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Beachfront vacation rentals in Highland Beach

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Highland Beach

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

4.95 out of 5 average rating, 281 reviews

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

A waterfront home is depicted with a screened-in porch and a gabled roof. A wooden pier extends from the shore, leading to the water. Lush greenery surrounds the property, and stone embankments partially border the shoreline.

Home in Shady Side

4.95 out of 5 average rating, 111 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

Located 35 minutes from Annapolis and 45 minutes from Washington DC, Shady Side is a quaint town. This waterfront home is perfect for families or small groups looking to enjoy a relaxing getaway on the Chesapeake Bay. Enjoy the large wrap-around screened in porch and private pier with ladder for easy access for swimming. Large yard, and an incredible view of the Bay Bridge. Free public boat ramp 5 min away in Parish Creek. Listed for 8 people max but contact us for approval of 1-2 more.

A charming cottage is nestled among lush trees, featuring a spacious yard of green grass. Ample sunlight filters through the leaves, casting playful shadows. The exterior showcases a combination of windows and porch areas, offering a welcoming appearance in a serene environment.

Cottage in Pasadena

4.97 out of 5 average rating, 186 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.

A wooden pathway leads to a relaxing outdoor space adorned with lush green grasses and a large umbrella. The Chesapeake Bay is visible in the distance, providing a serene backdrop. A flagpole with an American flag is positioned nearby, adding to the coastal ambiance.

Home in Annapolis

4.9 out of 5 average rating, 213 reviews

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.

Top guest favorite

A driveway leads to the garage of a two-story apartment building, framed by greenery on either side. The smooth, paved surface is bordered by neatly arranged flower beds and trees, with sunlight casting gentle shadows along the path.

Guest suite in Annapolis

5 out of 5 average rating, 243 reviews

Cape St Claire waterfront getaway "The Apartment"

This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.

Top guest favorite

An outdoor hot tub features a sleek design with built-in jets, illuminated by soft purple lighting. The surrounding area is draped with white curtains, creating a secluded atmosphere. Seasonal use is indicated, adding a touch of relaxation to the outdoor space.

Place to stay in Annapolis

4.94 out of 5 average rating, 123 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

*Hot tub* “Chesapeake Bay View Paradise" (3BR/2BA Penthouse Suite). Private penthouse level of a 2-level duplex, new deck, gorgeous Chesapeake Bay views, steps to sandy beach. 3 car parking. Gourmet kitchen, SS appl, granite counters, bar. Comfy living & dining areas. Entry handrail installed 9/20/24. 2 King BR, 1 Queen BR + Queen sleeper sofa in living area. Sleeps 8. 2 spa inspired baths, 1 jetted 2-person Jacuzzi tub inside. Outdoor Spa with Jets * Best Places To Stay Annapolis

The bungalow features a welcoming front porch enclosed by large windows, allowing natural light to fill the space. The exterior showcases white siding complemented by green trim and a simple pathway lined with landscaping stones, leading to the entrance surrounded by a grassy yard.

Bungalow in North Beach

4.86 out of 5 average rating, 110 reviews

Bayside Bungalow: Cozy North Beach Getaway

Sip your morning coffee while overlooking the Bay, hear the waves splashing up on the beach, and smell breakfast being made by the local bakery. Our little bungalow is located at the end of the Boardwalk, making for an easy stroll to the shops, a variety of eateries and ice cream shops, try a little shopping, or just relax on the beach all afternoon. Be on the water AND close to all that the beach has to offer for entertainment. *Beach Passes STAY with the home upon checkout*

A serene waterfront scene is captured just before twilight, showcasing calm waters reflecting the soft colors of the sky. Distant lights from nearby docks create a gentle glow, framed by the silhouettes of trees and the peaceful harbor setting.

Apartment in Annapolis

4.92 out of 5 average rating, 103 reviews

Dazzling day/night water views,1st class amemities

TREAT YOURSELF! YOU DESERVE THE VERY BEST! HUGE DISCOUNTS FOR WEEK AND MONTH LONG STAYS! Treat yourself to the good life while in Annapolis! Gorgeous 14yr. old custom designed & furnished 1470sq.ft. waterfront apartment, 9ft. ceilings, fantastic water views day & night! Private pier, firepit and 40ft. waterfront covered patio for guests use. Guest parking for 4 cars. Few minutes to US Naval Academy, Annapolis Harbor, restaurants, shopping. Pets are not allowed.

