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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Gwynn Island beachfront rentals
Pet-friendly beachfront home rentals
Home in Dunnsville
4.76 out of 5 average rating, 131 reviewsCozy & Content River Retreat Beach Hot Tub & Games
Feb 25 – Mar 4
Home in Cape Charles
4.95 out of 5 average rating, 118 reviewsHarbor View- (Sun - Sun rental June- Sept)
Jan 17 – 24
Cottage in Gwynn
4.96 out of 5 average rating, 26 reviewsIsland Get-A-Way on the Chesapeake Bay with Beach
Nov 10 – 17
Home in Moon
5.0 out of 5 average rating, 14 reviewsThe Retreat at Lilly's Neck
Jul 11 – 18
Home in White Stone
5.0 out of 5 average rating, 6 reviewsRelax Waterfront Hot Tub, Game Room, Frisbee Golf
Apr 13 – 20
Home in White Stone
5.0 out of 5 average rating, 50 reviewsOyster Creek Retreat: Waterfront | Dock | 2 Kings
Oct 20 – 27
Home in Christchurch
5.0 out of 5 average rating, 37 reviewsLuxury River House w/Private Beach
Jan 16 – 23
Home in Deltaville
4.96 out of 5 average rating, 26 reviewsSunset Pointe
Mar 1 – 8
Beachfront home rentals with a pool
Apartment in Cape Charles
4.98 out of 5 average rating, 183 reviewsCape Charles Plantation Home “Nevill’s Nook Suite”
Nov 26 – Dec 3
Camper/RV in White Stone
4.9 out of 5 average rating, 86 reviews“Old Smokey”A cozy, single bedroom, unique getaway
Jul 28 – Aug 4
Barn in Cobbs Creek
4.95 out of 5 average rating, 94 reviewsThe Barn at Pond Point - Riverfront Home
Sep 22 – 29
Home in Heathsville
4.92 out of 5 average rating, 25 reviewsWeekly discount 10% - cottage with pool and dock!
Sep 28 – Oct 5
Cottage in Heathsville
4.83 out of 5 average rating, 58 reviewsRiverfront Retreat with PRIVATE POOL and BEACH!!
Sep 29 – Oct 6
Vacation home in Cape Charles
5.0 out of 5 average rating, 15 reviewsCheerful 3 bedroom Beach House in Cape Charles, VA
Jan 23 – 30
Home in Cape Charles
5.0 out of 5 average rating, 9 reviewsBaydream
Nov 28 – Dec 5
Home in Cape Charles
5.0 out of 5 average rating, 8 reviewsCoastal Soul/spacious/updated/perfect beach escape
Dec 19 – 26
Private beachfront home rentals
Tiny home in Cape Charles
4.94 out of 5 average rating, 147 reviewsUnique, luxurious creekside stay in Cape Charles
Jan 9 – 16
Home in North
5.0 out of 5 average rating, 39 reviewsThe Llama House
Nov 2 – 9
Home in Gwynn
4.98 out of 5 average rating, 61 reviews‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
Nov 5 – 12
Home in Cobbs Creek
4.98 out of 5 average rating, 45 reviewsThe Gold Coast
Dec 24 – 31
Treehouse in Machipongo
4.96 out of 5 average rating, 25 reviewsTreehouse Couple's Retreat
Jan 6 – 13
Cottage in Deltaville
5.0 out of 5 average rating, 63 reviewsUnique & bright two-bedroom waterfront cottage
Apr 2 – 9
Place to stay in Machipongo
5.0 out of 5 average rating, 54 reviewsSmokehouse on the Chesapeake Bay
Aug 7 – 14
Home in Machipongo
5.0 out of 5 average rating, 31 reviewsPrivate Country Beach Retreat
Mar 21 – 28
Destinations to explore
- Virginia Beach Vacation rentals
- Ocean City Vacation rentals
- Richmond Vacation rentals
- Alexandria Vacation rentals
- Norfolk Vacation rentals
- Williamsburg Vacation rentals
- Lake Anna Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom