9 Best Vacation Rentals With Private Pool Near Williamsburg, Virginia - Updated 2024

Trina Joy Cassey
Trina Joy Cassey 
Updated
| 4 min read

Once the capital of Virginia Colony, Williamsburg is a beautiful city with an old-world charm, a rich history that dates back to the American Revolution, and fascinating attractions worth discovering. From admiring the pre-revolution beauty of the Governor’s Palace to immersing in art at the Muscarelle Museum of Art, memorable experiences await here. History buffs can travel back to the 18th century in Colonial Williamsburg Visitor Center. For families, a visit to the fun-filled Pirate’s Cove Adventure Golf is ideal. While there are plenty of superb accommodations within the city limits, there are also exceptional ones nearby, offering private pools. If you’re interested, browse through this list of the best vacation rentals with private pool near Williamsburg, Virginia.

We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on March 03, 2024.

1. Pet-friendly dwelling in a tranquil neighborhood (from USD 175)

Blissful family memories are made in this stunning Airbnb with vibrant interiors and a homey ambiance, situated in a peaceful community. Besides being conveniently furnished, it is pet-friendly, too, which tourists are fond of. Topping it all off is an outdoor pool in the fenced backyard where you and your loved ones can spend time splashing around. While in the pool, kids are required to use life vests for extra caution.

Stayed at this property?
Hampton, Virginia, United States
113 reviews   Wifi Available
ENTIRE HOME 3 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
and oh yeah the pool didn't hurt either
Cleanliness:
the house was very clean very accommodating
it was a very nice stay clean comfortable and very spacious
this place is awesome everything was neat and clean and had everything that we could ever need
shamus home was very clean great location i would stay here again if i return to va
the house is very clean the kids loves to stay in the house they feel like home
Host:
beautiful home & a great host 5 stars
five stars great host & beautiful home my family & i slept comfortably
amazing house and host i threw a pool party one day and had family night the next
also shamus was a great host
Location:
convient location and in a nice quiet neighborhood
perfect location to the rest of hampton
the pool was awesome and our kids loved it the location is good and close to busch gardens (approx
we had a wonderful time in shamus's place
it is nice place to stay away from home
Read more reviews

2. Renovated carriage house in Cumberland Estate (from USD 431)

Located in Cumberland Estate, this VRBO guarantees you a peaceful and quiet stay. Guests will sleep in a characterful carriage house and enjoy its amenities, including a kitchenette, a fitness room, and WiFi. From Memorial Day to mid-October, the swimming pool is usually open and accessible to guests. It is fenced, surrounded by verdant greens, and equipped with sunbeds where you can chill while reading a book.

Stayed at this property?
New Kent, Virginia, United States
Agritourism 6 Guests 3 Bedrooms 4 Bathrooms

Top guest reviews
Cleanliness:
it was clean and had everything we needed for our stay
Location:
this was a perfect location
we loved the accommodations but our experience was enhanced by the location
the property is beautiful and so relaxing to walk around
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3. Beautiful country retreat (from USD 365)

This VRBO bills itself as the perfect country retreat. It nestles in a lovely setting, showcasing a convenient fully furnished interior and a dreamy fenced outdoor pool with toys as its main attraction. The soaking facility is only seasonally open, usually from May to September. Should you need extra space, you can book the pool house at an additional cost. Since quiet hours start at 10 pm, you can only use the facility until 09:59 pm.

The private saltwater pool has a 10-ft (3-m) deep end, and access to it is rarely shared with the property’s owner. Its optional poolside lounge includes a wet bar, seating areas, a game table, a television, and a bathroom.

Stayed at this property?
Charles City, Virginia, United States
cottage 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
we enjoyed the views the pool deck and our dogs really took advantage of the fenced front yard
the pool and pool house were awesome and the cottage was very comfortable
nice pet friendly 3 bed 2 bath house outside of williamsburg
the house is charming and comfortable
Cleanliness:
the house was clean and extremely comfortable
the property is clean beautiful and relaxing
the house itself was a little outdated (bathrooms kitchen and bedding) but was clean bright and comfortable
Host:
lovely property and excellent host
really a wonderful host
the house was great and owner was attentive to concerns and questions during stay
you couldn’t ask for a better host than the owner steve
host was awesome and did all the little things that really made for a nice stay
Location:
there’s some great little fishing spots very close by if you’re into that
the house is outside of town and the surroundings were super quiet
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4. Spacious waterfront haven on Grandview Island (from USD 479)

If you seek accommodation that can fit big groups, this roomy vacation rental on Grandview Island might interest you. Apart from its comfortable space, it delights guests with mesmerizing water views and a heated indoor pool. The soaking facility measures 900 sq. ft.(83.6 sq m), and a hot tub can be found beside it.

