Vacation rentals with a pool in Surry County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Surry County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Condo in Williamsburg

4.95 out of 5 average rating, 130 reviews

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!

Aug 14 – 21

G$32,231 GYD per night

Guest favorite

Home in Gloucester Point

4.99 out of 5 average rating, 146 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.

Feb 1 – 8

G$73,458 GYD per night

Guest favorite

Boat in Poquoson

4.93 out of 5 average rating, 92 reviews

Invictus: A Romantic Sailboat

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. We purposely chose this marina location for the incredible seafood restaurant only steps from the boat. You must try their amazing SheCrab soup! Afterwards, snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love sleeping to the gentle sway of calm waters. Come enjoy a night aboard this amazingly cozy & romantic sail boat. ;)

Oct 10 – 17

G$35,858 GYD per night

Guest favorite

Apartment in Hampton

4.96 out of 5 average rating, 365 reviews

"Shangri-La", of Hampton, Virginia

2nd story 1200 square foot apartment with 2 BR's, Wi-Fi, microwave, fridge and bar with sink. Walk in glass enclosed shower & soaker tub. Private deck with gas grill down the spiral stairs below on ground level patio. Pool table in BnB. We share our pool with our BnB guests seasonally. Please inquire about pool availability if important to your booking. Local history, sites, nature and beaches abound. Security cameras surround the exterior of our home for our protection as well as yours!

Mar 28 – Apr 4

G$28,913 GYD per night

Guest favorite

Farm stay in Cardinal

4.95 out of 5 average rating, 111 reviews

Wtrfrnt aptmnt w/pool/dock on private farm

Come enjoy all the outdoors has on offer at this secluded, waterfront estate. The spacious studio apartment is fully equipped for comfort. 12 acres of waterfront grounds to enjoy including great outdoor seating, fabulous bayside salt water pool. Fish, canoe and kayak right off the farms private dock. Grill and fire pit. Just 10 mins from the charming villages of Mathews and Gloucesters farm to table amenities. Great local food, music, history and shopping right on the bay!

Nov 3 – 10

G$28,766 GYD per night

Guest favorite

Farm stay in Williamsburg

4.96 out of 5 average rating, 319 reviews

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.

Feb 12 – 19

G$40,469 GYD per night

Guest favorite

Apartment in Hampton

4.97 out of 5 average rating, 69 reviews

Penthouse Paradise On The Harbor

Enjoy a stylish experience at our brand new, centrally-located , downtown penthouse suite. This property, directly overlooking the historic Docks @ Downtown Hampton features many attractions such as Virginia Air and Space Science Center, Hampton Coliseum, Buckroe Beach and Park. This space is also located within walking distance of many quaint restaurants and speakeasy's such as Pour Girls, Marker 20, Baked Bistro and Pizza, and Stillwater Tavern.

Feb 23 – Mar 2

G$27,410 GYD per night

Guest favorite

Cottage in Chesapeake

4.95 out of 5 average rating, 111 reviews

The Cottage @ Captain Genes - Secluded Waterfront

Get away from the crowds! Private, secluded upscale waterfront cottage on ~5 acres; pool/hot tub feet from the back door (hot tub open year round). Waterview from most rooms. Direct Chesapeake Bay access on property via dock / kayak launch. ~15 mins to downtown. Fish/crab, kayak, screened porch views, relax by the pool, fire pit or hot tub with a drink. Bring your boat - marina ~4 mi away - put-in there & tie-up at our pier!

Dec 19 – 26

G$57,468 GYD per night

Guest favorite

Guesthouse in Gloucester

5.0 out of 5 average rating, 106 reviews

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.

Sep 15 – 22

G$32,273 GYD per night

Guest favorite

Apartment in Suffolk

5.0 out of 5 average rating, 70 reviews

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.

Aug 17 – 24

G$24,424 GYD per night

Superhost

Apartment in Williamsburg

4.82 out of 5 average rating, 146 reviews

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.

Feb 19 – 26

G$28,037 GYD per night

Guest favorite

Apartment in Williamsburg

4.86 out of 5 average rating, 154 reviews

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.

May 27 – Jun 3

G$30,103 GYD per night