Top guest favorite

A dining area features a glass-top table surrounded by rustic chairs. Sunlight filters through large windows, illuminating a vase of colorful flowers. The comfortable seating area, positioned by the windows, offers views of the bay, enhancing the tranquil ambiance.

Home in Tracys Landing

4.99 out of 5 average rating, 230 reviews

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

An open living area features plush seating arrangements in soft tones, complemented by a coffee table and an elegant fireplace beneath a mounted TV. Natural light filters through sheer curtains, enhancing the warm atmosphere of the space.

Cottage in Annapolis

4.94 out of 5 average rating, 18 reviews

Wonderful Cottage Nestled On Chesapeake Bay

Stunning home a short walk from Chesapeake Bay - a perfect blend of comfort and coastal charm. Stroll, jog or bike in the scenic neighborhood, and hear songbirds, see deer, and watch sailboats glide by. Open-concept design and natural light make our home ideal for entertaining, working from home, or relaxing on the spacious deck. Minutes from local eateries, and attractions in downtown Annapolis. Easy drive to DC or Baltimore. We allow one dog - max 25 lbs.

Top guest favorite

A serene riverfront scene features a reflecting water surface, with the sky painted in soft pinks and purples at sunset. Lush greenery borders the water's edge, and silhouettes of trees frame the tranquil landscape.

Guest suite in Pasadena

4.98 out of 5 average rating, 639 reviews

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!

Top guest favorite

A charming single-story house is framed by vibrant pink flowering trees. The facade features yellow siding, blue shutters, and a turquoise front door. A white picket fence encloses the front yard, which is well-maintained with green grass and landscaping.

Home in North Beach

4.97 out of 5 average rating, 161 reviews

Beach Home | King Bds | Firepit | Backyard Dining

Welcome to A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.

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Popular amenities for Highland Beach beachfront rentals

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Adirondack chairs are positioned on a brick patio, overlooking a serene view of the Miles River. The tranquil water reflects a partly cloudy sky, bordered by trees on the shore, creating a peaceful outdoor setting.

5 out of 5 average rating, 8 reviews

Ferry Bridge House

The main living area features a comfortable wicker chair with a blue cushion, complemented by a separate white armchair. Natural light pours in through several large windows with blinds, illuminating the light wood flooring and a cozy throw blanket draped over a nearby chair.

Houseboat in Stevensville

4.88 out of 5 average rating, 60 reviews

Chesapeake Houseboat Getaway

A sandy beach is shown along the shoreline, bordered by tall grasses and scattered vegetation. The view extends towards a two-story house positioned in the background, with soft clouds and a blue sky adding to the serene coastal atmosphere.

Home in Stevensville

4.9 out of 5 average rating, 60 reviews

Beachside Dream

Top guest favorite

The image captures a serene sunset over the Chesapeake Bay, with warm hues of orange and pink reflected on the water. A silhouette of a boat is seen in the foreground, creating a tranquil atmosphere. The distant horizon merges gently with the colorful sky.

Home in Rock Hall

5 out of 5 average rating, 29 reviews

Sunset at Rabbit Run

Top guest favorite

Adirondack chairs are placed on a sandy beach beside calm waters, with a wooded shoreline in the background. A dock extends into the water, framed by a soft pastel sky at sunset. Small waves gently lap at the shore, creating a peaceful ambiance.

Apartment in Arnold

4.93 out of 5 average rating, 83 reviews

Bring A Boat! Waterfront home-w/basement apt+dock!

A lush green lawn gently slopes toward the water, bordered by a decorative stone structure and a vibrant tree. A sailboat is anchored nearby, and a small dock features wooden chairs, inviting relaxation by the waterfront under a partly cloudy sky.

Private room in Pasadena

5 out of 5 average rating, 16 reviews

Pearl of the Magothy - Private Room 3*

A cozy room features a dark green vintage loveseat accompanied by a small lamp. A wooden desk with a vintage chair is positioned against the wall, surrounded by books and decorative items. Two windows allow natural light to filter in, enhancing the tranquil aesthetic.

Private room in North Beach

4.8 out of 5 average rating, 74 reviews

Room/house with panoramic view of Chesapeake Bay.

Beachfront home rentals with a pool

A large, clear swimming pool is surrounded by a well-maintained patio. A diving board is positioned at the edge, with a brick wall and lush greenery in the background. Sunlight reflects off the water's surface, enhancing the inviting atmosphere.

Home in Chestertown

4.97 out of 5 average rating, 32 reviews

Chestertown Watson Family Farm

Two red kayaks glide over the calm water of the Choptank River, surrounded by trees with autumn-colored leaves. The serene sky above is clear and blue, reflecting on the water's surface, creating a peaceful outdoor scene.

