Holiday rentals with beach access in Chesapeake

Perfect Escape with Ocean Breeze!

A new home constructed in 2021 that is a 5 minute walk to the beach from 25th Street. Located in the heart of Old Beach with numerous restaurants, bars, high end supermarket and the boardwalk all within walking distance from the home. The home consists of 3 bedrooms, a bonus room with a king size bed, and a media room/office with a queen size pullout sofa. The home is professionally designed with detailed amenities for our guests throughout the home. Transcendent Stays is a locally driven group

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.

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.

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.

Nates Nook on Back Bay

Welcome to Surfside at Sandbridge. We are located on the northern tip of the OBX...in Va!!!!! This tiny home is in the most secluded area of the resort. Offering tons of nature and beautiful surroundings. One of the 2 pools is only 150 steps away. the beach is 950 steps...or you can drive and park at the resort entrance. We have pickle ball and a boat ramp. You can park your boat behind your unit if you wish and the fishing is great! we provide all beach accessories!!

Summer fun at Summer Salt!

Awesome off road getaway! You will need 4 Wheel Drive (not awd) vehicle to access the property as there are no roads. Newer construction on the beach in Carova right next to the wild horse preserve. You will likely see horses on a daily basis! Home has 3 bedrooms and 3 baths with 3 deck areas to enjoy the ocean views, sunsets and breezes! Easy walk to the beach, parking passes included. New party deck with hot tub, grill, table, seating and string lights.

Sunrise, 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!

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.

FREE Luxury Golf Cart - across from CC Beach

🏖 Steps from the Sand – Unbeatable Location! This stunning, single-story ranch home is directly across from the Cape Charles beach, sitting on the corner of Bay Ave & Monroe Ave—the most coveted location in town! Enjoy breathtaking sunsets, walk to local dining, golf cart or bike through charming streets, all from your front door. Just purchased a 6 seater golf cart, and decided to make it free for the 1st year!