Holiday rentals in Highland Park

4.97 out of 5 average rating, 33 reviews

Pet-Friendly Slice of Heaven by Lake Geneva & Como

Experience the ultimate family retreat in this well-appointed getaway in Geneva, Wisconsin. Hilltop Haven provides the perfect blend of relaxation and access to adventure! Nestled near quaint Lake Como and a few miles from the renowned Geneva Lake, you can easily partake in water sports, stroll by the waterfront, or visit the plethora of shops, restaurants, activities, and attractions nearby. Or stay on the property to get a slice of nature and relax, it’s set up to be comfortable and enjoyable!

4.94 out of 5 average rating, 177 reviews

Flat in West Lake View

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

4.97 out of 5 average rating, 143 reviews

Bungalow in Lake Geneva

Private Cozy Cottage Lake Geneva, WI

Come stay at our top rated Bed & Breakfast, located two blocks from the beautiful Lake Geneva. Relax in our California king suites, each contains a spa tub and shower, with heated floors and towel rails in the bathroom. Your complimentary breakfast basket is placed in your fridge prior to arrival, as well as complimentary gift of wine & cheese. Free WIFI is available on the property. No Pets, ADULTS over 21 ONLY. *NOTE all guests are required to pay a 8% Lake Geneva Bed Tax at check in.

Top guest favourite

4.98 out of 5 average rating, 144 reviews

Updated luxury country getaway short walk to lake!

Luxury getaway close to private beaches, downtown Lake Geneva, and many area amenities. Relax in comfort in this newly renovated 3-bedroom. Enjoy all that the Lake Geneva area has to offer while unwinding in a modern, comfortable retreat. Conveniently located a 3-min walk to Lake Como and a 10-min drive to downtown Lake Geneva. Charming golf cart community with so much to do. Perfect for couples, families, and business travelers. Ideal space for up to 4 adults and great for families of 5.

4.92 out of 5 average rating, 271 reviews

Home in Kenosha

Where Family & Friends Gather to Create & Remember

Come gather, relax & celebrate at our 1 acre estate near beaches, dining & Carthage College! The designer interior features 5 BR/4 Bath, chef's kitchen with Viking & Subzero, Coffee/Espresso Bar, dining area for 12, 2 spacious family rooms with piano, fireplace and TVs. Enjoy dining, lounging & fun in the great outdoors w/hot tub, fire pit, basketball, pickleball, ping pong & lawn games! Beaches are walkable under a mile & near lively downtown w/ harbor, restaurants, shopping & museums.

Top guest favourite

4.96 out of 5 average rating, 80 reviews

Huge! Sleeps 12, Perfect getaway for a large group

Pretend you are lost in a magical place as you curl up on the porch on a rocking chair. Then fall asleep in a heavenly bedroom in a luxurious king size bed. When you wake up, all your worries have faded away and the espresso machine awaits. This is Como! We designed the most heavenly home for you so the minute you step inside you're on vacation. Perfect for all seasons! Two living rooms, game room, 5 bedroom, 2.5 bath, stocked with everything we can think of to make your stay perfect.

4.94 out of 5 average rating, 34 reviews

The Clean Slate, Walk to down town, pet friendly

The Clean Slate is the latest offering from Lake Geneva luxury Rentals. Half mile walk to downtown. Pet friendly The house can accommodate 8 guests, but can be rented with its sister property, The White House, to accommodate larger groups. Contact host to inquire about renting both houses. This newly built home will surely delight. Tastefully decorated with all modern amenities. Easy access to downtown Lake Geneva’s shops, restaurants, Riviera Beach, and Geneva Lake Shore Path.

4.92 out of 5 average rating, 12 reviews

Flat in Logan Square

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

4.97 out of 5 average rating, 153 reviews

NEW! Cozy Downtown Farmhouse, 5BR 3 BA Sleeps 15!!

Our gorgeous home is set in the heart of downtown Lake Geneva. 5 bedroom, 3 bathroom home that is two blocks from the lake and a few blocks from downtown shopping and restaurants. We just completed an extensive renovation of the home and it is now ready for you to stay for your dream vacation. Our homes are fully licensed and legal for short term rentals. We also rent the home two doors down and another in nearby Williams Bay!

5 out of 5 average rating, 26 reviews

Modern Downtown Lake Geneva Charm - Sleeps 8

Beautiful 3 bedroom home located in the heart of Lake Geneva and walking distance to restaurants, bars, & the beach. This recently remodeled house is the perfect place for an escape. With an open kitchen concept, leading out to a large composite (Trex®) deck, there is no shortage of space for any activity or just to get back to a quieter more relaxing pace. *** This property is Licensed & Legal for weekend rentals ***

4.87 out of 5 average rating, 124 reviews

Home in Fox Lake

Lakefront Paradise

Relax and have fun with the family and friends at this unique getaway! We are situated directly on the lakefront with private access to our pier where you can enjoy world class sunset views. Jump in and go swimming, roast s'mores over a campfire right next to the water, grill up some burgers on the spacious deck or get some rest in our luxurious suites in this newly renovated (June 2021) home.