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Holiday rentals with a pool in Williamsburg

Find and book unique homes with a pool on Airbnb

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Popular amenities for Williamsburg rentals with a pool

House rentals with a pool

Guest favourite
Home in Portsmouth
4.94 out of 5 average rating, 108 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

JustinRating, 5 stars1 week ago
We rented this property to visit the Virginia Tattoo and the beach and had a great trip!
Superhost
Home in Virginia Beach
4.83 out of 5 average rating, 123 reviews

THE OLD BEACON 1 | Beach Living

KyleRating, 5 stars1 month ago
Great place located walkable to the Boardwalk and the entire Beach. We loved have the grocery store a block away and walking everyday on the Boardwalk.
Superhost
Home in Cape Charles
4.75 out of 5 average rating, 4 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

CatherineRating, 5 stars3 days ago
The house and the host were incredible. Immediately upon arriving, we felt at home and ready to relax. There are so many five star touches in this house --- every room has its own sound machine; there is a top notch massage chair in the living room; and there is ample space to get away while all being in the same home. Our kids were asking within the first hour if this could be the forever house. I am looking forward to booking this space again in the future!
Superhost
Home in Portsmouth
4.84 out of 5 average rating, 31 reviews

Elegance Escape on Saunders Dr

TshepoRating, 5 stars2 weeks ago
Clean Place with thoughtful touches from the host. Place has a pool and mini cinema. Would definitely book this place again when am next in Virginia
Guest favourite
Home in Norfolk
4.95 out of 5 average rating, 99 reviews

Gorgeous Vacation House

VeronicaRating, 5 stars1 week ago
We were very pleased with the house. Just be careful w little ones, all vent covers were not secured to the floor properly and that could be safety hazard. One disappointment we had -although the beach was very close (5 minutes walk) there were runoff pipes all along the beach. Public beach a 5 minute drive. We ended up driving to Virginia Beach and had much better time there, 40 minute drive.
Top Guest favourite
Home in Irvington
4.99 out of 5 average rating, 113 reviews

The Rosé Retreat: Pool-Screened Porch-RELAX

LaurenRating, 5 stars2 weeks 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!
Top Guest favourite
Home in Locust Hill
4.97 out of 5 average rating, 131 reviews

Waterfront Cottage Getaway Pool/Kayaks/Fireplace

DamienRating, 5 stars1 week 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!
Superhost
Home in Virginia Beach
4.89 out of 5 average rating, 132 reviews

Beach Home, Upscale Croatan Resort + Private Pool

BetsyRating, 5 stars4 months ago
This is a wonderful beach home within walking distance of the oceanfront. Our extended family enjoyed a fantastic visit. The house is set up perfectly for multiple families with a large gathering space on the top floor next to the kitchen. There are several decks throughout the home to catch the sea breeze and air. Beverly was a great host and responsive to our needs.

Condo rentals with a pool

Guest favourite
Condo in Virginia Beach
4.9 out of 5 average rating, 52 reviews

Beach Luxury Beachfront

LuciaRating, 5 stars1 month ago
Amazing place. Recommended.
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 stars2 months 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 favourite
Condo in Virginia Beach
4.92 out of 5 average rating, 12 reviews

2BD2BA Condo w/Pool2Blocks2Beach

KrystleRating, 5 stars2 months ago
Came with my girls for a conference at the Beach. Salt and Serenity was super peaceful, felt private and quiet. Beds were super comfy and the water pressure in the showers was awesome. We had everything we needed in the kitchen and all amenities were as described. Susan was a great, responsive host and made accommodations for our early check-in. And all the restaurant suggestions were a hit! Would definitely come again!
Guest favourite
Condo in Virginia Beach
4.87 out of 5 average rating, 85 reviews

Good Vibes at the Beach

MarceeRating, 5 stars7 months ago
A great find. Everything we needed, including a grocery store, was walkable and convenient. Loved being 2 blocks from the ocean and boardwalk. Excellent space and very comfortable. Colin is an excellent host. Always addressed our questions and needs in a timely fashion. We will be back!
Guest favourite
Condo in Williamsburg
5 out of 5 average rating, 11 reviews

Wyndham Governor's Green (3 BD Deluxe)

GlennRating, 5 stars4 months ago
Great location, private and peaceful. Staff was very helpful and friendly.
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 favourite
Condo in Virginia Beach
4.86 out of 5 average rating, 137 reviews

Oceanfront, beachfront, boardwalk, fun, dolphins

AnitaRating, 5 stars2 weeks ago
We enjoyed staying at Kelly's place in VB. Its an ideal location for anyone who wants to stay right at the boardwalk. We witnessed amazing sunrises and moonrises. The ocean was right in front of us and from the 6th floor, the view was expansive. A lot of restaurants were also nearby. Kelly was always very communicative, polite and professional. The apartment was clean with the kitchen well stocked with utensils The bedrooms were of a pretty large size. And parking was on the premises. Overall, it was a wonderful experience and holiday for us. We strongly recommend Kelly's place.

Quick stats about holiday rentals with a pool in Williamsburg

  • Total rentals

    1.6K properties

  • Nightly prices starting at

    $46 AUD before taxes and fees

  • Total number of reviews

    7.4K reviews

  • Family-friendly rentals

    900 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    1K properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Williamsburg
  5. Rentals with pools