Vacation rentals with outdoor seating near Rupp Arena

4.97 out of 5 average rating, 139 reviews

A spacious outdoor area is illuminated with soft green lighting, featuring a round inflatable hot tub and a glass-top table surrounded by several chairs. A sunshade provides coverage while the wooden fence offers privacy, contributing to the inviting atmosphere.

Home in Georgetown

Hot Tub Hide-A-Way | Horse Park 11min/Ark 30min

Entire Luxury Home Hide-A-Way In Down Town Georgetown, KY. Featuring An Inflatable Hot Tub, Purple Mattress (Queen), Additional Pull Out Couch Bed, 65in 4K TV. *Please No Shoes* Security System/Cameras (Door Bell & Back Yard) 5 min Walk To Local Restaurants/Bars - Local Feed, Galvins etc 12 Min KY Horse Park 30 Min Ark Encounter 🚨 Ask about our 3 bedroom home “The Retro” directly behind this listing for traveling friends / family who would like to book close but stay in separate homes. 🚨

A contemporary home features a striking combination of metal and wood exterior. Large windows allow natural light to fill the entryway. A small, landscaped area with shrubs frames the stone pathway leading to the entrance, creating an appealing facade.

4.89 out of 5 average rating, 130 reviews

Mid-Century 3 BR In Heart of Downtown Lex

New contemporary home w/in walking distance to Rupp Arena, several breweries, coffee shops, restaurants & Transylvania University. Less than 2 miles to UK campus, 15 mins to Keeneland & the Ky Horse Park. We provide luxurious bedding, plentiful amenities, a chef's kitchen w/ stainless cookware, granite countertops & island. Stream your favorite channels using our hi-speed wifi on the 55" smart TV in the living room or the 43" smart TVs in each bedroom. (No cable.) Easy check-in w/ keyless entry.

4.93 out of 5 average rating, 149 reviews

A spacious living room is presented, featuring a gray sofa and two matching armchairs. A wooden coffee table is centered on a soft area rug. Natural light filters through a large window, complemented by decorative wall art and a floor lamp.

Guest suite in Lexington

The Fillys

This is our home and my Wife and I reside upstairs, The available space is our basement with a private entrance, large living room with YouTube TV, and comfortable seating for 7 people. Microwave & coffee machine with a mini fridge. Two bedrooms are available, each with a queen bed. A full bathroom and laundry. Back patio overlooking Cross Keys park with a pond and walking track. Downtown and Fayette mall are 10 minutes away, Keeneland race course and the airport are 5 minutes from the house.

4.99 out of 5 average rating, 120 reviews

A charming stone cottage with a gabled roof is set back from a winding driveway, surrounded by landscaped gardens. The entrance is flanked by trees and shrubs, creating a serene and inviting environment. A foggy atmosphere adds a touch of mystery to the scene.

Guesthouse in Lexington

West meets South in this Garden Cottage Retreat

STR PERMIT #15078463 A cozy backyard cottage nestled in historic Pensacola Park, part of the national register of historic places. Conveniently, located along Hwy 27 (Nicholasville Road). A stones throw from the University of Kentucky, Kroger Field, 3 hospitals (Baptist Health, UK, and Children's Hospital), and Lexington's celebrated state botanical garden: The Arboretum. This standalone cottage features one dedicated parking space, full amenities, garden views, and artistic embellishments.

A welcoming living area features a light gray sofa adorned with patterned cushions. A round pink coffee table is centrally placed, holding a tray of magazines. Natural light enters through large windows, illuminating the space, while a ceiling fan enhances airflow.

4.94 out of 5 average rating, 731 reviews

Adorable, Clean Lexington Cottage, Convenient to Everything

You'll love this bright, well-decorated home away from home! Located in an OPTIMAL location for all that Lexington and surrounding areas have to offer. Safe neighborhood. Xtra long driveway. Comfy beds. Fully fenced in backyard and large patio-NEW PHOTOS COMING SOON! *IF YOU HAVE MORE THAN 2 PETS, YOU MUST CONFIRM WITH ME BEFORE BOOKING. $40 P/PET FEE BEYOND 2. TOTAL # OF PETS ALLOWED DEPENDS ON TYPE/SIZE. YOU ARE RESPONSIBLE FOR ANY DAMAGE/STAINS TO BEDDING, FURNITURE, LANDSCAPING, ETC...

