Beachfront vacation rentals in Gwynn Island

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Gwynn Island

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Cobbs Creek

4.9 out of 5 average rating, 149 reviews

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!

Welcome to The Cottage at Misti Cove, where you can experience the epitome of relaxation and tranquility. Immerse yourself in the serene ambiance of our cottage, aptly named for its simplicity, which belies the luxurious amenities that await you. At The Cottage at Misti Cove, we understand that the essence of a fulfilling vacation lies in the delicate balance between embracing the simple life and indulging in modern comforts. Here, you will discover a haven that seamlessly blends these elements

Top guest favorite

A bright loft bedroom features large windows offering expansive views of the water, with soft natural light illuminating the space. A spacious bed is complemented by a ceiling fan and a comfortable chair, creating a serene environment for relaxation.

Guesthouse in White Stone

5 out of 5 average rating, 237 reviews

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

Guest favorite

A classic brick duplex features a large front porch supported by white columns. A ceiling fan hangs in the shaded area, while steps lead up to the entrance. Lush greenery lines the porch, and a clear blue sky complements the welcoming design.

Home in Cape Charles

4.95 out of 5 average rating, 139 reviews

Harbor View- (Sun - Sun rental June- Aug.)

Harbor View is an early 1900's brick duplex with high ceilings, transom windows, and crown molding. Best of all, this home is located in a quiet neighborhood just one block from the beach and two blocks from Mason Ave. where you can find unique shops, restaurants and other amenities. It's an easy walk to the pier for a magnificent sunset, or to Brown Dog's for homemade ice cream. We invite you to enjoy our comfortable home, and explore the quiet ambience of a historic beach town vacation!

Guest favorite

A light-filled living area features a simple sofa positioned on a textured rug, complemented by a wooden cabinet and a curved staircase. Natural wood accents and large windows enhance the inviting space, with greenery visible outside.

Barn in Cobbs Creek

4.95 out of 5 average rating, 112 reviews

The Barn at Pond Point - Riverfront Home

The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

Top guest favorite

A two-story blue house is positioned waterfront, with a white metal roof and multiple windows. A grassy area surrounds the property, complemented by large trees. The calm water reflects the house's exterior, creating a serene atmosphere.

Home in Gloucester Courthouse

4.97 out of 5 average rating, 310 reviews

"Bee-Z Haven" Waterfront Cottage on the Ware River

Curious about what makes Gloucester so wonderful? Live like a local at this Upscale Waterfront Retreat and find out for yourself why renters say "Enjoy the Breath Taking Views". Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our area is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Top guest favorite

A wooden dock extends over calm waters, leading towards a sandy beach bordered by grass. A two-story house is visible on a grassy hillside in the background, surrounded by trees. The sky features soft clouds, adding to the serene atmosphere.

Guest suite in Dunnsville

5 out of 5 average rating, 266 reviews

The Bird's Nest at Holly Bluff-Riverfront. Beach.

This is a spacious apartment above detached garage, with a roomy balcony. The property sits on the Rappahannock River- guests are welcome to use the beach and dock! Property has a private entrance. The bathroom which is located on the first floor. Apartment is up a flight of stairs above the garage. Plenty of parking. EV charger available. We have self check in and the host is extremely flexible.. We welcome all tenants! The Birds Nest is a perfect getaway destination for relaxing and fun.

Guest favorite

A modern beach house is set among tall pines, featuring large windows that provide sweeping views of nature. The exterior showcases a blend of wood and stone, while a spacious deck extends out, accommodating outdoor seating. A vehicle is parked nearby, emphasizing accessibility.

Home in Cape Charles

4.98 out of 5 average rating, 113 reviews

Wander Cape Charles

A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

Guest favorite

A sandy beach is visible from under a wooden pavilion, featuring a curved shoreline leading to calm waters. Footprints dot the soft sand, which extends toward the waterline. The structure has a thatched roof and offers shade, enhancing the serene coastal setting.

Home in White Stone

4.94 out of 5 average rating, 109 reviews

Coastal Farmhouse Getaway

Take it easy at this unique and tranquil getaway. This fully renovated historic farmhouse sits on 4 acres on Windmill Point. Spend the day on the expansive yard or our private beach on the Rappahannock/Chesapeake Bay. Perfect for fishing, crabbing, kayaking or just relaxing! The waterfront pavilions and tiki bar are the perfect oasis to set up camp. The house was completely renovated historic home that offers unmatched comfort and charm. Enjoy water views from almost every room!

Top guest favorite

Home in Deltaville

5 out of 5 average rating, 122 reviews

"No Bad Days" in this Fabulous Beachhouse w/ Dock!

You'll have "No Bad Days" in this beautiful beachfront home on the Rappahannock River with 123' of private beach and private dock with jetski lift. This stylish, comfortable home is well equipped with many inside and outdoor amenities. Watch sunset at the outdoor firepit table or choose the indoor fireplace in colder months. High speed internet and Smart TVs keep you connected while you kayak, bike, fish and enjoy river living at its finest. The town of Deltaville is 2 miles away.

Top guest favorite

The duplex features a light blue exterior with a welcoming front porch. Rocking chairs are arranged alongside the entrance, inviting relaxation. The well-maintained lawn is complemented by tidy landscaping and a concrete pathway leading to the front steps.

Home in Cape Charles

4.96 out of 5 average rating, 246 reviews

Steps to the Sea at Salt Box

Escape to The Salt Box, a charming 1915 duplex just one block from the beach in the heart of Cape Charles' Historic District. This cozy, private retreat sits on a peaceful, tree-lined street and is a short stroll to the beach, pier, shops, restaurants, and more! Check out our local Guidebooks or text us anytime—we're happy to share our favorite local spots! Looking for even more space? You can also book the other half of our duplex, Salt Box II!

Superhost

A spacious wooden deck overlooks the expansive Chesapeake Bay, framed by tall trees. The calm water stretches towards the horizon under a clear blue sky, with a sandy beach visible in the distance.

Cottage in Reedville

4.88 out of 5 average rating, 203 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

180 degree million dollar views in the quaint town of Reedville, VA. Away from all the noise, you won't want to leave our cottage once you get here. Upstairs bedroom has a private balcony with breathtaking views. Bay views from almost every window in the house. Perfect getaway for couples or the whole family. 60 inch Smart TV! Come build some memories!

Top guest favorite

A screened-in porch is highlighted, featuring a simple rectangular table paired with four chairs. A lantern sits on the table, while views of the serene water and trees are visible beyond the screen. The brick flooring complements the natural surroundings.

Cabin in Deltaville

4.97 out of 5 average rating, 286 reviews

"The Little Red Cabin" aka The Galley

Called the "The Galley". This is the first cabin built on the property. Right on the water with views of the Bay and beach. Galley kitchen, bedroom, small bathroom with shower, family room with a fireplace and dining area. Big screened in porch w/ fabulous breezes. Literally, right on the water!!! NO PETS. Parking for 1 car.