Holiday rentals with a kayak in Chesapeake

1-Bedroom Home Near Christopher Newport University

Sip a bourbon while you listen to a record on the vintage player. Create your CD playlist to pop in the 90s 5 disk changer while you cook on a seasoned cast iron on the new stove. Check out the coffee bar for home roasted beans. Soak in the hot tub, or get a high score on Dig Dug. Centrally located in Newport News near CNU. 25-30 minute drive to Busch Gardens, Water Country, and Colonial Williamsburg. 45 minute drive to the ocean front. Great neighborhood with sidewalks for running and walking.

The Green Bean Bungalow

Kick back and relax at The Green Bean Bungalow (400 sq ft) with peaceful waterfront views of Back Bay Sandbridge. This tiny home comes with full bay access (paddleboard provided), community pools (seasonal), tennis/pickleball court, basketball court, playground, a short distance to the beach (beach chairs & beach/pool towels included) and local restaurants. We are a part of the Surfside RV Resort in Sandbridge. You’ll be foot steps away from family fun and relaxation! *Please read all info below

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

If you enjoy majestic ocean views from almost every room & your own exclusive beach just steps below, Bay Bliss is for you! The panoramic views from this luxury home are unmatched & sure to relax you! Sip coffee from the grand deck or take a soak in the hot tub w/ breathtaking views. Cook/eat in the high-end chef's kitchen or watch a movie on a 75" TV all with stunning views! Wake up in the plush, king-sized bed and enjoy views of the water without having to get up. Your bliss at the bay awaits!

Stunning Views of Back Bay & Seconds to the Beach

Be our guest and enjoy some of the most spectacular views in all of Virginia Beach. Lounge in the pool and watch the sun set over Back Bay or enjoy exploring Back Bay with fishing and site seeing. With the beach being a block away, you can get your feet wet with surfing or snorkeling or simply relax on the beach with your favorite beverage. Little Island Park, Back Bay Wildlife Refuge & The Baja are just a few minutes away as well. This 6 bedroom home, with 11 beds will be the perfect get away.

3 bedroom 3 bathroom beach house pets welcome

Welcome to your perfect vacation getaway! This remodeled 3-bed, 2.5-bath ranch house is just a mile away from the ocean front. It's an ideal destination for families, friends & pets. All bedrooms have queen beds and smart tvs. Pet-Friendly (fee)The spacious backyard and deck are perfect for playtime and relaxation. Great location close to shopping and restaurants. You’ll feel right at home in this safe neighborhood. Please note: No parties. Only 9 people are allowed at the house at any time

The Sportman's Lodge

The Sportsman’s Lodge is a rustic and relaxing modern getaway with all the conveniences you are accustomed to but surrounded by the gorgeous Back Bay Wildlife Refuge. Enjoy the relaxing countryside at this waterfront property, while still being only a short drive away from Sand Bridge Beach. If you are looking to get away from the standard Virginia Beach Boardwalk tourist experience and get back to nature, this is the place for you. Free kayaking to Back Bay, access to fishing and crabbing.

Oceanfront Escape Private Beach

Our waterfront home on Willoughby Bay! Why You’ll Love It: With a small private beach in the backyard for a peaceful escape, and a larger beach just a 5-minute walk away Piano & guitar for music lovers to enjoy Game table for fun-filled nights 4+ private parking spots Spacious 2,800+ sqft open floor plan with bay views Close to Willoughby boat ramp great for boaters Whether you're soaking up the sun, making music, or watching the sunset over the water, our home is a perfect retreat.

Waterfront Family Stay:Kayaks, Theatre, Wifi, Desk

🎬 Movie Nights & Waterfront Fun 🌊 Host your own movie night on a 120" screen with high-end 3D projector, a library of 3D films, and rechargeable glasses for everyone. Step outside to a backyard retreat with outdoor dining, fire pit, and direct access to our private dock for fishing and kayaking. Sleep easy with a king bed in the master and two comfy doubles in the guest room. The home accommodates up to 6 guests. Please note: any visitors not on your reservation are $25 per person.

Quaint 2 Bedroom Cottage in Chicks Beach

This 2 bedroom 1 bathroom quaint cottage is the perfect small family getaway. Located 2 residential blocks to the beach. The beach is great for families with children. This unit is connected to a 1 bedroom rental. Back yard has a single detached unit also . Great for small families. There is a fenced in front yard Back yard and laundry area is shared with guest suite next door. 2 Car max allowed $100 pet fee with pre approval. ***Summer 2026 check in on Friday only ****

Island Lotus Yoga & Spa

A nature lover’s dream! Waterfront, ample natural light, serene beauty, and privacy can be all yours at our charming ranch right on the bay. The bay faces east, giving you the most breathtaking views of the sunrise and moonrise. Relax in the spa, adventure on kayaks, and chill and grill over the fire-pit. You’ll also local fresh eggs, and a private yoga class. Check us out on insta @islandlotusyoga! PS we’re not actually an island. Reach us by driving through Virginia Beach!

Oceanfront Cozy Beach Duplex

Wake up to stunning ocean views in this beachfront duplex in East Ocean View, Norfolk! Each 2BR unit offers cozy comfort, a full kitchen, fast Wi-Fi, and direct beach access just steps from your door. Perfect for family vacations, couples, or group getaways. Enjoy sunrise views from the bedroom, sandy strolls, and easy access to local dining. Free parking, smart TV, and self check-in included. Perfect spot for a family vacation.

The Sandbridge Rose: Beach and Bay Retreat

The Sandbridge Rose blends beach relaxation with bayfront beauty, offering a serene, stylish escape just 3 blocks from the ocean. Overlooking peaceful Back Bay, the private pool, expansive deck, and large yard invite effortless outdoor living. With water views all around and plenty of space to gather, it’s the perfect place to unwind, explore, and make lasting memories—every moment at The Rose feels refreshing and unforgettable.