Waterfront holiday rentals in Pasadena

4.97 out of 5 average rating, 473 reviews

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

4.94 out of 5 average rating, 181 reviews

An 80-foot private pier extends over calm water, lined with posts and surrounded by greenery. Two personal watercraft and a yellow pedal duck are visible at the end of the dock. The tranquil scene is enhanced by a blue sky with scattered clouds.

Home in Riviera Beach

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 .

Bungalow in Sparrows Point

The living area features a spacious layout with large windows allowing natural light to fill the room. Two patterned armchairs are positioned around a central console with a television. A light fixture hangs from the ceiling, complementing the hardwood flooring and neutral wall colors.

Boatyard Bungalow, 6 beds; 2 Full Baths-Waterfront

The original schoolhouse for Edgemere that was built in 1898 and converted to a residential home/marina in the 1950s. With over 2,200 sq. ft., it's a perfect environment for wedding venue preparations, family and friend reunions. Please don't exceed maximum number of twelve (12) guests at any one time in the house, during the day; or ten (10) staying the night in the house. Additional Pirate & Mermaid Bath House on property should extra toilets and showers be needed from April-November only.

4.95 out of 5 average rating, 169 reviews

4.99 out of 5 average rating, 152 reviews

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

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.

4.95 out of 5 average rating, 122 reviews

A spacious bed is adorned with decorative orange pillows and flanked by elegant bedside lamps. Framed artwork featuring floral designs hangs above the headboard, complementing the soft color palette of the room.

Home in Fells Point

Luxury Fells Home w/Hot Tub, Poker Room, & Parking

Treat yourself to a luxury getaway with a 6-person hot tub, poker room with record player, and a gorgeously renovated bathroom with a freestanding soaking tub. This opulently decorated, spacious, renovated townhouse is located in the heart of very safe Fells Point. Sleeping arrangements for 6. Blazing fast 1GB Wifi, dedicated work space, 1 street parking permit, 65" Smart TV, and only 3 short blocks (3 min walk) to the bustling Fells Point waterfront. Just far enough to sleep undisturbed!

4.96 out of 5 average rating, 196 reviews

A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.

Cottage in Pasadena

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.

4.9 out of 5 average rating, 231 reviews

A tranquil view of the Chesapeake Bay is captured, showcasing a grassy expanse leading to the water. Two stone boundary walls are visible, framing the lush landscape. A solitary beach umbrella and chair rest on the shore, inviting relaxation by the calm water.

Home in Cape St. Claire

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.

4.95 out of 5 average rating, 200 reviews

A cozy living area features a gray sectional sofa with a yellow throw draped over it. Wood accents and a patterned area rug complement the warm hardwood floors. An adjacent dining space is visible, showcasing a rustic brick wall and a dining table with elegant lighting.

Home in Fells Point

Charming 4 bedroom home just steps to the water!

Charming 4 bedroom home located in the heart of Fell's Point! Located just steps from Broadway Square and the waterfront, this unique space is surrounded by the best restaurants, bars, nightlife and entertainment in the city. This stylish home is the perfect place to stay for group trips and families looking to take in all that Baltimore has to offer. Please note that we allow a maximum of 8 guests and events and/or parties are strictly prohibited.

5.0 out of 5 average rating, 226 reviews

Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

Enjoy a peaceful waterfront getaway just 2 miles from Historic Downtown Annapolis and the U.S. Naval Academy. Located directly on the South River in a quiet neighborhood, this charming cottage features a full kitchen, 1 bedroom, washer/dryer, and sleeper sofa for up to 4 guests. Relax on the private patio with outdoor seating, grill, and fire pit, or enjoy the beautiful river views. Perfect for exploring Annapolis or simply unwinding by the water.

4.97 out of 5 average rating, 113 reviews

A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.

Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

Place to stay in Glen Burnie

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.

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

4.94 out of 5 average rating, 413 reviews

4.98 out of 5 average rating, 168 reviews

Cottage in Annapolis

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

Popular amenities for Pasadena waterfront rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

4.97 out of 5 average rating, 320 reviews

A serene view showcases the landscaped yard, featuring blooming pink flower clusters in the foreground. A large tree stands in the center with a backdrop of greenery and a peaceful waterway. The two nearby structures are connected by a deck, reflecting the tranquil surroundings.

Apartment in Essex

A place unique on sue creek

4.96 out of 5 average rating, 196 reviews

Apartment in Arnold

Celebrate Summer In Your Private Pool & Hot Tub

4.96 out of 5 average rating, 304 reviews

A cozy living area features a brown leather sofa next to a white coffee table. A decorative rug with star patterns lies on the floor. A green potted plant adds a natural touch, complemented by a television on a media unit. Light enters from the window.

Apartment in Chester

Cozy Waterfront Apartment Chester, MD

4.91 out of 5 average rating, 625 reviews

A serene waterfront scene is captured at sunset, displaying calm water reflecting soft hues of orange and blue. Silhouettes of trees line the shore, while gentle ripples can be seen across the surface, creating a peaceful atmosphere.

