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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Kent Island vacation rentals

Exterior

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, (52 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
$258 nightly
The price is $278
Aug 11 - Aug 12
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (45 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
$297 nightly
The price is $321
Aug 13 - Aug 14
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Outdoor dining

3. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (2 reviews)
"Very spacious property for a family of 14. Sleeping arrangements required a bit of creativity but everything worked out! Everyone had a great time by the pool and the property was very clean. Host was responsive and helpful during the stay!"
United States
Hoi C.
$1,158 nightly
The price is $1,228
Aug 30 - Aug 31
Total with taxes and fees
Waterfront Escape with Pool Nature Lover Paradise
Marina

4. 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
$425 nightly
The price is $485
Aug 10 - Aug 11
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Dining

5. 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, (15 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
$395 nightly
The price is $419
Aug 10 - Aug 11
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

6. 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.
$486 nightly
The price is $554
Aug 23 - Aug 24
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
Beach nearby, sun loungers, beach towels

7. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
$576 nightly
The price is $656
Aug 18 - Aug 19
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Coffee/tea maker, fridge, microwave, oven

8. 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.
$421 nightly
The price is $479
Aug 11 - Aug 12
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
Outdoor pool, a heated pool

9. 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
$392 nightly
The price is $447
Sep 1 - Sep 2
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Outdoor dining

10. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (74 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.
$623 nightly
The price is $710
Sep 9 - Sep 10
Total with taxes and fees
Charming Annapolis WaterVIEW Home
Terrace/patio

11. 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.
$329 nightly
The price is $375
Aug 12 - Aug 13
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Interior

12. 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.
$292 nightly
The price is $332
Sep 1 - Sep 2
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Coffee/tea maker, fridge, microwave, oven

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (11 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.
$504 nightly
The price is $575
Aug 12 - Aug 13
Total with taxes and fees
Renovated Bungalow | Walk to Beach | Dog-Friendly
1 bedroom, WiFi (free), bed sheets

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.
$269 nightly
The price is $306
Aug 10 - Aug 11
Total with taxes and fees
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Beach

15. 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.
$260 nightly
The price is $287
Aug 10 - Aug 11
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Living area

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

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
$585 nightly
The price is $667
Aug 11 - Aug 12
Total with taxes and fees
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Coffee/tea maker, fridge, microwave, oven

17. Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (12 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
$608 nightly
The price is $693
Aug 18 - Aug 19
Total with taxes and fees
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Coffee/tea maker, fridge, microwave, oven

18. 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, (18 reviews)
"Highly recommend this property! Great location. Place is clean and host was very accommodating."
United States
Abi O.
$204 nightly
The price is $232
Aug 17 - Aug 18
Total with taxes and fees
Cute, Cozy 2-bedroom house near Annapolis with water access
Coffee/tea maker, fridge, microwave, oven

19. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
$460 nightly
The price is $521
Aug 18 - Aug 19
Total with taxes and fees
Cute bungalow blocks to Stadium
Dining

20. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
$493 nightly
The price is $562
Aug 12 - Aug 13
Total with taxes and fees
Historic Row Home in Downtown Annapolis
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

8/10 Good
"The location was great and the staff was courteous and helpful. My wife and I were celebrating our fourth wedding anniversary and had reserved a room with a king sized bed. We were given 2 queen size beds, I am 6’6”tall and had to sleep on an angel.They did not tell us that at check in. We were switched to a king bed the next day. You only have one chance to make a great first impression."
Larry 2-night trip
Posted 1 hour ago
Hilton Garden Inn Kent Island Marina

Find out more about Kent Island

Everything you need to know about Kent Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kent Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kent Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kent Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kent Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Kent Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kent Island rentals

At Expedia, we put the best Kent Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kent Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kent Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kent Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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