Beachfront holiday rentals in Gwynn Island

Find and book unique beachfront homes on Airbnb

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Popular amenities for beachfront rentals in Gwynn Island

Pet-friendly beachfront home rentals

Top guest favourite
Home in Hudgins
5 out of 5 average rating, 9 reviews

Water front Coastal Bungalow with boat docks

KaraRating, 5 stars3 weeks ago
This was one of the cleanest, well thought out Airbnbs my Husband and I have ever stayed in! The host was quick to respond with any needs, the home was well stocked with essentials, and had notes with recommendations for the area. We loved drinking coffee on the dock and watching movies in the outdoor living area. The area is so quiet and peaceful.
Top guest favourite
Guest house in Cobbs Creek
5 out of 5 average rating, 16 reviews

Piankatank Riverfront Perch in Mathews County, VA

GreggRating, 5 stars1 month ago
Great place and location, we had a great time, we will be back !!! Thank you
Guest favourite
Cabin in Gloucester
4.95 out of 5 average rating, 19 reviews

Bill's Island

GeorgiaRating, 5 stars3 weeks ago
'A diamond in the ruff'. Our first AirBnB and we absolutely loved the cabin. Had everything we needed & very clean. We had wonderful weather, nice breeze off the water. Fish were biting. Very quiet . A great getaway cabin. Our hostess Lorena was great, checked on us to see if we needed anything. Well stocked kitchen. Thank You Lorena!
Top guest favourite
Guest suite in Dunnsville
5 out of 5 average rating, 269 reviews

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

AkaleiRating, 5 stars1 month ago
T’s place was absolute perfection! It was beautiful, tastefully decorated and the homemade muffins and cookies were amazing! She and John were so lovely and accommodating. Relaxing on the dock on the river was a sublime experience as well! I really can’t say enough about my time spent there and if I’m ever in the area again I will definitely be staying at T’s! Why would you stay anywhere else!?
Guest favourite
Home in Cape Charles
4.95 out of 5 average rating, 144 reviews

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

TheresaRating, 5 stars3 weeks ago
We absolutely loved the stay at Janie’s place! It was great and such a short walk to the beach. The beach wagon, chairs, and umbrellas were a nice touch and saved us from having to bring our own! There is also a propane and charcoal grill available for use, which is amazing. We look forward to booking our next trip to Cape Charles here, hopefully sooner rather than later! We have heard Christmas time is beautiful!
Top guest favourite
Home in White Stone
5 out of 5 average rating, 51 reviews

Waterfront Retreat w/ Hot Tub, Game Room, Kayaks,

ShaneRating, 5 stars3 weeks ago
I have a lot of experience not only traveling and staying at a variety of properties, but I have been a host and landlord for several years as well. Maria is a 5 Star Host who made the booking and entry process extremely easy with exceptional communication. The location and accommodations exceeded our expectations, and all of the guests agreed that this is a property we could see ourselves booking again in the future. Great place that is well worth the investment!
Superhost
Home in Dunnsville
4.75 out of 5 average rating, 144 reviews

Cozy & Content River Retreat Beach Hot Tub & Games

ChristineRating, 5 stars1 month ago
We had a great time at Nicholas and Dana's place! It was both fun and relaxing. We really enjoyed the little beach, the dock and the kayaks. We caught some catfish and one tiny crab in the crab trap (and threw everything back in). It was nice to have the firepit and hot tub to use too. And, the kids really liked being downstairs in their own space. The only issues were that the key pad wasn't working to get in to the front door which was frustrating after a long drive and the grill was very slow to heat up and probably needs to be replaced. Overall, this home was a really good choice for us and we would stay again when visiting family in the area.
Guest favourite
Cottage in Reedville
4.89 out of 5 average rating, 46 reviews

Waterfront Bay Cottage w/ Your Own Private Beach

BrandonRating, 5 stars2 weeks ago
We had a fantastic stay at this charming cottage on a private beach! The peaceful setting and direct access to the water made for a truly relaxing getaway. We especially loved the Adirondack chairs and firepit overlooking the Chesapeake Bay—perfect for amazing views and cozy evenings. The master bedroom and living spaces offered beautiful water views that made every moment feel serene and special. The owner was incredibly accommodating with check-in and shared thoughtful, personal tips that made our stay even more enjoyable. Highly recommend this spot for anyone looking to unwind by the bay!

