Vacation rentals with a pool in Winnebago County

HD Jameson House at River’s Edge

Nestled on the Rock River, the HD Jameson House, a National Historic Register gem, blends historic charm with modern amenities. Enjoy river views and with quaint shops and restaurants exploring the Village of Rockton is a perfect family-friendly retreat. This haven is surrounded by nature but close to numerous attritions, ideal for a romantic getaway or peaceful escape. The HD Jameson House offers a heavenly retreat, blending past beauty with present allure for everyone in the family.

Location · Family · Grill

Pool, Arcade, Hot Tub and more @16th and Aldeen

Do you want to be the Hero? Hero spouse, hero golf buddy, even Guitar hero?! You can be that and more at our hole-in-one nestled at the end of a quiet street right by a top 50 rated public golf course. Get in a round then head back to the hot tub to soothe that putting shoulder while the kids play in the pool. Then head inside to the arcade to play guitar hero till you win that Grammy you always wanted. Top it off with a family movie night! Pet fee $50/night per dog max 2 dogs

Value · Family · Check-in

Mulford Complex Private Estate • Spa & Pool

Private oasis in Rockford! Sleeps 23-25 featuring 7-9 bedrooms, 3 full baths, 3-4 half baths, hot tub, pool, pool house, & oversized living spaces--only 1 hour from Madison, WI, 90 minutes from Milwaukee & Chicago--you will have a unique getaway. Charming details, nooks, oversized deck, rose garden, fruit trees, massive garage/event space, 2 kitchens and 2 kitchenettes. Stay under the care of experienced Super Hosts. Memories are made here. Optional add-ons: Pool House, Events.

Family · Value · Heating

7mls HardRock Casino, 2mls RockCut State Prk, pool

Welcome to our specious home with Pool. Massage Chair. Each bedroom has dedicated workplace. 7mls to Hard Rock Casino. 2 minutes from IL Rock Cut State Park. 3 minutes from WoodWard Manufacturing. Close to lots of Hospitals and Immediate care facilities. 5-10 minutes from all convenience stores such as Woodmans, Aldi, Walmark, Target, Meijer. Close to several restaurants. The house has Pool in the back yard. Finished basement for more playroom or entertainer.

Andy's House *hot tub* *arcade* *theatre*

A great story starts with great moments of fun, laughter, and family! We are happy to welcome you into Andy’s House to start writing your own story. Enjoy our great amenities, from our Zen Zone massage room that doubles as a movie room, to the comfortable bedrooms and to the out of this world free-play arcade and lounge featuring a Toy Story pinball machine. You’ll have everything you need to relax and enjoy your time, except that nearby Pizza Planet.

Location · Family · Pets

Riverfront Nook - with Pool

Escape to a peaceful oasis tucked away in a secluded corner of Rockford. Nestled right on the banks of the beautiful Rock River, our spacious riverhouse is the perfect destination for groups looking to relax, recharge, and reconnect. Whether you're lounging by the pool, sipping coffee on the deck as the sun rises over the water, or enjoying evenings filled with laughter and good company, this home offers the ideal setting for making memories.

Family · Location · Cleanliness

The Outhouse

Country backyard living in a small town in a quite neighborhood ! Sauna inside the outhouse. The private back yard includes a hot tub, pool, chairs for lounging around the pool. The pool is above ground unheated and is open usually from Memorial Day to Labor Day. There will be times when we are working in the garden and we water our plants every morning. There is a pool table and dart board for entertainment!

Location · Family · Nearby

Arcade • Hot Tub • Movie Room Themed House

Welcome to your friendly neighborhood 🕷 Airbnb 🕷 Spend your afternoon relaxing in the hot tub while the kids chase high scores in the free play arcade. Then gather in the theater room for an epic movie night. Whether you're here for family fun or just a cozy escape, this hero hideout has it all—comfort, entertainment, and unforgettable memories, right in the heart of your favorite neighborhood.

Family · Location · Kitchen