Vacation rentals with a pool in Rockford

4.88 out of 5 average rating, 58 reviews

The exterior of a charming Barndominium is showcased, featuring a neutral color palette with a metal roof. The building displays large windows and a large garage door. Flower planters line the entrance, and well-maintained grass surrounds the structure, enhancing the rural ambiance.

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

An aerial view of a spacious deck surrounds a circular heated pool. Multiple lounge chairs and a table with an umbrella are arranged on the deck, providing ample seating. Lush greenery and trees frame the background, creating a natural setting.

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.

A cozy living area is highlighted by a gas fireplace and a large Smart TV mounted on the wall. A sliding glass door leads to a balcony with views of the green courtyard. Comfortable seating is arranged around a rustic coffee table that complements the relaxed atmosphere.

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

A patio area features multiple seating options and a glass door leading into the condo. Lush greenery and colorful flowers border the concrete walkway, providing a serene outdoor setting. A second-level balcony is visible above, adding depth to the outdoor space.

4.98 out of 5 average rating, 226 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

A view from the outdoor deck shows a circular pool surrounded by well-maintained green grass and trees. Colorful flowers are planted in decorative boxes along the railing. Umbrellas and lounge chairs are positioned around the pool area, providing shaded seating options.

Condo in Fontana-on-Geneva Lake

4.84 out of 5 average rating, 101 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!

The image showcases a clear swimming pool surrounded by a concrete deck. A shallow area is indicated, with safety signage specifying '3 ft 0 in No Diving.' Poolside loungers and umbrellas provide shade, while pool steps offer easy access for swimmers.

4.87 out of 5 average rating, 111 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.

5 out of 5 average rating, 11 reviews

A private outdoor pool is centered within a spacious concrete patio, surrounded by greenery. A pink float is visible in the clear blue water. The house features a light gray exterior with large windows, offering inviting views of the outdoor area.

Home in Rockford

Andy's House *pool* *hot tub* *arcade* *theater*

A great story starts with great moments of fun, laughter, and family! So, we’re 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 (dibs on Andy’s Room), and to the out of this world arcade and lounge area with featured Toy Story pinball machine. You’ll have everything you need to relax and enjoy your time, except that nearby Pizza Planet. Pool opens 6/15

4.97 out of 5 average rating, 96 reviews

The exterior of the HD Jameson House is captured in natural light, showcasing its historic stone façade and elegant columns. Lush greenery surrounds the property, enhancing the inviting atmosphere. A well-maintained lawn and pathway lead to the entrance, highlighting the home's charm and spacious outdoor setting.

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.

An outdoor pool area is surrounded by well-maintained landscaping, featuring several lounge chairs and tables. A patio with umbrellas provides shaded seating options. The pool is enclosed by a fence, with a clear view of greenery in the background. An adjacent gazebo offers additional space for relaxation.

4.95 out of 5 average rating, 155 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

An open living area features hardwood floors and a white brick fireplace. Comfortable red leather sofas are arranged around a white coffee table. A dining area is visible, adjacent to the kitchen, with a wooden table and chairs. Natural light filters through large windows.

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.

A breathtaking view of the sunset over Lake Como is framed by large glass doors. The patio features comfortable seating, adorned with potted plants, while the tranquil lake and lush greenery create a serene backdrop.

4.98 out of 5 average rating, 168 reviews

Serene Lakefront condo with magnificent view, pool

Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.