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 favourite
Apartment in Downtown Nashville
4.94 out of 5 average rating, 111 reviews

Nashlife Retreat WLK toBROADWAY w/Gym& Heated Pool

Welcome to The Nashlife Retreat! A stylish 1BR Luxury SUITE centrally-located in downtown Nashville and walking distance to Broadway & all other local attractions. We are: 0.2 miles from Music City Center 0.4 miles from Bridgestone Arena 0.4 miles from Country Music HOF 0.7 miles from Broadway 1.3 miles from Nissan Stadium 6.8 miles from Nashville International Airport Pool, Grills, 24hr Gym! On-site PAID parking available in our secure gated garage for $35 per night upon request.

Top guest favourite
A brightly lit living space features large windows offering city views. Unique net-style light fixtures hang above a custom-built oversized sofa and a dining table. Artworks are displayed on the walls, and a cozy area rug adds warmth to the wooden floor.
Condo in Downtown Nashville
4.97 out of 5 average rating, 176 reviews

Artisan Retreat | Rooftop Pool + Views | Walkable

★ "Tastefully decorated, comfortable, clean, and offers balance and harmony." ➪ Breathtaking city views ➪ Resort-style rooftop saltwater pool* w/ fire pit + BBQ + dining ➪ Sky lounge w/ poker + pool table ➪ Walk Score 90 (Walk to cafes, dining, shopping) ➪ Custom-built oversized sofa bed ➪ Gym w/ yoga + cycling studio ➪ Secured parking → 1 car ($25 nightly) ➪ 520 Mbps wifi ➪ Private conference room available to reserve upon request 1 min → Music City Convention Center 5 mins → Broadway+Ryman

Top guest favourite
Two light-colored armchairs are positioned near large floor-to-ceiling windows, offering views of the city skyline. A round woven table sits between the chairs, accompanied by a decorative lamp and a small plant. Natural light fills the space, enhancing its modern design.
Condo in Downtown Nashville
4.98 out of 5 average rating, 268 reviews

Broadway Bliss-Penthouse-Walkable-Pool-Lux Lounges

★"I have stayed at numerous Airbnbs and Abby was the most responsive and friendliest host I’ve ever had!" ~Penthouse w/breathtaking city views ~Prime location in the heart of Downtown Nashville ~Perfect for special occasions or small groups (sleeps 4) ~Secure, reserved parking* ($25 nightly) ~Rooftop pool ~Lux workspaces+lounges ~Modern fitness center, yoga, & cycling studio ~Fully equipped/stocked kitchen 1 min→Music City Convention Center 5 mins→Broadway+Ryman 10 min→Nashville Airport/BNA ✈

Guest favourite
The charming exterior of a historic two-story home is presented, featuring white siding and a welcoming front porch. Lush greenery surrounds the property, and a landscaped yard offers defined hedges and manicured bushes. Large windows allow natural light to fill the interior, enhancing the inviting entry.
Home in East End
4.95 out of 5 average rating, 564 reviews

Historic Gem: 4 BR with POOL, walk to all hotspots

Welcome to your Nashville Oasis in the heart of Five Points. This beautifully renovated four-bedroom historical home is in the city's most walkable neighborhood, surrounded by world-renowned restaurants and bars. Enjoy a heated saltwater pool, a fire pit, grill out with friends, relax on the front porch as the world strolls by. You're just a 5-minute Uber to Broadway. This home offers modern amenities, a fun bunk room, and the perfect blend of city excitement and tranquil neighborhood living

Top guest favourite
A comfortable seating area is highlighted by a dark gray sofa adorned with pillows in various textures and colors. A vibrant mural featuring bold colors and patterns acts as the backdrop. A wooden coffee table holds a small vase of fresh flowers, adding a touch of warmth to the space.
Apartment in Downtown Nashville
4.99 out of 5 average rating, 144 reviews

KING, Rockn' Retreat, 4 Blocks 2 Broad, Cozy Stay!

<b>HELLO THERE, DARLIN'!</b> Welcome to SoBro Station, a vibrant urban retreat in the heart of Music City, just a short walk from iconic sites like Country Music Hall of Fame, the Ryman, Honky Tonk Hwy, Music City Center, Johnny Cash Museum, Nissan Stadium, & more! Sip a flavored coffee on the sunlit balcony, lounge in the plush King Bed, enjoy 5-Star amenities. After a night on the town, chill in a romantically-lit space overlooking Nashville's downtown lights. Kick off those boots & relax!

Guest favourite
A spacious living area features a large, dark sectional sofa adorned with bright cushions. Artwork is displayed on the walls, and a mirrored accent piece adds depth. A coffee table sits in the center, while sliding glass doors open to a balcony overlooking serene views.
Condo in Downtown Nashville
4.95 out of 5 average rating, 780 reviews

Relax on the River, Close to the Action, Downtown

Walk EVERYWHERE!!! Hip 1st Avenue with peaceful views of the Cumberland River in the heart of the city. Close to Broadway, Downtown, Nissan Stadium, Sounds Stadium, Historic Germantown, the Farmers Market and so much more! You’ll love my place because of the location, the coziness, and the views. My place is good for couples, solo adventurers, and business travelers. Check out my other condo below: Copy, paste & search the following title ⤵ The Rad Pad on 2nd Ave ✦ Downtown Nashville ✦ NEW!

