Kent Island vacation rentals
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Top-rated vacation rentals in Kent Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Cottage in Edgewater
4.99 out of 5 average rating, 149 reviewsWaterfront Chesapeake Bay Sunrises w/Private Pier!
Comfortable and cozy cottage on the water. The back deck and enclosed porch was super nice and the view was amazing. Had it not been so cold during our stay we would have been outside more. Everything was as described and perfect for the two of us and my mom. The dock was easily accessible which was nice. Great stay and close to our Son we were there to visit.
Home in Deale
4.96 out of 5 average rating, 28 reviewsBeautiful Waterfront Escape w/ Gorgeous Views
This is the perfect place for an indoor vacation with a gorgeous view. The home has everything one could need and the photos do not do the panoramic window view justice. We went during the winter and saw plentiful bird species and hope to return in the summer to enjoy the water activities.
Cottage in North Beach
4.98 out of 5 average rating, 141 reviewsBell Estates-Brand New Bay View, Beautiful Cottage
Daniel’s place was amazing. We stayed for Christmas and it did not disappoint. Daniel had thought of everything from appliances in the kitchen, to games both inside and out and the place was spotless. The beds were extremely comfortable and I have no complaints at all. Would recommend and happily stay again. Enjoyed morning walks along the water.
Cottage in Chesapeake Beach
4.94 out of 5 average rating, 84 reviewsCozy Getaway - Breezy Point Beach
Wonderful place! So cute and very clean! The porch was my favorite. Host was very responsive. The kitchen had everything we needed. The only thing i would recommend is a mirror in the master bedroom.
Cottage in Pasadena
4.97 out of 5 average rating, 172 reviewsFt. Smallwood Overlook. Waterfront with Kayaks!
The place is wonderful. We were down for Thanksgiving with my family and were travelling with our 2 dogs, Wally & Dolly. The location was perfect, close to Riviera Beach where our Family Thanksgiving Dinner was, very private, no noise or distractions for the dogs (that was great). The property was surrounded by water on three sides, great views! It is right next to Ft. Smallwood Park where we took the dogs for walks every day, they loved it. As for the house it was perfect for us, just about the size of our home, so that made it very comfortable for us. All one level, which made it great for us older people. It was furnished with very comfortable furniture. Lots of information about the local surroundings, things to do, and restaurants. Keith was wonderful to work with, very easy to communicate with which made the whole process very easy for us. We even had a conversation over the phone once we were in the house to make sure everything was to our liking, and we were happy !
Home in Centreville
5 out of 5 average rating, 22 reviewsWater Oasis on the Eastern Shore
This is a beautiful property with all the amenities our group of 11 college friends needed to catch up and relax together. We loved morning coffee on the screened in porch and lounging around the pool. New hot tub was also a big bonus. Plenty of room for everyone to sleep and lounge comfortably. Thank you so much!
Cottage in Saint Michaels
4.84 out of 5 average rating, 31 reviewsCottage #8 Herons Nest Lg 2 rooms Under Main House
It’s super cute, quaint and has such character. Something for the whole family we will be back.
Cottage in Pasadena
4.88 out of 5 average rating, 121 reviewsChesapeake Cottages- 2 Quaint Waterfront Retreats
A nice stay with family. If you know what to expect it’s a lovely stay. The cottages are small but the scenery is beautiful. A little run down but perfectly fine just for sleeping for a weekend. We did encounter a lot of flies but we were right on the water. Overall a good stay. Definitely visit Tuggies if you love a good dive bar!
Home in Cambridge
5 out of 5 average rating, 14 reviews"Riverside Retreat"
I had such a great stay at this property and Doug was a great host! The location is fantastic—it's in a friendly, welcoming community that's just a short walk to great restaurants and coffee shops, which was super convenient. The space itself was clean, comfortable, and had a cozy, inviting vibe that made me feel right at home. If you're visiting Cambridge, Maryland, I definitely recommend staying here—it’s the perfect spot for a relaxing getaway. Would stay again in a heartbeat!
Cottage in Easton
5 out of 5 average rating, 101 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
This was a fantastic place for a relaxing break between the holidays! I loved being right on the river, it was so serene and comfortable. The house was wonderful with the windows looking right out onto the river. I'd definitely recommend this place and hope to return. Cheryl was there to greet me when I arrived and sent great information about things to do in the area.
Home in Cambridge
4.98 out of 5 average rating, 122 reviewsWaterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms
Betty’s place was absolutely immaculate and beautiful! It had everything we needed and was wonderful for creating fun family memories. We would definitely stay here again and have saved it for future visits to Cambridge! Thank you again to our host Betty!
Home in Annapolis
4.93 out of 5 average rating, 108 reviewsHistoric Downtown House with Off Street Parking
Christopher’s place in downtown Annapolis is perfectly located! There are so many great shops and restaurants in walking distance. The off street parking was so convenient. The house itself is so cozy with very comfortable beds and nice towels and linens. The decor is tastefully done and the kitchen was well equipped with everything we needed to cook Thanksgiving dinner. Our family, including our beloved Golden Retriever, had a great time! For others traveling with a dog, just know that the yard is not fully fenced… the walkway by the house is open to the street and the rear yard is connected to a shared parking area…so you will need to keep a close eye on your dog. Overall we were so happy with our stay and would love to stay again. Thanks, Christopher, for sharing your home in one of our favorite places to visit. We will be back!
