Holiday rentals with a pool in Rockford

A decorative wall sign displays the word 'WELCOME' prominently. Beneath it, a white vase filled with yellow flowers adds a touch of color, set against a soft green wall, creating a friendly and inviting ambiance.

4.93 out of 5 average rating, 163 reviews

Home away from Home

Our cozy and inviting home is designed for relaxation and fun, offering a wide range of amenities to make your stay unforgettable. Enjoy a refreshing dip in the in-ground heated pool, or relax in the Sunroom , cozy up by the fireplace in the fall/winter. Challenge your friends/family in the game room or with board games! Just a short walk from the downtown area with shops, restaurants, and attraction all while enjoying the peace and comfort of a relaxing retreat. Can’t wait to host you! V&T

4.97 out of 5 average rating, 106 reviews

Home in Janesville

*Family Retreat* *Indoor Pool* *Arcade*

The Pool House is the perfect family retreat for any group that wants quality time with quality amenities. Come enjoy everything our home has to offer and make all those wonderful memories with the ones you love. The indoor heated pool is perfect for that private party experience that can be followed up with the fully loaded arcade room. Enjoy the pinball machines and great classic arcade games then go off to the full size Golden Tee and Buck Hunter and see if you can get the new high score.

A spacious living area features a large sectional couch and a soft ottoman. A wooden table stands nearby, with a laptop resting on it. The kitchen area is visible, showcasing a bar with seating for four. Soft lighting enhances the neutral color palette.

4.88 out of 5 average rating, 122 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 Lodge Geneva National restaurant CRAFTED or just buy a bottle of wine from the guest store and watch the sunset. Quiet corner of condo complex. Completely furnished. Beautiful comfortable King bed, kitchen, cook and eat in! Balcony overlooking peaceful grounds. Private entry, laundry in building.

A manicured lawn gently slopes towards a serene body of water in the distance, framed by tall trees on either side. The landscape features lush greenery under a partly cloudy sky, creating an open and inviting outdoor space.

4.98 out of 5 average rating, 240 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.

A welcoming living area features a comfortable sectional sofa facing a gas fireplace and a 65" Smart TV mounted on the wall. Sliding glass doors provide access to the outdoor patio, allowing natural light to fill the space. A decorative wreath adorns the door.

4.93 out of 5 average rating, 122 reviews

Lake Geneva Retreat w/ Fireplace & WiFi

Your cozy getaway begins in a newly redesigned condo with patio (there are stairs to get to villa), conveniently located between Lake Como and Lake Geneva in Interlaken Resort! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, & more! The resort community is located by Lodge Geneva National, which adds additional restaurants and available amenities at an additional charge. Many local areas to explore & visit will await your arrival.

A spacious living area features light wood flooring and neutral-colored walls. A large window provides natural light and views of the outdoor space. Comfortable seating includes two armchairs and a sofa, with a coffee table centered on a patterned rug. A brick fireplace adds an element of warmth.

4.85 out of 5 average rating, 104 reviews

Best Pool View 2 BR 2 BA Abbey Villa D

Pool view sunlit 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. No Pets. New pool summer 2026!

An open living and dining area features a dark wooden dining table surrounded by black chairs. A light blue wall complements a cozy seating arrangement with armchairs and a sofa. Natural light enters through a large sliding door, with decorative elements and a chandelier enhancing the space.

4.9 out of 5 average rating, 208 reviews

Lakeview at CasaComo

Mi Casa Como es su Casa Como Escape the daily grind and plan your getaway to our newly remodeled condo on Lake Como in Lake Geneva. We’re located just 5 minutes outside downtown Lake Geneva, so very convenient for shopping & dining, but peacefully located on quiet Lake Como. We have an outdoor community pool and tennis courts and just a few steps for The Ridge Hotel. We have all that you could want or need within walking distance, so keep your car parked. Come to Casa Como, stay & enjoy!

A spacious living area features comfortable gray sectional sofas adorned with turquoise cushions. A light wooden coffee table is centered on a soft area rug. Soft lighting is provided by table lamps, and large sliding doors lead to an outdoor space with a view of greenery.

