Condo vacation rentals in Chesapeake

Find and book unique condos on Airbnb

Top-rated condo rentals in Chesapeake

Guests agree: these condos are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
Top guest favorite
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
4.99 out of 5 average rating, 158 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.

Top guest favorite
A spacious living area is shown, featuring a blue sectional sofa and a decorative rug in light tones. A flat-screen TV is mounted on the wall, and an adjacent dining area includes a white table with four chairs. Natural light filters through the windows.
Condo in Virginia Beach
4.9 out of 5 average rating, 268 reviews

2 Bedroom Condo One Block from the Oceanfront!

Our newly renovated 2 bedroom condo ONE block from the boardwalk accommodates 6 people and is also perfect for families. Each bedroom has a flat screen TV; one with a queen bed and the other with a king bed. There is also a pull out sofa bed in the living room along with a large TV. This is a 2nd floor unit with one designated parking spot. Plenty to do for the whole family with the beach, boardwalk, shopping, restaurants, amusement parks, and many more activities all within walking distance.

Guest favorite
A cozy living area features a brown leather futon accented by two blue cushions. The vibrant floral wallpaper creates a lively backdrop, complemented by a neon sign. A small dining table with two wire chairs is positioned by a window, allowing natural light to filter in.
Condo in Virginia Beach
4.94 out of 5 average rating, 124 reviews

Oceanfront Loft: Free Parking & 1 Block from Beach

Welcome to your stylish coastal retreat at the Virginia Beach Oceanfront, a thoughtfully designed 285 sq. ft. one-bedroom apartment just steps from the beach, boardwalk, dining, entertainment, and everything that makes Virginia Beach one of the East Coast’s favorite vacation destinations. This bright and modern condo combines comfort, convenience, and an unbeatable location in the heart of Virginia Beach Oceanfront. "Guest Favorite" for those looking for an easy, relaxing VA Beach getaway.

Top guest favorite
Condo in Sandbridge
4.94 out of 5 average rating, 157 reviews

Ocean & Bay Views - Newly Renovated! Local Family!

Just steps away from the sand, "Carolina on My Mind" is a 2b/2ba oceanside condo at the exclusive Sanctuary at False Cape, the only Oceanfront complex at Sandbridge in Virginia Beach. You'll enjoy a private patio with both Ocean and Back Bay views. The condo features a large open-concept living space, and a fully equipped gourmet kitchen, and high end finishes. Free access to all condo amenities, including free parking, 3 pools, grills, and a fitness center! Your beach vacation awaits!

Top guest favorite
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, 385 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!

Top guest favorite
The living area features a light grey sofa, two teal armchairs, and a wooden coffee table. A woven basket holds a soft throw. In the background, a kitchenette is visible, along with cabinets and appliances, illuminated by natural light from skylights.
Condo in Williamsburg
4.96 out of 5 average rating, 139 reviews

2 Bedroom Stylish Kingsmill condo

Located in the beautiful Kingsmill resort, this charming two bedrooms, two baths condo with stunning seasonal views over the pond is only a few minutes away from CW, Busch Gardens, water country, William and Maryand other Williamsburg attractions. All Kingsmill amenities are not included as they are strictly for Kingsmill residents Guests have access to the Spa and to the Mill Coffee House which is within walking distance from the condo and serves breakfast and lunch every day..

Top guest favorite
A bright living room features a green sofa and a light beige armchair, complemented by turquoise walls. A large mirror reflects the space, while a television is mounted above a decorative console. Soft lighting is provided by a floor lamp, enhancing the relaxed atmosphere.
Condo in Virginia Beach
4.96 out of 5 average rating, 120 reviews

Beach Chic Condo 1 Block from Boardwalk

If a get-away is what you need, then simply "My Beach Hideout’ is what you want. Completely renovated 2 Bedroom/1 Bath condo a short one-block walk from the oceanfront. Enjoy a stylish, relaxed coastal-vibe experience. Perfectly comfortable for 4 guests or a solo long-business stay. Dining, nightlife, entertainment, events, VB boardwalk & shops all within walking distance. Immaculate condo has queen bed + TV in both bedrooms, living room, stocked kitchen, bath + parking.

