Vacation rentals with a kayak in Jefferson County

5 out of 5 average rating, 4 reviews

Most Unique Eclectic Stay w/ Hot Tub in Louisville

Stay @the most unique & spacious home in East Louisville, Kentucky! Guests have the entire place to themselves. Conveniently located in the east end close to dining, shopping, golf courses, Thunder, Louisville Airport, KFC Yum! Center, Kentucky Bourbon Trail, Churchill Downs, Papa John’s Cardinal Stadium, Waterfront Park, Lynn Family Soccer Stadium, Louisville Bats Stadium, Louisville Slugger Museum, Downtown, Freedom Hall, The Big Four Bridge, Bourbon Distilleries, Valhalla, PGA Championship.

4.67 out of 5 average rating, 3 reviews

Vibrant 3 bedroom spacious vacation retreat

4.98 out of 5 average rating, 128 reviews

The Marie Airstream at Progress Park in Derby City

NOTE: FOR DERBY WE DON'T ALLOW CHECK INS OR OUTS ON FRI OR SAT. THURS-SUN MIN RQUIRED. This gorgeous silver bullet is our Marie Airstream! Marie is a 1996 Excella. She sleeps 5 and includes a private bathroom with shower, and a full kitchen. Your covered patio will have a firepit, grill & hammock & a short walk to all the fun & water activities. Boats & lifejackets provided. Progress Park is a shared glamping property with 11 total units on site. 2 houses, 8 airstreams & a bunk house.

Feel @ home even when you’re not

Updated 4 bedroom, 2 full & 2 half baths. Finished basement with pool table, gym, play area and large screen tv. Common areas with tvs and plenty of seating. Master suite with king bed, a guest room with king bed, second guest room with queen and nursery with crib that converts to a full size bed if requested. Property has a hammock, trampoline, 2 kids playhouses, large soccer and basketball goals, and other kid activities. Outdoor deck with a smoker, grill, patio furniture and dining table.

4.95 out of 5 average rating, 339 reviews

Cabin in Louisville

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 4 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

4.96 out of 5 average rating, 107 reviews

Stella Airstream at Progress Park in Derby City

This gorgeous silver bullet is our Stella Airstream, lovingly named after Wally Byam's wife Stella! She is a 1983 Airstream Classic. She's loaded with all the modern amenities! Stella can sleep 6 comfortably with 2 king beds and 2 bunk beds. There's a private toilet/shower with 2 add'l nearby. You'll have a kitchen & covered patio with grill & firepit. There are 11 total units on site. 2 houses, 8 airstreams & a bunk house. *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

4.99 out of 5 average rating, 136 reviews

Tiny home in Louisville

Mugsy's Bunkhouse @ Progress Park Airstream Resort

Mugsy's bunk house is cute as can be! While small in size, it's big on amenities and charm! It sleeps 7, and is complete with kitchenette, full bath and outdoor living room w/ couch & TV. Includes a hammock, table, firepit/chairs and charcoal grill. 2 add'l shared bathrooms avail. It is near our small fishing pond(no swimming). Progress Park has 11 total units on site. 2 houses, 8 airstreams & this bunk house. *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

4.96 out of 5 average rating, 226 reviews

502 House @ Progress Park w/ Game Room

Welcome to Progress Park! A true getaway for fun! Located on a 12 acre Airstream Glamping resort w/ a 2 acre swimming pond. Sleeps 8 comfortably in the beds with 2 leather futons. Enjoy all the luxuries of home w/ added amenities such as a custom game room & luxurious backyard with TV, firepit & grill. Relax, unplug and reconnect in our little slice of heaven. Progress Park has 8 total units on site. 2 houses, 5 airstreams & a bunk house. *DERBY IS A MIN THURS-SUN REQUIRED

5 out of 5 average rating, 7 reviews

Cozy, modern 4-bedroom ranch!

Enjoy our cozy and newly renovated 4-bedroom, 2-bath home at the centrally located Gaslight District of Louisville, KY. The area is safe and walkable to Kroger, Target, Starbucks, numerous restaurants, and more along Hurstborne Parkway. Only 20 minutes to Churchill Downs and Downtown Louisville. Sleeps 8 comfortably, or up to 12 with couches and air mattresses. With two living rooms, indoor fireplace, and spacious kitchen, this home is perfect for your Kentucky Derby stay!

4.97 out of 5 average rating, 312 reviews

The Grace Airstream at Progress Park in Derby City

Always wanted to experience the vintage airstream life? Here's your chance! The Grace is a 1974 Airstream Sovereign Land Yacht. All the amenities of a hotel, just on the water's edge. Enjoy your coffee in the hammock, spend your days hiking, fishing, swimming, kayaking or paddle boarding. A hidden gem, right in the city. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

4.97 out of 5 average rating, 31 reviews

Yaya Airstream at Progress Park

Our newest airstream is the Yaya. She is lovingly named after our owner Val's late mom. Yaya has all the modern comforts & amenities! It can sleep 3 adults. Possibly 2 adults/2 young kids with a full bed and a small pullout couch. There's a private toilet/shower with a full bath on side of our event ctr next door. You'll have a kitchen & covered patio with grill & firepit, as well as your own hammock. *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

5 out of 5 average rating, 122 reviews

The GiGi Airstream, Lakeside at Progress Park

Your stay in the Gigi Airstream at Progress Park will be anything but ordinary. Wake up to stunning views of the water, with the beach sand just outside your door. This 2022 Airstream Flying Cloud has all the bells and whistles and will ensure you are not roughing it while glamping in the city limits! We can't wait to host you! *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

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

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Jefferson County kayak rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

House rentals with a kayak

Superhost

Home in Brandenburg

4.94 out of 5 average rating, 271 reviews

Luxury lakehouse retreat with picturesque views

JenniferRating, 5 stars3 weeks ago

This was my second stay here and never disappoints! The place is always clean, with wonderful amenities and the host goes above and beyond to make you feel at home. I Would definitely continue coming.