4.95 out of 5 average rating, 101 reviews

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

✔ 1000 Sq. Ft. Ground Level Condo ✔ Patio overlooking expansive lawn ✔ Resort-like community ✔ New community pool ✔ Tennis,v-ball Courts ✔K-cup & drip coffee, Big Screen TV, Cable, FAST wifi ✔Steps to the Ridge Hotel w/ restaurant, coffee/wine shop ✔ Direct lake access w/boat launch, kayak, SUP board rental ✔ 5 min drive to Shops and dining in DT Lake Geneva ✔ Fully equipped kitchen ✔ Close to summer fun: Lake, golf, zipline, hiking ✔Close to Winter fun: Ice Castle, skiing, snowshoeing

4.97 out of 5 average rating, 105 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.

The living area features a dark leather sofa adorned with blue throw pillows, accompanied by a light gray couch. A round woven pouf and an antique-style trunk serve as accent furniture. Large glass doors provide access to a balcony, with lake-themed decor on the wall.

4.96 out of 5 average rating, 171 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.

A cozy corner of the living room features a brick fireplace with a warm fire. A decorative candle holder stands beside a beautifully lit Christmas tree. A plush sofa, adorned with a patterned pillow, invites relaxation, while a simple table holds a remote and holiday decor.

4.78 out of 5 average rating, 197 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 cozy bedroom features a plush king-sized bed with a light-colored duvet and decorative cushions. Natural light enters through large windows adorned with soft curtains. A comfortable bench sits at the foot of the bed, alongside a dark wood dresser and a small television.

4.97 out of 5 average rating, 143 reviews

The Landis, elegant condo w/ king bed & fireplace!

Kick back and relax in this calm, elegant one bedroom Villa with a KING size bed. This vacation rental is in a quiet area of Lake Geneva, but just minutes from all the vibrancy of downtown Lake Geneva or Williams Bay. It is within walking distance to Mars Resort, The Getaway or The Lodge Geneva National. This is a perfect spot for couples looking for a relaxing getaway. Local laws require all guests names and address be provided prior to check in.

Popular amenities for Rockford rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.79 out of 5 average rating, 28 reviews

Lodge Home 4BR - 2.8 Miles from Town - Lake Views

A refreshing pool surrounded by a wooden deck is visible, complemented by several loungers for relaxation. Lush greenery frames the area, providing a serene backdrop. Colorful flowers in the foreground add a touch of vibrancy to the peaceful outdoor setting.

4.98 out of 5 average rating, 42 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

Two black Adirondack chairs and a small side table are positioned on a patio, overlooking a lush green landscape under a cloudy sky. The view encompasses rolling hills and tree foliage, providing a serene outdoor setting.

5 out of 5 average rating, 57 reviews

Newly Updated Modern Lake Condo

4.94 out of 5 average rating, 54 reviews

An aerial view showcases the spacious property surrounded by lush greenery and vibrant autumn foliage. The home features a large front yard with colorful trees and a winding driveway leading to the entrance. The nearby creek adds a serene element to the landscape.

Home in Rockford

Mulford Complex Private Estate • Spa & Pool

4.89 out of 5 average rating, 88 reviews

The charming Victorian home features a welcoming front porch adorned with hanging flower baskets and a large American flag. A brick pathway leads through manicured hedges and colorful flower beds, enhancing the inviting outdoor space surrounded by mature trees.

Home in Woodstock

Grand 1800s Victorian Gem: Updated/by Downtown

An expansive outdoor area features a refreshing in-ground pool adjacent to a wooden deck. A hot tub sits nearby, sheltered under a pergola. Lush trees form a green backdrop, creating a natural setting for relaxation and outdoor activities.

5 out of 5 average rating, 10 reviews

Private Inground Pool Hot Tub

5 out of 5 average rating, 85 reviews

Home in Whitewater

Forest getaway; Alpacas, fire pit, trail access!

4.67 out of 5 average rating, 3 reviews

Home in Crystal Lake

Crystal Lake 4BR | Insurance & Repair Stays

Apartment rentals with a pool

A private balcony offers stunning views of the tranquil lake at sunset, framed by lush greenery and a well-manicured lawn. The sky is painted with soft hues of orange and blue, reflecting on the calm water's surface.

5 out of 5 average rating, 14 reviews

Glass Vista: Modern 2BR Condo, Lake Views

The spacious living area is illuminated by natural light from large windows. A leather sofa is paired with an accent chair, while a round rug centers the space. A modern coffee table sits atop the rug, and a dining counter with two bar stools is positioned nearby.

