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

Total holiday rentals
Explore 1,680 holiday rentals in Williamsburg

Nightly prices starting at
Williamsburg holiday rentals start at $42 AUD per night before taxes and fees

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

Family-friendly holiday rentals
1,090 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
990 properties have a dedicated workspace

Wi-Fi availability
1,680 of Williamsburg holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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!
ValueLocationNearby
4.95 out of 5 average rating, 224 reviews
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.
ValueLocationKitchen
4.99 out of 5 average rating, 226 reviews
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.
FamilyLocationLaundry
4.95 out of 5 average rating, 146 reviews
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?
ValueLocationHot tub
4.98 out of 5 average rating, 176 reviews
WaterVue at Kingsmill
Welcome to WaterVue; our Kingsmill, home-away-from-home in historic Williamsburg, Virginia. Be one of the first to stay in spacious style with completely updated amenities. You will be treated to fresh, clean accommodations, soft linens; everything you need is available for your stay. Sit and relax on any of the balconies that overlook Wareham's Pond. Catch wildlife passing by or hear the memorable train whistle from Busch Gardens next door. Close your eyes and experience serenity and peace.
FamilyLocationCheck-in
4.93 out of 5 average rating, 30 reviews
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
ValueLocationCheck-in
4.89 out of 5 average rating, 47 reviews
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)
LocationFamilyWi-Fi
4.72 out of 5 average rating, 147 reviews
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
ValueFamilyHeating
5.0 out of 5 average rating, 205 reviews
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!!!
LocationFamilyBeach
4.87 out of 5 average rating, 141 reviews
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.
LocationValueAccuracy
4.86 out of 5 average rating, 35 reviews
3 Bed, 3 Bath Sleeps 8 in Kingsmill
Welcome to your luxurious retreat at Kingsmill on the James River. This spacious and elegantly appointed 3-bedroom, 3-bathroom condominium is located on the serene first floor, offering refined comfort in a private, gated community, overlooking the 9th fairway of the famed Kingsmill River Course. For smaller groups, we also have a 2 bed, 2 bath option available. Please, no parties or pets.
FamilyLocationGetting around
4.98 out of 5 average rating, 41 reviews
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.
LocationFamilyBeach
4.93 out of 5 average rating, 123 reviewsPopular amenities for Williamsburg rentals with a pool
House rentals with a pool

Million $ Views! Pool! Private Hot Tub! EV Charger
FamilyValueWi-Fi
4.91 out of 5 average rating, 182 reviews
Gothic Cottage, Hot Tub, Walk to Town
ValueFamilyHot tub
4.95 out of 5 average rating, 182 reviews
Rappahannock Waterfront Pool, Kayak, Deck, Firepit
LocationValueCondition
4.97 out of 5 average rating, 178 reviews
The Great River Escape *Hot Tub!
ValueLocationBackyard
4.88 out of 5 average rating, 112 reviews
The Rosé Retreat: Pool-Screened Porch-RELAX
FamilyLocationWalkability
4.99 out of 5 average rating, 134 reviews
Gorgeous Vacation House
FamilyLocationCheckout
4.9 out of 5 average rating, 145 reviews
America's 250 Getaway | Pool | Busch Gdns | Wmbg
LocationFamilyAir conditioning
4.93 out of 5 average rating, 61 reviews
One Level Home | Boats Welcome! | Rockfish | Golf
LocationFamilyHospitality
5.0 out of 5 average rating, 8 reviewsCondo rentals with a pool

Colonial Williamsburg Spacious 4 Bedroom Suite!
FamilyLocationHospitality
4.91 out of 5 average rating, 156 reviews
Marriott's Manor Club Ford's Colony 2BD Villa Slee
LocationValueAmenities
4.96 out of 5 average rating, 55 reviews
Family reunion? Here ya go! 8BDR/8BA sleeps 24!
ValueFamilyNearby
4.79 out of 5 average rating, 14 reviews
Wyndham Kingsgate (2 BR)
FamilyLocationNearby
5.0 out of 5 average rating, 22 reviews
Wyndham Kingsgate- 1BR- Apartment with Resort Acce
LocationFamilyAccess
4.85 out of 5 average rating, 34 reviews
Charming 2BR Colonial Condo at Wyndham Kingsgate
FamilyLocationIndoor spaces
4.77 out of 5 average rating, 31 reviews
Wyndham Governor's Green, 3 BR Deluxe
ValueFamilyKitchen
4.83 out of 5 average rating, 53 reviews
Wyndham Kingsgate 3BD/3BA LO
ValueLocationAmenities
4.93 out of 5 average rating, 14 reviewsOther holiday rentals with a pool

Perfect for the family! 4BR townhouse near it all!
LocationFamilyQuiet
4.91 out of 5 average rating, 55 reviews
Kingsgate Resort 3 Bedroom Lockoff
ValueFamilyCheck-in
4.88 out of 5 average rating, 73 reviews
Kingsgate 2BR w/ Kitchen
FamilyValueIndoor spaces
4.96 out of 5 average rating, 24 reviews
Kingsgate one BEDroom
ValueAccessHospitality
4.89 out of 5 average rating, 9 reviews
KINgsgate 1 Bedroom
LocationFamilyHospitality
4.75 out of 5 average rating, 16 reviews
Cottage - Williamsburg Pet-Friendly, Heated Pool
FamilyValueHospitality
4.8 out of 5 average rating, 54 reviews
Family-friendly 1BR/1BA condo @ Kingsgate
FamilyLocationCleanliness
4.91 out of 5 average rating, 55 reviews
Two Bedroom Suite in Charming Williamsburg
FamilyLocationHospitality
4.58 out of 5 average rating, 292 reviewsWhen is the best time to visit Williamsburg?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $139 AUD | $149 AUD | $163 AUD | $187 AUD | $190 AUD | $195 AUD | $199 AUD | $178 AUD | $146 AUD | $159 AUD | $167 AUD | $136 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 |
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- Rentals with pools Virginia
- Rentals with pools United States
- 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
- The National
- Virginia Holocaust Museum
- Forest Hill Park
- Libby Hill Park
- The Mariners' Museum
- Town Point Park
- The Poe Museum





