Kent Island vacation rentals

We found 1,010 vacation rentals — enter your dates for availability

Welcome to Kent Island, a picturesque paradise where scenic waterfront views blend seamlessly with outdoor adventures and rich local history. This charming destination invites families and groups to explore its beautiful parks, marinas, and sandy beaches, perfect for hiking, boating, and creating unforgettable memories. With a variety of cozy cottages and modern apartments to choose from, you can enjoy the comforts of home while immersing yourself in the island’s enchanting atmosphere.

Holiday rentals with weekly discounts - Kent Island

Showing deals for:Dec 18 - Dec 25

Exterior
Kitchen
Kitchen
Kitchen
Exceptional
(31 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

12% off
$284
$1,988 for 7 nights
All fees included
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Private kitchen
Interior
Room
Interior
Exceptional
(107 reviews)

Cass-Away Luxury Houseboat

Grasonville

8% off
$170
$1,190 for 7 nights
All fees included
Cass-Away Luxury Houseboat
Interior
Interior
Dining
SuperMoon rising behind the house with moon beams on the bay
Exceptional
(47 reviews)

Sunset Lodge on the Bay

Rock Hall

9% off
$1,114
$7,800 for 7 nights
All fees included
Sunset Lodge on the Bay
Dining table- seats 10!
Pool
View from Pier back to house!
View from Foyer into Great Room
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

9% off
$1,059
$7,415 for 7 nights
All fees included
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Outdoor dining
Private kitchen
Room
Dining
Exceptional
(21 reviews)

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis

17% off
$713
$4,990 for 7 nights
All fees included
Captain's Retreat! Newly Renovated - few steps from the beach!
Lawn for yard games along the waterfront, or simply relax in the shade
Enjoy screened in porch with dining table and sitting area
Beautiful waterfront home on Burley Creek with private pier
West-facing screened porch with bar area and café lights for night ambience
Exceptional
(62 reviews)

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis

9% off
$654
$4,577 for 7 nights
All fees included
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Kitchen - Granite Island
Terrace/patio
Great Room
Exterior
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

8% off
$1,327
$9,286 for 7 nights
All fees included
Waterfront Architectural Masterpiece with private dockage available.
Upper level master bedroom
Kitchen
Kitchen
Dinning area
Exceptional
(16 reviews)

House near Patapsco River 2700 square feet

Pasadena

8% off
$824
$5,767 for 7 nights
All fees included
House near Patapsco River 2700 square feet
Another view from above.
The view off of the point, breathtaking.
Interior
Pool
Exceptional
(46 reviews)

Grandview- Main House

Bozman

27% off
$638
$4,469 for 7 nights
All fees included
Grandview- Main House
Exterior
Interior
Private kitchen
Interior
Exceptional
(14 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

9% off
$535
$3,742 for 7 nights
All fees included
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Upstairs Hall
Porch Dining Table
Swimming Pool
Kitchen
Exceptional
(35 reviews)

Waterfront Home near Annapolis, MD

Galesville

9% off
$1,739
$12,175 for 7 nights
All fees included
Waterfront Home near Annapolis, MD
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
Delightful front garden welcomes you when approaching house from driveway
Convenient open-concept design:  kitchen, dining and living areas
Exceptional
(163 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
$321
$2,246 for 7 nights
All fees included
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Interior
Exterior
Interior
3rd floor suite; queen and 2 twins; en-suite bath, sitting area, deck access.
Exceptional
(5 reviews)

Grand home located right on Main St, walk to Chesapeake Bay & great restaurants

Rock Hall

9% off
$752
$5,262 for 7 nights
All fees included
Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
upstairs bedroom w/ King size bed and space for queen air mattress
Terrace/patio
Living room with wood fireplace and second TV with basic channels
outdoor space
Exceptional
(94 reviews)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena

9% off
$490
$3,431 for 7 nights
All fees included
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Living area
Terrace/patio
Private kitchen
Exterior
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

11% off
$279
$1,950 for 7 nights
All fees included
Charming 3BDR Bungalow Near Annapolis​
Dining
Private kitchen
Living area
Dining
Excellent
(11 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

9% off
$449
$3,145 for 7 nights
All fees included
Fabulous 5-bedroom house with AC in charming Annapolis
Local artwork is displayed and for sale, if you wish to take a memory home.
Quiet, tree-filled neighborhood. The apartment is above the garage.
Separate entryway with electronic keypad.
Room
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

9% off
$216
$1,515 for 7 nights
All fees included
Annapolis Tree House Apartment- luxury shower, separate space
Property grounds
Outdoor dining
dining area
Marina
Exceptional
(39 reviews)

This is truly a Baydream!

