Vacation 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.

0 of 0 items showing

1 of 3 pages

Top guest favorite

Four white Adirondack chairs are arranged on a grassy area overlooking the tranquil Corrotoman River. The scene features trees lining the water's edge, with gentle hills in the background under a softly overcast sky.

Home in Weems

5 out of 5 average rating, 15 reviews

Waterfront River Escape w/ Pool, Kayaks, Detached

Spacious and luxurious private retreat on bluff overlooking the Corrotoman River. Bring your boat and explore! Lounge around the pool, or grab a paddle board or kayak and explore. We also have a fun Maui Mat. Large game room with ping-pong, foosball, and couches perfect for the kids. Separate in-law suite. Easy drive to Kilmarnock, Irvington, White Stone. Chef services, charcuterie boards, fishing charters, special occasion packages, and discounts for local activities. Book this popular vacat

Superhost

The living area features a spacious layout with two light-colored sofas positioned around a central white coffee table. Natural light fills the room through multiple windows, illuminating the hardwood floor. A dining table is visible in the background, complemented by a decorative area rug.

Home in Virginia Beach

4.82 out of 5 average rating, 22 reviews

The VIBE House with POOL!

This amazing home located in the happening ViBe district of the Virginia Beach Oceanfront has it all! Personal in-ground pool and backyard dining table! Walking distance to the Virginia Beach Convention Center and Sports center. Also, on 6 blocks off all the action at the Virginia Beach boardwalk and oceanfront. Amazing restaurants, beautiful beach and waves, and all the local hot spots for shopping are all walkable from this home. A farmers market located on 19th street is steps away from the h

Guest favorite

A refreshing outdoor pool is surrounded by a spacious deck. Lounge chairs are positioned around the pool, set against a backdrop of lush greenery and distant buildings. Clear blue skies and gentle clouds enhance the serene atmosphere of the area.

Home in Cobbs Creek

4.9 out of 5 average rating, 148 reviews

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

Superhost

A spacious home is set among lush greenery, featuring large windows that allow natural light to flood the interior. A private, inviting saltwater pool is surrounded by a deck, with steps leading up to the house and shaded areas provided by patio umbrellas.

Home in Lancaster

4.63 out of 5 average rating, 19 reviews

Peaceful bay retreat. Hot tub,water views,fire pit

Peaceful get away on the sandy shores of the Corrotoman "Rivah" full of water activities. Fast WiFi, private saltwater pool(open May-Sept), kayaks, canoe, private sand beach, hot tub, full kitchen, pool table, firepit, deck with grill, outdoor dining tables. Deep water dock bring or rent a boat. Yankee Point Marina offers boat rentals, live music & restaurant w/in walking distance! Ride free ferry into Kilmarnock for shopping, restaurants & wineries. Kayak w/dolphins, watch Rock fish from dock

Top guest favorite

Home in Gloucester Point

4.99 out of 5 average rating, 177 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.

Guest favorite

A saltwater pool is bordered by white lounge chairs, offering a view of the Atlantic Ocean in the distance. A deck with beach umbrellas is visible beyond the pool, while the sunny sky features a few scattered clouds.

Condo in Virginia Beach

4.89 out of 5 average rating, 210 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Nestled in the heart of the coastal city of Virginia Beach where all of the area’s greatest attractions will be right at your fingertips. This coastal beach studio offers a space-maximizing layout which includes kitchenette with full size appliances. All on the desirable north end of the Virginia Beach boardwalk. This small oceanfront complex is one of a kind, a great place for couples or a small family. Enjoy an early morning cup of coffee while enjoying beautiful views of the Atlantic Ocean.

Guest favorite

Home in Cobbs Creek

4.98 out of 5 average rating, 152 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?

Top guest favorite

A private backyard pool area is highlighted, featuring a large in-ground pool surrounded by a concrete deck. Lush greenery and trees provide a natural backdrop, while a wooden fence offers privacy. Pool accessories are visible, indicating a space for relaxation and enjoyment.

Guest suite in Chesapeake

4.95 out of 5 average rating, 560 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

Superhost

Vacation home in Sandbridge

4.89 out of 5 average rating, 37 reviews

VB Paradise / Private Pool, Hot Tub

Outdoor living is king at “A Secret Spot”, a lovely cottage located at the north end of Sandbridge. Offering a beautiful outdoor pool area, fenced yard for children, covered hot tub, and plenty of decks and space to spread out or gather together! Under the house offers an outdoor living room with seating, a ping pong table, and picnic table. Imagine steamed crabs and drinks while relaxing with family by the pool. ! Inside there are more games for everyone to enjoy.

Guest favorite

A spacious backyard features a saltwater inground pool surrounded by manicured grass. A two-level deck is visible with patio furniture, offering comfortable seating options. The exterior of the two-story house is seen in the background, under a partly cloudy sky.

Home in Suffolk

4.84 out of 5 average rating, 87 reviews

Perfect Getaway!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

Top guest favorite

A private saltwater pool is depicted, surrounded by a spacious patio area. The pool's clear blue water is inviting, with a ladder providing easy access. Lush greenery and a white fence frame the background, enhancing the serene ambiance near the Chesapeake Bay.

Cottage in Norfolk

4.97 out of 5 average rating, 240 reviews

Positano Villa

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

Top guest favorite

An outdoor swimming pool is surrounded by a spacious deck area. Several white lounge chairs are arranged neatly along the poolside, providing spots for relaxation. Shade umbrellas are positioned at intervals, enhancing the leisure space. The pool is bordered by landscaped greenery and residential buildings.

Home in Virginia Beach

4.96 out of 5 average rating, 194 reviews

Sunrise, North End Beach

The beach AND privacy! Wide open residential beaches, with plenty of "distancing space"! Best kept secret at the beach! Fully stocked, fully furnished, immaculate Vacation rental on Va Beach North End. 5 star rating says it all. Atlantic Ocean across the street. Public beach access. 3 flat screen TVs, Wifi, cable, beach cart, chairs &'umbrella. Outdoor grill. Private parking. 2025 Pool Season... May 23–September 7. NO HAIR DYE!