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Vacation rentals with a pool in Madison

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Madison

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A private swimming pool is covered and surrounded by a spacious patio area. Lush greenery and tall trees outline the backyard, creating a serene environment. A wooden pergola with climbing vines is visible, along with a small seating area featuring green picnic table seating.

Guest suite in Spring Green

4.91 out of 5 average rating, 167 reviews

Spring Green River Pines

Spend a few days in the beautiful countryside. A private entrance to the lower level of home (completely separate from our home) that includes a central room, 2 bedrooms with kitchenette, & 1 lg bath. WiFi >500 Mbps speed. Smart 60" TV, Bluetooth Airplay/stream compatible. Parking on sight. Great location 5 min from beautiful downtown Spring Green. Close to APT, Taliesin/Frank Lloyd Wrights Home/School, House on the Rock, WI River, Gov. Dodge State Park and 1/2 hr to Devils Lake State Park.

Top guest favorite

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.

Condo in Lake Geneva

4.98 out of 5 average rating, 232 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.

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.

Condo in Lake Geneva

4.88 out of 5 average rating, 115 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.

Condo in Wisconsin Dells

4.83 out of 5 average rating, 247 reviews

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown

INDOOR & OUTDOOR POOL ACCESS| DISCOUNTED ATTRACTION TIX | WATERFRONT The Riverwalk Retreat is the perfect spot to enjoy your next WI Dells trip with friends or family. This cozy vacation rental is located at the Sunset Cove Condo complex just 2 blocks off of Broadway & overlooks Crandalls Bay. Enjoy your morning coffee with a spectacular view of the WI River & the adjoining bay. This central location provides easy access to the area’s many athletics venues, nightlife, dining, & shopping.

Top guest favorite

The living area showcases a spacious layout with a leather pullout couch and armchair, complemented by a modern coffee table. A smart TV is mounted on one wall, while an electric fireplace adds warmth. The kitchen features a bar with three stools, enhancing the inviting atmosphere.

Condo in Wisconsin Dells

4.98 out of 5 average rating, 169 reviews

The Wanderlust at the Sunset Cove

Riverfront one bedroom condo in a tranquil area of Downtown Wisconsin Dells. Take a stroll near the beautiful River Walk and enjoy the magnificent scenery and unique attractions of Downtown Wisconsin Dells. Whether you need a few days to relax and decompress or if you are in town for business or games, our condo offers a fully equipped kitchen, a king size bed and a queen size pull out couch . There is an indoor community pool, hot tub and sauna. There is also a seasonal outdoor pool .

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.

Condo in Lake Geneva

4.96 out of 5 average rating, 158 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.

Top guest favorite

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.

Condo in Lake Geneva

4.98 out of 5 average rating, 162 reviews

Cozy Lake Geneva Condo | Amenities | WiFi

Discover Blue Lakes Escape, a newly-redecorated condo, steps away from Lake Como. Relax in the spacious great room with a smart TV, fireplace, desk area & access to quaint patio. Sit outside with a coffee, a good book, or a delicious BBQ. Enjoy free access to the shared amenities, including an outdoor pool, sports courts, & walking trails. Lake Como – 6 min walk Lodge Geneva National – 6 min walk Downtown – 8 min drive Book For Lasting Memories In Lake Geneva—See Details Below!

Top guest favorite

A family room showcases a comfortable seating area with a large sofa and armchair. A stone fireplace is positioned beneath a mounted television. Natural light is provided through the window that offers a view of the outside, while a wooden coffee table sits centrally.

Condo in Wisconsin Dells

4.97 out of 5 average rating, 125 reviews

The Dockview on Lake Delton - Pickleball & Pools

Upgrade to our Noah's Ark package after booking! NON-SMOKING The Dockview is located in a quiet neighborhood that is just blocks away from all the attractions on Wisconsin Dells Parkway. Situated on beautiful Lake Delton with a very large 2nd floor balcony, our guests will love relaxing and watching as life on the lake flows by. We have indoor and outdoor (open seasonally) pools and hot tubs, a beach that is exclusive to the neighborhood, and patios equipped with gas grills.

