A coastal town with a marina, a bridge, and a highway.

Kent Island Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Kent Island vacation rentals

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

1. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is ￥20,473
￥52,716 total
includes taxes & fees
Aug 26 - Aug 27
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A lighthouse with a white exterior, a balcony, and a metal roof.

2. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is ￥20,473
￥52,716 total
includes taxes & fees
Aug 27 - Aug 28
Charming Coastal/Country Home w/3 Acres & Sauna!
Three birds perched on a wooden structure by the water.

3. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (76 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is ￥128,352
￥222,023 total
includes taxes & fees
Sep 22 - Sep 23
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

4. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is ￥128,352
￥222,023 total
includes taxes & fees
Sep 22 - Sep 23
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

5. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (3 reviews)
"N"
United States
Maria S.
The price is ￥99,995
￥187,880 total
includes taxes & fees
Aug 30 - Aug 31
Waterfront Escape with Pool Nature Lover Paradise
A two-story house with a red roof, a brick chimney, and a small porch.

6. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
6.8 out of 10, (3 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveler
The price is ￥114,444
￥167,308 total
includes taxes & fees
Aug 26 - Aug 27
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A swimming pool with a waterfall feature surrounded by lush greenery.

7. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is ￥30,757
￥62,606 total
includes taxes & fees
Aug 26 - Aug 27
Waterfront Oasis of Annapolis Star
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

8. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is ￥39,738
￥67,395 total
includes taxes & fees
Aug 25 - Aug 26
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

9. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is ￥30,437
￥81,086 total
includes taxes & fees
Aug 25 - Aug 26
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

10. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ￥31,631
￥90,783 total
includes taxes & fees
Sep 15 - Sep 16
Annapolis Retreat - 7 mins from downtown Annapolis!

11. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is ￥30,614
￥77,665 total
includes taxes & fees
Aug 25 - Aug 26
Pool Loft Suite | Bay Access & Beach Passes
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

12. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (75 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is ￥52,771
￥107,815 total
includes taxes & fees
Sep 14 - Sep 15
Charming Annapolis WaterVIEW Home

13. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (12 reviews)
"Great place!"
United States
Chris A.
The price is ￥21,864
￥59,352 total
includes taxes & fees
Aug 26 - Aug 27
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
A house with a yellow door and a window with a lamp outside.

14. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very Good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is ￥20,743
￥53,002 total
includes taxes & fees
Aug 25 - Aug 26
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

15. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is ￥22,174
￥53,727 total
includes taxes & fees
Sep 1 - Sep 2
Large 2 bedroom house with private parking in a nice neighborhood
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

16. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (20 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is ￥13,590
￥37,418 total
includes taxes & fees
Aug 30 - Aug 31
Cute, Cozy 2-bedroom house near Annapolis with water access
A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

17. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is ￥39,165
￥102,813 total
includes taxes & fees
Aug 25 - Aug 26
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

18. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is ￥30,614
￥89,443 total
includes taxes & fees
Aug 27 - Aug 28
Renovated Bungalow | Walk to Beach | Dog-Friendly
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

19. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥19,710
￥47,014 total
includes taxes & fees
Sep 1 - Sep 2
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Kent Island Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Room was clean, staff was great. They should have notified in advance or had on line about all the construction and pool being closed."
Rick 1-night trip
Posted less than an hour ago
St Michaels Inn

Find out more about Kent Island

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