Vacation rentals for every style
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Popular amenities for Kent Island vacation rentals
Kent Island house rentals
Home in Lanham
4.89 out of 5 average rating, 72 reviewsModern 2 bedrooms house in prime location
Henok’s stay was absolutely as described. It was very spacious yet cozy space for our family. 2 bedrooms: 1 king size & 1 queen size bed. 1 shared bathroom that was very nice and clean. Appliances were updated, home was clean and comfortable couch. Attached laundry room to space. This is a shared space as this is the bottom space/“back house”. Private seperate entrance/paved walkway with no issues. Would love to visit again and see what this surrounding city has to offer.
Home in Millersville
4.85 out of 5 average rating, 26 reviewsA private space to celebrate
This home was beautiful, and we enjoyed our stay. It was in a quiet neighborhood and was the perfect place to celebrate Christmas. If we return to the area we would absolutely book here again! Michael was a wonderful host and we had only positive experiences. Thank you Michael!
Home in Tilghman Island
4.8 out of 5 average rating, 5 reviewsDreaming of a Cozy Winter? We’ve Got You Covered!
This was my first time utilizing Air BNB. I cannot say enough about Flaneur. Her home was exactly as described. Every T was crossed, every I was dotted. It was beautiful. It was perfect! We met the neighbors, who were beyond nice. It was just an amazing stay. My only regret is that it was not long enough. A group of us came down to charter a boat for a fishing trip. If Flaneur will have us, we will definitely be back! Thank you, Flaneur! Best regards, Michelle and Steve Simon
Home in Saint Michaels
4.83 out of 5 average rating, 78 reviewsHarrison House - in Town and on St Michaels Harbor
Very central location, easily walkable to everything in downtown St. Michael’s!
Home in Baltimore
4.76 out of 5 average rating, 21 reviewsUMB/Harbor/Stadiums/Convention Ctr - House 1 & 2
SPACIOUS!! If you have a large party size and don’t want to be on top of each other this is the house for you. We used both House 1 & 2 which was more than enough space.
Home in Arnold
4.81 out of 5 average rating, 26 reviewsEntire Private 2 bedrooms house, nice neighborhood
My children and I loved our stay!! It was very comfortable, clean, and had plenty of space. The host was very sweet and responsive, and it was nice to have our own little driveway and porch. We will definitely stay again!! Also, the location was great. Not too far from MANY shopping plazas and malls. Took my kids to the movies, Build a Bear, and bowling.... all in different locations, all less than a 25 miles (or way less) from this home!!
Home in Rock Hall
4.84 out of 5 average rating, 127 reviewsPirates Perch
Really enjoyed the stay. Great location. Quiet neighborhood and short walk to everything you need. Grocery store, coffee shop, pickleball courts, ice cream and so much more.
Home in Centreville
4.63 out of 5 average rating, 92 reviewsPeaceful Acres Guest House (A Nature's Getaway)
The house was comfortable, clean and quiet. It was exactly what I was looking for to participate in a nearby competition. There were minor issues that the host addressed quickly and we got back to our vacation. Would stay here again.
Other great vacation rentals in Kent Island
Home in Edgewater
4.91 out of 5 average rating, 139 reviewsHouse in Edgewater Maryland
The place was exactly what we needed. Location was perfect to get to everything we needed and wanted to do. We were able to check in a little bit early, which was amazing and helpful. Would definitely stay again!
Home in Deale
4.87 out of 5 average rating, 94 reviewsChesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home
Our group had such a lovely time at Shawn's home! The space itself was spacious and absolutely beautiful, even in the dead of winter. There were plenty of spaces to gather or take time alone, which was really important for our group. The kitchen was well stocked, and we had an easy time cooking our meals. The bedrooms were all nice and comfortable, and reflected the listing. Shawn was perfectly communicative and made it easy to contact her when necessary. We can't wait to return!
Home in Wye Mills
4.91 out of 5 average rating, 11 reviews⇚Family Getaway⇛| Lakeside + A Nature View |
Kevin is a great host to us year after year! we love staying at his place!
Home in Pasadena
4.85 out of 5 average rating, 54 reviewsBeautiful New Home Near Beach and Patapsco River
House looks even better than the pictures. Very nice, very modern and all amenities were wonderful. I am looking to come back in the summer and enjoy the lovely pool area.
Apartment in Baltimore
5 out of 5 average rating, 27 reviewsPatterson Park Apt; Walk to Hopkins, Bars, Cafes
Very responsive host. Apartment in fabulous location. In wonderful historic Baltimore house and neighborhood. Minor glitches addressed immediately and easily by host. If you’re looking for something fun and interesting this is it.
Home in Stevensville
4.97 out of 5 average rating, 31 reviewsCarolina Cottage - 2 story, pet-free home
We really enjoyed our stay here - it's so inviting, spacious, and "homey", and incredibly well-stocked. Tons of pots, pans, utensils, etc for cooking. We loved the main living area, bright and open. Large primary suite, mattress is quite firm. A couple of relatives joined us for a few days, and we had fun playing some of the games. Lots of local recommendations provided in guest book - we tried Harris' Crabhouse which was very good. Also walked to the Blue Heron preserve, wonderful place for a nature walk. Host communicated well and was very responsive to questions. Hope to return in warmer weather and use the deck.
Townhouse in Baltimore
4.96 out of 5 average rating, 134 reviewsArtsy, Historic Rowhouse with Striking Harbor Views
Baltimore! This is an excellent option for stays in the city. Walk the waterfront to Fells Point. Parking is free on Cambridge Street. The property is clean, spacious and has everything you need to make yourself feel at home.
Home in Stevensville
4.96 out of 5 average rating, 84 reviewsKent Island Beach House II by the Kentmorr Marina
Great place! Really cool location that makes you feel part of this unique community. We were in town for a family wedding and it was perfect. Our host Donna was exceptional (and friendly). We need to find a reason to go back soon!
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