
Holiday rentals with a pool in Jefferson County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Jefferson County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Cherokee Park Oasis with Pool and Hot Tub
1 bdrm basement apartment with private entrance, bedroom, bathroom, and common area located adjacent to Cherokee Park. 3/4 mile walk to shops, restaurants, and entertainment on Bardstown Rd. Heated saltwater swimming pool (seasonal) and cabana with wet bar. Hot tub. Centrally located within 10 minutes from downtown, Churchill Downs, the Zoo, the airport, golf courses, and Kentucky Kingdom. Situated in a quiet, park-like neighborhood with ample parking. Owner occupies the main floor upstairs.

Explore Jeffersonville & Louisville/Book for Derby
The hot tub is available year round. Perfect for relaxing and de-stressing during your stay. The pool is open May 1 ~ Oct 1. You can stay in and binge watch movies from our collection of DVD's or your Apple TV app favorites on the 110 inch screen in the theater room. Please browse through our photos & read the descriptions under them. You’ll love our home because we are close to downtown Louisville & Jeffersonville but tucked away enough for a peaceful, relaxing stay. No early check ins allowed.

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail
Welcome to the "Bourbon Barrel Retreat" where this truly unique property offers a one-of-a-kind getaway. This newly renovated 5-bed, 3 full bath ranch boasts two additional buildings on the property to provide a Kentucky experience like no other. Immerse yourself in the ambiance of the Bourbon Speakeasy or spend time at the Pickleball Sports Lounge. Unwind and relax however you would like! An ideal location where you are a short drive to Bardstown, Louisville, Lexington, Mammoth Cave and more!

Exclusive Farmhouse w/ a Romantic Garden View!
Discover rustic charm at this serene Prospect, KY retreat, nestled on a historic estate garden by the Smithsonian. Surrounded by retired thoroughbreds and saddlebreds, this unique stay offers a peaceful farm setting just 25 minutes from downtown Louisville. Perfect for weddings, family vacations, or romantic escapes, the home features a fully equipped kitchen, outdoor space, free parking, and self check-in. Unplug, recharge, and enjoy Kentucky’s natural beauty in a truly memorable setting.

Peppermint Cottage Norton Commons w Breakfast
Step into Peppermint Cottage ( breakfast included) and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, 3 pools and YMCA. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and summer Friday food trucks with live music . Your Louisville adventure awaits !

4th Street Suites - Beautiful King Bed Suite
Wake up to the best of Louisville! Imagine starting your morning in a cozy king bed, strolling to 4th Street Live for brunch, and exploring nearby restaurants, bars, and theatres. Spend the afternoon lounging by the pool or soaking in the hot tub, then watch the city lights twinkle from the 7th‑floor terrace. This stylish suite is your launchpad for urban adventure—and a quiet, relaxing escape when it’s time to rest. Come make it yours and experience the heart of the city!

Sleeps 16, Heated Pool , Hot tub, Close to Dwtn
5000 square foot house set on a beautiful lot backed to a nature reserve park. Total of six bedrooms, three and half bathrooms. 5 large bedrooms with 5 queen beds each, 3 singles on the second floor and a mother-in-law suite with a king size bed and a single bed on the first floor. pool and hot tub. Pool is open from May 15 to October 15 and will be heated from Sep 15 to Oct. 15. Inflatable Water Slide is upon request. Gas grill on the deck and propane tank is available.

Hot Tub | 5BR/5BA | King Beds | Expo
• Spacious 5BR, 5BA home—great for groups • 1st floor: king bedroom + full bath in hallway • 2nd floor: two king en-suites + queen w/ hall bath • Walkout basement: two king beds w/ privacy curtains, full bath + living room • Hot tub • Fast Wi-Fi • Easy street parking • Minutes to Expo Center, Churchill Downs & Downtown • Derby, Bourbon & Beyond & Louder Than Life guests must inquire first, strict cancellation policy required. • Rental agreement + damage deposit required

Cozy & fun Studio Near Churchill Downs/Fairgrounds
✨ Kick back in our bright and comfy studio on a peaceful 3-acre property! Just minutes from Churchill Downs, the Fairgrounds (perfect for concerts!), Iroquois Park, and downtown Louisville. Enjoy beautiful views, pool access, and even free training at our fitness gym. Ideal for event-goers, concert lovers, or anyone looking for a laid-back, unique stay. ☕ Grab a coffee on the back patio in the morning — you might spot our friendly family of deer wandering by!

