
Vacation rentals with a pool in Williamsburg
Find and book unique homes with a pool on Airbnb
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.

Waterfront Cottage Getaway Views/Kayaks/Fire Pit
A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

Chic Urban Living: 1BR in Kingsgate!
Furnished in the Colonial style, this resort offers all the modern amenities and activities you could want. Surrounded by the area's top attractions and historic landmarks, there's plenty to explore, ensuring that your getaway is one to remember. • Guest checking in must be 21+ with valid ID. • Guest must have debit/credit card to put $250 refundable security deposit on hold at resort check-in. . Resort Fee at $7 per night. • Name on reservation must match photo ID at check-in.

Colonial Williamsburg Spacious 4 Bedroom Suite!
This Resort is located on 256 acres of rolling woodland hills in historic Williamsburg, Virginia. The resort’s distinguished manor house that was originally built in 1735 captures the true essence of its Colonial surroundings. Discover the nation’s history at one of Williamsburg’s history museums, monuments or battlefields. The Resort features an indoor & outdoor pool, tennis court, playground. All suites have full kitchens, living/dining rooms & sleeper sofa.

3 BR Cottage on Mallardee Farm in Williamsburg
Enjoy all the comforts of home during your Williamsburg vacation at Mallardee Farm! Allow us to make our home, your home while you explore all of Williamsburg’s attractions-just a 15 minute drive away! You’ll find that Mallardee Farm will serve as its own attraction with our friendly, rescued farm pets, walking trails through the 57 acre property, complimentary fishing poles, canoe, row boat & kayaks to use on our 7 acre pond. Covid-19 precautions followed.

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)

Peaceful Haven: nature & charming town
Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen.

Creekside Guesthouse - Dock and Pool on 10 acres
With stunning views overlooking Bland Creek, this guesthouse is the perfect place to unwind or start your adventure. This two-bedroom apartment is nestled high in the treetops, perfectly situated on 10 acres of wooded and coastal beauty. When the time comes to explore, guests are only minutes away from eclectic shopping and dining in historic downtown Gloucester, with Williamsburg and Richmond an easy 45 minutes away.

2 Bedroom Greensprings Vacation Resort (Sleeps 6)
Located in historic Williamsburg, Virginia, Greensprings Vacation Resort features the essential amenities you need for an unforgettable vacation. Covid-19 Enhanced cleaning protocols in place. • Guest checking in must be 21+ with valid ID. • Guest must have debit/credit card to put $100 refundable security deposit on hold at resort check-in. • Name on reservation must match photo ID at check-in.

Westgate Historic Williamsburg One Bedroom
Offering a one bedroom apartment in Westgate Historic Williamsburg Resort with a king size bed, sofa bed and full kitchen. This fabulous resort has fantastic amenities and is a great location to visit the area attractions such as Colonial Williamsburg, Busch Gardens Williamsburg and Water Country USA. A great location to visit the local attractions.

Historic Powhatan Resort- 2 bedroom condo!
Peacefully situated amid 256 acres of rolling woodland hills, and boasting all the character of a distinguished manor house, The Historic Powhatan Resort captures the essence of its Colonial surroundings. Originally built circa 1735, this restored manor house offers a serene getaway during any season.
Popular amenities for Williamsburg rentals with a pool
House rentals with a pool

Wooded Wonderland Miniature Golf Hot tub Pool

Waterfront panoramic point with pool

Gorgeous Vacation House

Blue Heron WaterSide

The Rosé Retreat: Kayaks-Screened Porch-RELAX

Perfect Getaway!

Magical wooded cottage pool +priv hottub walk2town

Waterfront 4BR | Pool & Peaceful Deltaville Views
Condo rentals with a pool

Charming 1BR Colonial Condo at Wyndham Kingsgate

The Historic Powhatan, 2br suite, Saturday check-i

Historic Powhatan resort 2 bdrm

1br Colonial in Williamsburg -Fun by Busch Gardens

Kingsgate- 3 bedroom Williamsburg, VA

Williamsburg Vacation Villages Resort 2BR, 2BA

Club Wyndham Kingsgate One-Bedroom Condo

Wyndham Patriots Place | King Bed Studio
Other vacation rentals with a pool

Charming 2BR Colonial Condo at Wyndham Kingsgate

Patriots Place studio

Historic Powhatan Resort- 2 bedroom condo!

The Cottage @ Captain Genes - Secluded Waterfront

Historic Powhatan Resort- 2 bedroom condo!

Historic Powhatan Resort- 2 bedroom

Relaxing Retreat w/ Pool, Golf & Fireplace

Calm & Beautiful
When is the best time to visit Williamsburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$20,703 GYD | G$21,749 GYD | G$25,304 GYD | G$26,349 GYD | G$27,813 GYD | G$29,068 GYD | G$29,695 GYD | G$26,558 GYD | G$21,749 GYD | G$24,676 GYD | G$26,768 GYD | G$23,422 GYD |
| 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 |
Quick stats about vacation rentals with a pool in Williamsburg

Total vacation rentals
Explore 1,700 vacation rentals in Williamsburg

Nightly prices starting at
Williamsburg vacation rentals start at G$6,274 GYD per night before taxes and fees

Verified guest reviews
Over 9,850 verified reviews to help you choose

Family-friendly vacation rentals
1,000 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
1,010 properties have a dedicated workspace

Wi-Fi availability
1,700 of Williamsburg vacation rentals include wi-fi access

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

4.7 Average rating
Williamsburg stays receive an average rating of 4.7 out of 5 from guests
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- Chesapeake Bay
- Busch Gardens Williamsburg
- Buckroe Beach
- Carytown
- Water Country USA
- First Landing State Park
- Haven Beach
- Pocahontas State Park
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- Brown's Island
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