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

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Summer Waterfront โข Dock, Pool, & 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 - Firepit evenings, and true outdoor living - Dock, kayaks, fishing, and direct water access -Outdooring dining options and family-friendly - Immaculately clean and thoughtfully stocked for a seamless stay - Peaceful setting just minutes from downtown Gloucester

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

The Rosรฉ Retreat: Pool-Screened Porch-RELAX
Escape to The Rosรฉ 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 Rosรฉ Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosรฉ 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?

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.

Waterfront Cottage Getaway Views/Kayaks/Fire Pit
A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks โ perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

Beachfront with a View and Amenities Galore
Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with a breathtaking view of the beach and ocean.

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.

Va.Beach/Oceanfront Studio, Boardwalk, Beach, Pool
Nestled on the desirable north end of the boardwalk, close to the areaโs 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.

Peaceful Haven: nature & 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.

Historic Rousby Hall, Waterfront, Pool, Beach
Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).
Popular amenities for Eastern Shore of Virginia rentals with a pool
House rentals with a pool

The Glebe

Bayside community near OCMD great rates

Country Comfort Close to the Beaches

Private Pool at the Oceanfront in a Spacious Home

Gorgeous Vacation House

Sunrise, North End Beach

Perfect Getaway!

Mosaic Life Escapes -Bayfront Million Dollar Views
Apartment rentals with a pool

Luxurious Oceanfront Retreat with Amazing Views!

PENTHOUSE - 8TH Floor Boardwalk/Epic Views/Pool/

Kingsmill 1bed/1ba on Golf Course 9th Fairway

DownByTheBay 4601-Midtown/Oversize Sleep 15 w/Pool

Gone Coastal *Pool* Bayside with view* Top Floor

๐Carousel Oceanfront 2 Bedroom Amazing Amenities

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

Water Front Condo w/Pool Short Walk to Beach
Other holiday rentals with a pool

Waterfront Escape Pool Dock Kayaks Chesapeake Bay

Country Living Guest House (Upstairs/Downstairs)

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

Sanctuary on Sandpiper - Bayfront in Sandbridge

Hot Tub - Massage Chair - Golf Cart - Beach Gear

Nature's retreat @ the Bug-a-Boo. Beaches nearby

Amazing oceanfront view 3 blocks from boardwalk

Spring Hill Guest Cottage - Portsmouth
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- Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Assateague Island National Seashore
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- First Landing Beach
- Virginia Living History Museum
- Hampton University
- Neptune's Park
- The Mariners' Museum
- Virginia Air & Space Sci. Center
- Sandy Bottom Nature Park
- Cape Henry Light House
- Bluebird Gap Farm




