We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Some info has been automatically translated. Show original language

Airbnb your place

Beachfront holiday rentals in Chesapeake

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Chesapeake

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

0 of 0 items showing

1 of 3 pages

Flat

5 out of 5 average rating, 3 reviews

Beachside Bliss Block from the Shore

Welcome to our charming Norfolk townhouse(S), perfectly located just one block from the beach. Enjoy the best of coastal living with quick access to the sandy shores and refreshing ocean breeze. Our home is surrounded by an array of delightful restaurants, cafes, and shops, ensuring you'll never run out of things to do. It's tastefully decorated and fully equipped with modern amenities for a comfortable stay. Ideal for families, couples, or solo travelers looking for a relaxing beachside escape.

Guest favourite

Home

4.9 out of 5 average rating, 145 reviews

Beach Cottage #2 19th - 3 Blocks from Beach

Welcome to ResortCottages19. Cozy authentic beach cottage with many original features centrally located on 19th street, the heart of the VIBE district; boardwalk, beach, convention and sports center within 3 blocks. Walk or bike to local coffee shops, breweries, and restaurants. Take in the live music from various venues along the boardwalk. Shop at the Old Beach Farmer's Market on Saturdays. Enjoy the privacy of your own deck and backyard with plenty of parking. Easy access to the interstate.

Guest favourite

Apartment

4.85 out of 5 average rating, 128 reviews

Oceanfront, beachfront, boardwalk, fun, dolphins

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!

Cottage

4.79 out of 5 average rating, 117 reviews

Beach Cottage-Bay Views Loft on Beach & Veranda

We are on the Beach. Look at the Chesapeake Bay from the elevated veranda and living room from this second floor loft vacation rental. Our private wood walkways lead you from this rental to our beach. 100 year old duplex Cottage with large deck & Bay Views. Fully restored, modern & newly appointed. The rental isnt on the beach-side of the property so you will need to walk around the building to the beach which is only a few feet away. Read on about all of the amenities that await you here

Guest favourite

Apartment

4.93 out of 5 average rating, 59 reviews

VA Beach Retreat! Quiet and perfect for families!

Relax with the whole family at this peaceful place to stay. This property is ON the beach (unit itself is not facing the ocean) with access to 3 pools, a gym, local restaurants and much more! As you can see, guests LOVE my place! I frequently travel for work, spending a lot of time in hotel rooms. I know the NECESSITIES! ** I am currently replacing furniture! Pics may not match exactly but it is for the better. Expect brand new: King and queen mattresses. Bedding. Living room furniture.

Home

4.75 out of 5 average rating, 53 reviews

Cozy Coastal Cottage Steps from Ocean

This charming beach cottage is in the perfect location for your getaway! Nestled into a quiet, residential area in the city's desirable North Beach away from the hustle and bustle, but 2 BLOCKS FROM THE BEACH and the lively Oceanfront resort area and close to shopping, dining, and entertainment. Recently renovated with updated floors and finishes, with a fenced-in yard and a corner lot. Sit back, relax, and enjoy the beach breeze in the screened in porch. Your perfect vacation awaits!

Flat

4.83 out of 5 average rating, 155 reviews

THE OLD SALT A | Beach Living

Relax in the historic home of The OLD SALT. built in 1910 and renovated in 2021 this home is the perfect beach getaway. Nestled in heart of the highly sought after Virginia Beach Boardwalk area, close to the area’s best attractions, top restaurants and bars, you will find yourself right at home in this cozy haven. Just steps to the boardwalk and a beautiful view of the Atlantic Ocean. This unit is 3 bedrooms, 2 bathrooms, sleeps 6, and has the private second story deck.

Guest favourite

Flat

4.88 out of 5 average rating, 180 reviews

Va.Beach/Oceanfront Studio, Boardwalk, Beach, Pool

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 favourite

Home

4.96 out of 5 average rating, 188 reviews

Exit del Sol, North End Beach

The beach AND privacy! Wide open residential beaches, with plenty of "distancing space"! Best kept secret at the beach! Fully stocked, fully furnished, immaculate Vacation rental on Va Beach North End. 5 star rating says it all. Atlantic Ocean across the street. Public beach access. 3 flat screen TVs, Wifi, cable, beach cart, chairs &'umbrella. Outdoor grill. Private parking. 2025 Pool Season... May 23–September 7. NO HAIR DYE!

Guest favourite

Home

4.91 out of 5 average rating, 112 reviews

Cozy North End Cottage 1 block from the sand!