Condo in Wisconsin Dells

4.89 out of 5 average rating, 108 reviews

Lakefront Condo - Private Beach | Boat Slip| Pool

Experience lake life at our luxury, lakefront condo. Wake up to morning coffee on the balcony with breathtaking views of Lake Delton. Our spacious 2 bedroom, 2 bathroom condo features a beautiful master suite with a king bed, en suite bathroom complete with a jetted massage tub and walk in shower with 3 directional shower heads. It is the perfect escape for those who want to feel like they are a world away, but are also minutes from all the fun and excitement of the Dells.

Top guest favorite

A two-story house is set on a spacious lawn, framed by trees exhibiting autumn colors. The exterior features a welcoming porch with white railings. A paved driveway leads to a garage, and a privacy fence encloses the backyard, contributing to a tranquil environment.

Home in Spring Green

4.96 out of 5 average rating, 127 reviews

Hot Tub/$0 Cleaning Fee/Golf Course/The Hemlock

Our 4 bedroom, 2.5 bath home in downtown Spring Green, Home to Frank Lloyd Wright’s Taliesin, American Players Theater, the House on the Rock, and Tower Hill State Park, the vibrant village of Spring Green is a place where nature and art meet. Just 45 minutes from Madison, And the Dells Waterpark. Do You enjoy Golfing Or snow mobile Riding? Relax with the whole family at this peaceful place to stay. walk to downtown or the Rec Park with soft ball diamond and skate board Park.

A round swimming pool is situated within a spacious yard, surrounded by lush greenery and trees. The pool features a white safety cover and a set of steps leading down into the water. A wooden deck runs alongside the pool, enhancing the outdoor space.

Home in Madison

4.89 out of 5 average rating, 280 reviews

Luxurious BBQ and Pool House

Hosting a summer barbecue, a pool party, or just looking for a relaxing getaway with your friends? The unique combination of indoor and outdoor space provides something for everyone. This is a modern, spacious, and luxurious 3 bedroom, 2.5 bath home, conveniently located 15 minutes from downtown. Situated on a 3/4 acre lot, this house is fully equipped w/ premium amenities for your friends and family:Swimming pool, hot tub, big yard, deck with a gas grill and dining area

Top guest favorite

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.

Condo in Lake Geneva

4.98 out of 5 average rating, 173 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.

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Popular amenities for Madison rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Apple Canyon Lake

4.93 out of 5 average rating, 88 reviews

The Ho Hum East on Apple Canyon Lake

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

4.97 out of 5 average rating, 37 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

A spacious bedroom features a wooden bed frame with a large comforter in shades of blue. A flat-screen television is mounted on the wall above a faux fireplace. Natural light enters through a large window with dark blue curtains, complemented by a side table and a decorative plant.

Home in Wisconsin Dells

4.92 out of 5 average rating, 93 reviews

Family-Friendly Dells Stay | Sleeps 8 + Jacuzzi

Home in Wisconsin Dells

4.89 out of 5 average rating, 224 reviews

Spacious Pine Cabin at Island Pointe

A modern multi-level home is shown from the exterior, with a large deck extending from the second floor. A swimming pool is visible in the foreground, surrounded by a grassy area. The backdrop features a wooded landscape under a clear blue sky.

Home in Portage

5 out of 5 average rating, 11 reviews

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

4.94 out of 5 average rating, 33 reviews

Sunset retreat oasis Pool hot tub river fishngame

Top guest favorite

Home in Rockton

4.97 out of 5 average rating, 97 reviews

HD Jameson House at River’s Edge

Top guest favorite

Home in Elkhorn

5 out of 5 average rating, 9 reviews

Farmhouse with Heated Pool on almost 160 Acres!

Condo rentals with a pool

An outdoor pool area is surrounded by a forest of trees, featuring a curved shape with a spacious deck. Numerous lounge chairs are arranged nearby, and a shaded pavilion is visible in the background under a bright blue sky with scattered clouds.