Beachfront home rentals with a pool

Home in Heathsville
5 out of 5 average rating, 10 reviews

Gorgeous Historic Riverfront House

RobinRating, 5 stars45 months ago
My daughter found this gem online to book for my 65th birthday and a family get-together on the Northern Neck. We stay in Airbnb homes quite frequently all over the world and this is the loveliest home we've had the good fortune to stay in. Christine is the most gracious host and this home is special because she has made it that way for her family. It's a huge difference to stay in a vacation home that the host rents and a home that the host lives in. Christine's eye for beauty is exquisite and the home is comfortable as well as beautiful. It seldom happens that you say, "I wish the house had (fill in the blank)" and this house has it. The river is a gorgeous backdrop and there are kayaks to use. The saltwater pool is a great addition and a reason to hang at the house. And there is everything one needs to knock out a meal or if you don't want to cook, plenty of places to eat in the area. All in all, this house is a 15 out of 10!!
Home in Heathsville
5 out of 5 average rating, 10 reviews

Waterfront Escape Pool Dock Kayaks Chesapeake Bay

KarenRating, 5 stars2 weeks ago
My family and I had a terrific stay. The house was very accommodating, clean, and comfortable. Allison was a great help and responded quickly to every inquiry. The outdoor space is great - we used the fire pit every night and I brought my boat and kept it at the dock. We would definitely stay here again!
Home in White Stone

Rappahannock River House

LizbethRating, 5 stars19 months ago
Great host and great stay! Would definitely stay here again!
Home in Cape Charles
5 out of 5 average rating, 17 reviews

Coastal Soul/spacious/updated/perfect beach escape

RobertRating, 5 stars7 months ago
Excellent house in Cape Charles. The house was able to accommodate our group comfortably. Our only regret was not being able to stay longer.
Home in Heathsville
5 out of 5 average rating, 4 reviews

18 Acre Wood

NicoleRating, 5 stars1 month ago
This home was amazing - Jack and Beth were wonderful - everything we needed was right there - game room was perfect for the kids - the house was tremendous and spotless and perfect and I can’t say enough great things about my experience. I would 110% recommend this home to anyone!! Book it!!!
Home in Cape Charles
5 out of 5 average rating, 8 reviews

Handicap Accesible, with Beach, Pool & Tennis!

JRating, 5 stars8 months ago
Blue Belle was a fun and roomy place to spend a long weekend with our family! It’s in a great area and was easy to get anywhere you wanted to go in Cape Charles. We rented a golf cart but it wasn’t in the best of shape. That’s not Doug’s fault but that of the rental company. Therefore, we didn’t really use it as much as we would have liked. Doug was prompt in getting the washing machine repaired and it was needed. Our granddaughters enjoyed playing the ring on a string game on the back porch and walk to the beach nearby. I recommend staying here!
Home in Gloucester County
4.63 out of 5 average rating, 52 reviews

Private 5-acre Waterfront Peninsula with Beach

TroyRating, 5 stars1 month ago
This was a short trip for a bachelor/bachelorette party. Everyone who was coming was so impressed and was like we wish we were staying here longer than one night! Mary was very responsive and even popped out and said welcome when we arrived! Definitely would recommend this place for a fun get away! The bonfire was definitely a recommended opportunity! Thank you again Mary!!
Superhost
Cottage in Heathsville
4.84 out of 5 average rating, 80 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

YVisRating, 5 stars2 weeks ago
Awesome place with my t, we had everything we needed and more. Great location to disconnect and connect with one another. Plenty of space, locals, location and great amenities.

