Condo holiday rentals in Chesapeake

A charming private balcony offers a dining setup for two with white Adirondack chairs and a table, overlooking the beach. A stunning sunset illuminates the horizon, while the seaside view provides a serene backdrop for the table adorned with floral centerpiece and tableware.

4.88 out of 5 average rating, 250 reviews

Oceanfront Gem VaB Studio Exceptional Views

Newly renovated modern studio condo, owners personal getaway now open to guests. This corner unit, the largest and most private in Oceans ll Condominium complex, is on the 3rd floor and offers beautiful, expansive views at both sunrise and sunset. Just off the boardwalk with community pool, this unit sleeps three. Right on the oceanfront, you won't find a more peaceful getaway! Beach chairs & towels provided in season. Please note: due to the open layout of the building, there is no elevator.

A wide, sandy beach is outlined by spacious condos in soft pastel colors against a clear blue sky. Fishing rods are positioned in the sand near beach carts, indicating a relaxed atmosphere. Waves gently lap at the shoreline, creating a tranquil coastal setting.

4.88 out of 5 average rating, 257 reviews

Ocean Escape

Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Community pool area, complete with Jacuzzi tub, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

Two light blue Adirondack chairs are positioned facing the ocean, accompanied by a small table. The sandy beach stretches into the distance, meeting gentle waves under a pastel sky at dusk. A lounge chair rests nearby on the green grass.

4.9 out of 5 average rating, 234 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Nestled in the heart of the coastal city of Virginia Beach where all of the area’s greatest attractions will be right at your fingertips. This coastal beach studio offers a space-maximizing layout which includes kitchenette with full size appliances. All on the desirable north end of the Virginia Beach boardwalk. This small oceanfront complex is one of a kind, a great place for couples or a small family. Enjoy an early morning cup of coffee while enjoying beautiful views of the Atlantic Ocean.

The living room showcases two spacious leather sofas facing a flat-screen television. Natural light floods the room through two large windows, adorned with light-colored blinds. A coffee table centers the space, complemented by decorative plants and artwork on the wall.

4.95 out of 5 average rating, 132 reviews

Spacious Captain’s Beach Suite Near Rudee Inlet

Take advantage of the seasonal rates plan a winter escape to the beach! Don’t miss all the wonderful holiday activities to include the holiday lights, holiday parade & more! This spacious beautifully decorated 2-bedroom (each with ensuite baths) condo is near Rudee Inlet and all oceanfront activities. Walk across the street & relax on the beach, dine at great restaurants, walk under the bridge next to the city parking lot to enjoy all the water activities that originate from Rudee Inlet.

A bright and airy living space features a gray sectional sofa and a matching armchair, providing seating options. A white dining table with blue chairs occupies one side, and a flat-screen TV is mounted on the wall. Light enters through multiple window panes, accented with white shutters.

4.93 out of 5 average rating, 327 reviews

Beach Condo Block Off Oceanfront!

Come enjoy everything Virginia Beach has to offer. Our condo has all of the comforts of home and accommodates 4 adults or perfect for families. Bedroom has a king size bed and living room has sofa that pulls out into a full size sofa bed. TVs in both rooms. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do and you can walk to the beach in 3 minutes or less! Come have a relaxing and fun vacation at the beach.

4.92 out of 5 average rating, 111 reviews

3bd Sandbridge - Sunset Bay views! Newly Remodeled

Welcome to "Heels in the Sand", a 3bed-2bath luxury condo in the exclusive Sanctuary at False Cape, the only oceanfront complex at Sandbridge in Virginia Beach. Inside, there is space aplenty with a open-concept living area with Roku TV, a fully-stocked gourmet kitchen, high-end finishes & sleeping for 9! Two huge patios offer stunning views of the scenic Back Bay. Free access to all condo amenities, including free parking, 3 pools, grills, and a fitness center! Your beach vacation awaits!

A well-equipped kitchen and dining area are visible, with modern appliances and a stylish table set for six. A comfortable sofa in the living space is complemented by a soft area rug, enhancing the inviting layout. Natural light is allowed in by the open layout.

4.92 out of 5 average rating, 367 reviews

2 bedroom condo with oceanfront one block away!

Come enjoy everything Virginia Beach has to offer. Our cozy condo has all of the comforts of home and is perfect for families and accommodates 6 adults. Bedroom 1 has a king size bed w/TV, bedroom 2 has a queen size bed w/TV and the living room has a sofa that pulls out into a full size sofa bed w/TV. The Boardwalk, Shopping, Restaurants, and many more activities are all within walking distance. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach!

A bright living area is featured, displaying a gray sofa with decorative pillows, a wooden coffee table, and two armchairs. Natural light enters through windows dressed with light curtains. A dining table is positioned in the corner, complemented by a decorative lamp and wall art.

4.86 out of 5 average rating, 125 reviews

Condo living just steps from the sand

Come see what Virginia Beach has to offer. Our newly renovated condo has all of the comforts of home and accommodates 4 adults or perfect for families of 5. Bedroom 1 has a queen size bed, bedroom 2 has 2 twin beds, and Living room has a sofa that folds out into a twin size bed. Cable TVs and WiFi, and a beautiful lake view. We are located on the second floor so you will have steps to walk up. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach.