Rock Hall

8% off
$275
$1,926 for 7 nights
All fees included
This is truly a Baydream!
Interior
Property grounds
Dining
Private kitchen
Exceptional
(35 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

9% off
$629
$4,406 for 7 nights
All fees included
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Interior
New Kitchen 2022
Exterior
Dining room
Exceptional
(65 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

9% off
$496
$3,471 for 7 nights
All fees included
Circa 1700 Chesapeake Colonial home on the National Register.
Dining Room - Seats 6
View down the lane
Living Room with flat screen TV and sleeper sofa
Custom kitchen
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

9% off
$266
$1,860 for 7 nights
All fees included
Perfect Waterview Cottage - St. Michaels Getaway
Private kitchen
Exterior
Living area
Room
Exceptional
(24 reviews)

In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!

Rock Hall

9% off
$226
$1,585 for 7 nights
All fees included
In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!
Private kitchen
Dining
Private kitchen
Interior
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

9% off
$466
$3,263 for 7 nights
All fees included
Charming Waterfront Cottage Retreat near St. Michaels
Living area
Exterior
Dining
Property grounds
Exceptional
(25 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman

8% off
$391
$2,736 for 7 nights
All fees included
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Find the best place to stay - Kent Island

Private kitchen
Premier Host
10
Exceptional
24 reviews
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Kitchen
Premier Host
10
Exceptional
31 reviews
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Great views of the water from the sunroom.
Premier Host
10
Exceptional
138 reviews
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Beautiful deck and screen in porch for dining.
Premier Host
10
Exceptional
14 reviews
NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues
basement
Premier Host
10
Exceptional
16 reviews
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View
New Build - Accessible - Cozy
Premier Host
10
Exceptional
72 reviews
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
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Find out more about Kent Island

Why visit Kent Island

  • Outdoor Adventures: Kent Island offers a range of activities like hiking, biking, and water sports, perfect for nature lovers.
  • Scenic Beaches: Enjoy the beautiful coastline and relax on the sandy shores, ideal for family outings and picnics.
  • Rich History: Explore nearby historic towns with charming homes and local culture that reflect the island's heritage.
  • Family-Friendly Attractions: Kent Island features numerous parks and recreational spots that cater to visitors of all ages.
  • Diverse Accommodations: Choose from a variety of vacation rentals, from cozy cottages to spacious homes, for a comfortable stay.

Popular types of accommodation around Kent Island

Discover the perfect getaway on Kent Island with a variety of vacation rentals to suit your needs. Whether you're looking for houses, cozy cottages, or convenient apartments, we have options for everyone. From charming single-family homes to pet-friendly rentals near Kent Narrows, you'll find the ideal base for your adventure. Explore, relax, and create unforgettable memories in this beautiful destination.

  • Houses: The top choice among travelers, offering spacious and comfortable accommodations for families or groups.
  • Cottages: A charming option, perfect for a cozy getaway with a touch of rustic charm.
  • Apartments: A convenient choice for those seeking a home-like atmosphere with easy access to local attractions.
  • Condos: Ideal for vacationers wanting upscale amenities and stunning views.
  • Cabins: A delightful retreat for nature enthusiasts, providing a tranquil escape in the woods.**

Top attractions near Kent Island

Kent Island, Maryland, offers a perfect blend of outdoor activities for families, couples, and solo travelers. Visitors can enjoy urban parks, scenic beaches, and nearby national and state parks. With a variety of attractions catering to those seeking adventure, culture, and family-friendly experiences, Kent Island is an ideal destination for a memorable vacation. Be sure to explore the local points of interest to enhance your visit.