5 out of 5 average rating, 14 reviews

Home in Charlestown

The Quaint Cottage

HelenRating, 5 stars2 weeks ago

Awesome house for our family needs. We loved that one of the bedrooms was off the kitchen area cause we have a family member that snores!! Very clean, tons of towels & kitchen supplies. We loved the fire pit in the side yard.

5 out of 5 average rating, 27 reviews

Home in Shelbyville

Bourbon by the Lake

DarrellRating, 5 stars4 weeks ago

The location is superb is you are trying to see Kentucky. The distance to Louisville, Lexington and Frankfort are all about equal. Shelbyville is a few miles away and it has some great restaurants and nice shopping. While staying there we visited Churchill Downs, Buffalo Trace and Shelbyville. The house has kayaks and a little fishing equipment. We spend a lot of time on the decks and fishing on the dock. This was a great, peaceful getaway from life at home.

5 out of 5 average rating, 11 reviews

Home in Bloomfield

Quiet

SarahRating, 5 stars5 months ago

We had a fantastic quick stay on our long drive from Maine to Texas! Jack's place was absolutely beautiful, private and cozy! We felt right at home and had everything we could possibly need for our quick trip but it was well stocked for longer visits as well! We loved the views from the huge wrap around porch both morning and night, watched an incredible frosty sunrise and saw fantastic shooting stars on our arrival. We highly recommend Jacks place and would definitely stay again. Jack had excellent communication and his place was impeccably clean. Thanks again for a wonderful stay!

4.91 out of 5 average rating, 33 reviews

Home in Lawrenceburg

July 4 Bourbon Trail Lakefront Fire Pit Kayak

IanRating, 5 stars1 month ago

This was a lovely country getaway. I had a fantastic time fishing, kayaking, and enjoying the lakefront. If you're looking for a quiet, low-key trip, this is a great choice.

4.96 out of 5 average rating, 73 reviews

Home in Shelbyville

Bass N Bourbon Retreat - Lakefront * Bourbon Trail

SheriRating, 5 stars6 months ago

Great communication, very clean accommodations, and a perfect location for all of our activities. Would definitely stay again!

4.95 out of 5 average rating, 131 reviews

Home in Elizabethtown

Applewood Cottage Welcome Home

KenRating, 5 stars1 week ago

Beautiful home, everything we needed to cook and feel comfortable. Great coffee bar for waking up. WiFi and streaming services were top notch. Location was very accessible and convenient. Loved the back yard living area. Also appreciated the artwork and decor, very tasteful. Will definitely look to see if available next time in Etown.

5 out of 5 average rating, 45 reviews

Home in Shelbyville

Lakehouse Cove Road

JasonRating, 5 stars3 months ago

Had a great guys week visiting bourbon country. Beds were comfortable, entire house was clean. Great living area.

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Cabin rentals with a kayak

5 out of 5 average rating, 11 reviews

Cabin in Depauw

Little House of Oars

LaraRating, 5 stars2 days ago

Great, peaceful spot for fishing and boating. the cabin was very clean and had everything we needed for the stay. The hosts were friendly and responsive. thank you for hosting us!

5 out of 5 average rating, 58 reviews

Cabin in Willisburg

On Lake, Bourbon Trail, Kayaks, Fishing, Firepit

ChandaRating, 5 stars5 days ago

This was a great getaway for my boys and myself! We specifically booked this cabin because it was by the lake and we wanted to fish pretty much the entire time. If you're planning on using your own boat, like we did, you have to use the boat dock. It is about 4 miles from the cabin. The cabin is very peaceful and very secluded. Be very careful when walking to the lake from the cabin, it can be very slippery when it's wet. The stairs coming in and out of the cabin can be slippery as well. It was very clean and anything you need, Mary is just a call away!

4.98 out of 5 average rating, 106 reviews

Cabin in Lawrenceburg

Bourbon Trail Bliss by the Lake, HotTub, Kayaks

AmyRating, 5 stars4 days ago

This house and property is beautiful! We had such an amazing weekend. We love about an hour away and wanted to get away to the lake for our anniversary. Carolyn’s place did not disappoint! From the cozy beds and linens to the fully stocked kitchen and everything in between we felt truly at home. The space is open and airy and feels like you belong. The hosts have thought of it all. We spent 90% of our time outside on the deck or on the dock. It rained a good amount of the time but we still had a blast because the deck is fully covered. So much wildlife!! There’s a baby snapping turtle that lives in the yard and on the dock and deer were everywhere. The kayaks were a lot of fun too! This definitely won’t be our last visit here!