
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.

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.

Private Pool at the Oceanfront in a Spacious Home
Private Pool at the Oceanfront in a spacious 2600 sq ft home. 3 blocks from the Virginia Beach Boardwalk, Vibe District. 4 bedrooms in a three-story Private Home. 1st Flr: 2 bathrms, a bedrm with Full-bunk bds, kitchen, dining rm & living rm. 2nd lvl contains a lux Mstr ste with massive jacuzzi, dbl shwr and living rm . 3rd Lvl: 2+ bedrms, bathrms & prvt balconies (queen in 1 room and 2 doubles in the other). Two-car garage and driveway, NOT a duplex. Pool unheated. Modern Tvs and cable!

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!

Beach Front with Paddle Boards and Kayaks
You have your own private access to the beach AND water views of the Chesapeake Bay that no other home in the area has. The sunrises and sunsets are breathtaking! Paddle boards and kayaks are provided. My husband and I renovated the interior of the house this past year. We poured all of our love (and sweat) designing and crafting a home away from home with you in mind!! You'll find the kitchen stocked with all of the essentials. Towels, soap, shampoo, and conditioner are all provided.

Peaceful beach @Courtyard Cottage+No Cleaning Fee!
There is no congestion, crowds, or large commercial beach resorts here. Experience the exact opposite at Courtyard Cottage, steps away from a quiet, peaceful beach surrounded by sand dunes for a special getaway. A park across the street offers playgrounds and pet-friendly walks, and a local farmers' market opens from 9 a.m. to noon. Saturdays, May 4 - Nov 23. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax". No parties, quiet hours after 10 pm.

Quiet East Beach Bungalow, 1 block to beach!
Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

New Beach Home on the Chesapeake Bay
New Beach House on the Chesapeake Bay. Entire 2500 SF Home, 1st, 2nd and 3rd floors. Three King size bedrooms, third floor with 2 Sofa Beds. One Full kitchen and one Kitchenette. House on the dune 40 steps to the sandy beach. Balcony view of bay for sunrise coffee & sunset wine. New & old homes surround this newly built home in "East Ocean View." Restaurants short walk, more only a two min. drive. Summer Sailing regattas on Weds. and Sun. evenings, live music at the Pavilion.

Play by the Bay 1 MIN TO WATER
LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill, Washer-dryer. Great water views while you are relaxing on the deck. Many amenities! Just bring your bathing suit. Our guests have all said they love this place! Very close to many wedding venues, restaurants, state park, oceanfront boardwalk is closeby, military bases, etc.

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony
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 on the balcony 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.

Quaint and Comfortable Buckroe Beach Getaway.
Our quaint, cozy and comfortable, 1,100sf house is perfect for a small family or small group of friends, 4 guests MAX, to relax from the hustle and bustle of life. Take a nap or watch a movie while relaxing on the cozy and comfortable power reclining living room furniture. Enjoy the patio and firepit in the spacious fenced backyard. This getaway is located a short two-minute car ride or ten-minute walk from the beautiful and family-friendly Buckroe Beach.

Villa Positano
This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

Beachfront Exclusive Bay front Suite
This comfortable private beachfront suite with kitchenette has magnificent views of the sunrise and sunset that you can enjoy from your own private deck, with a 180 degree views of the beach front with easy access to the water's edge, just steps away. If you want to experience life on the beach this is as close as you can get. This suite represents our personalities and everything we love about living at the beach on the Chesapeake Bay.
Popular amenities for beachfront rentals in Chesapeake
Pet-friendly beachfront home rentals

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

Beachfront Getaway, Pet Friendly, Mermaid Suite

OceansideLuxuryCondo*Walk2Beach*Pool*Pets*NoStairs

Ocean Bliss: Cozy Apt Retreat(D)

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

Saltwater Seaclusion- Corolla-Walk to Everything!

Semi-Oceanfront Beauty and the Beach

Semi-Ocean Front|4x4 Beach|PET friendly|Hot Tub
Beachfront home rentals with a pool

Beachfront Condo/ Pool/ Surfing/ Fishing / EW 205

Discount Feb/Mar Htd pool/hotub, firepit oceanview

Beach Luxury Beachfront

Sunset Bay - Gorgeous Bay and Sunset Views.

Ocean Front, One Bedroom Condo, VA Beach (Z272)

Oceanfront Gem VaB Studio Exceptional Views

OBC - 1BR/1BA - Partial Ocean View - Great Pools!

Oceanfront Condo with Balcony & Pool
Private beachfront home rentals

Riverfront Oasis | Kayaks, Private Beach, & More

902C Coastal King Retreat Steps from Beach + Sauna

1 Block to Oceanfront & Boardwalk

FREE Luxury Golf Cart - across from CC Beach

Back Bay & Sandbridge Beach Escape

Private Beachfront Bay Kayaks Family Sleeps 10

Chic's Beach Rental and Fishing

Saint Salty | Private Beach, Hot Tub + Bay Views
Destinations to explore
- New York City Holiday rentals
- Washington Holiday rentals
- Myrtle Beach Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Cape Fear River Holiday rentals
- Jersey City Holiday rentals
- Ocean City Holiday rentals
- Rappahannock River Holiday rentals
- Beach house rentals Chesapeake
- Family-friendly rentals Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Flat rentals Chesapeake
- Guest house rentals Chesapeake
- Rentals with a firepit Chesapeake
- Rentals with outdoor seating Chesapeake
- Apartment rentals Chesapeake
- Townhouse rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- House rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with pools Chesapeake
- Waterfront rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with lake access Chesapeake
- Cottage rentals Chesapeake
- Rentals with a kayak Chesapeake
- Beachfront rentals Virginia
- Beachfront rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Hampton University
- Currituck Beach
- Currituck Beach Lighthouse
- Town Point Park
- First Landing Beach
- Old Dominion University
- Chrysler Hall
- Virginia Living History Museum