Private room in Trappe

5 out of 5 average rating, 3 reviews

B&B - Lawson

Top guest favorite

A tranquil heated pool is surrounded by lush green grass and vibrant flower beds. Lounge chairs are strategically placed around the pool for relaxation. In the background, a stationary RV and a multi-story building complement the charming outdoor retreat.

Camper/RV in Stevensville

5 out of 5 average rating, 9 reviews

Charming RV With A Water View

Vacation home in Queenstown

4.97 out of 5 average rating, 65 reviews

Heart of the Chesapeake

A bright and airy living area is showcased with large glass windows offering views of the waterfront. A modern dining table is accompanied by chairs, while a comfortable seating arrangement is positioned near the windows. Sunlight filters in, enhancing the serene ambiance.

Apartment in Southwest Waterfront

Luxurious Waterfront apartment in DC

A serene sunset view over the Chesapeake Bay is captured, showcasing the warm hues of orange and purple reflecting on the water. The exterior of the houseboat is softly illuminated, revealing a welcoming outdoor space with seating and a nearby sandy area.

Houseboat in Pasadena

Flohom 14 | Panoramic Chesapeake Bay Views

A serene in-ground swimming pool is surrounded by lush green grass and trees. The reflection of nearby trees is visible on the water's surface. A charming blue house stands in the background, with access to the waterfront just beyond the pool.

4.94 out of 5 average rating, 36 reviews

Chesapeake Bay Estate; 2 Houses, Beach&Heated Pool

Private beachfront home rentals

Top guest favorite

A charming one-story cottage is surrounded by lush greenery and colorful flower beds. The well-maintained lawn features clusters of lavender-colored flowers, complemented by shrubs and bushes, creating an inviting atmosphere. The front porch, with steps leading up, adds to the home's welcoming appeal.

Cottage in Annapolis

4.93 out of 5 average rating, 30 reviews

Bay View Cottage: Perfect for long or short stays

A collage showcases various areas of Breezy Bay Home. The living room features a comfortable gray sofa and modern decor. Outdoor views reveal a sandy beach and tranquil waters. A well-lit bedroom with a bed displays soft linens, while a spacious exterior highlights ample decking.

Home in Chesapeake Beach

4.89 out of 5 average rating, 47 reviews

Chesapeake Beach Charm: Cozy Home with Bay views

A cozy outdoor space features a circular arrangement of blue Adirondack chairs surrounding a firepit, set on gravel. A wooden picnic table sits underneath an umbrella, while a spacious green lawn is framed by a wooden fence and trees in the background.

Cottage in Grasonville

4.85 out of 5 average rating, 73 reviews

CoastalBeachCottage*BayViews*Close2WeddingVenues

Top guest favorite

A serene waterfront scene features a private pier extending over calm waters, bordered by lush green trees. Two Adirondack chairs in the foreground invite relaxation, complemented by a paddle board resting nearby. The soft hues of sunset reflect on the water's surface.

Guesthouse in Grasonville

5 out of 5 average rating, 24 reviews

Quaint Waterfront- access, Private Shorehouse-unit

The renovated cottage features a white exterior with blue accents, surrounded by lush greenery. A small porch with a light blue railing leads to the entrance. A brick pathway and outdoor seating area are visible in the well-maintained yard.

Cottage in Annapolis

4.95 out of 5 average rating, 55 reviews

Charming Waterfront Cottage on Historic Property

A charming cottage exterior is presented, featuring light-colored siding and a vibrant red door. Two teal Adirondack chairs are positioned on a grassy area, offering a cozy spot to relax. Lush greenery and small shrubs frame the entrance, enhancing the inviting appearance.

Cottage in Saint Michaels

4.79 out of 5 average rating, 29 reviews

Cottage #1 Lighthouse First Cottage down driveway

A wooden dock extends into a calm river, featuring three red Adirondack chairs at the end. Surrounded by trees, the still water reflects the overcast sky, providing a serene outdoor space for relaxation.

Home in Chestertown

4.98 out of 5 average rating, 59 reviews

Goose Haven, new waterfront house on Fairlee Creek

A modern kitchen features white cabinetry and dark countertops, with a double sink positioned beneath a window. Stainless steel appliances, including a gas stove and microwave, are visible. Hardwood flooring extends throughout the space, leading to a doorway that opens into an adjoining utility area.

Apartment in Dundalk

5 out of 5 average rating, 3 reviews

Cute Unfurnished 2 Bedroom on the Water

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