
Holiday rentals with a pool in Hampton Roads
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Hampton Roads
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

Wooded Wonderland Miniature Golf Hot tub Pool
Make yourself at home! This property offers a warm and welcoming environment for guest, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

"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!

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.

The Laughing King Retreat Honeymoon Island Cottage
Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

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!

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.

THE OLD BEACON 3 I Beach Living
The Old Beacon unit 3 is a two story unit with living space on the first floor and bedrooms on the second floor. It’s one of the units of the back cottage on the property. Adorable, cozy interior with access to the amazing outdoor common area - pool, cornhole, porch swings, outdoor dining area, and outdoor shower for when you return from the beach! Kick back and relax in this calm, stylish space that’s two blocks to the beach and Virginia Beach boardwalk!

Va.Beach/Oceanfront Studio, Boardwalk, Beach, Pool
Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

Oceanfront Studio: Boardwalk, Beach, & Pool Views
Atlantic Ocean views from the comfort of an Oceanfront studio, perfect for beach-loving travelers. Reserved parking space just steps from the beach, indulge in the sand & surf without having to cross a street. Park your car, & let your toes sink into the sand for a truly relaxing stay. Equipped with Wi-Fi & Roku TV, you can stay connected throughout your visit. Take a refreshing dip in the saltwater pool or lounge on the lawn just steps from the beach.

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.

Beautiful and Chic Studio Apartment
Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.
Popular amenities for Hampton Roads rentals with a pool
House rentals with a pool

The Golden Hour Pool is Open until October 5th!

Spacious 4BR Home w/ Pool • Family Friendly

The Sandbridge Jewel

The Seaglass Cottage

Private Pool at the Oceanfront in a Spacious Home

Stunning Views of Back Bay & Seconds to the Beach

Beach House with breathtaking sunsets

Sunrise, North End Beach
Apartment rentals with a pool

Beach Luxury Beachfront

New Oceanfront 2bd, 2bth / Beach / Pool / Boat

2BD2BA Condo w/Pool2Blocks2Beach

Paradise at the Beach

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Boardwalk Oceanfront Condo | Pool + Dining

Ocean Escape

Colonial Williamsburg Spacious 4 Bedroom Suite!
Other holiday rentals with a pool

Jen n John's Mini Mansion.

The Green Bean Bungalow

Ava’s Estuary

POOL, Pool House, Hot Tub, Grill, 2 bedroom

Oceanfront Queen Suite in Virginia Beach

Oceanfront Building Boardwalk Pool Beach 3 Beds

Beautiful 1BR at Williamsburg + Amenities

Oceanfront Views! 2 BR, 2 BATH!
Destinations to explore
- New York City Holiday rentals
- Washington Holiday rentals
- Myrtle Beach Holiday rentals
- East River Holiday rentals
- Philadelphia Holiday rentals
- Mount Pocono Holiday rentals
- Jersey Shore Holiday rentals
- Outer Banks Holiday rentals
- Ocean City Holiday rentals
- Charlotte Holiday rentals
- South Jersey Holiday rentals
- Virginia Beach Holiday rentals
- Smoking-friendly rentals Hampton Roads
- Rentals with breakfast Hampton Roads
- Townhouse rentals Hampton Roads
- Apartment rentals Hampton Roads
- Rentals with a hot tub Hampton Roads
- Fitness-friendly rentals Hampton Roads
- Beachfront rentals Hampton Roads
- Rentals with a patio Hampton Roads
- Family-friendly rentals Hampton Roads
- Rentals with beach access Hampton Roads
- Rentals with a firepit Hampton Roads
- Waterfront rentals Hampton Roads
- Rentals with a fireplace Hampton Roads
- Rentals with outdoor seating Hampton Roads
- Pet-friendly rentals Hampton Roads
- Flat rentals Hampton Roads
- Cottage rentals Hampton Roads
- Rentals with a kayak Hampton Roads
- House rentals Hampton Roads
- Rentals with a washing machine and dryer Hampton Roads
- Rentals with lake access Hampton Roads
- Rentals with pools Virginia
- Rentals with pools United States
- Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Kingsmill Resort
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Royal New Kent Golf Club
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Wilkins Beach
- James River Country Club