Vacation rentals with a pool in Westmoreland County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Westmoreland County rentals with a pool

House rentals with a pool

Guest favorite
Home in Montross
5 out of 5 average rating, 29 reviews

Waterfront+DOCK+Beach+Kayak+Paddlebd+Arcade

IanRating, 5 stars8 months ago
Beautiful location on the water with a lovely dock and the ability to do SUP and walk to a small bit of local beach. Quiet neighborhood though neighbors driveway light is too bright. Enclosed porch area with good AC is a great place to sit and watch the world go by. Kitchen has all you need. Bedrooms are fine but would be a bit better with nicer pillows and mattress toppers. This is a remote spot in that there are no restaurants or coffee shops to walk to. Everything is a drive. The community pool and tennis courts have to be driven to - not walkable. While nice to have them, they are a bit run down. Regardless we still used and enjoyed them. Overall I certainly recommend it and the hosts were very accommodating and responsive.
Guest favorite
Home in Montross
4.99 out of 5 average rating, 95 reviews

Waterfront+Kayaks l Beach+Pool l Gameroom+Firepit

LillianRating, 5 stars1 week ago
Our family had a great time at Connie’s! The kids had loads to do in the game room and we all enjoyed the scenic views and relaxing environment. Bathrooms were also super clean. The refrigerator is enormous and was helpful because there aren’t too many food places around so we cooked a lot. Connie was responsive and friendly. We would recommend her place!
Home in Kinsale
4.78 out of 5 average rating, 23 reviews

Riverfront Paradise w/ Hot Tub & Pool in Kinsale!

DruryRating, 5 stars9 months ago
This home was the perfect location for our family reunion. There are so many spaces inside and outside of the house, where we could spend time as a group or curled up with a book. The pool area was unbelievably perfect...from outside bathroom, to bar area with extra refrigerator, to lots of seating, to changing rooms, to floating devices...the list goes on...not to mention the incredible views from the pool area! The kitchen was stocked with everything you can imagine, including Keurig cups. All the beds were comfy and the grandkids loved the bunks and toddler bed. We loved the experience so much that we've already booked for next year. Many happy family memories were made there. Plus, we absolutely adore the town of Kinsale, the marina area, the Kinsale store and museum. It's a perfect place to just 'be'.
Top guest favorite
Home in Montross
4.98 out of 5 average rating, 41 reviews

Game-Themed Waterfront Fun! Dock-Boats-King Suite

NiyaRating, 5 stars3 weeks ago
I stayed here with my three kids for a little getaway, and we had the best time. The place was super clean and spacious, and the modern decor and finishes were clearly chosen with care—it just felt really good to be there. The game rooms were such a fun touch, each with its own theme, and the kids were obsessed! One of our favorite parts was the scavenger hunt—it was such a fun and unexpected surprise, and it gave us a memory we’ll definitely hold onto. The host was incredibly kind, polite, and respectful. Overall, it was just a great experience and a really special trip with my kids.
Guest favorite
Home in Colonial Beach
4.89 out of 5 average rating, 28 reviews

3 Little Birds

AlejandroRating, 5 stars1 week ago
This location was perfect for us. We came for a car show at Maryland international raceway, which was only about 30 to 40 minutes away from this air bnb. Lots to do and good area👍🏼.
Guest favorite
Home in Colonial Beach
4.88 out of 5 average rating, 8 reviews

Stay&Play:Games, Pool, FirePit, Beach & Boardwalk!

TriciaRating, 5 stars1 month ago
We had an amazing stay at Anthony’s place. The hosue was beautiful and inviting. Plenty of space and the decor was outstanding. We will most certainly be renting this property again. Anthony was an awesome host and was quickly responsive when I had a question. I highly recommend this home for a stay.
Guest favorite
Home in Montross
4.85 out of 5 average rating, 20 reviews

Idyllic Montross Vacation Rental Home w/ Views

Lisa JayneRating, 5 stars6 months ago
We really enjoyed the stay at the River House. We are a repeat customer and the house did not disappoint us. The host is very gracious and everything is just as the website has it listed. We enjoyed the amenities, lots of videos, games and the hottub. There is a short walk to the beach which we visited twice a day. We loved every minute of it! Thank you!

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