
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 1,630 vacation rentals in Williamsburg

Nightly prices starting at
Williamsburg vacation rentals start at €26 per night before taxes and fees

Verified guest reviews
Over 10,010 verified reviews to help you choose

Family-friendly vacation rentals
1,070 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
930 properties have a dedicated workspace

Wi-Fi availability
1,630 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!

The Great River Escape *Hot Tub!
Welcome to the River Escape, where the sun is hot and river breezes are cool! Located on the Hampton River, on a big fenced lot, with easy river access and just a 10 minute drive to sandy toes and the sound of crashing waves, this fantastic river house is made for the best family vacations around. It is furnished to comfortably sleep 6, featuring a spacious, well-stocked kitchen, private in-ground pool, hot tuband a gas grill in the backyard! Just add family, and you've got instant vacation fun!

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.

Peaceful Retreat w/ Fire Pit & Spa Services
Country living at its best! Quiet...peaceful & very special place to relax, release, and rejuvenate. We are surrounded by beautiful wineries, which are all minutes away. Gorgeous views of nature and seasonal flowers. Separate from the main house, our guest suite offers awesome privacy & comfort. You will enjoy this very quiet, cozy, peaceful retreat. It is the perfect hideaway with the utmost charm. Board Certified Reflexologist on the premises is available for appointments. So AMAZING!

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.”

Magical wooded cottage pool +priv hottub walk2town
Set among the trees on 2 peaceful wooded acres, this cottage delights with gothic architecture, sun-filled rooms, and a bathroom for every bedroom. Relax in the hot tub under the stars, sip local wines, eat oysters. Take a sunset boat cruise or learn oystering and crabbing from a local waterman. Farm stands, markets, and sea-to-table local fare. Live life in an historic working water town with lots of personality. Close to Tides Inn, Kilmarnock, White Stone, Compass Entertainment.

Summer Escape - Dock, Pool, Firepits, & Kayaks
A waterfront summer retreat tucked into 10 secluded wooded acres above Bland Creek, perfect for long days and relaxed evenings - Screened porch with water views and cool creek breezes - A Pool is available for rent for private use (open Memorial Day–Labor Day) - Dock, kayaks, fishing, firepits, and direct water access -Outdooring dining options and family-friendly - 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!!!

Pelican Place, Cozy Retreat | Pool | Walk to Tides
Unwind at this stylish apartment with view of Carters Creek and walking distance to the cutest little town and the iconic Tides Inn Resort. Take a refreshing dip in the pool, enjoy the charming outdoor shower, and star gaze under a blanket from the rooftop deck. Several outdoor spaces and large yard with whimsical touches. The perfect hideaway close to all the Northern Neck has to offer.

Clay Bank River Front Cottage
Recently updated waterfront cottage 2 bedroom - 2 queen beds, a pull out sofa, 28 private acres on the York River in Gloucester, Va. Great remote getaway with a pool, kayaks and private pier for fishing/crabbing. Lightly traveled river. Access to Yorktown, Newport News, Williamsburg, Jamestown, Richmond, Norfolk, Urbanna. Shares the property with the main house where owner lives.
Popular amenities for Williamsburg rentals with a pool
House rentals with a pool

Stand Alone 3 Bedroom Cottage

Chesapeake Bay Retreat Waterfront Indoor Pool

Luxury 3BR | Pool, Nature Trails + Walk to Town

Gorgeous Vacation House

Maddie's Place

The Rosé Retreat: Pool-Screened Porch-RELAX

Rappahannock Waterfront, Pool, Kayaks, Rose Garden

Serenity Farm Equestrian Retreat in Historic VA
Condo rentals with a pool

Wyndham Kingsgate 3BD/3BA LO

Wyndham Kingsgate (3 BD LO)

Wyndham Kingsgate (3 BD LO)

Powhatan Resort - 2 bdrm timeshare property (Q)

4BDR Williamsburg Resort Living!

Great value! Popular Powhatan Resort 2BDR

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

2BR Suite @ Historic Resort! Amenities Galore!
Other vacation rentals with a pool

Look Here! Great value 2BDR at Powhatan Resort.

Kingsgate 1 BedrooM

Historic Powhatan Resort 2 Bdrm! Sleeps 6

Governor’s Green 1BR Dlx Condo w/ Full Kitchen

Waterfront 4 bedroom home with marina facilities

Kingsgate Resort 3 Bedroom Lockoff

Eclectic and Cozy Apartment

Great value! Fantastic Powhatan resort vacation.
When is the best time to visit Williamsburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €87 | €93 | €101 | €110 | €116 | €122 | €124 | €111 | €91 | €99 | €104 | €85 |
| 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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- Busch Gardens Williamsburg
- Chesapeake Bay
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Pocahontas State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Greater Richmond Convention Center
- Old Dominion University
- Brown's Island
- Regent University
- First Landing Beach
- Chrysler Museum of Art
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Libby Hill Park
- The Poe Museum
- The National
- Forest Hill Park
- Virginia Holocaust Museum
- The Mariners' Museum





