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

Bay Creek Home~ King Suite & Family Friendly Loft!
Escape to your brand-new coastal beach retreat! This home features seaside decor and a serene atmosphere, blending comfort and elegance. Your kitchen is a chef's dream with a gas stove, granite countertops, and a bar area with a wine and drink fridge. You'll love the private beachfront access and community pool. Play pickleball or tennis, then relax with a drink on the front porch or play cards on the screened-in back porch. Shops and restaurants are just a 5-minute drive or golf cart ride away.

The Great River Escape *Hot Tub!
Welcome to the River Escape, where the sun is hot and river breezes are cool! Located on the Hampton River, on a big fenced lot, with easy river access and just a 10 minute drive to sandy toes and the sound of crashing waves, this fantastic river house is made for the best family vacations around. It is furnished to comfortably sleep 6, featuring a spacious, well-stocked kitchen, private in-ground pool, hot tuband a gas grill in the backyard! Just add family, and you've got instant vacation fun!

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

Hot Tub - Massage Chair - Golf Cart - Beach Gear
Whether you are looking for some rest and relaxation, a home-base for the beach or water activities, or a place that comfortably allows you to bring your pets, you are sure to find your desired experience at Paws at the Beach. Open concept space with large glass doors and window to bring in natural light. Sunset room with multiple entertainment options, a massage chair in the living room and a Hot Tub. Four bedrooms that comfortably sleep 10. Rental includes access to a four-seater golf cart!

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?

The Barn at Pond Point - Riverfront Home
The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

“Old Smokey”A cozy, single bedroom, unique getaway
"Old Smokey" is a 1965 pull-behind camper that has been beautifully remodeled. It is cozy, rustic and has been restructured with lots of love. You can enjoy breathtaking sunrises and sunsets. The camper has both air conditioning and a wood stove. "Old Smokey" is a unique and romantic glamping experience. You can cook delicious meals on the propane stove/grill or visit one of our charming local restaurants. This is the perfect location to relax and reset, either solo or with someone special.

"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!

Gorgeous Vacation House
This is is the perfect home away from home! Enjoy cozy furnishings and modern amenities in this 3bed/2.5 bath house located in the vibrant city of Norfolk oceanview. The house is renovated with top notch material and artistic touch. The kitchen, living room, and private backyard with deck/patio swimming pool make it the ideal place to relax. Shopping, restaurants, and entertainment are all within minutes; plus onsite parking and self-check-in make this an ideal destination for travelers.

East of the Sun Victorian - Private Pool
Back after a 2-year hiatus! East of the Sun is a fully-restored ca. 1890 Victorian (3 en-suites) with a large screen porch and private, 12' round plunge pool. Our place is ideally suited for 3 couples or families with older children. We welcome younger children as long as parents confirm they're okay with 3 floors/2 sets of stairs, antiques, and a pool. We have a strict limit of 6 guests (however, children under 2-years do not count). We offer a 3-night minimum both low and high season.

Heartsong Farmhouse , a nature lover's retreat.
Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

Oysterman's Pearl Golf Cart Included
Luxury Home with Golf cart included! Spacious beach house with a luxury touches. Great place to escape and enjoy the private amenities of Bay Creek while being a short walk or golf cart ride to downtown Cape Charles. Relax on the screened in porch or enjoy the breeze from the crows nest on the 3rd floor. This home has everything you need to have a relaxing beach vacation with the comforts of feeling at home. Bay Creek HOA pool, tennis courts, and YMCA pool and gym passes included.
Popular amenities for Cape Charles rentals with a pool
House rentals with a pool

Harbor Master

Waterfront panoramic point with pool

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

Chesapeake Bay Retreat Waterfront Indoor Pool

Waterfront Getaway w/ Pool, Firepit, Kayaks, Dock

Star by The Sea

14th & Hoos

Bay Creek (Pool!) Meets Historic Cape Charles!
Condo rentals with a pool

Rendezvous, a Resort Condo in Cape Charles

Updated Condo in Golf Community Featuring Access t

Spacious First Floor Condo in Golf Community With

Relaxing Condo in Golf Community With Access to Cl

Pool Across Street~ Kayaks, Beach, Bikes & Golf!

Ocean’s Eleven: A Steal of a Stay by the Bay

Bay Creek Retreat Near Beach & Golf + Incl. Bikes

Bay Creek Blessed at The Fairways
Other vacation rentals with a pool

Get away to the heart of Deltaville!

ShowTyme's Hampton Oasis

The Pearl | New Home w Pool, Beach & more!

Waterfront Studio | Walk to Downtown + HU

S/V Osprey - Sailboat

3-Bedroom house with a dock and pool access

Frank’s Landing

BEACH/ POOL HOUS, 1 min walk to the beach Norfolk
Quick stats about vacation rentals with a pool in Cape Charles

Total vacation rentals
Explore 40 vacation rentals in Cape Charles

Nightly prices starting at
Cape Charles vacation rentals start at G$18,804 GYD per night before taxes and fees

Verified guest reviews
Over 470 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Cape Charles vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cape Charles rentals

4.9 Average rating
Cape Charles stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with pools Northampton County
- Rentals with pools Virginia
- Rentals with pools United States
- Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- Cape Charles Beachfront
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Kiptopeke Beach
- Old Dominion University
- Hampton University
- First Landing Beach
- Regent University
- Town Point Park
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Neptune's Park
- Virginia Living History Museum
- Chrysler Hall





