Holiday accommodation with outdoor seating in Saint Matthews

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Saint Matthews

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite

Townhouse in Louisville

4.95 out of 5 average rating, 232 reviews

Louisville Charm: Walk to it All! Central & Quaint

Welcome to the charm and character of Louisville! WALKING DISTANCE to everything you can enjoy. You will be right off the main strip of Frankfort Ave near Nulu. Less than a 5min walk to local breweries, coffee shops, restaurants, bars +more! Your experience includes: -queen suite -clawfoot tub shower combo -rollaway twin bed -stocked kitchen w/blender & toaster -AT&T fiber wifi -wine fridge -smart tv -desk workstation -Levoit air purifier -coffee & tea -happy live plants -inviting neighborhood

Guest favourite

Home in New Albany

5 out of 5 average rating, 322 reviews

Welcome to the Bough House!

Listed on the National Registry of Historic Places, this beautifully renovated home offers vintage charm with modern amenities. Located just across the Ohio River from Louisville, only 6.6 miles from the Kentucky International Convention Center, 7 miles from the KFC YUM! Center, 12 miles from Churchill Downs, and one mile from shops and restaurants in historic downtown New Albany, IN, the Bough House is close to everything the Louisville region offers, with the peace of a quiet historic street.

Guest favourite

Rental unit in Louisville

4.98 out of 5 average rating, 263 reviews

Spacious & Artsy Highlands 3 Bedroom for Up to 6

There is more room than meets the eye in this surprisingly spacious and uniquely designed space! The lower level of our house (technically the basement) is designed to be an apartment, offering 1400 sq. ft. of relaxing and spacious fun. This is a great space and value for up to six people. The space is closed off from the rest of the house with total privacy. We’re located in a quiet neighborhood in the Highlands and conveniently located to a diverse set of restaurants, highways and grocery.

Guest favourite

Cabin in Louisville

5 out of 5 average rating, 109 reviews

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Guest favourite

Guest suite in Louisville

4.96 out of 5 average rating, 135 reviews

Derby City Hideaway

Whiskey Hollow offers you a unique stay with our Bourbon-themed space. Your stay in Kentucky is sure to be memorable and cozy. Our newly renovated space offers a full kitchen, cozy living area, bedroom and full bath with a private patio. Local attractions include Churchill Downs, home of the Kentucky Derby, Kentucky Derby Museum. Louisville Slugger Museum, Kentucky Bourbon Trail, local city eats, 4th Street Live, horse farms, hiking, waterfalls, parks, shopping, local arts, and much more!

Guest favourite

Home in Louisville

4.89 out of 5 average rating, 198 reviews

Quiet Neighborhood Home With Outstanding Location

Situated on a quiet hilltop neighborhood in Clifton Heights, this is the perfect location for a professional or personal visit to Louisville and very animal friendly. It is within 10 minutes of Downtown, Waterfront Park, Nulu, Frankfort Avenue, the Highlands, the Convention Center, and just 15 minutes from historic Churchill Downs. These neighborhoods feature the best dining and entertainment in the city. Just a block away is the Mellwood Arts Center complex with shops and dining.

Guest favourite

Home in Louisville

4.85 out of 5 average rating, 176 reviews

Private EAST END gem, minutes from everything!

Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

Guest favourite

Home in Louisville

4.9 out of 5 average rating, 104 reviews

Highlands House- Just off Bardstown Road!

*Please read all house rules before booking.* This home is located in the Highlands, only one block from Bardstown Road, where many of Louisville’s best restaurants, bars and breweries are located. This freshly updated house is in a quiet neighborhood, but close to the action on Bardstown Rd. You will have the whole house to yourself, no worrying about sharing spaces. Blazing fast wifi available. This is the perfect home for Derby and is only 4 miles from Churchill Downs.

Guest favourite

Guesthouse in Louisville

4.91 out of 5 average rating, 473 reviews

Cute Carriage House off Frankfort Avenue

Welcome to "The Cute Carriage House at Frankfort Avenue". Experience serenity in a genuine "tiny house” that comfortably accommodates two people. There are several sleeping options that I will mention below. We are located a short block from premier restaurants and shops on Frankfort Avenue in the classy Clifton Neighborhood...and close to Cherokee Park and the cool Bardstown Road. FYI https://www.leoweekly.com/2020/10/the-winners-of-the-2020-readers-choice-awards/

Guest favourite

Guesthouse in Louisville

4.97 out of 5 average rating, 119 reviews

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

Guest favourite

Rental unit in Crescent Hill

4.99 out of 5 average rating, 134 reviews

Urban Bourbon Farm Loft

Very unique second story 575sqft. duplex apartment with lots of amenities! A 15-20 minutes walk to reservoir park, swim club ($5.00), Blue Dog bakery, restaurants, coffee shops, salons, art galleries, a bookstore, and unique shops! The apartment is a 7 minute walk to the Southern Baptist Theological Seminary, which is a beautiful space to walk and enjoy. This is a second story apartment that is accessible through the backyard privacy fence gate.

Guest favourite

Guest suite in Louisville

4.99 out of 5 average rating, 165 reviews

Olive Branch Suite in East Louisville Neighborhood

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location.