Guest favourite
A private pool area is surrounded by lush greenery and features a shimmering blue pool. Sun loungers sit along the edge, while a shaded seating area with an umbrella provides a space to relax. A hammock is visible in the background, inviting comfort.
Barn in Hendersonville
4.86 out of 5 average rating, 255 reviews

Hendersonville Homestead

After spending several years living in the heart of Nashville, we bought this nearly 3 acre property as newlyweds and have dreams of turning it into a mini-farm some day. We love having the space and quiet and want to share it with you! This AirBNB is a small, one-bedroom apartment attached to our workshop behind our main house. Our guests can enjoy the quiet space including a full kitchen, dining area, living room, and patio area. The pool is open from May-October with a few rules/hours.

Top guest favourite
An open living area features a spacious sectional sofa adorned with decorative pillows. A wooden coffee table is centered on a herringbone floor, while a dining table is positioned nearby. The kitchen, equipped with modern appliances, is visible in the background, enhancing the inviting layout.
Home in Mt. Juliet
4.99 out of 5 average rating, 228 reviews

Carriage House On Lake sleeps8

Kick back, relax, and enjoy your lake vacation or get some quiet time if here on work, in our custom Carriage House on our very private property Built completely separate from the main house next door. The 3 acre property is situated in a private deep water cove on Old Hickory Lake and has a large Saltwater Pool 50'x20' with shallow end 1' for 1st 10' , gazebo, Hot tub & gym access! Fully equipped kitchen, 100% cotton sheets + mattress/pillow protectors. **Open to Elopements 👰‍♀️🤵💍***

Top guest favourite
A tranquil outdoor area features a swimming pool lined with lounge chairs and umbrellas. Nearby, a hot tub is set against a backdrop of greenery, creating a serene space for relaxation. The property includes two separate buildings with inviting architectural details.
Guest suite in Edgefield Historic District
4.98 out of 5 average rating, 338 reviews

Oasis in the East Just a Block From Five Points Area

DAVIDSON COUNTYSTRP#2018075308 Cozy up in the stone-lined hot tub or take an afternoon swim in the pool. Beautiful historic East Nashville neighborhood, 50+ eateries & bars within blocks. Walkable to Broadway, Nissan stadium, Bridgestone Arena, the riverfront and the Ryman. Come recreate Jessie and Deacon’s kiss from “Nashville”, Season 6, on the front porch where it was actually filmed. Feel free to reach out for any assistance, we hope you enjoy your stay !

Top guest favourite
A modern living space features a geometric accent wall with a large flat-screen TV. A comfortable chair and a round coffee table are positioned on a soft area rug. Large windows provide expansive views of the city, filled with natural light.
Apartment in Downtown Nashville
4.96 out of 5 average rating, 262 reviews

Private Downtown Penthouse with Rooftop Pool!

Unwind in this beautiful downtown Nashville penthouse suite! This complex is located walking distance from Broadway, the Bridgestone arena, and convention center. The complex offers amenities including a saltwater pool on an open rooftop deck, a lounge with panoramic views of the city, and a fully equipped gym! The unit is isolated on the top floor, so you can enjoy privacy to spend time with family and friends, or use our in unit workspace!

Top guest favourite
An inviting backyard space features a heated pool and hot tub, surrounded by sun loungers and a stone fire pit. A gas grill is positioned nearby, with a wooden fence providing privacy. The skyline is visible in the distance against a colorful sunset sky.
Home in Nashville
4.98 out of 5 average rating, 209 reviews

Skyline Stunner | Mins to Downtown, Pool & Hot Tub

Meet your new Nashville vibe. Dip in the year-round heated pool, soak in the hot tub, lounge by the fire pit, and catch skyline views from the rooftop that totally deliver. Just minutes from Broadway, this multi-level pad is your own private city oasis—made for good energy, great photos, and even better memories! Book your stay and discover why we’re one of Nashville’s top-rated Airbnbs—trust us, the hype is real! 🤠

Top guest favourite
A dining area is showcased with a wooden table surrounded by six soft, cream chairs. A striking piece of artwork featuring a face in soft hues of pink and red is prominently displayed on the textured wall. Natural light flows in from the floor-to-ceiling windows.
Apartment in Downtown Nashville
4.97 out of 5 average rating, 140 reviews

2 Blks to Bdwy | Corner Condo | Gym | Pool | King

We welcome y'all to our corner condo in the heart of downtown. Enjoy floor-to-ceiling windows, a private wraparound balcony and an open layout with room to spread out. Your comfort is our priority. We provide all the amenities you need to feel at home. ★ Check in: 3pm ★ Check out: 10am - NO EXCEPTIONS ★ Please read the full listing below for FAQs on parking, check-in/out, and the space.

Popular amenities for Madison rentals with a pool

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Quick stats about vacation rentals with a pool in Madison

  • Total vacation rentals

    Explore 500 vacation rentals in Madison

  • Nightly prices starting at

    Madison vacation rentals start at $69 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,820 verified reviews to help you choose

  • Family-friendly vacation rentals

    260 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    280 properties have a dedicated workspace

  • Wifi availability

    500 of Madison vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Madison rentals

  • 4.7 Average rating

    Madison stays receive an average rating of 4.7 out of 5 from guests

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