
Vacation rentals with a pool in Williamsburg
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Williamsburg

Total vacation rentals
Explore 1,680 vacation rentals in Williamsburg

Nightly prices starting at
Williamsburg vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

Verified guest reviews
Over 10,900 verified reviews to help you choose

Family-friendly vacation rentals
1,090 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
990 properties have a dedicated workspace

Wi-Fi availability
1,680 of Williamsburg vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Williamsburg rentals

4.8 Average rating
Williamsburg stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Williamsburg
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Kingsmill 1bed/1ba on Golf Course 9th Fairway
This beautiful 1 bed-1 bath unit is a cozy 400 sq.ft. and is located in the exclusive Kingsmill neighborhood. This first floor unit offers a king-size bed with a private patio that walks out onto the 9th Fairway of the River Course at Kingsmill. You'll enjoy the luxurious full bathroom with shower/tub combination and upgraded finishes. In the bedroom, you'll also find a computer desk, an over-sized sitting chair, a mini-fridge, a microwave, a Keurig coffee maker, and 50" Roku Smart TV w cable!

York River Vacation Home
This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

The Barn at Pond Point - Riverfront Home
The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

Blue Heron WaterSide
Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

Million $ Views! Pool! Private Hot Tub! EV Charger
Welcome to The Cottage at Misti Cove, where the Piankatank River is just steps from your door. Wake to sunrise views from bed, paddle the river by kayak or paddleboard, and unwind in your private waterfront hot tub as evening settles over the water. Enjoy the peaceful setting of a small community along with a seasonal pool, beach, pier and tennis court. It’s a cozy waterfront escape with exceptional views, thoughtful comforts and plenty of ways to slow down and say, “Now this is the life.”

3bdr Williamsburg Townhouse, sleeps 8
Discover Historic Powhatan, a Hilton Vacation Club managed property, in Williamsburg, Virginia. Nestled amidst timeless beauty, our resort offers a unique blend of history and modern comfort. Explore nearby historic sites, unwind by the pool, or embark on a culinary journey in our on-site restaurant. Experience a stay that bridges the gap between the rich heritage of Williamsburg and the indulgence of contemporary relaxation. 1,736sq ft 3BDR, 2BTH, 3-STORY SUITE

Log Cabin - Williamsburg Pet-Friendly, Heated Pool
Pet-friendly log cabin with 2 rooms, A/C & heat, free Wi-Fi, and cable TV. Includes a queen bed, breakfast bar, mini-fridge, microwave, and ceiling fan. No bathroom inside, but just steps from our first-class, professionally cleaned bathhouse. No kitchen. Outside: charcoal grill, picnic table, and fire ring. $20 per pet per stay. Linens/pillows not included—bring your own or rent a set for $20. Enjoy our 85° heated pool, free game room, and playground.

Great family vacation resort condo. Sleeps 12.
Welcome to Greensprings Vacation Resort. We combine two adjacent 2BDR/2BA units to create one huge 4BDR unit with 2 full kit/dining and 2 LR, each with a queen sofa sleeper. And we are near everything! Busch Gardens 7 miles (10-15 minutes) Colonial Williamsburg 5 miles (8 minutes ) Water Country USA 7 miles (10-15 minutes) Historic Jamestowne 5 miles (8 minutes) Newport News/Williamsburg International Airport 19 miles (30 minutes)

Cozy Fall Retreat - Creek Views & Fire Pits
A cozy waterfront escape tucked into 10 wooded acres above Bland Creek. Perfect for crisp fall days and peaceful evenings. - Elevated screened porch with colorful water and wooded views - Creekside fire pits for crisp fall nights - Dock, kayaks, fishing, and direct water access - Outdoor dining and hammocks beneath the trees - Immaculately clean and thoughtfully stocked for a seamless stay - Just 15 minutes from downtown Gloucester

The Cottage @ Captain Genes - Secluded Waterfront
Get away from the crowds! Private, secluded upscale waterfront cottage on ~5 acres; pool/hot tub feet from the back door (hot tub open year round). Waterview from most rooms. Direct Chesapeake Bay access on property via dock / kayak launch. ~15 mins to downtown. Fish/crab, kayak, screened porch views, relax by the pool, fire pit or hot tub with a drink. Bring your boat - marina ~4 mi away - put-in there & tie-up at our pier!