A comfortable living area is highlighted by a spacious sofa and a table with two high-backed chairs. Natural light enters through a window adorned with blinds. Wall art and a sign reading 'BEACH HOUSE' add a coastal touch to the space.

4.88 out of 5 average rating, 100 reviews

Cozy 1 Bd condo, 1 block from the beach!

Your family will be close to everything when you stay at this centrally-located, cozy condo. 1 bedroom, 1 bath just a block off the beach. Queen bed in master and pull out couch and futon in living room. (comfortably sleeps 4, could sleep up to 6) Cute, fully equipped kitchen and dining area for 2. Walking distance to the popular board walk and beach, restaurants, bars, shopping and nearby activities and attractions. Perfect for a couples get away or a small family stay!

A cozy living area showcases a teal sectional sofa and a light-colored armchair, accompanied by a round side table. A flat-screen TV is mounted on the wall, while a light wood dining table and white chairs complete the space. Natural light filters through windows, creating a welcoming ambiance.

4.93 out of 5 average rating, 309 reviews

2 Bedroom Condo ONE Block from the Oceanfront

Come enjoy a Virginia Beach vacation ONE block from the oceanfront and boardwalk. Our 2 bedroom condo accommodates 4 adults and is also perfect for families. Bedroom 1 has a queen size bed and bedroom 2 has a king size bed. There is also a pull out sofa bed in the living room. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do for the whole family.

A bright sleeping area features a spacious bed with light bedding, flanked by two armchairs. Natural light fills the space through large windows, revealing a view of trees outside. Soft, warm tones are complemented by a piece of art above the headboard.

4.84 out of 5 average rating, 159 reviews

WOW Location! Beach Paradise on Boardwalk w/Pool

Enjoy a piece of the Oceanfront with this gorgeous updated condo! Walk out your front door to the beach, pool, boardwalk, the historic Cavalier hotel, restaurants, shops and many entertainments on the beach! Newly renovated, this beachy North End paradise is the perfect getaway for a couple. One parking spot, deck area , a lawn on the beach with lounge chairs and coin operated laundry available on premises.

4.89 out of 5 average rating, 182 reviews

A well-furnished living room is depicted, featuring a dark blue couch adorned with patterned throw pillows. Two abstract art pieces hang above, and a flat-screen television is mounted on the wall. Light is provided by a table lamp, creating a bright and inviting space.

Condo in Newport News

*Mid/Long Term Rental* Cozy Home at Mary Roberts

Bring the whole family to this great place with lots of room for fun. Less than 10 minutes away from Fort Eustis Military Base. Less than 15 min away from Newport News Airport, Christopher Newport University, and plenty of shopping and dining. Short drive to Williamsburg with shopping at the outlet mall, dining and entertainment for the family at Busch Gardens and Water Country USA theme parks.

Popular amenities for Chesapeake condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

The exterior of the house is shown, featuring a three-story structure with a light-colored facade and multiple balconies. A spacious lawn surrounds the property, providing an open area for outdoor activities. Clear blue skies and well-maintained landscaping enhance the inviting appearance.

5 out of 5 average rating, 34 reviews

*NEW -25ft to Beach, 2br. Oceanviews.Pool.Hot Tub

5 out of 5 average rating, 66 reviews

Sandbridge Beach - DeepSeaSide Retreat

An aerial view showcases the Boardwalk Resort & Villas, a tall building with large windows, prominently situated along the Virginia Beach Boardwalk. Lush landscaping with green lawns and palm trees is visible in the foreground, while the beach and cityscape extend beyond.

5 out of 5 average rating, 5 reviews

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!

A serene bedroom is highlighted by two spacious beds, each adorned with light teal blankets and decorative pillows. A dresser with a woven texture is positioned against the wall, while natural light filters in through a window dressed with dark curtains.

4.95 out of 5 average rating, 41 reviews

Oceanfront & Brdwalk 1 blck away! Save on Summer!

A comfortable living area features a brown leather sofa and an armchair, complemented by decorative pillows. A television is positioned on a media console, while a vibrant floral artwork hangs on the wall. Soft lighting is provided by a ceiling fan and a lamp.

4.86 out of 5 average rating, 28 reviews

Just a block from beach

A spacious balcony features several blue adirondack chairs, offering a view of the surrounding buildings and the outdoor area. Clear skies with a few clouds create a bright atmosphere. The ocean is visible in the distance, providing a scenic backdrop.

5 out of 5 average rating, 24 reviews

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym

A comfortable living area features two beige sofas and a circular patterned area rug. Large windows provide natural light and showcase a view of the ocean. A wall-mounted TV is positioned for easy viewing, and sliding doors lead to an ocean-view balcony.

