Holiday rentals with a pool in Rockford

4.88 out of 5 average rating, 58 reviews

Farm stay in Clare

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.

5 out of 5 average rating, 21 reviews

Home in Oregon

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.

4.97 out of 5 average rating, 152 reviews

Cozy LG Retreat! King Bed! Fireplace! WiFi!

Your cozy & relaxing getaway begins in a newly redesigned condo with balcony (courtyard view), and is conveniently located between Lake Como and Lake Geneva in peaceful Interlaken Resort community! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, and more! The resort community is located by Lodge Geneva National (formerly The Ridge Hotel), which adds additional restaurants and available amenities at an additional charge. Walk to the

4.98 out of 5 average rating, 224 reviews

Lake Geneva Cloud 9

A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Ridge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

Superhost

Condo in Fontana-on-Geneva Lake

4.84 out of 5 average rating, 100 reviews

Best Pool View 2 BR 2 BA Abbey Villa D

Pool view sunlight Villa. It's great for a girls weekend, golfing trip or a family reunion. The condo next door is also available. Located adjacent to the Abbey Resort, Avani Spa & Big Foot Golf. Our 2-bedroom, 2-bath Villa features an open floor plan and has the comforts of resort living, including a pool. The second floor, walk-up unit has an outdoor dining area with seating for six and and a deck overlooking the pool and grounds. Essentials included. No parties. New pool coming summer 2026!

4.93 out of 5 average rating, 29 reviews

Home in Albany

Sunset retreat. Pool n hottub and tubing river.

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 glares 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.

4.87 out of 5 average rating, 110 reviews

Lake Geneva relaxation!

4 mi to Downtown Lake Geneva, WI. Rent kayaks on Lake Como. New pool and tennis courts, amazing wildlife. Snowboard, cross country ski, sled on hills during our amazing Wisconsin winters. Dine at The Ridge restaurant CRAFTED or just buy a bottle of wine from the guest store and watch the sunset. Quiet corner of the condominium complex. Completely furnished. Beautiful comfortable King size bed, kitchen, cook and eat in! Balcony overlooking peaceful grounds. Private entry, laundry in building.

4.97 out of 5 average rating, 96 reviews

Home in Rockton

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.

4.95 out of 5 average rating, 154 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

Enjoy your stay at our family's Serene Lake condo with outdoor pool. NEWLY UPDATED Stylish and comfortable with amenities for any family to feel at home. Part of Interlaken community and set on Lake Como, we are surrounded by peaceful woods and often seen wild life, yet a quick drive into down town Lake Geneva, William's Bay and Fontana. Enjoy golfing, dining, water sports and all the region has to offer, then cozy up and relax with a view. NO RV, BOAT or TRAILER parking is allowed.

Superhost

Condo in Fontana-on-Geneva Lake

4.79 out of 5 average rating, 187 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

Enjoy a fun romantic get away or time away to connect with family and friends in Fontana-on-Geneva. Condo is an open concept kitchen, dining, and family room with fireplace. Enjoy the outdoors while relaxing on the screened in porch attached to the great room. First floor Master Bedroom has a semi-private full bath. Downstairs has a large second bedroom and full bath. There is also an office area which has a large double bed and a common area with TV and 2 extra twin beds.

4.95 out of 5 average rating, 44 reviews

Home in Rockford

Father of the Bride Private Estate •Spa• Sleeps 25

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.