
Holiday 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.

Beautiful 1BR at Williamsburg + Amenities
Built on the lush grounds of a former golf course, this quiet resort community is surrounded by the stunning landscape and historic spirit of Williamsburg. A great retreat any time of year, its central location also provides convenient access to explore all the area has to offer. • 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. • Name on reservation must match photo ID at check-in.

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.

Wyndham Kingsgate (3 BD LO)
The Wyndham Kingsgate resort is less than a mile away from Historic Williamsburg and seven miles from Busch Gardens. The resort has a friendly staff that is available 24/7. The unit we have available for rent is a spacious 3 bedroom 3 bath lock off with a separate living and dining rooms, private balconies, washer/dryer and a full kitchen. . My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups.

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.

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. Sumptuous, spacious accommodations offer a private balcony, loft and hot tub. Originally built circa 1735, this restored manor house offers a serene getaway during any season.

Country Living Guest House (Upstairs/Downstairs)
This country living guest suite is conveniently positioned on Lone Star Lakes Park. It is located in a quiet, private drive. Prepare quality meals in the down-stairs fully equipped eat-in kitchen with built-in cabinets, spacious countertops, a full-sized fridge, an electric stove, and everything you need to feel at home. Just off the kitchen is a half-bath. NO PETS ALLOWED.

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.
Popular amenities for Williamsburg rentals with a pool
House rentals with a pool

Wooded Wonderland Miniature Golf Hot tub Pool

Beautiful country house with 5 bedrooms 4.5 baths

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

Patriots Place, one bedroom condo, cozy space

1BR Colonial Suite at Kingsgate | Williamsburg, VA

Wyndham Patriots Place | King Bed Studio

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

1br Colonial in Williamsburg -Fun by Busch Gardens

Williamsburg Vacation Villages Resort 2BR, 2BA

Club Wyndham Kingsgate One-Bedroom Condo

Colonial Williamsburg Spacious 4 Bedroom Suite!
Other holiday rentals with a pool

Historic Powhatan Resort 2 Bdrm! Sleeps 6

Charming 1BR Colonial Condo at Wyndham Kingsgate

Chesapeake Bay Retreat Waterfront Indoor Pool

Historic Charm & Modern Comfort at Hilton Powhatan

2 bedroom at The Historic Powhatan Resort

Historic Powhatan Resort- 2 bedroom condo!

Patriots Place 2 BEDroom

*Historic Powhatan Resort- 2 bedroom
When is the best time to visit Williamsburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $153 AUD | $160 AUD | $187 AUD | $194 AUD | $205 AUD | $214 AUD | $219 AUD | $196 AUD | $160 AUD | $182 AUD | $197 AUD | $173 AUD |
| 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 holiday rentals with a pool in Williamsburg

Total holiday rentals
Explore 1,700 holiday rentals in Williamsburg

Nightly prices starting at
Williamsburg holiday rentals start at $46 AUD per night before taxes and fees

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

Family-friendly holiday rentals
1,000 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

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

Wi-Fi availability
1,700 of Williamsburg holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Buckroe Beach and Park
- Pocahontas State Park
- Brown's Island
- Grandview Beach
- Jamestown Settlement
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