Vacation rentals with a pool in Jessamine County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Jessamine County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Jessamine County rentals with a pool
House rentals with a pool
Guest favorite
Home in Lexington
5.0 out of 5 average rating, 51 reviewsPOOL! Game room! 5 beds an 4 bedrooms
Guest favorite
Home in Lexington
4.86 out of 5 average rating, 51 reviewsThe NightinGayle - Pool, Hot Tub
Guest favorite
Home in Midway
5.0 out of 5 average rating, 64 reviewsMidway Cottage, Keeneland, Distilleries, Pool
Guest favorite
Home in Midway
4.99 out of 5 average rating, 68 reviewsThe Bees Wing
Guest favorite
Home in Lexington
5.0 out of 5 average rating, 54 reviewsHouse w/private pool & hot tub, dogs ok
Superhost
Home in Lexington
4.85 out of 5 average rating, 53 reviewsSouthland Swim House
Superhost
Home in Lancaster
4.76 out of 5 average rating, 42 reviewsThe Herrington
Home in Harrodsburg
5.0 out of 5 average rating, 4 reviewsBluegrass Charm
Condo rentals with a pool
Guest favorite
Condo in Lexington
5.0 out of 5 average rating, 14 reviewsCondo downtown Lexington
Condo in Lexington
4.8 out of 5 average rating, 99 reviewsAttend UK Sports From a Downtown Condo With a Heated Pool
Condo in Lexington
4.97 out of 5 average rating, 39 reviewsParadiso - Divine Condo, Perfect Downtown Location
Guest favorite
Condo in Lexington
5.0 out of 5 average rating, 8 reviewsThe Big Blue Wave - 2-Bedroom Condo by Rupp Arena
Guest favorite
Condo in Lexington
5.0 out of 5 average rating, 91 reviewsLuxe - Your Bourbon Trail Adventure Starts Here
Condo in Lexington
4.71 out of 5 average rating, 48 reviewsCozy & Classic Downtown Lexington Getaway
Destinations to explore
- Rentals with pools United States
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