Holiday rentals with a hot tub in Milwaukee

Hot Tub, Arcade, 4 bath, Sleeps 16, Chef's Kitchen

Spacious 4BR, 4BA home perfect for families & groups! Sleeps 16 with 11 beds. Enjoy a chef’s kitchen w/ 48” oven and everything you need to host the perfect meal, hot tub, game room, BBQ, smoker, patio, & 85” TV w/ surround sound. Plenty of space for all in group with cozy nooks for quiet conversations, group gathering spaces and play spaces. 2 dedicated work spaces. Modern upgrades throughout. TV in each room. Great for reunions, retreats, or getaways - comfort, space, and fun all in one place!

Bark Lake, Entire Home, Private Lake Frontage 50ft

A 1,700 sqft home with 3 bedrooms, 2 baths, sofa bed and couch, large outdoor deck, hot tub, grill, 50 feet of lake access. Enjoy the morning sunrise from the East and relax by the waterfront and watch the sunset on the West. Bring the family and enjoy some lake life where the days linger on longer. During the Summer months we have a pier available to fish off of. There are two fire pits, one by the lake and another tucked away near the house. You will love it here, it is very calm and relaxing.

Downtown Oasis: Hot Tub, Garage, 2 King Huge yard!

Bring the whole family to this great place with lots of room for fun. A rock throw away to Milwaukee central featuring the city's best restaurants, bars, shops, and attractions. This exclusive 1800sqft Ranch 3 bedrooms, 9 beds, 2 full and 1 half bathrooms to sleep up to 14 guests. It features everything your family & friends need: Large Kitchen, Wash/Dry, Outdoor Patio, large back yard and a 8 person Hot Tub! Walking to the Fiserv Forum and downtown. Attached Garage w/ Driveway. 1 Gig Internet

Quiet, Comfy Craftsman 2-BR with Private Hot Tub!

This special place is close to everything that makes Milwaukee GREAT! Short drives lead you to downtown, State Fair Park, Am Fam Field, Fiserv Forum, Summerfest grounds, Milwaukee Zoo, and many great local hangouts. Enjoy the quiet, neighborly, & historic Washington Heights area in your own 2-BR lower apartment (of a duplex). Private access to a large 6-Person Hot Tub in the backyard during your stay! Free Off-Street parking for one vehicle. Also close to the Milwaukee Regional Medical Center.

Brew City Inn with Hot Tub | Summerfest House

Welcome to another property by “GNRHomes”! Make some memories at this luxurious, unique and family-friendly residential home on a quiet street. Newly renovated 1900’s home with both historic charm and modern luxury. Walkable to many major bars and restaurants. A few minutes to most popular MKE attractions, DM for more info. By booking this home you have access to the entire space and private hot tub with an garage oasis. Great central location to discover all that Milwaukee has to offer.

Belleview House: Hot Tub, Backyard, Fire Table

Welcome to Belleview House, a delightful pet-friendly 3-bedroom home nestled in the heart of the vibrant Murray Hill/East Side neighborhood. We have renovated and redecorated the entire home and backyard (November 2025)! ✔ Hot Tub - closed during quiet hours ✔ Fast Wi-Fi ✔ Workspace ✔ Smart TVs ✔ Comfy king, queen, and twin beds ✔ Fenced Backyard with outdoor fire table ✔ Lawn bowling, horseshoe & cornhole ✔ Outdoor dining table ✔ 0.9 mi to Bradford Beach on Lake Michigan ✔ Stocked kitchen

Arcade Victorian Mansion · Sleeps 23 · 7 BR

Prepare to be WOWED! This restored historic Victorian offers 5,000 sq ft across 4 levels with 7 bedrooms, 11 beds, 2 full baths, and 3 half baths—sleeping up to 23 guests. Minutes from downtown Milwaukee. Enjoy a full game floor with 2 arcade machines, N64, foosball, poker table, and more. Outside features a huge backyard with a massive playset, swings, slides, basketball court, and plenty of space for the whole group to relax, play, and make unforgettable memories together.

6BR house, yard, hot tub - 5 min drive downtown

My spacious home spreads out over three levels on 1/3 acre in a quiet residential neighborhood, and is about one mile from most downtown restaurants, bars, breweries, and entertainment venues. Having easy access to the freeway and downtown it's a perfect location from which to explore the city, or to relax and have fun in the home with its many included amenities. Don’t forget your swimsuits so you can enjoy the new salt water hot tub with moto massage seats.

Happy Days Home close to all MKE attractions

Welcome to the Happy Days House! The cozy house is updated with a fully-equipped kitchen, full dining room with views, a charming living room anchored with a fireplace, completed with a queen sofa sleeper. Enjoy coffee on the porch overlooking a quaint tree lined street. Gather around the fire pit, dine outdoors, or pop into the hot tub (a spring to late fall amenity) in the private backyard. Location is central - AMF, Zoo, Fiserv, downtown, etc.

Spacious Family Retreat w Hot Tub & Movie Lounge

🏡Large Milwaukee retreat offering 2,157 sq ft of modern comfort, ideal for families, groups, and business travelers. Thoughtfully designed for comfort and togetherness, this home features modern interiors, spacious living areas, and carefully selected amenities for a relaxing and seamless stay. Whether you’re unwinding after a busy day or making memories with loved ones, it offers the ideal mix of comfort, convenience, and enjoyable city living.

Barclay House in Walker's Point

Our Walker's Point house is recently renovated, nearly everything is new. Relax in this stylish space which includes a private backyard, w/rear & front decks. Located next to cafes and some of Milwaukee's best restaurants. It is also within walking distance to the Summerfest grounds. We are minutes from Downtown Milwaukee, bike trails and the pedal taverns are just a block away from the house. We just recently added a new hot tub!

The Little Gray House

Spring is here and it's time to share what we've been up to! Those of you staying with us after April will be treated to new kitchen counter tops, roof, windows and siding :) It'll still be the LGH, but with a little something more! We'll update the photos as soon as it's completed! The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!