
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.

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

“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.

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.

Magical wooded cottage pool +priv hottub walk2town
Set among the trees on 2 peaceful wooded acres, this cottage delights with gothic architecture, sun-filled rooms, and a bathroom for every bedroom. Relax in the hot tub under the stars, sip local wines, eat oysters. Take a sunset boat cruise or learn oystering and crabbing from a local waterman. Farm stands, markets, and sea-to-table local fare. Live life in an historic working water town with lots of personality. Close to Tides Inn, Kilmarnock, White Stone, Compass Entertainment.

Big Cozy Loft Overlooking the Farm and River
The cozy loft is located above the apiary workshop. It is a spacious, kind suite with a walk-in bath featuring a rainforest shower. Windows overlook the donkey pasture, river, farm, and gardens. Designed for a true retreat, there is no WiFi, TV, or smoking. For breakfast, travel on over to Sugar Water Restaurant to have a free breakfast with coffee, tea, juice, and more. The Loft includes a small refrigerator plus coffee and tea essentials. Please note: children are not permitted.

Artful Retreat with a Private Pool
Take a break and unwind at your private pool! Stylish, updated interior and a spacious backyard with pool and lounge area. Rinse off at the outdoor shower after a day at the beach and enjoy your private retreat! The Rudee Inlet is less than a block away with great restaurants, fishing, and water activities. A path along the Rudee Inlet leads to the beach and shops - a quick 4 block trip with the included bikes! Outdoor seating and gas fire pit added for the cooler months!

Summer Escape - Dock, Pool, Firepits, & 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 (open Memorial Day–Labor Day) - Dock, kayaks, fishing, firepits, and direct water access -Outdooring dining options and family-friendly - Immaculately clean and thoughtfully stocked for a seamless stay - Just minutes from downtown Gloucester

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.

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU
BEFORE BOOKING: Pool will be open 4/05/26 Unless PRIOR AUTHORIZATION….. NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your party are allowed on the property. Fully restored top to bottom 1920s farm house. Every bedroom has its own full bathroom Full laundry room with extra refrigerator RH furniture All bedding/towels/paper towels/toilet paper/body wash/shampoo/conditioner/spices/laundry detergent included;Total turn key

Peaceful Haven: nature, pool, 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.
Popular amenities for Eastern Shore of Virginia rentals with a pool
House rentals with a pool

Retreat with Pool, Walk to Beach

Wooded Wonderland Miniature Golf Hot tub Pool

Waterfront, Pool + Beach, Dock + Kayaks, Potomac

Harbor Master

The Glebe

Coastal Waterfront Escape + Hot Tub & Kayaks

Hot Tub - Massage Chair - Golf Cart - Beach Gear

Perfect Getaway!
Apartment rentals with a pool

Boutique Moments OC • Pool • Walk to Boardwalk

Bluewater Couples Escape

Oceanfront Gem VaB Studio Exceptional Views

Completely Renovated Luxury Bay Front Condo

Oceanview Oasis with 2 private balconies

Oceanfront Bldg.| 2 pools | Tennis | Game Room

Love Above the Waves-OceanView/Rooftop Heated Pool

Water view at Ocean Pines Yacht Club Condo
Other holiday rentals with a pool

Waterfront Escape Pool Dock Kayaks Chesapeake Bay

Rivah Getaway!

Waterfront home-225' pier kayak firepit pool beach

East of the Sun Victorian - Private Pool

Rosses Chance Guest House

Holiday Cottages -"Sea Star"~POOL~3 mi. to Beach

The Cozy Cottage At Grateful Meadows

The Sportman's Lodge
Destinations to explore
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Ocean City Holiday rentals
- Raleigh Holiday rentals
- Virginia Beach Holiday rentals
- Wilmington Holiday rentals
- Newark Holiday rentals
- Jersey City Holiday rentals
- Baltimore Holiday rentals
- Richmond Holiday rentals
- Carolina Beach Holiday rentals
- Rentals with a washing machine and dryer Eastern Shore of Virginia
- Hotel rooms Eastern Shore of Virginia
- Rentals with a firepit Eastern Shore of Virginia
- Tiny house rentals Eastern Shore of Virginia
- Cottage rentals Eastern Shore of Virginia
- Family-friendly rentals Eastern Shore of Virginia
- Rentals with a kayak Eastern Shore of Virginia
- House rentals Eastern Shore of Virginia
- Apartment rentals Eastern Shore of Virginia
- Rentals with a cinema Eastern Shore of Virginia
- Rentals with outdoor seating Eastern Shore of Virginia
- Flat rentals Eastern Shore of Virginia
- Rentals with a fireplace Eastern Shore of Virginia
- Rentals with a patio Eastern Shore of Virginia
- Rentals with lake access Eastern Shore of Virginia
- Waterfront rentals Eastern Shore of Virginia
- Rentals with breakfast Eastern Shore of Virginia
- Rentals with a hot tub Eastern Shore of Virginia
- Cabin rentals Eastern Shore of Virginia
- Rentals with beach access Eastern Shore of Virginia
- Fitness-friendly rentals Eastern Shore of Virginia
- Villa rentals Eastern Shore of Virginia
- Bed and breakfasts Eastern Shore of Virginia
- Pet-friendly rentals Eastern Shore of Virginia
- Rentals with an EV charger Eastern Shore of Virginia
- Beachfront rentals Eastern Shore of Virginia
- Townhouse rentals Eastern Shore of Virginia
- Rentals with an accessible-height bed Eastern Shore of Virginia
- Rentals with an accessible-height toilet Eastern Shore of Virginia
- Rentals with pools Virginia
- Rentals with pools United States
- Chincoteague Island
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chesapeake Bay
- Assateague Island National Seashore
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Norfolk Botanical Garden
- Outlook Beach
- Neptune's Park
- First Landing Beach
- The Mariners' Museum
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House
- Virginia Beach Convention Center
- Sandy Bottom Nature Park
- Hampton Coliseum
- Willoughby Beach
- Virginia Air & Space Sci. Center
- Bluebird Gap Farm
- NASA’s Wallops Flight Facility Visitor Center





