Holiday rentals with outdoor seating in Jefferson County

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Jefferson County

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Top guest favourite

Loft in Madison

4.92 out of 5 average rating, 92 reviews

Downtown Historic Maddox House - on Main Street

The Historic Maddox House is owned by the former president of the South Carolina Bed and Breakfast Association and a retired Air Force Fighter Pilot. Once you arrive and walk up a few steps standing on the wraparound front porch facing historic Madison Main Street your senses will be heightened knowing that this home was built during the Civil War in 1863. We hope you enjoy as much as we do, the original windows, the original trim and the original architecture. Welcome to this piece of history.

Top guest favourite

Flat in Madison

4.98 out of 5 average rating, 245 reviews

Rivers Edge-Historic Hunger House-Upstairs-Madison

A unique blend of historic character and contemporary comfort! Floor to ceiling windows, amazing staircase and hardwood flooring with modern kitchen & bathroom, this UPSTAIRS unit with private entrance will be your oasis. The balcony, w/view of the Ohio river, is perfect for early morning coffee or relaxing after a busy day of touring Madison. WELCOME to the River's Edge! Extended stay (week-mo) discounts 21%-49%. Rent one or both floors (See "River's Edge II-listing) SEND INQUIRY FOR PRICING

Guest favourite

Home in Madison

4.95 out of 5 average rating, 65 reviews

Your Madison Home Away from Home

While staying in this cozy home, you can enjoy a peaceful morning with a small view of the Ohio River then use the golf cart to explore the historic town. Take a leisurely stroll along the Ohio River waterfront, visit the local winery, or indulge in the local restaurants and cafes nearby. Whether you're visiting Madison for a weekend getaway or a business trip, our home offers the perfect blend of comfort, convenience, and local charm. Book your stay today and make unforgettable memories.

Top guest favourite

Townhouse in Madison

4.99 out of 5 average rating, 227 reviews

Cozy downtown home with patio. Walk to everything.

Your family will be close to everything in downtown Madison when you stay at this conveniently located, updated home built in 1880. First floor open concept floor plan includes living room equipped w/electric fireplace and an eat-in kitchen w/bar stool seating for 4. Upstairs offers two bedrooms and full bath w/shower and old old-fashioned soaker tub. Enjoy nice weather on the fenced back patio. Note: This property contains stairs and is not recommended for guests with mobility issues.

Guest favourite

Cottage in Madison

4.86 out of 5 average rating, 142 reviews

Cozy Cottage downtown *Pets*Trails*firepit*Clean

Sue’s Cottage is a quaint two bedroom cottage with a porch over looking the Heritage Trail of Madison. It is perfect for pets. It is a home to many species of birds and wildlife. Relax on the deck bird watching or stroll through the heritage trail & scenic railroad tracks surrounding the cottage, which leads to the river walk. We are walking distance to all historic Madison offers. We are less than a mile from Clifty Park. A portion of each stay is donated to local charity.

Top guest favourite

Home in Madison

4.98 out of 5 average rating, 143 reviews

Riverview Historical Retreat

Full time Airbnb home in Historic Downtown Madison. This two bed, two bath home overlooks the Ohio River and includes a fully stocked kitchen, washer/dryer, screened in back porch, internet, keyless entry, and more Centrally located next to Bicentennial Park, enjoy one of the many restaurants, bars, parks, and local events, or enjoy a quiet weekend away with a weekly Music/Movie by the river, a local farmers market, and shops. There is something for everyone to enjoy in Madison

Top guest favourite

Cabin in Madison

5 out of 5 average rating, 38 reviews

Cedar Rustic Cabin at Lost Trails

Tucked into 45 acres of wooded forest this cabin is just minutes to Madison's Historic Downtown district. Walking trails, ponds, and daily wildlife sightings make this stay a peaceful and serene getaway from the hurriedness of daily living. Offering a full kitchen with washer and dryer and family room with double recliner, this one-bedroom cabin is perfect for two people. The wraparound deck provides comfortable seating to relax and enjoy beautiful views to both water features.

Top guest favourite

Flat in Madison

4.98 out of 5 average rating, 123 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful hills of Kentucky. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

Superhost

Cottage in Madison

4.9 out of 5 average rating, 182 reviews

Cozy Farmhouse Retreat in Historic District

Located in the Historic District in Madison! Lisa and Richard co-own and co-host this recently updated cottage. Welcome to our cozy, chic Farmhouse Retreat. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings for which Madison is famous. Only three blocks from the mighty Ohio and a short five-minute drive to Clifty Falls State Park. We fell in love with Madison and know you will, too.

Top guest favourite

Townhouse in Madison

4.98 out of 5 average rating, 110 reviews

209 King Beds, River View, Deck, Parking

Stay at General’s Quarters (209) — a stylish 3-level home in historic downtown Madison! Just steps from the Ohio River, Bicentennial Park, shops, bars, and restaurants. Sleeps 10 with 4 bedrooms & 3.5 baths. Enjoy modern comforts, fast Wi-Fi, a full kitchen, reserved parking and walkable access to festivals and local charm. Perfect for families or group getaways!

Top guest favourite

Cabin in Madison

4.99 out of 5 average rating, 183 reviews

Stoney Creek Cabin - Sit back and unwind

Welcome to Stoney Creek Cabin. This charming 2 bedroom cabin is nestled in the hills of Madison, IN. Situated far enough away to offer all the privacy you want, yet only 8 miles from historic downtown, where there are so many gems nearby to explore. Enjoy the HOT TUB, wrap around porch, and patio! There could not be a more relaxing place to unwind.

Top guest favourite

Home in Madison

5 out of 5 average rating, 180 reviews

Charming shotgun in the heart of downtown Madison

This charming, stylish 2-bedroom shotgun house is located on Main Street in historic downtown Madison, IN. You'll be just steps away from locally owned shops, bars, and restaurants, and within walking distance of the Ohio River and Madison's many festivals and events. Enjoy off-street parking, modern amenities, and the perfect front-porch view.