Holiday rentals with a pool in Racine

Rosie’s Eastside Garden Bungalow

Classic 1920's bungalow 10 minutes from Fiserv Forum, and across from the Oak Leaf trail— Rosie’s is truly a hidden gem on the East Side of Milwaukee. Wake up to birds chirping and enjoy your morning coffee on the air conditioned sun porch. Walk to Collectivo on the Lake, Bradford Beach, UWM, North Avenue, Brady Street, among countless cafes, restaurants, pubs, and more. This is your home away from home with welcoming hosts living next door for any recommendations or questions during your stay.

Family · Value · Long stay

Unplug - Boat, pool, hot tub on Lake Michigan!

Have you stayed in a boat allowing the sun to wake you up? Have you experienced the joy of doing nothing? In the lazy waves of Lake Michigan lies UNPLUG where we encourage you to practice the joy of doing nothing. Unplug has one large bed on board that can sleep 2 (Q size), a smaller Full bed, a small sofa, and a kitchen on board with basic amenities. The bathroom on board is not usuable but guests can use the clean well kept marina bathrooms and showers just a short walk away. Come unplug!

Value · Location · Barbecue

Kalo House | Mid-Century Modern Retreat with Pool

A beautifully preserved mid-century modern home with pool designed by noted architect Edward Humrich. The Kalo House blends iconic architecture with warm, curated interiors. Clean lines, expansive windows, and thoughtful design throughout. Peaceful and stylish, it’s the perfect retreat for design lovers visiting Chicago’s North Shore, Lake Michigan, or nearby Great Lakes Naval Station. Thoughtfully, curated and hosted with care…Perfect for Navy graduation stays and gathering families together.

Location · Family · Comfort

Close to Lake with Great Ammenities & Breakfast!

I want you to be able to do things here that you can't do in a hotel. If you're grillilng out, having a bonfire or watching movies all night long, you can turn up that volumn as loud as you want all night long! I posted my listing under "entire home" as you do get so much more than just renting "a room". When I have guests I stay in my office or bedroom so my guests feel more comfortable utalizing entire home & yard. In fact, if you don't ask for breakfast, you may not even see me at all.

Family · Location · Check-in

Fall Retreat near Lake Geneva & Apple Orchards

TOP 5% GETAWAY✨ - Private backyard & cozy fire table, ideal for s’mores & memories 🔥 - 15 min to Lake Geneva boutiques 🚤 🛍️ - Near ziplining adventures, orchards & boating 🏞️ - Near local skiing & tubing ⛷️ - Gameroom: foosball, basketball & Simpsons bowling 🏀🎳 - Oversized heated pool (May-Sept) - Quiet neighborhood: baseball fields, basketball courts & walking trail ⚾️🏀🚶 - 5 min to Country Thunder - 1 hour to ORD/MKE/RFD airport ✈️ - 40 min Six Flags & Great Lakes Navy Base 🎢🇺🇸

Location · Family · Backyard

7 1/2 Acre Private Estate w/inground pool, hot tub

Any event needs to be approved. First 4 guests 10 y/o and up are included in the nightly rate. Then I charge per person per night over 4 guests. PETS ALLOWED FOR $200.00 3 Bedroom, 3 Bathroom, 3000 Sq/ft Heated Pool!!, Hot Tub!!, Fishing Pond!!, Game Room all on 7 1/2 Acres!!!!!! It is a ONE OF A KIND!! NEW REC ROOM!! 1/2 Acre Fishing pond Stocked with MANY FISH!!! Sand Beach and Pier with boat, Paddle Boards. heated in ground pool, (open May1 - October 1st), hot tub.

Family · Location · Pets

2-acre retreat steps from Nagawicka Lake

Private Lake Country Retreat on 2 Acres | Pool, Park & Prime Location Relax at this private Lake Country retreat on 2 secluded acres surrounded by mature trees. Enjoy a private outdoor pool, spacious yard, and peaceful setting just steps from a county park with trails and a public beach. A nearby boat launch makes lake days easy, while shopping, restaurants, and coffee spots are only minutes away. Perfect for families, couples, or extended stays seeking privacy with convenience.

Family · Location · Cleanliness

"A" Frame Brandenburg Lake

Getaway to a cozy 1 bedroom w/loft for 2, up to 6 people. Full kitchen 1.5 bath all season getaway. There is a piano as well. A tranquil home steps from a private lake. Oak and Pine surround you plus a stone fireplace, it feels like the North Woods. The A Frame guest house shares a 5 acre compound ( total 20 Acres) with the owners residence and caretaker cottage. The Volo Bog 800ft away. No hot tub Nov - May. Swimming pool, June-October often cool to use in early June.

Value · Location · Kitchen

Private Pool and Hot Tub! Private Backyard Oasis!

Escape to a Summer Splash Pad, a private backyard oasis featuring a deep pool, relaxing hot tub, and space for families and groups. Enjoy a fully stocked coffee bar with espresso, perfect for starting your morning. Located minutes from Lake Michigan, North Beach, downtown Racine, and a short drive to Milwaukee. Whether you're planning a family vacation, weekend getaway, or summer retreat, Nautical Splash Pad offers the perfect blend of comfort, fun, and relaxation.

Location · Family · Nearby

Home away from Home

Welcome to Home Away From Home! Our warm and inviting retreat is the perfect place to relax, reconnect, and make lasting memories. Enjoy the in-ground heated pool, unwind in the sunroom, cozy up by the fireplace in fall and winter, or have fun in the game room with family and friends. Just a short walk to downtown Lake Geneva, you’ll be close to shops, restaurants, and attractions while enjoying the peace of a quiet neighborhood. We can’t wait to host you! V&T

Location · Value · Indoor spaces

The Dragonfly Loft

The second floor of this house is a spacious private lofted area that is very open and has high Located in the back of home, Private entrance and close to the city. Pets allowed! But note backyard is not available for bathroom time due to garden/pool and people walking barefoot. Near small bars, stores and short walk to buses that can take you into the city. I live on the lower unit, If you have any questions or request before check-in please message.

Location · Value · River

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.

Location · Value · Check-in