Kent Island Vacation Rentals from $208: Search Short-Term Rentals

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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!

Stevensville

Anthony P.

$242 nightly

Oct 20 - Oct 21

Total with taxes and fees

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Stevensville

Michael V.

$288 nightly

Oct 25 - Oct 26

Total with taxes and fees

Three birds perched on a wooden structure by the water.

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

Stevensville

barbara s.

$1,200 nightly

Oct 20 - Oct 21

Total with taxes and fees

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

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

Stevensville

David R.

$1,142 nightly

Oct 20 - Oct 21

Total with taxes and fees

A two-story house with a red roof, a brick chimney, and a small porch.

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

Stevensville

"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...

Michele F.

$994 nightly

Oct 20 - Oct 21

Total with taxes and fees

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Pamela B.

$440 nightly

Nov 3 - Nov 4

Total with taxes and fees

A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.

7. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

West Annapolis

Jill R.

$407 nightly

Nov 5 - Nov 6

Total with taxes and fees

A wooden dock extending into a calm body of water with boats docked at the end.

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

Historic District

Nancy N.

$423 nightly

Oct 21 - Oct 22

Total with taxes and fees

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Top Kent Island Hotel Reviews

Best Western Annapolis

10/10 Excellent

"Super nice staff, Clean rooms, comfortable bed, good breakfast and close to restaurants and less than 5miles to City Dock. I was in Annapolis for work for 5 days, I recommend this hotel, thank you!"

Sonesta ES Suites Annapolis

8/10 Good

"My husband and I were traveling with our 14 month-old son. The room was a good size and had two separate bedrooms, which worked out really well for us. There was a strong odor when we first arrived to our room. We travel with an air purifier for our son, as he sometimes has sinus issues, so that helped. The room itself was a bit dated, although well laid out. The fridge, microwave and dishwasher were all really nice to have. We didn’t get to use the fireplace, as we purchased a log, but we didn’t have a lighter or matches and the property didn’t either. The breakfast every morning was great! Fresh food snd fresh ingredients. Kitchen staff was incredibly friendly and good with our son, too. I’d say 7.5/10, but if they were to update the room and eliminate the odor, I feel like it’d be a 9/10."

240' Private Beachfront @Kent Island Love Point - Great for Families

10/10 Excellent

"This place was wonderful for family get togethers. So incredibly home-y! Beautiful views from every window. The place is better stocked than any home I’ve ever rented and we’ve stayed in over twenty across the USA. Tissues in every room. Can never find tissues in other rentals! Also paper products, foil, every possible cookware and dish available for use. Loads of drawer and closet space if you like to unpack. Beautiful landscaping and waterfront views. Even the driveway was landscaped perfectly. I am a bird watcher / listener and the birds sing their hearts out in the trees surrounding the property. We utilized the kayaks and super wide paddleboard. We put the crab traps out and caught two dozen crabs. We all had fun and spent quality time together. Best rental experience EVER! Host Hal was very responsive to any questions we had too!"

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10/10 Excellent

"What a great experience!! The hosts couldn't have been kinder, the house and property were beautiful, and the communication was great! They were so responsive, and obviously were working very hard to make sure everyone had a great stay. Tons of room for people to sleep, visit, and hang out. The house is on a huge wooded lot, and the outside was great too. Highly recommend!"

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 $208 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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Check prices for these dates

Our top choices for Kent Island vacation rentals

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

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

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

4. 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

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

7. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

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

9. Secluded Cozy Cottage in Historic Downtown

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

11. Pool Loft Suite | Bay Access & Beach Passes

12. Annapolis Retreat - 7 mins from downtown Annapolis!

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

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

15. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

16. 18th Cent. Charm in Historic Downtown Annapolis

17. Family Home on Mayo Peninsula | Deck | Sleeps 10

18. 8 Bells Bungalow - Cozy, Stylish, Prime Location

19. Mins to DTA - King Beds - Parking

20. Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Find vacation rentals that suit your style

Top Kent Island Hotel Reviews

Best Western Annapolis

Find out more about Kent Island

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