Welcome to our one-of-a-kind 3-bedroom beach bungalow in the heart of Virginia Beach’s historic North End. Located one block from wide, white-sand beaches and one block from the serene trails of First Landing State Park, we offer stylish and pragmatic accommodations all tucked gracefully under two beautiful Live Oaks. If you’re looking for the most relaxing house in Virginia Beach’s most relaxing neighborhood you have found it.

Home

4.92 out of 5 average rating, 12 reviews

Endless Beach #unitA-3bedrooms-steps to the ocean

Endless Beach A, located at 7707 Atlantic Ave. Just 270 steps to the beach, makes it easy to take a cup of coffee to watch the early morning sunrise! This part of the beach is a well-known dolphin watching spot nearly year-round! Barefeet Retreat offers 3 bedrooms and 1.5 bathrooms indoors, along with an outdoor shower in fenced back yard.

Guest favourite

Apartment

4.99 out of 5 average rating, 218 reviews

Chic's Beach Rental and Fishing

Duplex on Chic's Beach, expansive water view and private beach access right out the back door. Everything needed for the House & Beach included, including Coffee. We also offer Fishing Trips, Fish for Sale, Dolphin Cruises and Seafood & Greek Dinners! Michael Griffith, President/Manager, Chic's Beach Rental and Fishing LLC

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for beachfront rentals in Chesapeake

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Guest favourite

Cottage

4.97 out of 5 average rating, 237 reviews

Villa Positano

Guest favourite

Home

4.96 out of 5 average rating, 128 reviews

Water Oaks at Chic's Beach

Guest favourite

Home

4.92 out of 5 average rating, 137 reviews

Cozy beach cottage! One block to the beach!

Guest favourite

Home

4.93 out of 5 average rating, 116 reviews

3 bedroom private home a block from the beach!

Guest favourite

Home

4.89 out of 5 average rating, 130 reviews

Modern. Spacious. Pets Yes! 2Min Walk to Beach

Tiny home

4.86 out of 5 average rating, 122 reviews

☼ Beach Bungalow- 5 min walk to beach | parking ☼

Guest favourite

Home

5 out of 5 average rating, 102 reviews

Quiet East Beach Bungalow, 1 block to beach!

Guest favourite

Home

4.95 out of 5 average rating, 135 reviews

Family hideaway

Beachfront home rentals with a pool

Guest favourite

Home

5 out of 5 average rating, 12 reviews

Private retreat renovated pool/hot tub wild horses

Apartment

4.92 out of 5 average rating, 122 reviews

Ocean & Bay Views - Local Family Owned & Operated

Home

4.75 out of 5 average rating, 12 reviews

Beachfront/Pool/Hot Tub/Dog Friendly/Winter Specia

Guest favourite

Apartment

4.98 out of 5 average rating, 84 reviews

Paradise at the Beach

Guest favourite

Apartment

4.88 out of 5 average rating, 179 reviews

Oceanfront Jewel VB Studio Mesmerizing Ocean View

Guest favourite

Home

4.95 out of 5 average rating, 22 reviews

Sandbridge- Great Escape Saltwater Pool &Boat Ramp

Guest favourite

Home

5 out of 5 average rating, 22 reviews

Pool, hot tub, walk to beach, family friendly home

Guest favourite

Campsite

5 out of 5 average rating, 7 reviews

RV Lot (No RV) near all amenities

Private beachfront home rentals

Guest favourite

Holiday home

5 out of 5 average rating, 7 reviews

3 yr old home in Carova Beach! 6 person hot tub

Guest favourite

Home

4.96 out of 5 average rating, 25 reviews

Private Beachfront Modern Villa: Outdoor Shower!

Guest favourite

Home

4.99 out of 5 average rating, 78 reviews

Breathtaking Ocean views at Pinch Me, 8bdrm, 6bath

Guest favourite

Home

4.94 out of 5 average rating, 114 reviews

Lakefront House @ Oceanfront

Guest favourite

Home

4.96 out of 5 average rating, 69 reviews

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

Guest favourite

Home

4.99 out of 5 average rating, 186 reviews

Play by the bay beach house,

Guest favourite

Home

4.99 out of 5 average rating, 77 reviews

Beachfront 2 Dwellings EV charger

Home

4.72 out of 5 average rating, 18 reviews

Beach Front - Hot Tub - Game Room - 3500SQFT

Destinations to explore