We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals with outdoor seating in Jessamine County

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Jessamine County

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

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Home in Lexington

4.84 out of 5 average rating, 219 reviews

Garden Suite at Castleton

Lounge in style on the oversized sofa for movie-night with a huge 70” TV with Dolby Atmos surround sound. Play Chef de Cuisine in the fully equipped kitchen with bar and table dining spaces available. Retreat to the master bedroom where you’ll find a king-size Tempur-Pedic bed, two sets of French door closets with ample clothes space, and a motorized standing desk to optimize your work/study/reflection time. Active lifestyles can also take advantage of the light dumb-bells and modern water-rower provided, while a full sized washer and dryer are located in the dedicated wash room.

Sep 28 – Oct 5

ﺩ.ﺇ365 per night

Cottage in Wilmore

4.98 out of 5 average rating, 164 reviews

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

Sep 26 – Oct 3

ﺩ.ﺇ463 per night

Townhouse in Lexington

4.81 out of 5 average rating, 232 reviews

Spacious Lexington Townhouse

ALL NEW TEMPUR-PEDIC MATTRESSES (September 2023) This spacious townhome is located in a quiet residential neighborhood minutes away from downtown, Commonwealth Stadium, Rupp Arena and the University of Kentucky. You will be centrally located so as to be a short drive from Lexington's best shopping and dining in the Fayette Mall or Hamburg Pavilion. This townhome is situated on a cul-de-sac to maximize quiet and privacy while still in the heart of Lexington. It is attached to Mount Tabor Park.

Aug 23 – 30

ﺩ.ﺇ455 per night

Guesthouse in Nicholasville

4.98 out of 5 average rating, 298 reviews

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Aug 16 – 23

ﺩ.ﺇ348 per night

Farm stay in Nicholasville

4.93 out of 5 average rating, 240 reviews

Moonlit Meadows: A Kentucky 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.

Feb 3 – 10

ﺩ.ﺇ380 per night

Farm stay in Lancaster

5.0 out of 5 average rating, 143 reviews

Serene barn loft in the heart of the Bluegrass

Relax and unwind in this charming barn loft nestled amidst 13 rolling acres on Honey & Vine Farm. This loft is the ideal honeymoon and anniversary space! Enjoy coffee in the morning from Adirondack chairs overlooking the pond, spectacular sunsets from the deck, and absolute serenity in this peaceful setting. Queen bed, private entrance, and beautiful sunsets. The goats and two horses love meeting new friends! 20 minutes to Danville and near hiking, lake Herrington, and Shaker Village.

Mar 20 – 27

ﺩ.ﺇ756 per night

Apartment in Lexington

4.99 out of 5 average rating, 201 reviews

Lexington Apt. with parking & private entrance

Lower level apartment with parking and two entrances. Light painted walls, ceiling lighting/fan, plus free washer and dryer. Approximately 10-15 minutes from Bluegrass Airport, 15-20 minutes to the University of Kentucky campus, stadium and 20-25 to Rupp Arena, 10-15 minutes from main entrance to Keeneland Race Track Main entrance, 20-25 minutes to downtown Lexington, 10-15 minutes to shopping mall/restaurants located in mall area, 50 minutes from the ARK ENCOUNTER AND CREATION MUSEUM.

Apr 2 – 9

ﺩ.ﺇ278 per night

Home in Lexington

4.88 out of 5 average rating, 117 reviews

Perfect for Traveling Professionals & Vacation!

Traveling professionals, relocation guests, vacation guests, this is the perfect house for you! This 3 bedroom 2 bath ranch-style home w/ a garage has a gourmet kitchen and an open floor plan. Perfectly located in the heart of Lexington in a family-friendly neighborhood near Trader Joes, hospitals, restaurants, the Summit Shopping Center, Fayette Mall and a short trip to Keeneland or downtown Lexington. This is the perfect home away from home. All are welcome! Pet Friendly, per request!

Mar 19 – 26

ﺩ.ﺇ554 per night

Home in Lexington

4.91 out of 5 average rating, 566 reviews

Lower Level of Home near UK, Eateries, 1000 sq ft

Large private sunny apt w/ lovely deck in a safe, quiet neighborhood 5 mins from LEX airport. 15 minutes from UK. Walking trail in neighborhood. 2Q beds in separate rooms, full private bath, pool table, microwave, coffee maker, frig, large flat screen TV with Roku, Netflix. Deck with view of beautiful yard with mature trees, swing, chiminea, bridge and path through garden. Welcome from Chris! NOTE! As ALWAYS, ALL bed linens & bath towels washed, bleached & sanitized after every guest!

Dec 2 – 9

ﺩ.ﺇ262 per night

Home in Nicholasville

4.92 out of 5 average rating, 213 reviews

Cali King beds w/ Koi pond Oasis. 15 min from LEX

Nicholasville's finest short term rental! We recently finished remodeling this spacious ranch home in Nicholasville Ky and are extremely excited to share it with future guests. It looks brand new on the inside and has an awesome oasis in the backyard with water effects/ koi pond. It is close to all the great things to do in Lexington including Keeneland and the University of Kentucky. Mattresses are top of the line and will ensure you have a very comfortable stay.

Oct 1 – 8

ﺩ.ﺇ510 per night

Guesthouse in Wilmore

4.95 out of 5 average rating, 133 reviews

Coach House at the 1898 Red Bud B & B

Lovingly renovated coach house unit was originally the workshop attached to the back of the coach house. It is a ground floor accommodation with private entrance located behind the main bed & breakfast. We are only two city blocks from Asbury! We make a perfect base to explore the area. The Bourbon Trial, numerous horse farm tours, vineyards, Keeneland, the Horse Park, and historic sites such as Shaker Village of Pleasant Hill. Only 11 miles from Lexington.

