Apartment holiday rentals in Waukesha County

4.97 out of 5 average rating, 36 reviews

A winding staircase is shown, featuring a wooden railing and a textured carpeted surface. A framed artwork of a chicken decorates the wall, alongside potted plants in light, neutral tones. Natural light illuminates the space, enhancing the warm wooden accents.

Private room in Pewaukee

Huge private loft by lake

Relax with your family at this peaceful setting. Enjoy lake life in this private loft with separate entrance. Next to bike trail, lake access to kayak, and boat launch nearby. Near Pewaukee and Delafield. 25 minutes to Milwaukee. Enjoy lake country fun, shopping, restaurants and festivals. You’ll feel like you’re up north sitting on the front patio or the fire pit in the backyard, looking up at the stars. It’s a gem! Owner lives on site in separate lower level. Shared laundry/garage access.

A bright living area is presented with a plush blue sofa and a matching loveseat, adorned with colorful throw pillows. A wooden ladder holds a towel in the corner, while a decorative map hangs on the wall. A small red table complements the space.

4.82 out of 5 average rating, 33 reviews

Ideal4Contractors/Sleeps6/Parking/Laundry/FastWiFi

Quiet & Safe Central location - Minutes from Hospitals, Highways, Shopping, Parks, Restaurants Central Air/Heat, Fast WiFi, Smart TV Black-out Blinds Perfect for business travelers, digital nomads and students Newly renovated, beautiful brick building Spacious floor plan Two parking slots; one garage space In Unit washer/dryer combo to make your stay efficient Medical College of WI - 8 mins Froedret Hospital - 8 mins Children’s Hospital- 8 mins Minutes from HWY 41 & 45

A bright living area features a mix of cozy seating, including a leather sofa and light-colored accent chairs. A coffee table sits at the center, surrounded by a large area rug. Decorative pillows and a painting add character to the space, complemented by natural light from nearby windows.

5 out of 5 average rating, 36 reviews

Historic Luxury |Walk to Downtown| King bed |Shops

✨ 1870s Elegance Meets Modern Comfort | Steps from Dining & Shopping ✨ Welcome to Downtown Delafield’s most charming and highly-rated historic stay! This stunningly restored 1870s apartment offers a luxury experience with vintage charm, all within walking distance to top-rated restaurants, boutique shops, and lakeside trails. Whether you’re visiting for a romantic escape, work trip, or weekend getaway, this unique property is designed to make your stay unforgettable.

5 out of 5 average rating, 55 reviews

Historic Downtown Gem| Walk to Dining, Shops, Lake

✨ 1870s Elegance Meets Modern Luxury ✨ Welcome to Downtown Delafield’s most sought-after Airbnb stay! This beautifully restored historic apartment offers a 5-star luxury experience with original 19th-century charm and modern amenities—all within walking distance to the best dining, shopping, and nature spots in the area. Bonus perk: this cozy gem is perched just above one of downtown’s favorite restaurants—so you’re literally steps away from an unforgettable meal.

A spacious living area features a large window providing natural light, an entertainment center with a Smart TV, and a comfortable seating arrangement. A blue futon and an accent chair are positioned near a wooden coffee table, while a decorative rug adds a cozy touch.

4.73 out of 5 average rating, 15 reviews

Delafield Vacation Rental Near Lakes & Parks!

From hosting afternoon picnics in Oak Street Park to making memories on the waters of Nagawicka Lake, this vacation rental has everything you need for a blissful stay! Nestled in the heart of Delafield, this cheerful 1-bedroom, 1-bathroom apartment features natural lighting, a Smart TV, a dining area, and a well-stocked kitchen. Stroll the boutiques, dining, and sights of Main Street, or take an adventure to greater heights at the Lapham Peak Observation Tower.

4.99 out of 5 average rating, 104 reviews

A historic Victorian home showcases intricate architectural details, featuring a turret and a welcoming front porch. The light blue exterior is complemented by vibrant red accents. Lush greenery surrounds the property, enhancing its inviting presence in a serene neighborhood.

Flat in Oconomowoc

Charming Historic Upper•Walk to Downtown+Festivals

✨Experience a memorable Wisconsin getaway at the Blue Belle, a beautifully preserved Victorian home nestled in the heart of Lake Country. 📍This charming small town offers the perfect blend of adventure and relaxation, with shops, restaurants, wedding venues and activities all within walking distance. 🗓️Browse our host profile for additional listings if your preferred dates are unavailable or if you're traveling with a larger group or a 🐶furry friend.

5 out of 5 average rating, 60 reviews

Luxury Delafield Retreat | Walk to Lake & Shops!

⭐ 5-Star Comfort | Prime Location |Historic Downtown| Self Check-In ⭐ Welcome to Your Ultimate Delafield Getaway! Nestled in the heart of Historic Downtown Delafield, this luxury apartment is steps from Lake Nagawicka, top-rated restaurants, boutique shops, and scenic parks. Designed for both relaxation and adventure, this stylish retreat offers modern comforts, high-end finishes, and a perfect location for exploring everything Delafield has to offer.

A neatly arranged living area showcases a light-colored sofa and a matching loveseat, both adorned with dark cushions. A round wooden coffee table sits on a textured area rug. Natural light enters through the window, complemented by dark curtain panels, adding to the cozy ambiance.

Flat in Elm Grove

2-Bedroom Condo in Elm Grove/Brookfield, WI

Experience Elm Grove like a local in this 2-bedroom condo. Step into this welcoming and adorable property, featuring 2 queen beds in the cozy bedrooms. You'll find everything you need for a comfortable stay, from a hair dryer in the bathroom to AC and WiFi throughout. The fully equipped kitchen and washing machine ensure convenience during your visit. This condo is located near the Brookfield, WI area and a short 7 minute drive from Froedtert Hospital.

A bright and inviting living space is depicted, featuring a white sofa adorned with colorful decorative pillows. Two accent chairs, angled for comfort, are complemented by a small side table. A floor lamp provides ambient lighting, and a decorative ladder holds a cozy throw.

3 Bedrooms/LaundryOnsite/FreeParking/Near Hwy

Guest favourite

A comfortable living area features a dark brown leather sofa adorned with multiple decorative pillows. A cozy ottoman is positioned in front. Soft, ambient lighting is provided by a nearby lamp, with a light-colored area rug adding warmth to the polished wood flooring.

4.94 out of 5 average rating, 32 reviews

Long Stay Discount/Free Parking, Washer/Dryer

A spacious living area features a green sofa positioned in front of a wooden coffee table. A light area rug lies beneath, and a window draped with sheer curtains allows natural light to illuminate the room. Decorative plants and wall art enhance the ambiance.

5 out of 5 average rating, 5 reviews

Extended Stays:/Garage/WasherDryer/FastWiFi

Two Bedrooms, Quiet & Safe Central location - Minutes from Hospitals, Highways, Shopping, Parks, Restaurants Central Air/Heat, Fast WiFi, Smart TV Black-out Blinds Perfect for business travelers, digital nomads and students Newly renovated, beautiful brick building Spacious floor plan Two parking slots; one garage space In Unit washer/dryer combo to make your stay efficient

A cozy living area features a spacious bed adorned with a plaid blanket. Two reclining chairs create a comfortable seating arrangement. A television is mounted on the wall, and sheer curtains softly filter light. Dark rugs complement the neutral-toned walls.