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Villa holiday rentals in Eastern Shore of Virginia

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Top-rated villa rentals in Eastern Shore of Virginia

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Superhost
A sandy pathway leads from a wooden fence to a wide, open beach. The calm ocean stretches into the horizon under a clear blue sky, with gentle waves lapping at the shore. Dune grass flanks the sides of the path, creating a natural border.
Villa in Frankford
4.73 out of 5 average rating, 11 reviews

Milo's By the Beach

Welcome to your home away from home at the Delaware Shore! Our home is minutes away from Bethany Beach, and just a short drive from Rehoboth Beach, Dewey Beach, Fenwick Beach, and Ocean City, MD. Along with our beautiful beaches, this area is a golfer's dream with Bear Trap Dunes just 2 1/2 miles away and many other beautiful golf courses nearby. This 2025 coastal 4-bedroom villa hosts 2400+ square ft of great modern living space with a one-car garage and driveway for your parking convenience.

Superhost
The image captures a waterfront view of the condo complex, showcasing a series of boats docked at wooden piers. Calm water reflects the blue sky, while landscaped areas with low-growing plants line the docks. The colorful buildings of the complex are visible in the background.
Villa in Chincoteague
4.85 out of 5 average rating, 20 reviews

Sunset Bay 105-Waterfront w/ Boat Slip, Pool & Gym

Just a few miles from Assateague Beach & the Chincoteague National Wildlife Refuge Bayside & Beyond (Sunset Bay Villa #105) is a well appointed 1st floor Waterfront Condo w/ Boat Slip, Pool (Seasonal) & Gym Located in the heart of historic downtown Chincoteague Bayside & Beyond is walking distance to restaurants, shopping, town park, fishing pier & carnival grounds. Enjoy beautiful sunsets, fishing, crabbing & kayaking from just outside your door! Relax & soak in the sunshine by the shared pool!

Superhost
A sandy pathway leads from a wooden boardwalk through grassy dunes towards the beach. The open sky is filled with fluffy white clouds, and the calm water of the bay is visible in the distance.
Villa in Norfolk
4.81 out of 5 average rating, 31 reviews

LOVE n the Air! 5StarBeachVilla+CoffeeBar+W/D+WiFi

See YouTube: Zoe Bay Properties 5 Star Beach Villa video tour. VA is for lovers and you'll love our family-friendly spacious beach villa at tip of Willoughby Spit, Willoughby Bay on 1 side of the Spit, Chesapeake Bay the other. Only 3-minute walk to beach. No direct beach views, just marina. Fully stocked kitchen, coffee/ tea bar, gameroom, corn hole and the essentials! 4 BR 2 full BA w/tubs, 65" Smart TV w/ROKU, fast WIFI w/elite streaming. Beach cart/chairs/umbrella. Fire pit, outdoor seating.

Superhost
A tiki-style gazebo with a thatched roof is positioned near the waterfront, overlooking calm waters as the sun sets in the background. Soft, warm colors fill the sky, reflecting on the water's surface, while wooden posts line the shore.
Villa in Chincoteague
4.57 out of 5 average rating, 42 reviews

Beautiful 2BR Snug Harbor Waterfront villa!

It is a beautiful WATERFRONT, newly renovated villa overlooking the Assateague lighthouse, the National Park, the Wildlife Refuge and the spot where the wild ponies hang out! There is a marina right on the premises with motor boat, kayak and SUP rentals as well as organized guided kayak tour, nature boat tours and sunset cruises. The villa has fully stocked kitchen with full size fridge, stove, oven, coffee maker, toaster, pots, pans, utensils etc. Bring the family and enjoy our island!

Guest favourite
A spacious living area features light wooden flooring, a comfortable white sofa, and a coffee table. Natural light floods through the windows, illuminating the adjacent kitchen area, which includes modern appliances and a dining space. A ceiling fan and wall-mounted TV enhance the inviting atmosphere.
Villa in Virginia Beach
4.88 out of 5 average rating, 103 reviews

Beach House Just Blocks From Oceanfront Boardwalk.

This 3 story town-home (similar to a Duplex House) is the perfect getaway to enjoy a day at the beach! Only 5 minutes walk to the Oceanfront Boardwalk, you can enjoy an evening walk or have dinner at one of hundreds of restaurants in the area. First master bedroom and 2 other rooms are at second floor. Second master bedroom is third floor. Also we provide key less entry for all door inside, outside the house. Beach chair, grill, etc.... also available for you during the time you stay.

