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.

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. Pool closed for the season

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.

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

Spacious bi-level home in a great neighborhood.

Come on in and enjoy the spacious interior of this home. The upstairs hosts 4 bedrooms. Meander your way through the quiet, scenic living room into the formal dining area. The eat in kitchen offers additional seating for diners. is living space meanders throughout. Get comfy in the cozy family room off the kitchen. Start a fire to add ambiance to your evening. The lower level includes a theatre from, full bath, pool table, bar and kitchenette. Perfect for a family vacation.

Retro Revival mini Hot Tub | Indoor Pool | Arcade

Our Atomic Alcove Retro Revival Stay is apart of our Rockford Retro Revival Stay. You will have access to our master Suite and our 2 Queen Suite and three bathrooms in the house. Our Atomic Alcove offers the perfect blast from the past kind of stay with our Free play retro arcade, heated indoor pool, hot tub, and sauna. Tucked away in a quiet neighborhood and offers access to our downtown area and located near local restaurants. Perfect for a small weekend getaway.

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!

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.

The Hills

Come stay at The Hills where style meets comfort. We offer an open floor plan for family and friends to enjoy. Across the street you can find a walking path, tennis courts, and a playground. In the backyard guests can enjoy their own private pool. We ask that guests be respectful of our community being mindful of quiet hours between 10 PM and 6 AM.

Entire home in Rockford. Pool/Dart/HotTub/Gym

Make some memories at this unique and family-friendly place.