Modern DT Apt – Gym, Pool, Hot Tub & Golf Sim
Enjoy an elevated stay in this spacious one-bedroom apartment in the heart of downtown, just steps from everything Louisville has to offer. Start your morning with complimentary coffee, then hit the state-of-the-art gym or head out to explore. Walk to top restaurants, bars, live music, and entertainment including 4th Street Live! all right outside your door. Comfort, convenience, and location come together for a stay that’s easy and memorable. Book today.

Louisville KY Home w/Hot Tub & Pool
Come celebrate the holidays Kentucky style! Bring the whole family to our beautiful 4-bedroom - We can even host your family holidays! (One room in basement with no egress), 3-bathroom Louisville retreat with a Pool (open May-Oct), Jacuzzi Spa (Year round), Mini Gym with Dumbbells, and Recreation room with other amenities. The entire house is open for your experience. Kid and Family friendly, this guest favorite home is what you've been looking for.

Cozy City Condo in Norton Commons
Norton Commons – Your Perfect Getaway! This beautifully designed short-term rental combines modern comfort with timeless charm, offering an ideal stay for both leisure and business travelers. Whether you’re here for a weekend escape, a family visit, or a work trip, 9440 Norton Commons Blvd offers the perfect blend of style, comfort, and convenience. Book now and experience the best of Prospect, KY!
Popular amenities for Jefferson County rentals with a pool
House rentals with a pool

Home in Jeffersonville IN

DERBY! The Ville Getaway! Centrally Located

No Guest Fees, NEW Pet Friendly, Shops, Downtown

Beautiful house in suburban neighborhood

ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/

Sunsets on Bourbon Street! Waterfront views!

East End Bungalow

Urban Lakeside 3BR Retreat w/ Private Pool
Other holiday rentals with a pool

4th Street Suites - Luxury King Bed Suite

Acadia II Apt. in the Commons

1br Condo

Luxury, Modern 1-Bedroom High Rise Condo

Charming & Cozy Cottage in Quiet Neighborhood

Spacious 3 bedroom 2 full bath

Be easy Speak easy Sleep easy

Pink Castle Babe’cation of Indiana!
Destinations to explore
- Boutique hotels Jefferson County
- Townhouse rentals Jefferson County
- Bed and breakfasts Jefferson County
- Family-friendly rentals Jefferson County
- Rentals with a washing machine and dryer Jefferson County
- Rentals with a fireplace Jefferson County
- Rentals with breakfast Jefferson County
- Condo rentals Jefferson County
- Private suite rentals Jefferson County
- Rentals with an accessible height toilet Jefferson County
- House rentals Jefferson County
- Waterfront rentals Jefferson County
- Rentals with a patio Jefferson County
- Rentals with a fire pit Jefferson County
- Loft rentals Jefferson County
- Rentals with an EV charger Jefferson County
- Rentals with a hot tub Jefferson County
- Rentals with a kayak Jefferson County
- Apartment rentals Jefferson County
- Fitness-friendly rentals Jefferson County
- Hotel rooms Jefferson County
- Smoking-friendly rentals Jefferson County
- Rentals with outdoor seating Jefferson County
- Guesthouse rentals Jefferson County
- Pet-friendly rentals Jefferson County
- Rentals with lake access Jefferson County
- Rentals with pools Kentucky
- Rentals with pools United States
- Buffalo Trace Distillery
- Kentucky Derby Museum
- Kentucky Exposition Center
- Churchill Downs
- Kentucky Kingdom & Hurricane Bay
- Valhalla Golf Club
- Louisville Slugger Museum & Factory
- Muhammad Ali Center
- Angel's Envy Distillery
- Louisville Slugger Field
- Big Four Bridge
- Falls of the Ohio State Park
- Kentucky Science Center
- Waterfront Park
- James B Beam Distilling
- Evan Williams Bourbon Experience
- University of Louisville
- Four Roses Distillery Llc
- L&N Federal Credit Union Stadium
- Kentucky International Convention Center
- Castle & Key Distillery
- Marengo Cave National Landmark
- Jefferson Memorial Forest
- Bernheim Arboretum and Research Forest