  • U.S. Naval Academy: Located 9 miles from Kent Island, this historic academy offers breathtaking architecture and rich maritime history, making it a must-visit for history buffs and those interested in military traditions.
  • Chesapeake Bay Bridge: Just 6 miles away, this impressive modern bridge connects the Eastern and Western shores, providing stunning views of the bay and a unique urban experience.
  • Sandy Point State Park: Situated 7 miles from Kent Island, this national park is perfect for outdoor enthusiasts, offering scenic trails, picnic areas, and adventurous activities along the beautiful waterfront.

Things to do recommended for couples

For a romantic getaway on Kent Island, visit St. Michaels Winery for a delightful wine tasting, or set sail with Annapolis Sailing School for an adventurous day on the water. Don’t miss a captivating performance at the Ballet Theater of Maryland to complete your memorable experience.

Things to do recommended for families

Your family will have a blast at the Navy-Marine Corps Memorial Stadium, just 10 miles away, soaking in the sports atmosphere. For more fun, visit the Annapolis Bowl, 13 miles away, for an arcade adventure, or catch a game at Alumni Hall, only 9 miles from Kent Island.

Things to do recommended for groups

Explore the craftsmanship at Paul Reed Smith Guitars, only 4 miles from Kent Island. For shopping and entertainment, visit Queenstown Premium Outlets, located 10 miles away. If your group enjoys sports, the Queenstown Harbor Golf Club, 9 miles away, offers a fantastic outdoor golfing experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Kent Island

When traveling with a group, family, or pets, or if you're seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Kent Island with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Kent Island with young kids: Traveling with young children can be quite a challenge. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's worthwhile to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Kent Island: For many, a family vacation isn't truly a family vacation without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds to ensure everyone feels comfortable and at home.
  • Planning for a long term stay visiting Kent Island: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly locate and save on monthly accommodations. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Kent Island

Kent Island, the largest island in Maryland, offers a peaceful getaway perfect for outdoor adventures and family vacations. With its beautiful coastline and charming homes, visitors can relish in a relaxing atmosphere while exploring nearby towns rich in history and friendly locals. Whether you're seeking a romantic retreat or a rustic experience, Kent Island provides a unique blend of sunny weather and scenic views that will make your stay unforgettable.

  • Annapolis: Located a mere 9 miles from Kent Island, Annapolis is the charming capital of Maryland and a hub for family-friendly activities and urban exploration. Visitors can enjoy a variety of attractions, from educational landmarks such as the United States Naval Academy to shopping experiences at local malls and unique boutiques. The city is also renowned for its waterfront, where you can take leisurely strolls along the scenic beach and enjoy picturesque views of the lake. Whether you’re exploring the historic district or indulging in local cuisine, Annapolis provides a vibrant city experience that caters to all ages.
  • Northern Chesapeake Bay: Just 1 mile away, Northern Chesapeake Bay is a picturesque retreat known for its stunning outdoor scenery and romantic settings. This area is perfect for those who appreciate nature, offering a range of recreational activities from kayaking in tranquil waters to golfing at scenic courses. Visitors can explore the beautiful beaches, visit notable monuments, or cross the impressive modern bridge that connects various waterfront attractions. It’s an ideal spot for couples looking to enjoy a peaceful getaway or families seeking outdoor adventures.
  • Stevensville: A short 3 miles from Kent Island, Stevensville is a delightful city that invites visitors to immerse themselves in outdoor activities and family fun. The area boasts a vibrant recreational scene, including well-maintained parks and a charming boardwalk perfect for leisurely walks. Shop at local centers or explore nearby beaches and the stunning national state park, which offers hiking trails and breathtaking views. With its inviting atmosphere and numerous attractions, Stevensville is a great destination for those looking to experience the beauty of Maryland’s coastline.