Apartment in Deale

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise

4.98 out of 5 average rating, 55 reviews

A spacious dock area displays two Adirondack chairs positioned for enjoying the water views. The wooden platform features a vibrant finish, with boats visible in the distance and trees lining the shoreline under a partly cloudy sky.

Apartment in Pasadena

Relaxing Waterfront Apartment!

4.95 out of 5 average rating, 81 reviews

A serene sunset is viewed over calm waters, reflecting warm orange and gold hues. Silhouettes of trees and a boat dock are visible in the foreground, with a few boats gently resting on the still water.

Apartment in Dundalk

Waterfront Romantic Studio

4.86 out of 5 average rating, 37 reviews

Apartment in Annapolis

Annapolis 4 Steps to Harbor Backs to Gate 1

Apartment in Stevensville

An aerial view showcases a large grassy area surrounding a heated pool, with several lounge chairs positioned nearby. A fire pit is set with white adirondack chairs. Two properties are visible, featuring balconies and umbrellas enhancing the outdoor space.

Heron Roost

5.0 out of 5 average rating, 96 reviews

Waterfront house rentals

4.78 out of 5 average rating, 100 reviews

The exterior of the waterfront home showcases a spacious wooden deck with a ramp leading to double glass doors. The structure is framed by large windows, and the surrounding greenery adds a natural touch to the entryway.

Home in Essex

Waterfront getaway Essex, MD

4.97 out of 5 average rating, 108 reviews

Home in Annapolis

Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit

4.99 out of 5 average rating, 145 reviews

A spacious living area is highlighted by large windows allowing natural light. Modern furniture includes a sectional sofa and accent chairs, complemented by a sleek coffee table. A large television is mounted on the wall, while indoor greenery adds a touch of nature.

Home in Edgewater

Luxury Modern Home on Water+Hotub- Annapolis 25min

4.94 out of 5 average rating, 335 reviews

A spacious rooftop deck features a shaded seating area surrounded by greenery. Comfortable couches provide ample seating, and a glass table holds decorative items and refreshments. The backdrop showcases colorful buildings and autumn foliage.

Home in Canton

Luxury Home, Gorgeous Roof Deck (By Marina & Park)

4.96 out of 5 average rating, 161 reviews

A serene bedroom is presented with a spacious bed, featuring soft gray bedding and illuminated by wall-mounted lamps. Two windows provide natural light, while a large mirror reflects the room's calming decor. A 43" Smart TV is mounted on the wall opposite the bed.

Home in Fells Point

3FL 1Block 2 Water wParking,85tv,Fireplace,1 K bed

5.0 out of 5 average rating, 217 reviews

Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

4.98 out of 5 average rating, 191 reviews

An inviting front yard is presented, featuring a pathway of round stones leading to the entrance of a two-story guesthouse. Lush greenery is framed by ornamental plants and mulched beds, creating a serene outdoor setting surrounded by trees.

Home in Annapolis

Quiet Waterfront

4.82 out of 5 average rating, 150 reviews

A two-story home built into the hillside is framed by lush greenery. A wooden porch, supported by stone pillars, features a railing and an American flag. The exterior showcases a mix of siding and stone, with large front windows allowing natural light into the interior.

Home in Ellicott City

Mello-Ray River House

Waterfront condo accommodation

4.86 out of 5 average rating, 291 reviews

A modern living area features a sleek flat-screen television mounted above a stone fireplace. On either side, wooden shelving units are filled with decorative items and books. The ambient light from the fireplace creates a cozy atmosphere, complemented by neutral wall colors.

Condo in Inner Harbor

Historic Federal hills urban lifestyle

4.98 out of 5 average rating, 124 reviews

Captains Quarters | Waterfront & Pool

A light-filled living area features a comfortable sectional sofa with pillows and a cozy throw. A round coffee table sits in the center, surrounded by a woven basket and a wooden armchair. The kitchen area is visible in the background, equipped with dark cabinetry and stainless-steel appliances.

4.75 out of 5 average rating, 85 reviews

Amazing Views from Spa Creek 2BD Condo with Pool

4.85 out of 5 average rating, 13 reviews

Waterfront Eastport Condo w Pool & Parking

4.8 out of 5 average rating, 20 reviews

Condo in Inner Harbor

Luxury Harborplace Condo Near Orioles, Ravens, M&T

The bedroom features a queen-sized bed with light bedding and decorative pillows. Two windows with brown shades allow natural light. A desk and chair are positioned nearby, with a mounted television above. Warm wood flooring adds to the room's comfort and style.

Condo in Georgetown

Historical Georgetown Modern Penthouse 12 min DCA

4.66 out of 5 average rating, 138 reviews

A modern, multi-story resort building is prominently displayed under a clear blue sky. Light-colored brick and stone create a contemporary façade, while balconies and large windows emphasize the welcoming design. The entrance features a sheltered area, enhancing accessibility for guests.

Condo in National Harbor

Luxury @ Wyndham National Harbor

4.91 out of 5 average rating, 38 reviews