Guest favourite
A charming lakefront home is situated on a well-maintained lawn, featuring a mix of shrubs and trees. The exterior showcases a combination of brick and siding with gabled roofs and an arched window. The driveway leads to a two-car garage.
Villa in Virginia Beach
4.85 out of 5 average rating, 40 reviews

Executive Lakefront Oasis - Center of Va. Beach

Lakefront home with huge deck over the water. This amazing 4 bedroom 3 bath home just got updated. Minutes from the beach, make this location ideal. Beautiful screened in porch for enjoying the lake views. At night, the landscape lighting in the front and back gives an elegant touch. Close enough to enjoy the beach and you'll appreciate the quite relaxing lake when it's time to wind down and make memories with the family. There's a large park directly across the street for the kids.

Guest favourite
A tranquil bayside view is captured, with calm waters reflecting the clear sky. A small outdoor table adorned with a silver bucket and glasses sits on a deck, framed by white railings that lead to the water's edge.
Villa in Bethany Beach
4.81 out of 5 average rating, 16 reviews

Beach Cove Bliss

Bayfront Villa in Bethany Beach – Sleeps 16, Walk to the Beach! Beach Cove Villa #15, a stunning 5-bedroom, 4-bath bay view vacation home in Bethany Beach, Delaware. With 2,700 square feet of beautifully designed space, this coastal getaway is perfect for large families, multi-family groups, or friends traveling together. Just minutes from Bethany Beach boardwalk and sandy shores, this villa offers breathtaking water views from six private decks, plus all the comforts of home.

Superhost
A serene view of a private beach meets the calm waters of the bay under a clear blue sky. Gentle waves lap at the sandy shore, with a wooden dock extending into the water. Soft grasses frame the beach area, contributing to the tranquil atmosphere.
Villa in Montross
4.85 out of 5 average rating, 110 reviews

Beach Retreat

Relax with the whole family at the Beach Retreat! Enjoy the beautiful Sunrise and Sunsets in the Hot tub overlooking your own private beach! There is plenty to do in the Northern Neck of Virginia! We have Wineries, a Brewery, historical sites, boating, swimming, fires on the beach, bike rides, kayaking, plenty of Summer and Fall Festivals and so many great places to eat on and off the river! The Northern Neck of VA is a hidden gem! Just a 90 minute drive from the DC area

Top Guest favourite
The living area features comfortable seating options arranged around a central area rug, with a fireplace adding warmth. A large television is mounted on the wall opposite, while natural light streams through the windows, which are adorned with blinds.
Villa in Ocean City
4.99 out of 5 average rating, 74 reviews

Walk to the Beach! Firepit-Grill-Bikes-Fence-N64!

Escape to the Blue House, a pet-friendly retreat just 6-mins to the beach. - Full kitchen and charcoal grill - Coffee bar (k-cups, espresso, coffee grinder, french press, and pour over) - Fully fenced patio with a fire pit and ping pong - Outdoor shower - 5 Bikes - Northside Park - 2 min walk away - N64 - 48W EV charger - Rrecord Palyer Sleep 10 (8 Adults 2 Children) in our 3 bedrooms - 1 king, 1 queen, 1 full over full bunk bed, and full sofa bed. NOT POSTED ON C.LIST

Superhost
Villa in Chincoteague
4.7 out of 5 average rating, 10 reviews

Sand Dollar Villa

The Sand Dollar Villa @ The Reef Features two bedrooms upstairs and 1/2 bath. Each bedroom has a Queen Bed Downstairs has a fully equipped kitchen, bathroom with a shower and a sleeper sofa in the living room The Reef Vacation Villas has an indoor pool, bikes, stand up paddle boards, corn hole, and Two passes to MAUI JACKS WATERPARK just a short walk away Stay with us and beat the traffic to the beach since we are located just over a half mile from the beach

Guest favourite
An outdoor dining area is shown, featuring a light blue picnic table surrounded by four matching chairs. A patio umbrella stands upright in the center, offering shade. A tall tree is visible in the background along with a white fence that encloses the space.
Villa in Ocean City
4.93 out of 5 average rating, 44 reviews

Cheery & Cozy Beach Villa - Walk to Beach

This Villa Offers All The Items You Want For A Perfect Vacation! Beautiful Spacious 3 BR 2 Bath With Sleep Sofa To Sleep Up To 8 Comfortably. Master BR Has A King Bed With A Private Bath. BR 2 has A Queen Bed and BR 3 Has Twin Bunk Bed. Both Have Windows Facing The Coastal Hwy. The Second Full Bathroom Is In The Hallway. Located At 90th St It Is Convenient To A Supermarket And Within Walking Distance To Popular Restaurants.