Best time to go to Kent Island

If you're planning a trip to Kent Island, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyLowSlightly Low
February37.9°F (3.3000000000000003°C)Light RainMostly SunnyAverageSlightly Low
March44.6°F (7.0°C)Light RainMostly SunnyAverageSlightly Low
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.900000000000002°C)Light RainMostly SunnyAverageAverage
June73.0°F (22.8°C)Light RainMostly SunnyHighSlightly High
July78.4°F (25.8°C)Light RainMostly SunnyHighSlightly High
August76.8°F (24.9°C)Light RainMostly SunnyHighSlightly High
September70.7°F (21.5°C)Light RainMostly SunnyAverageAverage
October60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
November48.7°F (9.3°C)Light RainMostly SunnyLowAverage
December41.5°F (5.300000000000001°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial savings. To discover a Vrbo property that suits your budget, utilize our filters to narrow down options by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can effortlessly plan new trips, resume your previous work, or manage your travel arrangements. You can easily access your saved or booked properties, organized into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Kent Island

Enjoy the history and other features of Kent Island. Well known for its island views, boating and biking, this relaxing city won't disappoint. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Kent Island

Do you want to find top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Kent Island a fun place to get away. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Queenstown Harbor Golf (9.4 mi / 15.1 km)
  • St. Michaels Winery (12.2 mi / 19.7 km)
  • Maryland Renaissance Festival (14.6 mi / 23.5 km)
  • Thanksgiving Farm Wines (16.7 mi / 26.8 km)
  • Chesapeake Beach Water Park (20.3 mi / 32.6 km)
  • Paul Reed Smith Guitars (3.6 mi / 5.7 km)

Exploring the natural features in Kent Island

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Kent Island is a great place to get outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Northern Chesapeake Bay (2.1 mi / 3.4 km)
  • Sandy Point Beach (6.3 mi / 10.1 km)
  • Bay Ridge Beach (6.9 mi / 11.1 km)
  • Eastern Neck National Wildlife Refuge (8.6 mi / 13.9 km)
  • Maryland Quiet Waters Park (9.1 mi / 14.6 km)
  • Fort Smallwood Park (16.5 mi / 26.6 km)

Frequently asked questions

What is the most popular type of vacation rental accommodation in Kent Island?
Villas are the most popular kind of vacation rental in Kent Island, according to our data. Even if you have a different idea about what you'd like, Vrbo has vacation homes in loads of sizes and shapes. Filter our options to find your perfect Kent Island pad.
How much does it cost to rent a vacation rental in Kent Island?
Property type, length of stay and time of year are some of the conditions that can influence the price of a vacation home. Simply add your travel dates to find your ideal fit. From homey country cottages to expansive luxury villas, all Vrbo vacation rentals provide amazing value.
How much does it cost to rent a beach house in Kent Island?
When you travel and the size and style of the property will determine the cost of your beachside escape. Type in your Kent Island travel dates to view your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to pick the features and amenities you need.
What are popular rental amenities in Kent Island?
Some of the most popular rental amenities people search for in Kent Island are a barbecue grill, a sauna and an ocean view. Whether you're on the road with your besties, family or even pets, Vrbo vacation rentals come with the best amenities for beginning new traditions with the people closest to you.
Can I find two-bedroom vacation rentals in Kent Island?
Gather your family and enjoy peace, privacy and comfort in one of the three two-bedroom vacation rentals Kent Island has to offer.
Are there vacation rentals with WiFi in Kent Island?
You can pick from 26 vacation rentals with WiFi in Kent Island. If you'd like to disconnect from daily life on your escape, but still want to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a vacation rental in Kent Island?
The minimum age is usually 16, 18 or 21. It can differ across properties on Vrbo, so look at the rules of your chosen Kent Island stay before booking your stay.
How long can I rent a vacation rental in Kent Island for?
The amount of time you can rent a Kent Island vacation home for differs depending on the property. Simply tap in your preferred travel dates to browse available options that offer extended stays. They have all you require to make your extended trip more comfortable and enjoyable, such as kitchens and backyards. Some vacation homes might also offer discounted weekly or monthly prices, so you can stick around for longer for less.
Does Vrbo offer discounts for vacation homes in Kent Island?
In Kent Island, you'll find some incredible discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether it's a mini escape or a couple of weeks away, we've got a variety of options that'll suit your style.

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