4.83 out of 5 average rating, 54 reviews

Lovely Beachfront 3-Bedroom Condo

4.95 out of 5 average rating, 43 reviews

Condo in Elizabeth City

Water Front Condo with Boat Slip: The Dock House

Pet-friendly condo rentals

4.78 out of 5 average rating, 112 reviews

A guest room features two spacious beds adorned with patterned linens. An artistic display of vintage vinyl records decorates the wall above, enhancing the room's character. Warm wooden flooring complements the overall design, while a small nightstand stands between the beds.

Condo in Hampton

Cozy & Fun Hampton Condo, WIFI & W/D! Dogs welcome

4.99 out of 5 average rating, 98 reviews

A workspace with a wooden desk and a comfortable chair is situated by large windows, offering expansive views of the ocean. Natural light streams in, highlighting the tranquility of the beach outside. The windows are framed by light-colored blinds, with a small plant placed on the desk.

Condo in Willoughby

Beachfront Getaway, Pet Friendly, Mermaid Suite

4.96 out of 5 average rating, 114 reviews

A tranquil lakeside scene captures two individuals on paddleboards gliding across calm water. Sandy shores are lined with chairs, offering a peaceful spot to relax. In the background, a spacious building features a wraparound deck, providing views of the serene landscape.

Condo in Williamsburg

Walk to beach lovely 2/2 in "Kingsmill on James"

5 out of 5 average rating, 29 reviews

A fenced backyard features a picnic table, two lounge chairs, and a firepit. String lights hang overhead, providing soft illumination. Lush greenery surrounds the space, enhancing the outdoor setting, while nearby structures indicate the proximity to the rental property.

Condo in Ocean View

Ocean Bliss: Cozy Apt Retreat(D)

The open living area features a comfortable sofa accompanied by a patterned armchair, creating a relaxed atmosphere. A coffee table sits in front, adorned with a small decorative arrangement. Modern cabinetry and stainless steel appliances are visible in the adjoining kitchen, complemented by a spacious dining area.

5 out of 5 average rating, 40 reviews

Enjoy Sea Life! Steps to the Beach!

The modern kitchen features sleek white cabinetry and quartz countertops. Stainless steel appliances, including a microwave and a refrigerator, are visible. An island with bar seating and a wine cooler complements the open layout, leading into the dining area illuminated by a stylish chandelier.

5 out of 5 average rating, 28 reviews

Oyster & Pearl Beautiful New Single Level Condo

A modern kitchen and living area showcase an open layout with high ceilings. A large island with bar seating invites gatherings. The cozy living room features a sectional sofa adorned with decorative pillows. Natural light fills the space through multiple windows, enhancing the welcoming atmosphere.

4.94 out of 5 average rating, 18 reviews

Off The Hook-Luxury Cottage - Heart of Corolla!

4.85 out of 5 average rating, 20 reviews

Condo in Willoughby

1b/1bath beach condo, unobstructed ocean views

Condo rentals with a pool

4.88 out of 5 average rating, 8 reviews

A serene beach sunset is captured over gentle waves, with vibrant hues of orange and pink reflecting off the water. The shoreline features soft sand, inviting relaxation and peaceful moments by the sea.

Condo in Cape Charles

Rendezvous, a Resort Condo in Cape Charles

The exterior of the duplex showcases a welcoming entrance with a sign reading 'Salty Vibes.' Lush landscaping features colorful flower beds and well-maintained grass. The home is framed by a modern fence, providing a clear view of the architectural design and neighboring units.

4.97 out of 5 average rating, 34 reviews

2 bdr: Steps to Sand, Dog-Friendly!

A clear view of a rectangular pool surrounded by a patio area. Lounge chairs are positioned near the pool, and a hot tub is visible adjacent to the water. Greenery and potted plants line the space, and a building with large windows is in the background.

4.87 out of 5 average rating, 109 reviews

Good Vibes at the Beach

The kitchen features modern appliances, including a stainless steel refrigerator and oven, set against white cabinetry. A central island with seating for six enhances the open layout, while large windows allow natural light to brighten the space.

5 out of 5 average rating, 18 reviews

2BD/2BA Villa across Currituck Beach Lighthouse

A sunset view over the ocean is captured from a balcony, where warm colors blend in the sky. Gentle waves lap at the shore, and silhouettes of distant boats are visible on the horizon. The sandy beach offers a serene atmosphere.

4.87 out of 5 average rating, 154 reviews

Oceanfront, beach, boardwalk, fun, dolphin, sunris

The outdoor pool area features a well-maintained pool surrounded by lounge chairs. A clear blue sky is noted above, with clouds adding texture. Nearby greenery and structures contribute to the atmosphere, allowing for a relaxing outdoor experience.

4.98 out of 5 average rating, 104 reviews

Paradise at the Beach

A modern living area is showcased with a comfortable leather sofa, light wood dining table, and light-colored walls. Large windows allow natural light to fill the space, offering a view of the balcony. Decorative accents include artwork and curtains, contributing to a welcoming ambiance.

4.89 out of 5 average rating, 35 reviews

Coastal Beach condo-amazing view and indoor pool

A dining table is set with an array of fresh fruits and cheeses, complemented by a vibrant blue arrangement of hydrangeas and two blue candles. The ocean can be seen in the background, enhancing the inviting beachside dining experience.