Vacation rentals with a pool in Kilmarnock

Find and book unique homes with a pool on Airbnb

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Popular amenities for Kilmarnock rentals with a pool

House rentals with a pool

Guest favorite
Home in Montross
4.99 out of 5 average rating, 95 reviews

Waterfront l Beach+Pool Kayaks I 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!
Guest favorite
Home in Montross
4.97 out of 5 average rating, 87 reviews

Waterfront Gem: Dock, Hot Tub, Beach, Pool, Kayaks

NoraRating, 5 stars3 months ago
Andrea was extremely proactive and responsive to our questions, even reaching out ahead of time to make sure we were aware of work being done and arranged for late check-out, a huge help for our group. The local recommendations were really appreciated, and it's such a beautiful location along the water.
Top guest favorite
Home in Irvington
4.99 out of 5 average rating, 113 reviews

The Rosé Retreat: Pool-Screened Porch-RELAX

LaurenRating, 5 stars1 week ago
We loved our stay at the Rosé Retreat and are so sad to leave! The place was spacious and beautiful- we felt right at home. The surroundings were so peaceful and serene. Roxanne and Tara were very responsive and helpful. This was the perfect place for our family to spend a fun weekend together. When we come back to Irvington, we will absolutely stay at the Rosé Retreat again!
Guest favorite
Home in Montross
4.99 out of 5 average rating, 151 reviews

Beach Please! River cottage w/private beach & dock

AudreyRating, 5 stars3 weeks ago
This was our second stay at Beach Please and it was just as delightful as the first! The house was again squeaky clean, thoughtfully decorated and had plenty of room for our multi-generational family to spread out. Grandparents appreciated the first floor master bedroom and kiddos loved the game room, and the crafts and puzzles upstairs. The neighborhood is peaceful and cozy, with beautiful views in every direction. The addition of the acoustic guitar for songs by the firepit was a major plus, as our ten year old is a music lover and almost brought her own. We had a great stay and would recommend this AirBnB to anyone! Grab a week (or two) and don't think twice.
Top guest favorite
Home in Locust Hill
4.97 out of 5 average rating, 131 reviews

Waterfront Cottage Getaway Pool/Kayaks/Fireplace

DamienRating, 5 stars4 days ago
We had an absolutely wonderful stay at this beautiful cottage by the water! The home itself is cozy, spotless, and thoughtfully decorated — it felt like a true retreat. Waking up to the peaceful views of the water every morning was just magical. The location is perfect, with some fantastic restaurants just a short drive away — everything from fresh seafood to charming cafes. Heather was incredibly welcoming and made sure everything was perfect for our stay. I can’t recommend this place enough and can’t wait to come back!
Top guest favorite
Home in Montross
5 out of 5 average rating, 13 reviews

Water View Cozy Getaway- beach/Kayak/fishing/pool

SharenRating, 5 stars6 months ago
it was right across the street from the beach. It was a great time. Easy to walk to the beach. Kite flying was fun. Great place for your family.
Top guest favorite
Home in Gloucester
5 out of 5 average rating, 13 reviews

Serenity Farm Equestrian Retreat in Historic VA

LisaRating, 5 stars2 days ago
When we had some communication issues related to AirBnB, William called me directly and patiently helped me work out concerns with the company. He was proactive, considerate, & helpful. I could not have asked for better! Hope we can get down to Serenity Farm as a family in the future!
Top guest favorite
Home in Irvington
5 out of 5 average rating, 43 reviews

Blue Oyster: Perfect Getaway, Kayaks, Quiet

JeniferRating, 5 stars5 months ago
The Blue Oyster was a lovely and relaxing oasis for our girls weekend getaway. The house was so well appointed anything you could need or want was available and accessible. The screened in porch was wonderful for having conversation, wine and cheese to relax before dinner. Bathrooms were clean and well appointed. Beds were very comfortable. Extra blankets in case we needed them. Gas fireplace in the living room provided lovely ambiance and warmth as the day cooled off. Highly recommend stay at The Blue Oyster if you find yourself in Irvington!

Condo rentals with a pool

Superhost
Condo in Williamsburg
4.8 out of 5 average rating, 5 reviews

Williamsburg Plantation ThanksGiving Large Condo 2

KitRating, 5 stars9 months ago
Amazing experience! communication was amazing! I'm a firm believer that communication sets the tone for an experience. The resort is beautiful! the amenities were top tier. The biweekly poolside party was a hit with the family. We felt safe and very welcomed. Great experience!
Superhost
Condo in Williamsburg
5 out of 5 average rating, 3 reviews

Relax in Style: 2BR Condo w/ Balcony at Wyndham GG

JamesRating, 5 stars1 month ago
We were very pleased with our stay. Check-In was very easy with plenty of text notifications. Check out was easy as well. We were greeted by Club Wyndham timeshare staff and invited to attend a presentation, but the offer was very friendly and not pushy at all. It was a very good experience, and we would love to stay again. We visit our Aunt who lives in Ford's Colony and found this location we'll suited for all of Williamsburg.
Guest favorite
Condo in Williamsburg
4.9 out of 5 average rating, 10 reviews

Wyndham Kingsgate (3 BD LO)

JohnRating, 5 stars1 week ago
Our family of 6 has a great time. Plenty of space at the unit and the amenities were even more than described. We'll be coming back!
Condo in Williamsburg
4.8 out of 5 average rating, 10 reviews

2 Bdrm Condo at The Historic Powhatan Resort

LoriRating, 5 stars23 months ago
Very nice. I highly recommend this place. Very nice inside and I love the Powhatan Resort also.
Superhost
Condo in Williamsburg
4.9 out of 5 average rating, 10 reviews

Upscale condo with Golf Course views

MaryRating, 5 stars8 months ago
The condo is well appointed with everything I needed. Kingsmill is a special place. Rodica was very quick to reply when I had a few different questions. Very comfortable bed and reading chairs. Top notch.
Guest favorite
Condo in Williamsburg
5 out of 5 average rating, 7 reviews

3BDR 2 bath, Sleeps up to 8 Guests

CatherineRating, 5 stars6 months ago
This was a great place for a weekend In Williamsburg. Lots of comfy beds, functional kitchen, plenty of places to sit and chat.
Guest favorite
Condo in Williamsburg
4.91 out of 5 average rating, 65 reviews

2BR Suite @ Historic Resort! Amenities Galore!

DonnaRating, 5 stars1 month ago
We really enjoyed our stay. Everything was as described and exceeded our expectations. It was a good value; we have no complaints. Thank you so much for your professionalism, everything went as planned.
Superhost
Condo in Williamsburg
4.6 out of 5 average rating, 5 reviews

Spacious Family Friendly Two Bedroom Suite.

AndreRating, 5 stars9 months ago
This was my family's first stay in Williamsburg and the unit met our needs and expectations. I will definitely use Suite Spaces again.

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