Holiday rentals with outdoor seating in Lexington

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Top-rated rentals with outdoor seating in Lexington

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

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Guest favourite

Home in Lexington

4.94 out of 5 average rating, 661 reviews

Adorable, Clean Lexington Cottage, Convenient to Everything

Browse the host's binder of hand-picked places to visit and dine; many menus are included. Cozy up with a good book from the host's large and diverse collection of books. Fully equipped kitchen that's great for cooking or entertaining. 4-legged visitors will appreciate the big, fenced-in yard. You'll love this bright, clean and airy Lexington cottage. Ten Reasons to stay here: 1. Bright and spacious despite it's small size. 2. So many personal touches that not only make this house feel homey, but also unique to Lexington. 3. I've tried to think of everything as far as making your stay as livable and care-free as possible. 4. Large kitchen with just about anything you’ll need for cooking meals or hosting dinner for a small group. 5. Great, large, fully fenced-in backyard (fire-pit coming soon!) 6. Comfy beds with nice linens and a shower with good water pressure 7. Good water pressure in kitchen and bathroom. 8. A binder with lots of hand-picked, local restaurant and activity suggestions. Menu's included! 9. TV with local channels and Netflix PLUS a blue ray player if you want to rent a Redbox movie to watch. 10. Probably the most convenient location in all of Lexington in that it's either close to where you need to be or it's easily accessible to where you need to be. You'll have the entire house, driveway, and yard all to yourself! **Driveway is located on the left side of house. Text me or message me any time of day or night if you need something or have questions. I'm happy to help and try to be quick to respond. Truly convenient to everything Lexington (and the surrounding area) has to offer! The University of Kentucky is less than 2 miles away and the area hospitals are all approximately one mile away. Rupp Arena/Downtown is a 5 min drive and Keeneland Race Track is less than 10 min away. Other Lexington attractions such as horse farm tours, the KY Horse park, and Bourbon Tours are all easily accessible from here. Safe, family-friendly street with large, fenced in backyard. Free parking in xtra long driveway (no garage or carport) ,close to bus stop. Biking distance to pretty much anywhere. Easy access to downtown...Plus there's always UBER! Great house and great neighbors. Feel free to bring your furry loved ones (potty trained and well-behaved only, please). I've had my dogs in the backyard many times and there is no escaping, so you can have a total peace of mind keeping your dog outside if you choose to do so. I'm fine with cats too as long as you can promise they won't scratch the furniture or pee on anything :) Southland drive is in walking distance. A few Southland notables include: Good- Foods Co-op grocery and cafe, Marrikas Bar (tons of beers on tap), Wenchell's (local food, sports bar), Southland Bowling Alley, Coffee Shop, Donut Days Bakery, Two Chicks & Company (gifts and accessories store), and a local farmers market on Sundays. University of Kentucky, The Arboretum, and downtown are all within a 3 mile radius (2.7 miles from downtown city center and approx. 1.3 miles from UK). Keeneland, KY Horse Park, Bourbon Tours, and Horse Farm tours are all within 15-30 min away regardless of time of day or traffic.

24 Apr – 1 May

$189 SGD per night

Guest favourite

Home in Lexington

4.96 out of 5 average rating, 322 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

16–23 Jan

$255 SGD per night

Guest favourite

Flat in Lexington

4.99 out of 5 average rating, 175 reviews

City Chic Loft - Downtown

Discover urban living at its finest in this impeccably clean and stylish boutique. Nestled in the vibrant heart of downtown Lexington, enjoy proximity to trendy cafes, bars, and restaurants. Relax on a plush California King bed and take advantage of the full kitchen and laundry. Whether for short or long stays, this sparkling-clean haven offers style and convenience. Immerse yourself in the city's vibrant energy while having a peaceful retreat. Don't miss out on this unforgettable urban escape!

30 Dec – 6 Jan

$169 SGD per night

Guest favourite

Cottage in Lexington

4.94 out of 5 average rating, 653 reviews

Little House Dwntwn - Close to Rupp & Restaurants

1 BR, 1 bath, restored house on quiet street in downtown. Patio (with umbrella), & front porch - each with table & chairs, Off-street parking, TV in Living Room and in Bedroom, Broadband Internet, Cntl A/C, Complete kitchen w/microwave, refrigerator - freezer, toaster oven, regular oven and stove, flatware, dishes and cooking utensils, dishwasher, and washer-dryer. 15 min. to Keeneland or Horse Park. 1.5 miles to UK. 1/2 mile to Rupp (10 minute walk.) Walk to many restaurants and attractions.

