Vacation rentals with a pool in Winnebago County

Haven Estates_: Cozy Barn, Hot Spa & heated Pool

Enjoy a peaceful countryside retreat at this charming Barndominium set on 6.5 private acres, accommodating up to 8 guests This spacious getaway features an 18' x 36' private pool with a hot spa and a solar-heated pool room for year-round relaxation. The Great Room offers open-concept living with comfortable seating, recreation space, and four sleeper sofas. The cozy bedroom includes a king-size bed, while the fully equipped chef’s kitchen boasts an oversized island & a stove with an air fryer.

Skip & Reed's River Retreat

Wonderful riverfront home located just south of Castle Rock on the Rock River in Oregon, IL. Enjoy beautiful views of the river while enjoying the heated pool (open May 15th through Oct 10th). Enjoy fishing off the lower yard. Must love cats as there are friendly outdoor cats! The Oregon area has plenty to do including exploring the nearby state parks, climbing Castle Rock, visiting John Deere's home, antiquing, tubing and boating down the river & enjoying the quaint area shops & restaurants.

Fall Specials Family friendly & dogs welcome

Enjoy time with family & friends in this cozy home, just one block from beautiful Delavan Lake! Our home has 3 bedrooms, 2 full baths & multiple living spaces. The fully fenced backyard can't be beat! Patio with gas grill and fire pit, swingset for kids, & above ground pool (seasonal). Have a blast with ping pong, foosball & board games. Perfect location to fish and golf! An easy drive from Chicago, it's a great getaway for families! Come enjoy all that Delavan & Lake Geneva have to offer!

Spacious Delightful 2 Bedroom Home

Entering the front door you'll feel right at home. Full Bathroom with walk-in shower and amenities. Living Rm and separate Reading/Work Den with 60" HD Roku TV. Complete Fully Functional kitchen. An additional Twin or Queen size air bed, set up with bedding, is available by request to sleep a total of six. Conveniently close 2 min. from Beloit Hospital, Grocery Store, Drug/Convenience Stores, restaurants, bike/hiking paths along the scenic Rock River, Beloit College and Downtown activities.

Sunset retreat oasis Pool hot tub river fishngame

Take it easy at this unique and tranquil getaway. romantic dinners. tranquil evenings. pool and hot tub. big yard. Foosball . yard games. close to ice age trail and multiple parks dams and waterfalls. . neibors r cool. u should be too. available for tubing and kayaking thru snb or minihaha. sugar river raceway. New Gllarus brewery and Monroe shops. bonfires n cookouts. bands down the road on sat. parties available 4 rental of both houses. please enquire. extra or tenting available.

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

Family Home w/ Deck, Yard, Dock on Rock River

Leave your busy schedules behind for lazy river days at this vacation rental in Janesville. Located on Rock River, this 5-bedroom, 3.5-bath property invites you to indulge in an all-American vacation as you cook burgers on the balcony, play football in the backyard, and take the boat out from the public launch a half-mile away! With botanical gardens, historic districts, a charming downtown, and the world’s best weekly water-ski shows, Janesville is the hidden gem of Wisconsin!

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.

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.

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!