Holiday rentals with a pool in Rockford

4.9 out of 5 average rating, 82 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, 34 reviews

An aerial view reveals a spacious riverfront property surrounded by lush greenery. A heated pool is seen adjacent to the house, complemented by a deck with lounge chairs. The Rock River flows peacefully nearby, adding to the natural landscape.

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.

4.98 out of 5 average rating, 103 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, 121 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 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!

4.97 out of 5 average rating, 102 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, 169 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.

The spacious living room features a large sectional sofa in neutral tones, focused around a gas fireplace. A flat-screen smart TV is mounted above the brick hearth. Sliding glass doors open to the outdoor patio, allowing natural light to fill the space.

4.98 out of 5 average rating, 180 reviews

Lake Geneva Getaway | King Bed • Fireplace • Pool

Relax & enjoy a quaint getaway at Blue Lakes Escape! This newly redecorated ground-level condo with patio is located in peaceful Interlaken Resort between Lake Como and Lake Geneva, making it the perfect spot for a romantic retreat, friends getaway, or small family vacation. Short peaceful walk to lake, pool, tennis courts, craft rentals, boat launch and lakeside dining! Minutes from downtown LG with boutique shops, restaurants, gorgeous walking paths & unique experiences. Enjoy!

Superhost

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.

4.94 out of 5 average rating, 51 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

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.

Popular amenities for Rockford rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 42 reviews

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.

Home in Lake Geneva

Cozy cabin getaway near Lake Como and Lake Geneva

5 out of 5 average rating, 57 reviews

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.

Home in Lake Geneva

Newly Updated Modern Lake Condo

Home in Fontana-on-Geneva Lake

The exterior of a two-story home is shown, featuring a wooden deck with steps leading to the entrance. Lush green grass and landscaped gardens surround the house, with smooth stones arranged along a small water feature, providing a natural setting.

5 out of 5 average rating, 13 reviews

Treetop Lakehouse at Abbey Springs

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

Superhost

Home in Loves Park

New place to stay

7mls Hard Rock Casino, 2mls RockCut State Park, pool

4.92 out of 5 average rating, 37 reviews

A charming two-story house with a front porch is surrounded by lush green grass and trees. The property includes an additional structure to the right, showcasing a well-maintained landscape that enhances the serene atmosphere of the setting.

Home in Albany

Sunset retreat oasis Pool hot tub river fishngame

4.95 out of 5 average rating, 97 reviews

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.

Home in Lake Geneva

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

Superhost

Home in Fontana

4.6 out of 5 average rating, 5 reviews

North Shore Hideaway |Abbey Springs|Fireplace|Deck

Apartment rentals with a pool

A spacious living area is characterized by light-colored leather sofas and a fireplace, providing a cozy atmosphere. A large television is mounted on the wall, and sliding glass doors lead to an outdoor space with seating visible beyond. The room features wooden flooring and brick walls.

4.88 out of 5 average rating, 26 reviews

Charming 1BR Condo with Patio, Near The Lake Genev

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, Stunning Views

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

A balcony features a small table surrounded by two chairs, offering a view of the lush greenery and trees beyond. The scene reflects a peaceful outdoor setting, with a road visible in the distance under a clear sky.

4.97 out of 5 average rating, 35 reviews

Elegant 4-Season Lake Geneva Condo w/ Fireplace!

4.96 out of 5 average rating, 24 reviews

Sunset + Lake View Stylish Condo in Lake Geneva

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.

4.75 out of 5 average rating, 53 reviews

Abbey Springs - Lake Geneva - 2 BR - Sleeps 6

Other holiday rentals with a pool

A spacious living room features comfortable seating arrangements, including a sleeper sofa and armchair. Natural light filters through large sliding doors, leading to a balcony. A cozy gas fireplace adds warmth to the space, complemented by a round coffee table and a flat-screen TV mounted on the wall.

4.94 out of 5 average rating, 209 reviews

Beautiful Villa with Amenities Galore

4.81 out of 5 average rating, 26 reviews

A light-filled living area features a soft gray couch accompanied by a small black coffee table. Large windows allow natural light to illuminate the space, with views of the outdoors visible through sliding glass doors. A piece of nautical wall art adds a subtle decorative touch.

Flat in Lake Geneva

Geneva's Edge, Newly remodeled lake front escape

A red pool house with a green metal roof is positioned behind a well-maintained grassy yard. Stone pavers lead towards a large deck, where various seating arrangements are visible. Lush trees provide natural shade, and a spacious pool can be seen in the background.

Place to stay in Davis Junction

country living

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

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.

4.97 out of 5 average rating, 197 reviews

Lakefront condo with magnificent view & fireplace

4.94 out of 5 average rating, 16 reviews

A spacious living area features a large sectional couch with decorative pillows, a wooden coffee table, and a woven rug. Two windows allow natural light to fill the room, with light curtains gently blowing in the breeze. A media console and dining table complete the inviting space.

Flat in Lake Geneva

Peaceful Geneva Matterhorn Villa

A living area features a dark sofa and two accent chairs, complemented by a wooden coffee table. A large window offers a view of the green outdoor space. Nautical-themed decor is visible, adding to the relaxed ambiance of the room.

4.08 out of 5 average rating, 12 reviews

Cute n Cozy Lake Geneva Interlaken Condo!

The living area features a light-colored sofa and armchairs arranged on a soft rug, complemented by a glass coffee table. A dining table with white chairs is positioned nearby, alongside large windows allowing natural light to fill the space. A ceiling fan provides ventilation.