Aug 12 – 19

ﺩ.ﺇ358 per night

Guest suite in Lexington

5.0 out of 5 average rating, 116 reviews

The Gainesway Suite-Near UK/Hospitals/Keeneland

A posh Guest Suite in popular Gainesway! Centrally located in a friendly, established neighborhood. Minutes to Lexington's best Concert Venues, Restaurants, UK, Rupp, Hospitals, and Shopping! Private entrance, luxurious and stylish furnishings, plus your own laundry room! Perfect for a night in town, traveling for a ballgame or show, visiting our famous distilleries and Keeneland! The suite is also equipped for longer stays, business travelers, you name it!

May 23 – 30

ﺩ.ﺇ368 per night

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Jessamine County outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Home in Lexington

5.0 out of 5 average rating, 166 reviews

Super Clean 3BR getaway - *King Bed* and Snacks!

Jul 16 – 23

ﺩ.ﺇ529 per night

Home in Lexington

4.91 out of 5 average rating, 116 reviews

Light Filled Guest Suite STR #15063219-1

ﺩ.ﺇ358 per night

Home in Lexington

4.93 out of 5 average rating, 171 reviews

By The Summit, 10 Min to Airport/Keeneland

Nov 18 – 25

ﺩ.ﺇ838 per night

Home in Lexington

4.93 out of 5 average rating, 28 reviews

Hartland Bungalow/Newly renovated! 2 King beds

Dec 12 – 19

ﺩ.ﺇ517 per night

Home in Lexington

4.97 out of 5 average rating, 36 reviews

Cozy 2-bedroom Home Designed for Travelers Alike

Jul 19 – 26

ﺩ.ﺇ368 per night

Home in Wilmore

5.0 out of 5 average rating, 29 reviews

*KY Charm*Asbury/Lex-King bed-foosball-piano-games

Apr 5 – 12

ﺩ.ﺇ478 per night

Home in Lexington

5.0 out of 5 average rating, 65 reviews

Newly renovated upscale house with high ceilings

Jul 31 – Aug 7

ﺩ.ﺇ583 per night

Home in Wilmore

5.0 out of 5 average rating, 36 reviews

Milk & Honey Farm Cottage House

Nov 27 – Dec 4

ﺩ.ﺇ850 per night

Apartment rentals with outdoor seating

Apartment in Lexington

4.97 out of 5 average rating, 169 reviews

Studio Apartment on Urban Farm

Jun 19 – 26

ﺩ.ﺇ221 per night

Apartment in Winchester

4.92 out of 5 average rating, 100 reviews

The River House Floor 2 Getaway, w/a river view.

Jul 15 – 22

ﺩ.ﺇ330 per night

Apartment in Lexington

4.98 out of 5 average rating, 167 reviews

"Uptown Retreat" - Cozy Fireplace & Sauna

May 25 – Jun 1

ﺩ.ﺇ394 per night

Apartment in Richmond

4.96 out of 5 average rating, 294 reviews

East Unit Apartment in Historic Tenant House on Main Street

Jul 1 – 8

ﺩ.ﺇ430 per night

Apartment in Lexington

4.95 out of 5 average rating, 146 reviews

Distillery 1 Block Away! Downtown with Deck

Apr 2 – 9

ﺩ.ﺇ426 per night

Apartment in Lexington

4.98 out of 5 average rating, 397 reviews

Game of Thrones - Downtown

Dec 1 – 8

ﺩ.ﺇ570 per night

Apartment in Richmond

4.83 out of 5 average rating, 235 reviews

Spacious Downstairs Apartment

Jul 12 – 19

ﺩ.ﺇ297 per night

Apartment in Georgetown

4.83 out of 5 average rating, 116 reviews

Man O'War @ The House on Main | KHP 11m | Ark 30m

Jul 2 – 9

ﺩ.ﺇ598 per night

Condo rentals with outdoor seating

Condo in Lexington

4.94 out of 5 average rating, 201 reviews

Top Shelf the only Airbnb in KY above a Distillery

Jan 15 – 22

ﺩ.ﺇ1,392 per night

Condo in Frankfort

4.97 out of 5 average rating, 120 reviews

Bourbon Trail R&R

Jul 15 – 22

ﺩ.ﺇ511 per night

Condo in Lexington

4.95 out of 5 average rating, 77 reviews

Mid-Century Mod Vibes in Lexington

Nov 21 – 28

ﺩ.ﺇ533 per night

Condo in Lexington

4.88 out of 5 average rating, 52 reviews

The Weekender

Jun 7 – 14

ﺩ.ﺇ275 per night

Condo in Lexington

4.97 out of 5 average rating, 32 reviews

Federico's Historic Studio - Downtown

Aug 10 – 17

ﺩ.ﺇ409 per night

Condo in Lexington

4.93 out of 5 average rating, 88 reviews

Downtown Gallery House (Pet Friendly-Walk to Rupp)

Aug 16 – 23

ﺩ.ﺇ475 per night

Condo in Lexington

4.96 out of 5 average rating, 27 reviews

Historic Downtown Condo

Apr 7 – 14

ﺩ.ﺇ390 per night

Condo in Richmond

5.0 out of 5 average rating, 3 reviews

Robin’s Nest: Walk EKU/Downtown

Jan 31 – Feb 7

ﺩ.ﺇ541 per night

Destinations to explore