
Monthly Rentals in Gwynn Island
Discover long-term rentals that feel like home for stays of a month or longer.
Nearby monthly rentals
Guest favorite

Cottage in Gwynn's Island
4.91 out of 5 average rating, 35 reviewsLittle Gray Beach House
MarkRating, 5 stars1 week ago
Great experience, easy to get into, as advertised. Right on the water, awesome view. Instructions were easy to follow, all in all, I would definitely recommend staying there.
Guest favorite

Home in Gwynn
5 out of 5 average rating, 11 reviewsStill Waters Point
NatashaRating, 5 stars1 month ago
We had a wonderful Easter weekend at Tony’s home. This was our second time staying here, and we truly hope to come back again. It has become our special place of peace and energy. The view of the bay is breathtaking, and the sunsets are absolutely stunning. If you bring binoculars, you’ll enjoy birdwatching—there’s a favorite spot for birds right near the house. Beautiful, spacious beaches are just 20 minutes away, and the island itself is peaceful and quiet, with a very relaxing neighborhood atmosphere. The house is located in one of the best places on the island. It is cozy, spacious, and spotless, with large windows offering views of the Chesapeake Bay from almost every room. The big deck became our favorite place to enjoy breakfast and morning coffee. The home is thoughtfully equipped with everything you need for a comfortable stay. Tony and Paula are wonderful hosts who clearly pour their hearts into every detail of the house and genuinely care about their guests.
Guest favorite

Home in Gwynn
4.97 out of 5 average rating, 79 reviews‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
ToshaRating, 5 stars3 weeks ago
The host did a fabulous job explaining everything. The location was easy to find with GPS. The place has up dated furniture and appliances. One bedroom and full bathroom downstairs and 2 bedrooms and full bathroom upstairs. The kitchen was fully stocked with everything to cook with. The ocean is directly in front of the back porch. Its about 5 minutes away from a restaurant called "The Hole in the Wall". I had blackened tuna and it was delicious. 10 minutes away from a 7 eleven. 20 minutes away from Food Lion and a few other restaurants. The only thing that was a concern was our phone service went completely out at the location. We have AT&T service. The wifi was very useful. The neighbors were nice, but doesn't like the smell of medical marijuana. It's legal in VA to have marijuana with a medical card. You can't smoke outside the house. You will have to walk away from the house to smoke.
Superhost

Home in Hudgins
4.83 out of 5 average rating, 6 reviewsChesapeake Bayfront Home with Amazing Views!
KezeRating, 5 stars3 weeks ago
Definitely will be going back! Liked it so much I didn’t want to go home lol. Probably rent again in June. Only thing I recommend them to do is to update the pier it is useable. Just use extreme caution! Otherwise absolutely outstanding place!
The comforts of home and great monthly rates
Amenities and perks for longer stays
Furnished rentals
Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.
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Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*
Simple monthly prices
Special rates for long-term vacation rentals and a single monthly payment without additional charges.*
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*Some exclusions may apply in certain geographies and for some properties.