5 out of 5 average rating, 56 reviews

Chic Condo in Lake Geneva.

A bright and open living space is visible, showcasing a seamless transition from the kitchen to the dining area. Light wood floors run through the area, while large glass doors provide views of the outside greenery. Soft furnishings add a touch of comfort to the inviting atmosphere.

4.99 out of 5 average rating, 69 reviews

2 BD 2 BA Abbey Villa with Pool

A cozy living area features a grey sectional sofa with patterned cushions and a comfortable armchair. A flat-screen television is mounted on a brick wall above a fireplace, complemented by nautical décor. Light enters through adjacent windows, enhancing the relaxed ambiance.

5 out of 5 average rating, 11 reviews

Sailor’s Delight: lakefront condo w/fireplace

4.92 out of 5 average rating, 50 reviews

A cozy living area is depicted, featuring a brick fireplace beneath a mounted television. Soft furnishings include a gray couch adorned with decorative pillows, positioned around a dark coffee table. Sheer curtains filter light from the nearby window, adding a touch of warmth to the space.

Apartment in Geneva

Quaint, quiet condo minutes from Lake Geneva

Enjoy onsite Waterpark in this family friendly 1BD

4.95 out of 5 average rating, 39 reviews

Sunset + Lake View Stylish Condo in Lake Geneva

A stylish open-plan living area features a cozy seating arrangement with plush chairs and a modern coffee table. The fireplace serves as a focal point, complemented by a large wall-mounted TV. A kitchen bar with blue stools adds a vibrant touch, promoting an inviting atmosphere.

4.89 out of 5 average rating, 37 reviews

Modern Lake Geneva Condo with Pool and Patio

Other holiday rentals with a pool

5 out of 5 average rating, 27 reviews

A charming porch is furnished with two rocking chairs, inviting relaxation. A well-maintained garden bed with green plants and flowers surrounds the entrance, while a spacious lawn connects to the driveway. The home's exterior features neutral siding and shutters, framed by mature trees in the background.

Home in Delavan

Relax by the Lake! Family friendly & dogs welcome

A spacious backyard features a private in-ground pool surrounded by a well-maintained lawn. A wooden deck with red umbrellas offers seating areas for relaxation. The home, highlighted by large windows, is framed by lush trees and greenery, enhancing the outdoor gathering space.

5 out of 5 average rating, 23 reviews

Lake Geneva Home w/ Pool near the Lake!

A comfortable living area features a beige sofa accented with blue decorative pillows. A wooden coffee table sits centrally, accompanied by a flat-screen TV mounted on the wall. The space opens into a modern kitchen visible in the background, creating a warm and inviting environment.

Townhouse in Fontana-on-Geneva Lake

5 out of 5 average rating, 3 reviews

Lake Geneva Yacht Club Sunsets

The exterior of the condo is displayed, featuring a well-maintained facade with a combination of dark wood and beige accents. A manicured lawn stretches in front, leading to a concrete pathway. Symmetrical windows and entryways characterize the building's design, adding to its inviting appearance.

Flat in Lake Geneva

4.62 out of 5 average rating, 13 reviews

Charming, Cozy Condo in Lake Geneva

A serene marina scene is captured at sunrise, with boats docked in calm waters. Sunlight reflects off the lake, creating a glimmering effect. Lush green grass borders the scene, complemented by trees in the distance, enhancing the tranquil atmosphere.

5 out of 5 average rating, 21 reviews

Abbey Harborfront Villa on Lake Geneva

4.98 out of 5 average rating, 48 reviews

The exterior of the home is shown, featuring a well-maintained lawn with lush green grass. A large tree provides shade in front of the house, which has a combination of stone and siding. A welcoming porch is visible, inviting guests to enjoy the outdoors.

Home in Oregon

Rock River Relaxation Home

A serene view of Lake Como at dusk, with calm water reflecting soft pastel hues of pink and purple in the sky. The distant shoreline is framed by trees, and small lights from boats can be seen twinkling along the lake.

4.64 out of 5 average rating, 288 reviews

Flexible rental In Lake Geneva Area

A serene lakeside scene features a wooden dock extending into the water, with several boats anchored nearby. Lush greenery and gentle waves can be seen in the background, creating a peaceful atmosphere. The clear sky hints at a warm day, inviting outdoor leisure activities.