Holiday rentals with beach access in Pasadena

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!

View · Beach · Bathroom

Waterfront Cheerful 5 home

Welcome to this brand-new relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 4 Bathroom .one bedroom on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

View · Walkability · Amenities

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.

Walkability · View · Parking

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Walkability · View · Wi-Fi

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

Beach · View · River

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

Walkability · Beach · Check-in

Beach Access, Hot Tub, Pet Friendly, Fully Fenced

A serene escape awaits you at our cozy hot tub 4-bedroom retreat, minutes away from Historic Downtown Annapolis. As the sun sets, the deck comes alive under the soft glow of string lights beckoning you to unwind in our 8-person Bullfrog hot tub or outdoor firepit where your worries will melt away! Indulge in the culinary delights of fresh local seafood and world-renowned crabcakes just moments away. Truly indulge in our paradise getaway and experience everything Annapolis has to offer!

View · Walkability · Comfort

Luxury Waterfront Annapolis/ Private Beach & Dock

Stunning Contemporary Home recently renovated on the Severn River with magnificent views of the Chesapeake Bay Bridge, a private dock & gorgeous sand beach w/ games, fire pit & hammock. Just minutes to downtown. Water views from all rooms, two propane fireplaces, designer kitchen, wine unit, electronic blackout shades, private office, screened-in porch, front patio w/grill. Master bedroom w/stand-alone tub & walk-in closet. Private road w/room for 3 cars. Spectacular Sunrises.

View · Beach · Backyard

Iconic Chesapeake. Unparalleled Luxury.

Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.

View · Beach · Quiet

Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit

Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier/dock! Gorgeous sunrises! Experience fresh Maryland Crabs & fish caught from your private pier & enjoy the peace, serenity, bay breezes & waterfront green space! Connect to nature and explore Meredith Creek on the Chesapeake Bay by kayak or boat! Super CLEAN & new with water views from dining, living room, kitchen and bedroom! 1.5 miles to the Beach!

Walkability · View · Hospitality

Captain’s Retreat! Newly Renovated - Beach House!

Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay. Steps to the Beach and a large community playground. With three large decks, enjoy nature, sitting with a glass of wine or coffee in the morning. Gourmet Kitchen opens to a deck with plenty of seating to enjoy outdoor entertaining. Perfect for large groups or multiple families. Custom solid wood bunk beds - Twin XL's over Kings!

Walkability · View · Hospitality

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Beach · View · Getting around