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.

Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 149 reviews

Waterfront Chesapeake Bay Sunrises w/Private Pier!

EricRating, 5 stars1 month ago
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.
Guest favorite

Home in Deale

4.96 out of 5 average rating, 28 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

JanessaRating, 5 stars1 week ago
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.
Guest favorite

Cottage in North Beach

4.98 out of 5 average rating, 141 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

JonathanRating, 5 stars1 month ago
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.
Guest favorite

Cottage in Chesapeake Beach

4.94 out of 5 average rating, 84 reviews

Cozy Getaway - Breezy Point Beach

JenniferRating, 5 stars4 months ago
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.
Guest favorite

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars2 months ago
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 !
Guest favorite

Home in Centreville

5 out of 5 average rating, 22 reviews

Water Oasis on the Eastern Shore

KatjaRating, 5 stars4 months ago
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!
Superhost

Cottage in Saint Michaels

4.84 out of 5 average rating, 31 reviews

Cottage #8 Herons Nest Lg 2 rooms Under Main House

NicoleRating, 5 stars19 months ago
It’s super cute, quaint and has such character. Something for the whole family we will be back.
Superhost

Cottage in Pasadena

4.88 out of 5 average rating, 121 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

AlexaRating, 5 stars2 months ago
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!
Guest favorite

Home in Cambridge

5 out of 5 average rating, 14 reviews

"Riverside Retreat"

ValerieRating, 5 stars4 months ago
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!
Guest favorite

Cottage in Easton

5 out of 5 average rating, 101 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

KathleenRating, 5 stars1 month ago
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.
Guest favorite

Home in Cambridge

4.98 out of 5 average rating, 122 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

BeverlyRating, 5 stars2 months ago
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!
Guest favorite

Home in Annapolis

4.93 out of 5 average rating, 108 reviews

Historic Downtown House with Off Street Parking

LisaRating, 5 stars2 months ago
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!

Popular amenities for Kent Island vacation rentals

Kent Island house rentals

Guest favorite

Home in Lanham

4.89 out of 5 average rating, 72 reviews

Modern 2 bedrooms house in prime location

JubileeRating, 5 stars1 week ago
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.
Guest favorite

Home in Millersville

4.85 out of 5 average rating, 26 reviews

A private space to celebrate

NoahRating, 5 stars1 month ago
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!
Superhost

Home in Tilghman Island

4.8 out of 5 average rating, 5 reviews

Dreaming of a Cozy Winter? We’ve Got You Covered!

MichelleRating, 5 stars5 months ago
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
Superhost

Home in Saint Michaels

4.83 out of 5 average rating, 78 reviews

Harrison House - in Town and on St Michaels Harbor

PamelaRating, 5 stars1 week ago
Very central location, easily walkable to everything in downtown St. Michael’s!
Superhost

Home in Baltimore

4.76 out of 5 average rating, 21 reviews

UMB/Harbor/Stadiums/Convention Ctr - House 1 & 2

AjaniRating, 5 stars2 months ago
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.
Superhost

Home in Arnold

4.81 out of 5 average rating, 26 reviews

Entire Private 2 bedrooms house, nice neighborhood

BrandyRating, 5 stars6 months ago
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!!
Guest favorite

Home in Rock Hall

4.84 out of 5 average rating, 127 reviews

Pirates Perch

AndrewRating, 5 stars5 months ago
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.
Superhost

Home in Centreville

4.63 out of 5 average rating, 92 reviews

Peaceful Acres Guest House (A Nature's Getaway)

AnneRating, 5 stars3 months ago
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

Guest favorite

Home in Edgewater

4.91 out of 5 average rating, 139 reviews

House in Edgewater Maryland

StephanieRating, 5 stars3 months ago
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!
Guest favorite

Home in Deale

4.87 out of 5 average rating, 94 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

AmiRating, 5 stars3 weeks ago
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!
Superhost

Home in Wye Mills

4.91 out of 5 average rating, 11 reviews

⇚Family Getaway⇛| Lakeside + A Nature View |

LisaRating, 5 stars8 months ago
Kevin is a great host to us year after year! we love staying at his place!
Superhost

Home in Pasadena

4.85 out of 5 average rating, 54 reviews

Beautiful New Home Near Beach and Patapsco River

VeronaRating, 5 stars2 months ago
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.
Guest favorite

Apartment in Baltimore

5 out of 5 average rating, 27 reviews

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

KimberlyRating, 5 stars3 weeks ago
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.
Guest favorite

Home in Stevensville

4.97 out of 5 average rating, 31 reviews

Carolina Cottage - 2 story, pet-free home

ValerieRating, 5 stars1 month ago
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.
Superhost

Townhouse in Baltimore

4.96 out of 5 average rating, 134 reviews

Artsy, Historic Rowhouse with Striking Harbor Views

ThomasRating, 5 stars3 weeks ago
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.
Superhost

Home in Stevensville

4.96 out of 5 average rating, 84 reviews

Kent Island Beach House II by the Kentmorr Marina

GregRating, 5 stars7 months ago
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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