12–19 Aug

$122 SGD per night

Guest favourite

Farm stay in Versailles

4.91 out of 5 average rating, 394 reviews

Bluegrass Country Cottage

Enjoy a quaint, private, quiet & charming little place to call your own, on a small, working (seasonal) Thoroughbred horse farm. Green acreage, lovely scenes and sunsets. Located in horse country, between historic Winstar Farm and Lane's End Farm, just a short drive to small town USA, Versailles; historic Midway; and to the nearby City of Lexington, home of the Kentucky Wildcats, Horse Capital of the World, Bourbon Country & so much more. Pets allowed (2 max), well behaved, pet fee applies.

19–26 Jul

$220 SGD per night

Guest favourite

Farm stay in Nicholasville

4.93 out of 5 average rating, 240 reviews

Moonlit Meadows: A Tranquil Getaway for Travelers

Escape to the heart of Kentucky's countryside in our modern guest suite, set across a 17-acre landscape. Immerse yourself in the serenity of nature with views of a pond and beautiful rolling fields. Ideal for both business and leisure travelers as well as those visiting Asbury University. Our guest suite has continued to offer a tranquil haven where you can relax and rejuvenate! Enhance your experience by visiting the great grandson of the legendary Secretariat, stabled just 4 miles away.

17–24 Aug

$144 SGD per night

Guest favourite

Home in Versailles

4.93 out of 5 average rating, 121 reviews

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

14–21 Apr

$184 SGD per night

Guest favourite

Guest suite in Lexington

4.98 out of 5 average rating, 124 reviews

Close to Keeneland Charming Guest Suite

Great location in beautiful well established neighborhood. 5 mi to Keeneland & airport, 2 mi to downtown, Rupp Arena, Univ of Kentucky campus & football stadium. Centrally located within one mile of all major hospitals. Lexington is located along the Kentucky Bourbon Trail. Enjoy distillery, horse farm & historic home tours, unique and fine dining, craft breweries, sporting events, theater, concerts, boutique shopping. Nearby horse farms, rolling hills, hiking and boating/canoeing

14–21 May

$115 SGD per night

Guest favourite

Guest house in Winchester

4.98 out of 5 average rating, 175 reviews

Escape and unwind in the country

Relax and unwind in the country! Close to Lexington, Red River Gorge, Pilot Knob and Natural Bridge with easy access to the Mountain Parkway. We now have Wi-Fi!! Pets are welcome but we request that dogs are either crated or not left unattended. There is a $25 pet cleaning fee. Our guest house has a fully equipped kitchen, washer/dryer, queen size Sleep Number Bed, queen size sleeper sofa, and patio with gas grill. An air mattress is available by request.

30 Oct – 6 Nov

$107 SGD per night

Guest favourite

Flat in Lexington

4.89 out of 5 average rating, 158 reviews

Sunset Over Lex-Downtown w Deck at Rupp Arena

Spacious, light-filled apartment across from Rupp Arena, walkable to downtown and UK's campus. The bedroom features a king sized Sealy mattress and plush bedding. Enjoy a gorgeous bathroom, full kitchen, and huge second level deck overlooking Rupp. Located in a historic building but newly renovated, top to bottom. Equipped for remote work or relaxation with high speed internet and a Smart TV. Free parking for easy access to conventions, concerts, and games.

6–13 Dec

$160 SGD per night

Guest favourite

Cabin in Lawrenceburg

4.98 out of 5 average rating, 442 reviews

Bourbon Trail Cabin on the Farm

Recognized by AirBnB as the “2021 Top New AirBnB in the State of KY”!Overlooking rolling hay fields, and surrounded by wooded farm land, this cabin features barn wood walls, hardwood floors, handcrafted bourbon barrel sink, king bed, leather sleeper sofa, and custom built kitchenette. Located on a working cattle farm, see cows, goats, a donkey and horse, & our pet free-range pig! In the heart of the Bourbon Trail in the home of Wild Turkey and Four Roses.

20–27 Nov

$156 SGD per night

Guest favourite

Barn in Lexington

4.94 out of 5 average rating, 294 reviews

Stay with our horses and goats on a private farm

Lovely and private studio barn apartment in super safe neighborhood. Stay with our horse and goats on 12 private acres, minutes from downtown Lexington. Hiking trails around property, and just minutes to several state parks. Three miles to 75 and 64, and 15 minutes to downtown Lexington, the Kentucky Horse Park, UK campus, and 10 minutes to the Hamburg area of Lexington full of restaurants, sports bars, and movie theaters. 50 amp EV charging station

28 Jul – 4 Aug

$124 SGD per night