
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!

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!
Welcome to The Cottage at Misti Cove, where you can experience the epitome of relaxation and tranquility. Immerse yourself in the serene ambiance of our cottage, aptly named for its simplicity, which belies the luxurious amenities that await you. At The Cottage at Misti Cove, we understand that the essence of a fulfilling vacation lies in the delicate balance between embracing the simple life and indulging in modern comforts. Here, you will discover a haven that seamlessly blends these elements

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: Pool-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?

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.

Suitable 1BR Near Top Attractions!
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 $15 per night. • Name on reservation must match photo ID at check-in.

Best Resort/$$$ for Colonial Wburg & Busch Gardens
Our place is close to restaurants, supermarkets, dining and family-friendly activities. The resort is great for couples, solo adventurers, business travelers, families (with kids), and big groups. We are 10 minutes from Colonial Wburg & Jamestown and 20 minutes from Busch Gardens. We can provide either a 1st FL unit with a King in the MBR and 2 twins in the 2nd BR or a 2nd FL unit with Queen beds in each room. Your choice. If available at the resort, default will be 1st FL.

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 minutes from downtown Gloucester

Peaceful Haven: nature, pool, 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.

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.

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.
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

Perfect Getaway!

Rappahannock Waterfront, Pool, Kayaks, Rose Garden

Serenity Farm Equestrian Retreat in Historic VA

POOL OPEN | Deltaville Riverfront Getaway | 4BR

𓂃Tidal Creek Retreat: Near CNU, JLab and Busch𓂃
Apartment rentals with a pool

Spacious, 4 Bedroom Family Suite in Williamsburg!

Charming 1BR Colonial Condo at Wyndham Kingsgate

Vacation Village at Williamsburg

Mini Golf | Arcade | Pool @ Club Wyndham Kingsgate

Greensprings 4BDR for 12. Great location. $269 up

Wyndham Governor's Green, 2 BR Deluxe

Kingsgate- 3 bedroom Williamsburg, VA

Williamsburg Vacation Villages Resort 2BR, 2BA
Other holiday rentals with a pool

Kingsgate Resort 3 Bedroom Lockoff

Suitable 1BR Near Top Attractions!

Two Bedroom Suite in Charming Williamsburg

The Cottage @ Captain Genes - Secluded Waterfront

Waterfront Getaway w/ Pool, Firepit, Kayaks, Dock

The Colonies at Williamsburg: 4-BR, Sleeps 12

Club Wyndham Kingsgate One-Bedroom Condo

Private 5-acre Waterfront Peninsula with Beach
When is the best time to visit Williamsburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $127 SGD | $136 SGD | $148 SGD | $161 SGD | $170 SGD | $178 SGD | $182 SGD | $163 SGD | $133 SGD | $145 SGD | $152 SGD | $124 SGD |
| 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 1,630 holiday rentals in Williamsburg

Nightly prices starting at
Williamsburg holiday rentals start at $38 SGD per night before taxes and fees

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

Family-friendly holiday rentals
1,070 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
930 properties have a dedicated workspace

Wifi availability
1,630 of Williamsburg holiday rentals include wifi 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!
Destinations to explore
- Norfolk Holiday rentals
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Myrtle Beach Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Outer Banks Holiday rentals
- Rentals with breakfast Williamsburg
- Rentals with a hot tub Williamsburg
- Villa rentals Williamsburg
- Serviced apartment rentals Williamsburg
- Bed and breakfasts Williamsburg
- House rentals Williamsburg
- Rentals with a fireplace Williamsburg
- Rentals with a sauna Williamsburg
- Pet-friendly rentals Williamsburg
- Flat rentals Williamsburg
- Rentals with a cinema Williamsburg
- Hotel rooms Williamsburg
- Rentals with beach access Williamsburg
- Fitness-friendly rentals Williamsburg
- Apartment rentals Williamsburg
- Cottage rentals Williamsburg
- Resort rentals Williamsburg
- Rentals with a washing machine and dryer Williamsburg
- Rentals with lake access Williamsburg
- Rentals with outdoor seating Williamsburg
- Rentals with a patio Williamsburg
- Rentals with a firepit Williamsburg
- Family-friendly rentals Williamsburg
- 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
- Greater Richmond Convention Center
- Jamestown Settlement
- Pocahontas State Park
- Brown's Island
- Norfolk Botanical Garden
- Outlook Beach
- Kingsmill Resort
- Chrysler Museum of Art
- Libby Hill Park
- Old Dominion University
- First Landing Beach
- Nauticus
- Neptune's Park
- The Poe Museum
- Kiptopeke Beach
- Colonial Williamsburg's Merchants Square
- Regent University
- Science Museum of Virginia





