Photo by Jennifer Crim

Vacation rentals in Kent Island

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Top vacation rentals in Kent Island

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

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

6.88 mi from city center
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This vacation home features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

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

0.67 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

2 out of 5
2.38 mi from city center
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This houseboat features barbecue grills.
Kitchen
Pet friendly
Circa 1700 Chesapeake Colonial home on the National Register.

Circa 1700 Chesapeake Colonial home on the National Register.

1.4 mi from city center
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An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

3.46 mi from city center
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A sauna is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

3.84 mi from city center
$240 nightly
The price is $254 total per night
$254 total
Sep 28 - Sep 29
Total with taxes and fees
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Chesapeake Houseboat Getaway on Kent Island, Maryland

Chesapeake Houseboat Getaway on Kent Island, Maryland

2.41 mi from city center
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This houseboat features barbecue grills.
Kitchen
Pet friendly
25-50% Off~Private Beach~Hot Tub~Fire Table~

25-50% Off~Private Beach~Hot Tub~Fire Table~

4.01 mi from city center
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A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

3.73 mi from city center
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This vacation home features free WiFi in public areas, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Kent Island Waterfront Cottage

Kent Island Waterfront Cottage

5.78 mi from city center
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This condo features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

1.57 mi from city center
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This vacation home features free WiFi in public areas, a garden, and laundry facilities. Families will appreciate the playground and barbecue grills.
Kitchen
Washer
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

11.95 mi from city center
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This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

9.11 mi from city center
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A gym is featured at this vacation home, along with limo/town car service and a garden. Laundry facilities, concierge services, and barbecue grills are also on offer.
Pool
Kitchen
Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

4.97 mi from city center
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Stay at this houseboat in Grasonville. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chesapeake Bay Environmental Center and Paul Reed Smith Guitars are located nearby.
Kitchen
Free WiFi
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

8.97 mi from city center
$1,088 nightly
The price is $1,240 total per night
$1,240 total
Oct 13 - Oct 14
Total with taxes and fees
This vacation home features a garden, laundry facilities, and concierge services. Barbecue grills are provided for your convenience.
Kitchen
Washer
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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.

The Best Way to Find your Vacation Rentals in Kent Island

How cheap can a vacation rental in Kent Island be?

You can find vacation rentals in Kent Island for as low as $254 per night.

How do you look for the best vacation rental deals in Kent Island with Travelocity?

Travelocity provides the best vacation rental deals in various locations throughout Kent Island so you can create the perfect plan for you. You can search and filter by type of property, amenities, neighborhood, price range, number of bedrooms, and more.

Are cancellations free on vacation rentals with Travelocity?

Each vacation rental has its own cancellation policy. It’s essential to understand the terms of your agreement before booking. Most rentals in Kent Island can be canceled for free when notifying the property before the cancellation deadline.

What types of vacation rentals are available in Kent Island?

Short term rentals come in all shapes and sizes. Choose from properties for a wide range of budgets and types of holidays. Families, couples, outdoor adventurers, and leisure travelers alike will find the perfect place for them. Check out our Kent Island vacation apartments to get started building your trip.

What are the benefits of booking a short-term rental in Kent Island?

Whether it’s for a summer getaway, a winter excursion, or a routine business trip, Kent Island vacation homes are often an excellent choice. You can enjoy group vacations with short term rentals to fit your party size. You might take a romantic weekend for two or plan a family reunion, and all stay under one roof. The options are endless, and you can find them on Travelocity.

Why is Travelocity the best site to find your vacation rental in Kent Island?

With Travelocity, all your travel needs are taken care of in one convenient platform. We offer fantastic deals on our large selection of vacation rentals to get you the most savings and rewards back on every booking. Save more when you bundle bookings together, including car rentals, flights, and activities. Here, you can build custom Kent Island vacations.

How to cancel your vacation rental with Travelocity?

To cancel your vacation rental, contact the property manager. You can find their contact information in the ‘Itinerary’ section of your Travelocity account. Most properties receive a full refund when you cancel before the cancellation deadline. Policies vary by property, so it’s important to understand the terms before booking. For more information, visit our customer service portal.