Waterfront vacation rentals in Pasadena

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Pasadena

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

4.99 out of 5 average rating, 155 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Superhost

A spacious waterfront house is shown surrounded by lush trees, with multiple balconies and large windows. A sandy area extends toward the water's edge, and smooth stones form a barrier along the shore, reflecting the natural beauty of the Chesapeake Bay.

Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

Accepting 2025 bookings as of June 1st.... "Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take our kayaks to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acres in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home.

Guest favorite

The exterior of a multi-story building features a combination of brick and clapboard siding in pastel colors. Large windows with green shutters are visible, and the front is lined with small trees. Two parked cars are positioned on the street in front.

Townhouse in Old Town

4.92 out of 5 average rating, 136 reviews

Lord & Patrick House at Old Town

Enjoy a phenomenal family experience! Escape on a friends vacation, getaway or retreat filled with fun and exciting things to do at the Old Town Waterfront, the nation’s capital or MGM at National Harbor. Visit The Smithsonian Institution with 21 museums, 14 education and research centers, and the National Zoo. To top it off, Old Town Alexandria is humming with more than 200 independent restaurants and boutiques alongside intimate historic site museums and happenings right on the waterfront.

Top guest favorite

A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.

Home in Stevensville

5 out of 5 average rating, 110 reviews

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.

Guest favorite

A serene lakeside scene features silhouetted trees framing a view of the water at sunset. A person sits in a plastic chair at a small table, overlooking the calm waters, creating a peaceful and reflective atmosphere.

Cottage in Pasadena

4.97 out of 5 average rating, 173 reviews

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.

Guest favorite

A well-maintained inground pool can be seen surrounded by a spacious deck featuring lounge chairs and shaded seating areas. Lush greenery and trees create a natural backdrop, enhancing the outdoor space’s tranquility with direct views of the water.

Apartment in Arnold

4.96 out of 5 average rating, 174 reviews

Celebrate Summer by Your Private Pool

Lovely 2 acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Top guest favorite

A serene waterfront scene features three colorful kayaks resting on the grassy shore, with a private dock extending into the calm water. The dock is equipped with seating, surrounded by trees and residential landscapes in the background, creating a peaceful outdoor setting.

Home in Deale

4.99 out of 5 average rating, 143 reviews

Chesapeake Waterfront HotTub-Kayaks-Crabbing

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Make wonderful memories. Great place for families and multi family groups.

Top guest favorite

A wooden pier extends over calm waters at sunset, with the sun setting at the horizon. The scene features reflections of the colorful sky on the water's surface, creating a serene atmosphere. Smooth rocks line the edges of the pier.

Cottage in Stevensville

4.95 out of 5 average rating, 157 reviews

Cottage on the Bay - Kent Island

Chesapeake Bay Waterfront home on Kent Island! Enjoy year round big sky and water views from the comfort of the screened porch & family room. Fish & crab from the pier or take a dip in the bay. Open concept living and rear bedroom/rec room are perfect for relaxing and having fun with family & friends. Close to popular wedding venues, local marinas & charter fishing boats, restaurants, Tiki bars, beaches, golfing, parks, & bike trails.

Guest favorite

A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.

Guesthouse in Glen Burnie

4.93 out of 5 average rating, 336 reviews

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

Guest favorite

A wooden dock extends into the water, equipped with boat slips on either side. Lush green grass frames the foreground, while calm waves ripple in the background. The scene is set under a soft, cloudy sky, providing a serene waterfront view.

Home in Pasadena

4.89 out of 5 average rating, 101 reviews

Beautiful Waterfront Home With Theater Room

This beautiful Pasadena Beach House(Chesapeake Bay waterfront with Pier) private beach access and is in close proximity to Celebrations At the Bay, Fort Smallwood Park, a Golf Course, Mike’s Crab House, BWI Airport, Baltimore, Live Casino, Arundel Mills, Naval Academy, and more. **Swim at your own risk** Every Winter!!! Price Drop!!!!! Enjoy the Same Space at a Lower Rate!!!!! October to March!!!!!!!!

Top guest favorite

An aerial view captures the waterfront cottage situated on the South River. The property is surrounded by water and greenery, featuring a manicured lawn with a patio area. A private dock is visible, leading from the house to the water, alongside a pool nestled within the landscaping.

Guesthouse in Annapolis

4.99 out of 5 average rating, 163 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Guest favorite

A screened-in porch provides a serene setting with two wicker chairs facing a small table. Peaceful views of the calm waterfront and surrounding greenery are visible, enhancing the connection with nature.

Home in Glen Burnie

4.97 out of 5 average rating, 141 reviews

12 M to Naval Acadmey | Waterfront

Discover the perfect blend of tranquility and convenience at our charming waterfront property. Nestled away in a serene setting yet close to all the action, this home offers an ideal escape. Imagine unwinding on the expansive screened-in porch, taking in the peaceful views of calm waters, or dropping a crab pot to catch some of Maryland's renowned Blue Crabs.