Condo in Wisconsin Dells

4.97 out of 5 average rating, 29 reviews

Condo in Wisc Dells for 10-14 ppl

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.

Condo in Lake Geneva

5 out of 5 average rating, 14 reviews

Glass Vista: Modern 2BR Condo, Stunning Views

Top guest favorite

A circular swimming pool is surrounded by a spacious patio with numerous lounge chairs. Lush greenery and trees frame the area, while nearby, a gazebo offers shaded seating. The multi-story condominium buildings in the background complete the inviting outdoor environment.

Condo in Fontana-on-Geneva Lake

4.99 out of 5 average rating, 69 reviews

2 BD 2 BA Abbey Villa with Pool

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, 192 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

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.

Condo in Lake Geneva

5 out of 5 average rating, 10 reviews

Sailor’s Delight: lakefront condo w/fireplace

Top guest favorite

A scenic view of the outdoor pool area is displayed, with clear blue water surrounded by lush green trees. Guests are seen enjoying the pool, while the resort's lounging area is visible in the background, featuring wooden structures and sunlit spaces.

Condo in Wisconsin Dells

5 out of 5 average rating, 26 reviews

Spacious 3BR Condo Retreat

Condo in Wisconsin Dells

4.79 out of 5 average rating, 145 reviews

Beautiful Condo at Chula Vista!

A cozy living area is presented, featuring a light blue sofa adorned with various throw pillows. A matching armchair sits nearby, and a coffee table with decorative items occupies the center. Natural light enters through a glass door, highlighting the warmth of the space.

Condo in Geneva

4.95 out of 5 average rating, 20 reviews

Cozy 2 Bedroom Condo - Lake Geneva

Other vacation rentals with a pool

The outdoor water park features multiple waterslides and a spacious pool area. Sun loungers and umbrellas are arranged around the pool, alongside playful water attractions. The lodge-style buildings are visible in the background, enhancing the resort atmosphere under a blue sky with scattered clouds.

Condo in Baraboo

4.91 out of 5 average rating, 11 reviews

Wyndham Glacier Canyon |1BR/1BA King Suite w/ Balc

Apartment in Wisconsin Dells

4.93 out of 5 average rating, 14 reviews

Chula Vista Resort Condo

A serene backyard scene features a clear blue swimming pool surrounded by a spacious patio. Comfortable seating arrangements, including lounge chairs and a patio table with chairs, are positioned nearby. A red patio umbrella provides shade, and lush greenery frames the area, enhancing the outdoor setting.

Home in Fitchburg

4.88 out of 5 average rating, 16 reviews

Country Living/Downtown Access

Home in Edgerton

4.75 out of 5 average rating, 36 reviews

Boat Dock & Backyard: 'Rock River Retreat'

The cabin's entrance is framed by vibrant autumn leaves, with a wooden bench placed on the front porch. Its log exterior features inviting architectural details and large windows, allowing natural light to enhance the entrance.

Cabin in Apple Canyon Lake

4.89 out of 5 average rating, 55 reviews

Spacious 4BR Log Cabin Getaway | Hot Tub, King Bed

A spacious pool area is surrounded by a secure fence, featuring a covered pool with a soft green safety cover. A gray water slide is positioned nearby, and a small shed is visible at the back. Lush trees and greenery provide a natural backdrop.

Home in Poynette

4.81 out of 5 average rating, 47 reviews

Your Home Away From Home!

An outdoor balcony features a large table surrounded by six chairs, with a bright red umbrella providing shade. Green Adirondack chairs are positioned nearby, overlooking the grassy lawn that leads to the waterfront.

Home in Janesville

5 out of 5 average rating, 83 reviews

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

Condo in Wisconsin Dells

4.85 out of 5 average rating, 162 reviews

Mel’s Marina, on the River, walk downtown.

Quick stats about vacation rentals with a pool in Madison

Total rentals
60 properties
Nightly prices starting at
G$4,183 GYD before taxes and fees
Total number of reviews
880 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Destinations to explore