
Family-friendly vacation rentals in Kent Island
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Kent Island
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Boutique by the Bay
Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Cass-Away A Luxury Houseboat
Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

Old Bay Bungalow
This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Luxe Modern Chesapeake Waterfront Oasis - 5 Star
The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

Just Like Home - Private Entrance Apt in DMV Area
288 SQ FT PRIVATE ENTRANCE Mother-in-law suite/ studio apt, full bed, sofa, roll-away single bed, kitchen, bathroom with small shower stall & 55” Smart TV w/cable, Netflix & WiFi. No guests under 12 years of age. Excellent location: Ft. Meade (14.4 miles), Annapolis (15 m), Andrews AFB (19 m), Washington DC (19 m), Baltimore (29 m) Nearby airports: DCA (23 m), BWI (27 m), IAD (48 m) Public Transportation: Metro Bus Stop (0.2 m), New Carrollton Station Metrorail, Amtrak, & Greyhound (9 m)

Kent Island Waterfront Home with Amazing Sunsets
Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

Cozy Retreat w/Private Beach Access
Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a perfect blend of comfort and convenience. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtful interiors and modern amenities, our Airbnb promises a memorable stay for your solo trip, couples romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!

Calico Cottage Guest House, king bed, free parking
Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Chill in The Crib! Easton, Maryland
Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Annapolis Garden Suite
Welcome! We’re tucked away on a forested residential street, roughly a 7 minute drive from restaurants, coffee shops and all that Annapolis has to offer. 15m from the coast, 30m from Baltimore and 35m from DC. Tl;dr: this is a private ground-level guest suite with 3 beds, 2 bedrooms, 1 desk (optional standing desk), 1 kitchen with oven, dishwasher + Nespresso/pour over, 2 tvs, laundry room with washer/dryer, fast wifi, a pool, patio and a forest view. We live on the top floor.

Waterfront Getaway - View of bay from your bed
Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Sea Dreamer
Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!
Popular amenities for Kent Island family-friendly rentals
Family-friendly home rentals with a hot tub

Kone Oasis- hot tub, pool, theater/game rm.

Cozy Cottage, Winter Promo, Hot Tub, BlockToBeach

Red, White & Waterview Studio Apt with pool

Cozy 3-bedroom home w/ Hot tub & firepit

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

Coastal Comfort Suite Near Annapolis, Hottub, EV

Fall Oasis - hot tub, fire pit, fully fenced

Luxury Modern Home on Water+Hotub- Annapolis 25min
Family- and pet-friendly home rentals

Lofty Dreams, 2016 Brookstone RV - Waterfront

Outrange at Blue Heron Farm

Beautiful Waterfront Chestertown Getaway

The Crab House - a Private, Waterfront Guest House

Chestertown Private cottage with NFL Sun Ticket

Fox Cottage *Pet Friendly*

Home away from home

New Hotel Chic
Family-friendly home rentals with a pool

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cozy, Cute and Clean rowhouse w/ 2 Masters!

Rollingside: Two-Room Guest Suite

Patterson Park Penthouse with Rooftop Deck!

Charming Annapolis Waterfront Condo

Bright and Cozy 2nd floor apt

Patuxent River View

Rosses Chance Guest House
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- Rentals with a fireplace Kent Island
- Fitness-friendly rentals Kent Island
- Rentals with a kayak Kent Island
- Waterfront rentals Kent Island
- Rentals with pools Kent Island
- Rentals with a patio Kent Island
- Rentals with a fire pit Kent Island
- Rentals with lake access Kent Island
- Rentals with outdoor seating Kent Island
- Pet-friendly rentals Kent Island
- House rentals Kent Island
- Rentals with a washer and dryer Kent Island
- Rentals with beach access Kent Island
- Family-friendly rentals Maryland
- Family-friendly rentals United States
- Nationals Park
- Georgetown University
- The White House
- National Mall
- M&T Bank Stadium
- District Wharf
- Oriole Park at Camden Yards
- Smithsonian National Museum of Natural History
- National Museum of African American History and Culture
- Betterton Beach
- Hampden
- Sandy Point State Park
- Arlington National Cemetery
- Georgetown Waterfront Park
- National Harbor
- Caves Valley Golf Club
- Washington Monument
- Crystal Beach Manor, Earleville, MD
- Great Falls Park
- Six Flags America
- The Pentagon
- Patterson Park
- Smithsonian American Art Museum
- Killens Pond State Park