If you’re looking to enjoy a more natural playground, Buckroe Beach is only 3.8 mi (6.1 km) from the property.

Stayed at this property?
Hampton, Virginia, United States
PRIVATE VACATION HOME 10 Guests 5 Bedrooms 4 Bathrooms

Top guest reviews
Amenities & Room:
beautiful views and nice pool and hot tub
the back room was nice also to look out on the water chill and relax
we were not disappointed the house is so spacious - large rooms and all the amenities
between the pool the nature reserve the beach and the dock we were in heaven
the rooms were very comfortable the kitchen well equipped
Cleanliness:
nice clean area & neighborhood
the house was clean well stocked and we really enjoyed the pool and hot tub
this property was exactly like the pictures clean spacious quiet and cozy we had so much fun
Host:
the owner was very responsive and helpful
property manager was very responsive and helpful
the owner is really nice and he responds quickly
the host was great to work with always prompt with any questions
owner took us at a day notice and was very responsive and kind
Location:
great location to beach shopping & restaurants
quiet location but with easy access to grocery stores etc
close to everything shopping and fun
the neighborhood is quiet and peaceful
we couldn’t ask for a better place for a getaway the house was huge
Read more reviews
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5. Ware Haven Cottage (from USD 345)

Set along Ware River, the Ware Haven Cottage offers mesmerizing vacation views. Birdwatching and occasional dolphin-watching are activities guests can enjoy on-site. Also, the fully furnished property provides holidayers with their own fenced outdoor pool, which is seasonally open from May to September. The in-ground facility measures 20 ft by 40 ft (6.1 m by 12.2 m). It is 3-ft (0.9-m) deep from the pool steps while the water at the slide area has a depth of 6-ft (1.8 m).

The unheated pool is set on a rustic deck, which offers sets for drinking tropical fruity beverages and reading a book.

Stayed at this property?
Gloucester Courthouse, Virginia, United States
PRIVATE VACATION HOME 6 Guests 2 Bedrooms 1 Bathroom

Top guest reviews
Amenities & Room:
quite and cozy cottage by the river with a nice pool
Cleanliness:
steve was amazing the house was immaculate and it was the best vacation we have ever had
Host:
the hosts were wonderful and available if needed
steve is a great host
steve and cindy are wonderful hosts and were only a text away
steve and cindy were wonderful hosts; i almost felt like family
Location:
great house and wonderful location on the water great for kayaking
Read more reviews
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6. Upscale abode with a fire pit area (from USD 421)

From the scenic waterfront setting to the classy and well-equipped interiors, everything you look for in an ideal vacation home is here - and more.

Outside, a fire pit area and a saltwater pool await. The private swimming facility is heated for your comfort and offers lovely views of the Hampton River. The host only asks that you always return the cover of the pool when not using it. Also, avoid messing with the pump and heater. Should you come across any pool complication, be sure to contact the host instead of trying to fix it yourself.

Stayed at this property?
Hampton, Virginia, United States
141 reviews   Wifi Available
ENTIRE HOME 4 Beds 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
great place and the heated pool was tons of fun
a beautiful heated pool and fire pit and plenty of outdoor seating
outdoor space is wonderful and heated pool was by far my favorite part
the heated pool was the everyone’s favorite place to be
great house we really enjoyed the heated pool
Cleanliness:
everything was very clean
very spacious updated and clean house
place was very clean and kitchen had everything we needed
place was clean and very functional for our group
house was large enough for our needs clean offering a perfect outdoor living space
Host:
host was nice and made accommodations good
the host is extremely communicative and helpful
great house and great host
the rooms are spacious you can tell the host is very thoughtful about their guests
directions were clear and shamus was extremely responsive
Location:
amazing house in an amazing location
beautiful house in a great location
great location and house was just as described
the location is great in a very nice neighborhood with plenty of parking space
great place beautiful pool and great location for fishing
Read more reviews

7. Siren Cove (from USD 859)

This vacation rental charms travelers with its tourist-friendly location near Mellen Street and the attractions along with it. Also, the beautiful water views and elegantly furnished bright interiors are a hit with guests. The property has a backyard with an outdoor pool, so you can enjoy a refreshing dip. Since there’s no lifeguard to oversee the happenings there, parents are required to keep an eye on their kids for safety.

