
Condo holiday 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.

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.

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

Oceanfront, beach, boardwalk, fun, dolphin, sunris
Fantastic condo on the beach. Floor to ceiling windows in living-room, bedrooms. Watching waves, sunrise, dolphins. Enjoy the ocean, boardwalk, beach gym, playground right at downstairs. Extra-large end-unit with fully equipped kitchen, saves you $$$ on meals. One free parking. Walking distance to restaurants, bars, stores, beach concerts, activities, art shows, performance. New 65” QLED TV, new sofa and dining set. Ask for extended stay discount! Up to 45% off Winter Special Deals. Book now!

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.

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.

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!

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!

Beach Bliss Oasis • Walk to Ocean & Boardwalk
Stylish beach retreat just blocks from the ocean & boardwalk 🌊 Walk to the Virginia Beach Convention Center (3 blocks), top restaurants, and local attractions. Perfectly located for a relaxing getaway with everything you need just steps away. Please note: This is a multi-level home with multiple flights of stairs inside the property. Guests will need to use stairs to access different areas of the home, including the bedrooms. This may not be ideal for guests with mobility concerns.

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!

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.

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

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.
Popular amenities for Chesapeake condo rentals
Weekly condo rentals

Beach Luxury Beachfront

Clean, Calm, Contemporary home mins from Beach

Oceanfront Condo with Spectacular Beach View

* Modern Victorian 2 bdr, 1 bath, eat in kitchen

2BD/2BA Villa across Currituck Beach Lighthouse

Coastal Beach condo-amazing view and indoor pool

Oceanfront Condo with Balcony & Pool

OceanSands Oceanfront AquariumChairsBikes
Pet-friendly condo rentals

Bay Breeze At Ocean View Beach Home

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

OceansideLuxuryCondo*Walk2Beach*Pool*Pets*NoStairs

Ocean Bliss: Cozy Apt Retreat(D)

Enjoy Sea Life! Steps to the Beach!

Oyster & Pearl Beautiful New Single Level Condo

Comfy cozy condo for four and so much more!

*Mid/Long Term Rental* Cozy Home at Mary Roberts
Condo rentals with a pool

2 bdr: Steps to Sand, Dog-Friendly!

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

Oceanfront Gem VaB Studio Exceptional Views

Off The Hook-Luxury Cottage - Heart of Corolla!

NEW! Prime Location @Beach Club -Tranquil Seascape

The White Pearl A Modern 3 Bed w/Private Hot Tub!

Lewis Villa | 2 Min Walk to Beach + Heated Pool

VB Boardwalk Getaway (2b2ba) - Long or short term!
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $144 AUD | $156 AUD | $156 AUD | $150 AUD | $147 AUD | $143 AUD | $142 AUD | $144 AUD | $153 AUD | $144 AUD | $151 AUD | $146 AUD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
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 $70 AUD per night before taxes and fees

Verified guest reviews
Over 1,070 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, 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
- Norfolk Holiday rentals
- New York City Holiday rentals
- Washington Holiday rentals
- Myrtle Beach Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Outer Banks Holiday rentals
- Charlotte Holiday rentals
- Ocean City Holiday rentals
- Cape Fear River Holiday rentals
- Jersey City Holiday rentals
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with lake access Chesapeake
- Beachfront rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with a kayak Chesapeake
- Apartment rentals Chesapeake
- Guesthouse rentals Chesapeake
- Waterfront rentals Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with pools Chesapeake
- Townhouse rentals Chesapeake
- House rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Fitness-friendly rentals Chesapeake
- Family-friendly rentals Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Cottage rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with a fire pit Chesapeake
- Beach house rentals Chesapeake
- Condo rentals Virginia
- Condo rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Grommet Island Park
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Old Dominion University
- Currituck Beach Lighthouse
- Neptune's Park
- Kiptopeke Beach
- Colonial Williamsburg's Merchants Square
- First Landing Beach
- Nauticus
- Regent University
- Town Point Park
- Virginia Zoological Park
- Currituck Club