Top Guest favourite
A bright and modern kitchen features sleek white cabinets and quartz countertops. A spacious island with seating for four is complemented by stylish pendant lighting. Stainless steel appliances, including a refrigerator and oven, are neatly integrated, providing an inviting space for meal preparation.
Villa in Ocean View
5 out of 5 average rating, 37 reviews

Luxury Bethany Beach Villa in Bishop's Landing

Attention Guests - you must be at least 27 years of age or older to book this property. A Community Specific Rental Guest Form Agreement will be emailed and is required to be signed, also to include guest names so to register for pool & shuttle passes. Failure to agree to these terms will result in denial of your reservation. Please message or contact the host if you have questions about these terms. Enjoy your vacation!

Popular amenities for Eastern Shore of Virginia villa rentals

Kitchen
Wi-Fi
Pool
Free parking on premises
Air conditioning

Private villa rentals

Superhost
A light blue two-story building features white railings and a spacious deck. Large windows provide natural light, while air conditioning units are positioned for comfort. A gravel area surrounds the property, enhancing accessibility and outdoor space.
Villa in Chincoteague
4.67 out of 5 average rating, 9 reviews

Sol Villa

The exterior of a spacious home is surrounded by greenery, featuring large windows that invite natural light. A gravel driveway leads to the entrance, which is accented with steps and a circular front window.
Villa in Ocean Pines
4.43 out of 5 average rating, 72 reviews

Luxe Homey Get-Away Beach Cove

Guest favourite
The rear view of the Italianate home showcases a spacious, multi-level structure with a tile roof and wrap-around porch. Green lawns and trees frame the property, providing a serene backdrop. Large windows and multiple seating areas invite outdoor relaxation.
Villa in Claremont
4.92 out of 5 average rating, 53 reviews

River Retreat with Eagle's Eye View

Superhost
A waterfront scene features a docked boat against a striking sunset, reflecting warm hues of orange and pink on the water's surface. Nearby, a two-story cottage stands with a sloped roof, complemented by a tranquil backdrop of the coastal landscape.
Villa in Chincoteague
4.68 out of 5 average rating, 25 reviews

Waterfront cottage with the most peaceful view!

Superhost
A compact bathroom is presented with neutral-colored walls and a tiled floor. A round mirror is mounted above a small pedestal sink, and a toilet is positioned against the wall. A shelf is located above the sink, providing additional storage.
Villa in Chincoteague
4.62 out of 5 average rating, 13 reviews

Surfers Villa

A picturesque villa is set beside a tranquil pond, with vibrant red roses in the foreground. Lush greenery frames the property, while a grand entrance features classical columns. Soft clouds drift in a blue sky, enhancing the serene atmosphere of the surroundings.
Villa in Williamsburg
4.71 out of 5 average rating, 17 reviews

Quiet Villa with Bowling Alley, Pools, +Mini Golf

Top Guest favourite
A cheerful living space features light blue walls and a starfish-patterned rug. A navy blue couch is complemented by patterned curtains and decorative poufs. Two windows provide natural light, and a lamp stands on a side table. A wall sign conveys a family-oriented theme.
Villa in Millville
4.92 out of 5 average rating, 13 reviews

Firepit/Beach Shuttle/Pools/Office/Smart TVs

Superhost
A functional kitchen is displayed, featuring a white refrigerator, microwave, and coffee maker. Dark wood cabinetry lines the walls, complemented by a light-colored countertop. A door leads outside, allowing natural light to illuminate the space, while a window invites fresh air.
Villa in Chincoteague
4.56 out of 5 average rating, 9 reviews

Coral Villa

Luxury villa rentals

A spacious living area is furnished with a comfortable dark sofa and a light green armchair. A wooden coffee table centers the room, complemented by a TV on a stand. The room features a fireplace and leads to an open kitchen area visible in the background.
Villa in Williamsburg
4.94 out of 5 average rating, 35 reviews