Management rules state that the owners will not be liable for accidents and injuries on the property.

Stayed at this property?
Hampton, Virginia, United States
47 reviews   Superhost Wifi Available
ENTIRE HOME 6 Beds 10 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
cozy house with amazing amenities
plenty of rooms and the backyard is excellent with a dock and pool and firepit
Cleanliness:
kim and her team were very accommodating the house was clean and beautiful they made our stay memorable
this is a beautiful fully functional home for a family vacation it was very clean and nicely decorated
the home is super clean beautifully decorated and well appointed with everything you will need during your stay
Host:
the host was a pleasure to deal with
very helpful and pleasant host
amazing property with a super great host
hosts were very responsive on any issues that arose
Location:
close to great sights
this was the ideal place for our group of 10 an amazing view & location
great place for a large family gathering
kim’s house was the perfect place for our large family gathering
wonderful place for a family getaway
Read more reviews

8. Scenic vacation home on York River (from USD 342)

Are you on the hunt for scenic accommodations on York River? This lovely vacation home with spectacular water, sunrise, and sunset views might pique your interest. It is fully furnished and fun-filled, thanks to a private dock, kayaks, and a riverfront saltwater pool with 35,000 gal (132,489.4 l) of water.

Kids are prohibited in the pool area without accompanying adults. Life vests are also available for the children’s safety. Diving and jumping into the facility are not allowed, too, as well as running and playing with balloons that can burst and get stuck in the filtration system.

Stayed at this property?
Gloucester Point, Virginia, United States
142 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the pool was awesome and the view of the river was great
great place with an awesome view and pool we had a great time and can't wait to stay again
Cleanliness:
the house was super clean and had everything you could need
the house is spacious clean and beautiful
place was incredibly clean and there were so many thoughtful touches
everything is bright and clean
this property is amazing- very spacious and super clean
Host:
the hosts are wonderful
they were so kind and thoughtful
very nice recent renovations carol and gene are excellent hosts and quick to answer any questions
carol & gene were great hosts the home is gorgeous with an absolutely beautiful view
gene is very nice and accommodating
Location:
house is in a great location for fishing crabbing sunsets
the home is beautiful inside and out and the location is perfect
beautiful space close enough to towns but secluded enough to have an amazing relaxing time along the water
Read more reviews

9. Good Vibes Villa (from USD 385)

At Good Vibes Villa, guests can enjoy a circular above-ground pool on a fenced deck. The professionally maintained 27 ft (8.2 m) outdoor soaking facility is equipped with accessories and a single life vest for young swimmers. With a 4.5 ft (1.4 m) depth measurement, it is mostly safe for kids, but adult supervision is also required at all times. While the pool is only seasonally open from June to September, it is operational 24/7 during its season.

A roofed lounge area can be found on the deck, offering a shady retreat to guests in between swims.

Stayed at this property?
Hampton, Virginia, United States
41 reviews   Wifi Available
ENTIRE HOME 4 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
was really impressed with the amount and quality of kitchen “stuff” lol
the beds were very comfortable
the pool area was so beautiful and relaxing
Cleanliness:
the house was clean and well stocked with basic essentials
it was easy to access and was very clean
courtney’s place is very clean
fun place & great for a summer stay clean spacious and all the essentials for a comfortable experience
Host:
the host was very responsive
she is very responsive
Location:
i loved staying at this location
as soon as you walk in the door it feels like a home away from home
great home with a very convenient location comfortable beds and decorations were awesome
Read more reviews

Have fun in your private pool

Williamsburg has a lot to offer in terms of history and must-visit attractions for the whole family to enjoy. Take your holiday experience up a notch by booking a stay from this list of the best vacation rentals with private pools near Williamsburg, Virginia.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Trina, a preschool teacher, is a working mom and a devoted wife to an analyst programmer. She's also a writer, cook, and travel enthusiast. Trina firmly believes that travel is a valuable...Read more

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