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.

%{current} / %{total}1 / 1
Top guest favorite
Condo in Virginia Beach
4.99 out of 5 average rating, 136 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 favorite
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, 251 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.

Guest favorite
The pool area is showcased with a clear blue water feature and adjacent Jacuzzi. Surrounding lounge furniture and a nearby seating arrangement provide space for relaxation. The backdrop features a low, stone wall and buildings with a warm color palette, enhancing the community atmosphere.
Condo in Sandbridge
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.

Guest favorite
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, 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.

Guest favorite
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.
Condo in Virginia Beach
4.87 out of 5 average rating, 109 reviews

Good Vibes at the Beach

Boutique style building with a pool, designated parking, and coded door access. 2 bedrooms and 2 baths with a full kitchen and all amenities. Enjoy the pool during the summer months (May28th-Sept. 30th) or walk another block to enjoy the Beach at all times of the year. Multiple restaurants of all types surrounding this location and a large Harris Teeter grocery store only steps away. Come enjoy the Beach Life where music and arts are abundant. Primary booking guest must be at least 21 yrs old

Top guest favorite
A living area features comfortable seating with plush couches and a woven coffee table. Large windows provide natural light, and a dining area with a blue fabric table set is visible. Decorative elements include a ceiling fan and wall art.
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.

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, 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!

Guest favorite
A well-lit living area features a gray sofa positioned next to a cozy chair, with a yellow accent pillow adding a touch of color. Light streams through large windows with plantation shutters, illuminating the open layout that connects to a modern kitchen with granite countertops.
Condo in Virginia Beach
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 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.

Guest favorite
Condo in Virginia Beach
4.93 out of 5 average rating, 310 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
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 favorite
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, 183 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.

Guest favorite
Condo in Virginia Beach
4.86 out of 5 average rating, 153 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.ﺇ404ﺩ.ﺇ404ﺩ.ﺇ400ﺩ.ﺇ393ﺩ.ﺇ386ﺩ.ﺇ375ﺩ.ﺇ371ﺩ.ﺇ378ﺩ.ﺇ400ﺩ.ﺇ378ﺩ.ﺇ397ﺩ.ﺇ382
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.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 1,000 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 Cinemark Chesapeake Square

Destinations to explore

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