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

Kent Island Vacation Rentals

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Our top choices for Kent Island vacation rentals

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is CA $119
CA $392 total
includes taxes & fees
Nov 11 - Nov 12
Charming Coastal/Country Home w/3 Acres & Sauna!

2. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is CA $144
CA $422 total
includes taxes & fees
Nov 15 - Nov 16
Relax on Kent Island in 4 Bedroom Home w/Waterview

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, (75 reviews)
"Great stay, exactly as advertised, Donna was great!"
United States
Sam C.
The price is CA $987
CA $1,778 total
includes taxes & fees
Dec 1 - Dec 2
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

4. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is CA $987
CA $1,778 total
includes taxes & fees
Dec 1 - Dec 2
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

5. 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
8.6 out of 10, Excellent, (7 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 traveller
The price is CA $1,017
CA $1,414 total
includes taxes & fees
Nov 11 - Nov 12
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

6. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is CA $127
CA $366 total
includes taxes & fees
Nov 12 - Nov 13
Cass-N-Reel Luxury Houseboat

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, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is CA $292
CA $666 total
includes taxes & fees
Nov 16 - Nov 17
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

8. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (87 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is CA $304
CA $613 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 2br home w/ parking in downtown Annapolis

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

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
9.0 out of 10, Wonderful, (4 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is CA $318
CA $744 total
includes taxes & fees
Nov 11 - Nov 12
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

10. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (24 reviews)
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."
United States
Bridget C.
The price is CA $635
CA $1,004 total
includes taxes & fees
Nov 14 - Nov 15
Secluded Cozy Cottage in Historic Downtown

11. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (15 reviews)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
The price is CA $329
CA $568 total
includes taxes & fees
Nov 11 - Nov 12
18th Cent. Charm in Historic Downtown Annapolis

12. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 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 CA $272
CA $650 total
includes taxes & fees
Nov 11 - Nov 12
Pool Loft Suite | Bay Access & Beach Passes

13. Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay!"
United States
Michaell M.
The price is CA $403
CA $930 total
includes taxes & fees
Nov 16 - Nov 17
Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

14. 5 bedroom house with EV charger Near Downtown Annapolis

5 bedroom house with EV charger Near Downtown Annapolis
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"In town for a regatta, exactly what we required. "
United States
Jacob V.
The price is CA $477
CA $822 total
includes taxes & fees
Nov 22 - Nov 23
5 bedroom house with EV charger Near Downtown Annapolis

15. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is CA $967
CA $1,400 total
includes taxes & fees
Nov 28 - Nov 29
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

16. 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 CA $297
CA $784 total
includes taxes & fees
Nov 29 - Nov 30
Annapolis Retreat - 7 mins from downtown Annapolis!

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 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 CA $272
CA $748 total
includes taxes & fees
Nov 11 - Nov 12
Renovated Bungalow | Walk to Beach | Dog-Friendly

18. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
United States
Heather B.
The price is CA $315
CA $813 total
includes taxes & fees
Nov 30 - Dec 1
Cute bungalow blocks to Stadium

19. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (10 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is CA $311
CA $771 total
includes taxes & fees
Nov 11 - Nov 12
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

20. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (6 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is CA $292
CA $707 total
includes taxes & fees
Nov 11 - Nov 12
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
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

Find out more about Kent Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kent Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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