Guest favorite
An open living area features a sectional sofa, a flat-screen TV mounted on the wall, and a small side chair. Light-colored cabinetry is seen in the kitchen area, accompanied by a dining table. Soft natural light brightens the space through large windows.
Condo in Virginia Beach
4.91 out of 5 average rating, 328 reviews

2 Bedroom Beach Condo Block Off Boardwalk

Come enjoy everything Virginia Beach has to offer. Our newly renovated condo has all of the comforts of home perfect for families. Bedroom 1 has a king size bed, bedroom 2 has a queen size bed, and Living room has sofa that pulls out into a full size sofa bed. TVs in all rooms. 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.

Top guest favorite
A view of the beach stretches towards the horizon, framed by green grass and a flower pot. White lounge chairs are arranged for relaxation, while colorful umbrellas dot the sandy shore, providing shade to beachgoers enjoying the ocean.
Condo in Virginia Beach
4.97 out of 5 average rating, 183 reviews

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen

Nestled on the desirable north end of the boardwalk, close to the area’s 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

Guest favorite
Condo in Virginia Beach
4.92 out of 5 average rating, 144 reviews

Vibe District • Walk to Beach • Parking • Sleeps 6

Stay in the heart of Virginia Beach's Vibe Creative District—just a short walk to the beach and Boardwalk 🌊 Enjoy Atlantic Park, which is home to year-round surfing, along with The Dome concert venue and numerous new restaurants—all within two blocks. The Virginia Beach Sportsplex is also nearby. This 3-story condo offers a fully equipped kitchen, in-unit laundry, and a comfortable layout—perfect for families, small groups, or a fun coastal getaway.

Top guest favorite
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 Norfolk
4.99 out of 5 average rating, 103 reviews

Beachfront Getaway, Pet Friendly, Mermaid Suite

Escape to a serene, semi-private beach with breathtaking views and everything you need for the perfect vacation. Welcome to Big Blue, where unforgettable memories await. Beach access, Fully stocked kitchen, modern upgrades, comfy beds, large open floor plan, bbq pit, outdoor patio, beach gear & many personal touches. Condo not suitable for children under 7. Pet fee $100 for max of 2 with approval.

Guest favorite
The living area features a light-colored sofa positioned across from a modern coffee table. A bar area with two stools is visible in the background, leading to a kitchen with white cabinetry. Natural light illuminates the space, creating a bright and open atmosphere.
Condo in Virginia Beach
4.87 out of 5 average rating, 166 reviews

Beach Bungalow on the Boardwalk

If you are looking for convenience, comfort, and a pleasant experience than Beach Bungalow on the Boardwalk is for you. We are located only a block from the beach and boardwalk, and there is no shortage of restaurants and entertainment in the area. Our condo has been completely renovated with all new furniture. We know you will enjoy your experience and look forward to being your host.

Popular amenities for Chesapeake condo rentals

When is the best time to visit Chesapeake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 378ﺩ.ﺇ 408ﺩ.ﺇ 408ﺩ.ﺇ 393ﺩ.ﺇ 386ﺩ.ﺇ 375ﺩ.ﺇ 371ﺩ.ﺇ 378ﺩ.ﺇ 400ﺩ.ﺇ 378ﺩ.ﺇ 397ﺩ.ﺇ 382
Avg. temp6°C7°C10°C16°C20°C25°C27°C26°C23°C18°C12°C8°C

Quick stats about condo rentals in Chesapeake

  • Total vacation rentals

    Explore 40 vacation rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 1,070 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Chesapeake vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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 Cinema Cafe-Greenbrier Mall

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Chesapeake
  5. Condo rentals