Holiday rentals with a hot tub in Milwaukee

Peaceful Woodland Escape with Hot Tub & Lake Path

Escape to this serene 2-bedroom, 3-bathroom home nestled in the woods, just 25 minutes from downtown Milwaukee. Each bedroom has its own bathroom with jet tubs and wardrobes with full-length mirrors. The spacious living room features three sofa sets, a sofa bed, and a dining table. Enjoy the open-concept kitchen, gas BBQ, fire pit, and hot tub in the private backyard. Conveniently located near Walmart, Aldi, Costco, and dining options, this home is perfect for relaxation or adventure. Book now!

Bathroom · Hot tub · Breakfast

6BR Home•Hot Tub•Game Room•Near Downtown•Sleeps 14

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. Sleeps 14 with room to spread out!

Hot tub · Outdoor spaces · Hospitality

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.

Hot tub · Bathroom · Access

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.

Hot tub · Bathroom · Condition

Belleview House: Hot Tub, Fire Table, Fenced Yard

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

Outdoor spaces · Bathroom · Cleanliness

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.

Bathroom · Hot tub · Grill

Spacious Family Retreat w Hot Tub & Movie Lounge

🏡 Spacious Milwaukee retreat offering 2,157 sq ft of elegant comfort, perfect for families, groups, and business travelers. Enjoy a pleasant getaway in this thoughtfully designed home, featuring contemporary décor, generous living areas, and convenient amenities for a restful stay. Ideal for families, groups, business travelers, and extended stays, it offers a great blend of comfort, convenience, and easy access to all the city has to offer.

Bathroom · Outdoor spaces · Access

The Little Gray House

The Little Gray House is better than ever! This spring we completed many upgrades inside and out - check out our photos! We've got a few small openings left this summer, maybe they work for you? Time to book for fall and winter holidays so you can get in on the best little Airbnb around! The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!

Outdoor spaces · Hot tub · Air conditioning

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!

Bathroom · Outdoor spaces · Amenities

Brewers Hill Gem w/hot tub & seasonal shared pool

Your family will be close to everything when you stay at this centrally-located place. Walking distance to Brady Street, the Milwaukee River Walk, shops, restaurants and coffee houses. Less than a mile from Fiserv Forum, downtown Milwaukee and just minutes from Bradford Beach. This pet friendly unit has a private fenced in yard, BBQ grill, off street parking for your vehicles and motorcycles, and a hot tub for your use.

Outdoor spaces · Bathroom · Walkability

Large Downtown Home w/ Hot Tub & Huge Backyard

Enjoy a stay in a beautifully renovated historic cream city brick home in Milwaukee, ideal for groups. Enjoy a bright living room with fireplace, a fully equipped kitchen, and a large dining table for 10. This space is ideal for gatherings, consisting of 2 full bathrooms, 4 bedrooms, and flexible sleeping options. Walkable to downtown, restaurants, and breweries, this home offers comfort, space, and a prime location.

Hot tub · Bathroom · Air conditioning

Beautiful 6 bedroom with Heated Pool & Jacuzzi

Relax with the whole family at this peaceful place to stay right in the middle of beautiful Whitnall Park. You won't find a more peaceful view of the woods and park. Our beautiful home has a large heated pool with brand new 6 person jacuzzi. Brand new Kitchen and updated bathrooms. Master suite is very romantic with steam shower, jacuzzi tub, and luxury bed and fireplace. Family Friendly OR Romantic Getaway!

Bathroom · Outdoor spaces · Indoor spaces