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

Guest favourite
A modern kitchen is featured, equipped with high-end appliances including a double oven and gas cooktop. A 15-foot white quartz island provides seating, complemented by sleek white barstools. Large windows allow natural light to brighten the space, creating a welcoming atmosphere.
Villa in Frankford
4.83 out of 5 average rating, 6 reviews

Summer Breeze – 4BR Villa. Fall & Winter Gateway

A spacious deck overlooks the water, featuring potted plants and an umbrella for shade. The marina is visible in the background, showcasing boats docked along the waterfront against a clear blue sky.
Villa in Hampton

Luxe 5-Star Waterfront Retreat - Water-Beach Views

Guest favourite
The exterior of the home displays a charming two-story design with a mix of dark and light siding. Large windows allow natural light to enter, while the inviting entrance features a well-maintained front yard with a young tree and a driveway leading to a one-car garage.
Villa in Ocean View
5 out of 5 average rating, 7 reviews

Spacious Retreat Near the Beach.

Top Guest favourite
A bright living area is presented, featuring two white sofas and a dark wood coffee table at the center. Large windows allow natural light, showcasing views of the pond outside. A patterned rug complements the space, adding a playful element to the decor.
Villa in Selbyville
5 out of 5 average rating, 8 reviews

Fenwick Island-GOLF CART-Bayfront pool and beach!

A three-story beach house features large windows and a balcony overlooking the sandy beach. An American flag is displayed, and a wooden pier leads to the water. White chairs are arranged on the porch for relaxation with a view of the shoreline.
Villa in Dewey Beach
5 out of 5 average rating, 9 reviews

Beachfront Townhome - Spectacular Sunsets, Parking

Villa rentals with a pool

Guest favourite
The front exterior of the villa features a light-colored facade with stone accents and a symmetrical roof. Two garage doors are visible on the left, complemented by well-maintained landscaping and a walkway leading to the entrance, under a blue sky adorned with fluffy clouds.
Villa in Millville
4.88 out of 5 average rating, 51 reviews

Spacious Villa 3 miles to Bethany Beach Water Acc

Top Guest favourite
The living area features a dark blue sofa adorned with plaid and nautical-themed cushions. A matching upholstered chair is present, along with a decorative ottoman. Wall art depicting coastal scenes is mounted above, flanked by oars. Two lamps provide ambient lighting beside the sofa.
Villa in Bethany Beach
4.89 out of 5 average rating, 36 reviews

Sea Colony West-Summer Breeze, villa 2bdrm/2bth(8)

An indoor pool is illuminated by bright overhead lights. The clear blue water reflects the light and surrounding windows. Lounge chairs are positioned along the edge of the pool, providing a space for relaxation. Large windows allow natural light to fill the area.
Villa in Williamsburg
4.81 out of 5 average rating, 31 reviews

Quiet Villa with Access to Amazing Amenities

A balcony view is presented, overlooking the surrounding landscaped grounds and several white multi-unit buildings. Clear blue skies and wispy clouds can be seen above, while distant views of water and greenery add to the serene atmosphere.
Villa in Clarksville

Condo w/ water views and amazing amenities!

A spacious outdoor pool area is shown, surrounded by lounge chairs and shaded areas. Tall trees provide greenery in the background. A lifeguard chair is positioned next to the pool, with swim lanes visible, inviting guests for leisure and relaxation.
Villa in Bethany Beach

3BR Sea Colony Stay | Full Access to Resort Perks

Villa in Norfolk
4.89 out of 5 average rating, 45 reviews

Spacious 4 bedrms, pool, close proximity to beach

Two adirondack chairs are positioned on a balcony, facing a golf course with lush green grass and a serene lake. A small table holds two cocktails, complemented by the backdrop of trees and a clear sky.
Villa in Ocean Pines
5 out of 5 average rating, 4 reviews

Lakeview/Golf course front home - 4 Bed/3 baths

Top Guest favourite
The exterior of the villa is shown, featuring a modern design with a combination of stone and painted siding. The first-floor unit is highlighted, showcasing a private entrance and a small patio area. Large windows offer a view of the well-kept landscaping.
Villa in Ocean View
5 out of 5 average rating, 9 reviews

Cozy, Brand New Villa - Bethany Beach, DE

Destinations to explore