
Gwynn Island vacation rentals
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Top-rated vacation rentals in Gwynn Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Gwynn Island vacation rentals
Other great vacation rentals in Gwynn Island
Top guest favorite

Home in Kilmarnock
5 out of 5 average rating, 58 reviewsSecluded beach front cottage on the Chesapeake Bay
AngieRating, 5 stars4 days ago
My absolute favorite airbnb ever ! This was the 3rd time I've stayed here, and if I could afford it, I'd go monthly. The location is perfect, right on the water, small private beach, lots of privacy and soooo incredibly relaxing. The house is very well laid out, super clean and comfortable. Keri provides more than most hosts, from the kitchen and bathrooms, to beach gear, movies, books, games, and the kayaks ! I love love love this house and location so very much. It feels like "my" home away from home and I'll continue to go back as much as possible. THANK YOU again Keri, for another amazing getaway !
Guest favorite

Home in Port Haywood
4.91 out of 5 average rating, 32 reviewsAnne's Beachfront Shangri-La
AntinnetteRating, 5 stars4 months ago
Our family Thanksgiving was great! What a beautiful home with a breathtaking view of the water!! Just waking up each day with that beautiful sunrise over the water was wonderful to see. What a hidden gem! Everything you possibly have needed was provided in the home. The fireplace was very nice especially on those cold evenings! We can't wait to return! Thank you Brandon for opening up your home to my family. We all felt relaxed & right at home!! Thanks Again Nicholas & Crouch family
Superhost

Home in North
4.82 out of 5 average rating, 44 reviewsWaterfront Sunsets With Pickleball Court & Hot tub
GregRating, 5 stars2 weeks ago
This is such a unique property! It was perfect for our family. We knew the weather was going to be cold and rainy for ~half our visit, but Jessica’s house did not disappoint. There is so much to do, which resulted in priceless family time. When the weather cleared, we fully enjoyed the outside amenities. The pickleball court, sauna, and hot tub were big hits. Jessica is a great communicator and enabled a memorable Spring Break for our kids.
Guest favorite

Cottage in Gwynn's Island
4.93 out of 5 average rating, 27 reviewsLittle Gray Beach House
AshleyRating, 5 stars4 days ago
This is a super cute place right on the water! It’s arranged in a way that feels comfortable and maximizes the space. It has everything you need! We loved staying here with our dog and one year old. The beach is a very easy walk and watching the sunrise on the deck is magical. Don’t miss the kind of hidden second bathroom tucked in with the laundry, it’s very handy!
Superhost

Home in Williamsburg
4.59 out of 5 average rating, 209 reviewsGR8 Family Vacation Rental
BrianRating, 5 stars4 weeks ago
Very well setup home with a great location for all of the historic triangle activities. Walkable for a few restaurants (<1mi) and very easy to get in an out of. Only item to be aware of is the morning traffic if you are sensitive to road noise but it doesn't pickup until closer to 7AM. The home has everything you need and enough space to relax after a full day walking the historic sites. Spence is a fantastic host and extremely quick to respond to any questions. He even provided some recommended activities and family friendly options for the kids. We will be looking to return once the kids are a bit older for our Busch Gardens trip.
Superhost

Home in Deltaville
5 out of 5 average rating, 5 reviews4 Bedroom plus loft walk to bay beach
ThomasRating, 5 stars9 months ago
The house was very nice, it was cleaned very well when we got there and there were plenty of amenities for everyone. The beach is accessible with maybe a two minute walk. The area is pretty, we saw horseshoe crabs and jellyfish at the beach, and the neighbors are friendly. The jellies can sting, but the kind of jellyfish here are painless enough that I initially thought I got bumped into by a floating stick, and the locals at the beach completely ignored the one in the water. The nearby restaurant/bar stays pretty busy, but it’s really nice as well.
Superhost

Apartment in Williamsburg
4.79 out of 5 average rating, 14 reviewsGovernor’s Green 2 Bedroom
LindsayRating, 5 stars5 months ago
Check-in was smooth. Deluxe 2 bedroom was very nice and large enough for my entire party. Beds were comfortable and everything was clean. Sorry we couldn’t stay longer to enjoy the resort amenities - but had a lovely stay. Would stay again.
Top guest favorite

Cottage in Irvington
4.98 out of 5 average rating, 162 reviewsCharming cottage next to Tides Inn with big yard
MadeleineRating, 5 stars1 month ago
Great stay for our family! Cute house, nice sense of design, very responsive host. Lots of good recommendations for things to do nearby.
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