Private beachfront home rentals

Guest favourite
Home in Lancaster
4.94 out of 5 average rating, 85 reviews

River Home on Sea Glass Beach

RosemarieRating, 5 stars2 weeks ago
We loved our mini vacation at Darrell’s. The home had everything one would need and it’s located in a quiet, private area with plenty to do. And one can’t not mention the friendly neighbors and beautiful surroundings. We would love to come back again. Thank you for hosting us!
Guest favourite
Home in Gloucester
4.92 out of 5 average rating, 90 reviews

Beach Heron Retreat

JoyRating, 5 stars1 month ago
This beautiful home is truly a gem! We mostly enjoyed the screened in porch with comfy furniture, ceiling fans, and a fantastic view. The quiet, peacefulness was a great escape. We didn't want to leave! Thank you Ashley for sharing your gorgeous home with us and for being so attentive to our needs. You put a lot of thought into creating a special experience for your guests and it shows. We hope to return soon.
Superhost
Cabin in Reedville
4.73 out of 5 average rating, 22 reviews

"Elderberries" Chesapeake Bayfront Cottage

JoelRating, 5 stars3 weeks ago
We enjoyed our stay here. Very quiet area, nice comfortable space. The gravel road leading in (maybe a half-mile long) and driveway gave us a good area for morning and evening dog walks. We did not end up doing any fishing but the pond looked like a great place for kayak fishing. Not specific to the house but in the area: Rita's Cafe in Weems was great (food truck on a small road)--Chef Craige usually has a special and some regular menu items. Leadbellys (at Fairport Marina) had good oysters and hush puppies and was convenient for our first night. River Market in White Stone has good food to be ordered at the rear counter and prepared items in the coolers. Out of the Oven Bakery (White Stone) had great bread Miss Mary's seafood, also in White Stone had great fresh fish and prepared items. The three places in White Stone are very close to each other so convenient when running out.
Superhost
Cottage in Port Haywood
4.67 out of 5 average rating, 3 reviews

Beach Music Chesapeake Bay Getaway for all Seasons

AnnaRating, 5 stars10 months ago
Our stay at this property was truly an amazing getaway. The breathtaking views and stunning sunrises from the porch were a daily delight. The home is exactly as described and absolutely beautiful. We felt like we were at home. Each room is uniquely decorated. The doors opening up from the upstairs living room to the porch outside with a comfortable couch was so wonderful. We enjoyed the quietness Beach Music offered. We look forward to coming back soon one day.
Guest favourite
Home in Jamaica
4.91 out of 5 average rating, 64 reviews

Waterfront Sandy Beach Retreat near Urbanna

NancyRating, 5 stars5 days ago
Karen was very quick to respond to our questions. The house was lovely. There were canoes, kayaks and water boards for the family to use. Baby pool for the kids. Fishing and crabbing was great entertainment for all. Kitchen well stocked with anything you needed.
Guest favourite
Cottage in Cape Charles
4.93 out of 5 average rating, 27 reviews

The Crew's Quarters: Steps from the Bay

SueRating, 5 stars1 week ago
Caryn’s home was perfect for our needs. She was very responsive to our question and provided valuable information about the area.
Top guest favourite
Home in Reedville
5 out of 5 average rating, 90 reviews

The View at Jerk Cove - River Escape

QuynhRating, 5 stars2 weeks ago
The house was beautiful, clean and plenty of space for our family of five. The view is amazing. Overall, we really enjoyed our stay and hope to come back again soon.
Guest favourite
Home in Reedville
4.93 out of 5 average rating, 40 reviews

Summer Breeze waterfront new home-Private Beach

StormyRating, 5 stars1 week ago
This is a perfect spot for a girls weekend to just be. The surroundings are gorgeous and the home is fantastic. It is a quiet neighborhood for those who enjoy early morning walks. Every room of the home feels airy and comfortable. I would return for sure.

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Mathews County
  5. Gwynn
  6. Gwynn Island
  7. Beachfront rentals