Condo holiday rentals in Chesapeake

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Top-rated condo rentals in Chesapeake

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Top Guest favourite
A modern living room features a gray sofa adorned with decorative pillows, paired with a light blue coffee table. Two lamps provide ambient lighting. Artwork of coastal scenes decorates the walls, while a patterned area rug enhances the room's coastal theme.
Condo in Virginia Beach
4.98 out of 5 average rating, 132 reviews

Tropical 2BR Condo Getaway 1 Block from the Beach!

Unwind at this gorgeous fully renovated getaway for your family and friends! This two bedroom, one bath beach home is one block from the ocean. This unit accommodates up to 4 adults. Each room is equipped with a smart TV and internet is provided. Our kitchen provides refrigerator, microwave, oven, dishwasher, toaster, Keurig, dishes, cutlery, bowls, pots and pans, and much more! Steps away from shopping and restaurants! This highly sought after vacation spot really is a home away from home.

Guest favourite
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.
Condo in Virginia Beach
4.9 out of 5 average rating, 233 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.

Top Guest favourite
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.
Condo in Virginia Beach
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.

Guest favourite
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.
Condo in Virginia Beach
4.93 out of 5 average rating, 321 reviews

Beach Condo Block Off Boardwalk

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.

Top Guest favourite
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.
Condo in Virginia Beach
4.92 out of 5 average rating, 359 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!

Guest favourite
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.
Condo in Virginia Beach
4.85 out of 5 average rating, 123 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.

Superhost
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.
Condo in Virginia Beach
4.88 out of 5 average rating, 248 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 and towels provided. Please note: due to the open layout of the building, there is no elevator.

Guest favourite
Condo in Sandbridge
4.92 out of 5 average rating, 110 reviews

3bd Sandbridge - Sunset Bay views!

A stone's throw from the sand and water, this is a 3bed-2bath luxury condo in the exclusive Sanctuary at False Cape, the only Oceanfront complex at Sandbridge in Virginia Beach. Two huge private patios with scenic views of the Back Bay await you! Inside, there is space aplenty with a open-space concept living area, a fully-stocked gourmet kitchen, & 3 separate bedrooms with sleeping for 8! Free access to all condo amenities, including 3 pools! Your beach vacation awaits!

Guest favourite
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.
Condo in Virginia Beach
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!

Guest favourite
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.
Condo in Virginia Beach
4.93 out of 5 average rating, 305 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.

Superhost
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.
Condo in Virginia Beach
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.

Guest favourite
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
4.89 out of 5 average rating, 180 reviews

*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

When is the best time to visit Chesapeake?

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Quick stats about condo rentals in Chesapeake

  • Total holiday rentals

    Explore 40 holiday rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake holiday rentals start at $75 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,000 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Chesapeake holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Chesapeake rentals

  • 4.8 Average rating

    Chesapeake stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square

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