanked by decorative planters. A spacious driveway provides access to an attached garage.

4.64 out of 5 average rating, 14 reviews

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

5 out of 5 average rating, 34 reviews

The two-story home features a light-colored brick façade and a spacious driveway leading to a three-car garage. Lush green landscaping frames the entrance, complemented by well-maintained grass and a large tree, creating an inviting exterior.

Home in Green Bay

Spacious Green Bay Packer Home

A spacious living area features a large, dark gray sectional sofa with decorative pillows, set on a patterned area rug. A small side table is positioned nearby, and natural light filters in through sheer curtains covering a window. The walls are adorned with a 'HOME' sign.

4.5 out of 5 average rating, 4 reviews

Cozy 4 bedroom home. Minutes to Eaa grounds.

A spacious dining area features a large marble table surrounded by upholstered chairs. A modern chandelier hangs above, providing ambient lighting. Floor-to-ceiling windows offer views of the outdoor greenery, enhancing the dining experience with natural beauty.

4.95 out of 5 average rating, 39 reviews

Riverfront Appleton Home with Pool & Boat Dock!

4.98 out of 5 average rating, 128 reviews

A spacious kitchen and dining area is visible, featuring modern white cabinetry and a large island with a stone surface. A wooden dining table is surrounded by four chairs, and sunlight is let in through multiple windows that offer a bright atmosphere.

Home in Ashwaubenon

Indoor Pool, 5 Bedrooms, 10 Min Walk to Lambeau

Condo rentals with a pool

A cozy bedroom features a spacious bed with a light-tone blanket, complemented by two wooden nightstands. A large window with a sliding door offers access to a balcony. Dark curtains frame the window, and a flat-screen television rests on a wooden dresser.

4.27 out of 5 average rating, 15 reviews

Siebkens 1 bedroom condo

4.71 out of 5 average rating, 21 reviews

A spacious bedroom features a king-sized bed with a rich burgundy and cream bedspread. Two bedside tables with lamps sit beside the bed, and a comfortable armchair is placed in the corner. Soft carpet covers the floor, enhancing the cozy atmosphere.

Condo in Mishicot

Lake Michigan and Door County Fun

5 out of 5 average rating, 19 reviews

The Lake Street Kickback in Elkhart Lake!

An open layout features a cozy sleeping area with a spacious bed framed by light walls and large windows. A modern kitchen with dark cabinetry and stainless steel appliances is complemented by a round coffee table on a textured area rug. A comfortable seating area is visible.

5 out of 5 average rating, 8 reviews

Private Beach, Pools & Full-Kitchen

5 out of 5 average rating, 22 reviews

Lakefront Condo, Private Beach/Pools, Walk to Town

Other vacation rentals with a pool

A clear swimming pool is framed by a spacious wooden deck, featuring floating loungers and a ladder for easy access. Trees and houses are visible in the background, providing a serene environment for relaxation.

Home in Omro

4.33 out of 5 average rating, 3 reviews

Perfect Oasis for EAA guests

A single-story ranch-style home is captured from the front, showcasing a light blue exterior and a symmetrical garage door. A driveway leads to the garage, surrounded by neatly trimmed grass, with simple landscaping elements visible along the front of the house.

Hotel room in Elkhart Lake

Perfect for E.A.A. 4 Bedroom with Pool

A spacious room features two large beds adorned with patterned bedding. Natural light filters through sliding glass doors leading to a balcony. A ceiling fan enhances airflow, while a large mirror and dresser provide functional space. A blue area rug adds a cozy touch to the hardwood floor.

4.33 out of 5 average rating, 6 reviews

Stay in the heart of Elkhart Lake at Victorian Inn Resort

The exterior of the house features a combination of brick and gray siding under a clear blue sky. A manicured lawn surrounds the home, with a stone pathway leading to the entrance. Windows provide natural light to the interior spaces.

4 out of 5 average rating, 5 reviews

Excellent location near Lambeau and EAA

Home in Neenah

Poolside Retreat - EAA Rental

An inviting exterior view of the spacious home showcases multiple large windows framed by greenery. The property is set against a colorful sunset sky, with a manicured lawn and vibrant flower beds enhancing the scene. The driveway leads to a two-car garage.

Home in Green Lake

Lawson Poolside Escape (gym and pool!)

A clear blue pool is framed by a spacious patio area. Several lounge chairs in various colors are arranged around the pool. A two-story house stands in the background, featuring a wooden entrance and balconies on either side.

The Schmidt Haven