4.97 out of 5 average rating, 104 reviews

A spacious backyard is shown, featuring well-maintained green grass and tall trees providing shade. A hot tub and outdoor dining area are placed next to the house. A colorful playground is visible in the background, adding to the inviting atmosphere of the outdoor retreat.

Home in Georgetown

The Luxe/HotTub/Playground/12min KHP/30min Ark

Experience the perfect blend of old charm and contemporary. Nestled on a tranquil street, you'll find yourself just a short stroll away from boutique shops, delectable dining options, Georgetown College, and picturesque parks. Additionally, the Kentucky Horse Park and interstate access are conveniently minutes drive away. Outside, indulge in your very own private backyard retreat, complete with a soothing hot tub , stone grill for al fresco dining pleasure, and a playground for the kiddos.

4.98 out of 5 average rating, 474 reviews

A custom California King wooden bed is featured within an immersive room, surrounded by dark hues and dramatic lighting. Adjacent is a unique chair and a traditional rug, enhancing the room's historical charm and fantasy theme.

Apartment in Lexington

Game of Thrones - Downtown

Be the lord or lady of this palatial chamber, in the center of downtown‘s hottest spots. Your OMG stay comes w/royal features inspired by your favorite fantasy series. •Custom Calif. King wooden bed w/playroom features and a mini-dungeon (not just for containing dragons!) •Luxurious bathroom w/steam shower for two •Decor from Old World Europe: hand-crafted torch sconces, medieval-style weaponry and an iron throne •Custom Coffee Bar w/touch-screen access to your favorite cafe coffees

4.95 out of 5 average rating, 256 reviews

An inviting outdoor deck features two wooden lounge chairs and a sofa overlooking a serene creek. A textured rug adds comfort underfoot, while soft lighting from above enhances the peaceful atmosphere. The view of the water and surrounding greenery creates a relaxing environment.

Treehouse in Georgetown

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

Superhost

The kitchen features a spacious layout with modern appliances, including a refrigerator and stove. White cabinetry contrasts with natural wood paneling. A large window allows natural light to fill the room, enhancing the granite countertops and laminate flooring.

4.92 out of 5 average rating, 123 reviews

Mid-Century Modern

Mid-Century modern home with an open floor plan in a quiet neighborhood. Located near Versailles Road and Cardinal Hill Hospital. Close to Bluegrass Airport and Keeneland. 10 minutes from downtown. Small pet friendly (<25lb) with a large fenced in backyard. Three bedrooms, two full baths. Extra Trundle bed and desk in one of the bedrooms. Washer and dryer. Fully equipped kitchen with Keurig coffee / tea. Wifi. Large rear patio. Large screened-in porch. Carport and plenty of parking.

A cozy living area features a comfortable grey sectional sofa, two modern chairs, and a round wooden coffee table. The space includes a wall-mounted TV above a fireplace, with natural light streaming through the windows, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 187 reviews

Hot Tub | 7 Beds | Fire Pit | Patio & Grill

Totally remodeled, one and half story in the heart of Southland. The open floor plan includes new hardwood flooring, a totally equipped kitchen with new stainless steel appliances and granite countertops, all leading to a new deck off the eat in kitchen. The first floor offers two bedrooms with an updated bath and 2 linen closets. Upstairs you will find 2 very large bedrooms, with great closet space and tons of natural light, sharing a jack and jill bath with 48 inch vanities.

A spacious living room features modern furnishings with a blue sofa and a brown armchair, creating a cozy atmosphere. Natural light illuminates the room, highlighting the decorative fireplace and mounted TV above it. A kitchen and dining area are visible in the background.

4.98 out of 5 average rating, 102 reviews

Bluegrass Retreat with Hot Tub! Near Horse Park!

Unbeatable location for the best experiences in Central Kentucky! You will be close to the Kentucky Horse Park, historic Keeneland, downtown Midway, the Ark Encounter, Rupp Arena and downtown Lexington, UK sporting events, golf courses, and several highly desirable distilleries including our personal favorite - Buffalo Trace Distillery. There are so many great restaurants nearby! Be sure to check out our Guidebook when you book a stay at Bluegrass Retreat.