4BD home w/ game room & pool near Langley & PTC!
Welcome Home! Be the next to rent this beautifully renovated, modernized home with beautiful kitchen, amazing bathrooms and generous bedrooms and closets. Come in and relax in this centrally located neighborhood - convenient ten minute trip for shopping, restaurants and military bases. Great for families coming in town for Boo Williams tournaments! This is the one! DONT FORGET TO ASK ABOUT OUR YACHT RENTAL OPTIONS!!!

1br Colonial in Williamsburg -Fun by Busch Gardens
Discover Club Wyndham Kingsgate in historic Williamsburg! This cozy 1-bedroom resort suite sleeps up to 4 and features a king bed, queen sleeper sofa, mini kitchen, washer/dryer, and comfortable living space. Enjoy indoor & outdoor pools, mini golf, tennis, fitness center, movie theater, arcade, and easy access to Colonial Williamsburg, Busch Gardens, shopping, dining, and Virginia's top historic attractions.
Popular amenities for Williamsburg rentals with a pool
House rentals with a pool

Magical wooded cottage pool +priv hottub walk2town

Rappahannock Waterfront Pool, Kayak, Deck, Firepit

The Rosé Retreat: Pool-Screened Porch-RELAX

The Great River Escape *Hot Tub!

Gorgeous Vacation House

America's 250 Getaway | Pool | Busch Gdns | Wmbg

Pine Cove on the Severn

One Level Home | Boats Welcome! | Rockfish | Golf
Condo rentals with a pool

Colonial Williamsburg Spacious 4 Bedroom Suite!

3 Bed, 3 Bath Sleeps 8 in Kingsmill

WaterVue at Kingsmill

Lovely 2 Bedroom Condo in 4Diamond Historic Resort

Marriott's Manor Club Ford's Colony 2BD Villa Slee

Family reunion? Here ya go! 8BDR/8BA sleeps 24!

Charming 2BR Colonial Condo at Wyndham Kingsgate

Wyndham Kingsgate (2 BD)
Other vacation rentals with a pool

Perfect for the family! 4BR townhouse near it all!

Kingsgate Resort 3 Bedroom Lockoff

Wyndham Kingsgate 3BR Apartment with Resort Access

Two Bedroom Suite in Charming Williamsburg

Private 5-acre Waterfront Peninsula with Beach

Club Wyndham Kingsgate One-Bedroom Condo

Pet Friendly Cabin in Williamsburg, VA

4BR Williamsburg Retreat – Pool, Tennis & BBQ
When is the best time to visit Williamsburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 364 | ﺩ.ﺇ 389 | ﺩ.ﺇ 426 | ﺩ.ﺇ 488 | ﺩ.ﺇ 496 | ﺩ.ﺇ 510 | ﺩ.ﺇ 521 | ﺩ.ﺇ 466 | ﺩ.ﺇ 382 | ﺩ.ﺇ 415 | ﺩ.ﺇ 437 | ﺩ.ﺇ 356 |
| Avg. temp | 5°C | 6°C | 9°C | 15°C | 19°C | 24°C | 26°C | 25°C | 22°C | 16°C | 11°C | 7°C |
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- Chesapeake Bay
- Busch Gardens Williamsburg
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Pocahontas State Park
- Outlook Beach
- Greater Richmond Convention Center
- Old Dominion University
- Norfolk Botanical Garden
- Regent University
- First Landing Beach
- Brown's Island
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Virginia Holocaust Museum
- The National
- Forest Hill Park
- Libby Hill Park
- The Mariners' Museum
- Town Point Park
- The Poe Museum





