
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.

The Rosé Retreat: Fireplace-Screened Porch-RELAX
Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

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?

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.

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.

Waterfront Escape • Pool, Dock & Creek View
A peaceful waterfront retreat tucked into 10 wooded acres above Bland Creek, perfect for long summer days and relaxed evenings. - Private screened-in porch with cooling creek breezes - Pool days, firepits under the stars, and quiet moments outdoors - Kayaks, a floating dock, fishing, and nature right outside your door - Immaculately clean and thoughtfully stocked for a stress-free stay - Quiet setting just minutes from downtown Gloucester

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.

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.

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.

1 Bedroom @ The Historic Powhatan Resort
Step back in time at The Historic Powhatan Resort, located on 256 acres of rolling woodland hills in historic Williamsburg, Virginia. • 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.
Popular amenities for Williamsburg rentals with a pool
House rentals with a pool

Wooded Wonderland Miniature Golf Hot tub Pool

Chesapeake Bay Retreat Waterfront Indoor Pool

Our Home Away from Home

Gorgeous Vacation House

Perfect Getaway!

Magical wooded cottage pool +priv hottub walk2town

𓂃Tidal Creek Retreat: Near CNU, JLab and Busch𓂃

4BD home w/ game room & pool near Langley & PTC!
Condo rentals with a pool

Apartment Resort Williamsburg 2bdrm

Charming 3BR Colonial Condo at Wyndham Kingsgate

Wyndham Governor's Green (3 BD Deluxe)

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

Greensprings Vacation Resort-2 bdrm

Lovely 2 Bedroom Condo in 4Diamond Historic Resort

Big family 4BR (12) townhouse.

Patriots Place 2 Bedroom
Other holiday rentals with a pool

Amazing 2 bdrm at The Colonies

Kingsgate one bedroom

Historic Powhatan Resort- 4 bedroom condo!

Patriots Place studio

Waterfront Hot-Tub, Canoe & Firepit w/ Dock

The Cottages at King's Creek Plantation -- 1BR4

Club Wyndham Kingsgate One-Bedroom Condo

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 | $141 AUD | $148 AUD | $173 AUD | $180 AUD | $190 AUD | $198 AUD | $203 AUD | $181 AUD | $148 AUD | $161 AUD | $170 AUD | $138 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 1,690 holiday rentals in Williamsburg

Nightly prices starting at
Williamsburg holiday rentals start at $43 AUD per night before taxes and fees

Verified guest reviews
Over 10,640 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
960 properties have a dedicated workspace

Wi-Fi availability
1,690 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
- Carytown
- Water Country USA
- First Landing State Park
- Pocahontas State Park
- Buckroe Beach
- Jamestown Settlement
- Brown's Island
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Outlook Beach
- Libby Hill Park
- Chrysler Museum of Art
- Science Museum of Virginia
- The Poe Museum
- Hollywood Cemetery
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- Greater Richmond Convention Center
- Forest Hill Park
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- The NorVa
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