Beachfront vacation rentals in Westport

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Westport

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

A sandy beach stretches along the tranquil shoreline, with a beach house positioned nearby. Soft waves lap at the shore, and the horizon reveals a serene water view. The sky is partly cloudy, providing gentle lighting to the landscape.

Home in Milford

4.94 out of 5 average rating, 137 reviews

#2 Milford Beach (across street) Charles Isle 2BR

Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

Superhost

A serene beach scene features gentle waves lapping at the shore under a sky filled with soft, fluffy clouds. A dog is seen running playfully on the sandy beach, creating a sense of leisure and tranquility.

Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

Superhost

Aerial view of the property along a sandy beach, surrounded by other homes. The two-story original home is highlighted, with its location indicated. The beach area stretches out in front, leading to the water, set against a backdrop of greenery and adjacent residential structures.

Cottage in Milford

4.78 out of 5 average rating, 32 reviews

Cheerful 2 bedroom cottage on beach

Take it easy at this unique and tranquil getaway with friends or family. Located on Cedar beach, this quiet original 2 story 1915 home is the perfect place to sit back, relax and remember the good ol’ days. Enjoy the private beach and views. Property has off street parking for 2 small cars and public street parking only a block away. AC window units, office, WiFi, coffee bar and tv w/Roku (guest to login.)Master bed has private balcony overlooks yard to beach. This is rear house on property.

Guest favorite

A bright sunroom features a comfortable white sofa adorned with colorful pillows. Large glass sliding doors provide unobstructed views of the water, while natural light floods the space. A small outdoor seating area is visible, enhancing the connection to the beach outside.

Home in New Haven

4.95 out of 5 average rating, 108 reviews

Beach Haven - waterfront, near Yale, sunsets

Everything you need for an amazing vacation, year-round, in our comfortable home right on the beach! Walk out the back door and dip your toes in the sand and in Long Island Sound. Enjoy spectacular views from the back patio, sun room, and most rooms in the house. Watch the sunset while soaking in the hot tub. Sit by the gas fireplace with a book. Stroll along the lovely nearby sea wall. 10-minute drive to Yale and all downtown New Haven has to offer. 5-minute drive to Lighthouse Point Park.

Guest favorite

The open living area showcases a modern kitchen with a central island and several bar stools. Sunlight streams through large glass doors, highlighting the neutral tones of the furnishings and the expansive water view. Wood detailing adds warmth to the atmosphere.

Home in Milford

4.98 out of 5 average rating, 209 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Guest favorite

A shaded porch is visible, featuring a round table with a floral tablecloth and several chairs. The tranquil ocean is seen in the background, while distant land can be discerned on the horizon. Soft light illuminates the space, enhancing the inviting setting.

Home in Woodmont

4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

Looking for an island-feel getaway? You've arrived! Welcome to La Spiaggia. Come enjoy this 4 bedroom, 2 bath home and wake up to the sound of waves crashing on your private beach. Have a cup of coffee watching the beautiful sunrise, work from home on the oversized front porch, and enjoy the evening with beautiful lighting and sunset views. Take a stroll along the ocean to Bay View Beach, or simply relax and take in the expansive oceanfront views. Soak up the summer sun at La Spiaggia!

Top guest favorite

The exterior of a newly renovated cottage showcases a light-colored façade adorned with turquoise shutters and flower boxes filled with vibrant flowers. The entrance is highlighted by a staircase leading up, while a parking area and garages are visible beneath the elevated structure.

Cottage in Fairfield

4.97 out of 5 average rating, 119 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

Charming Beach Cottage – Steps from Private Beach! Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

Top guest favorite

Home in Milford

5 out of 5 average rating, 101 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Superhost

A light-filled room features a large sliding glass door providing views of Long Island Sound. The serene ocean scene is complemented by a small table set for two and a potted plant, enhancing the inviting atmosphere of this waterfront home.

Home in East Haven

4.8 out of 5 average rating, 143 reviews

Casa al Mare Beachfront Retreat Oceanview

Welcome to Casa al Mare! If you are looking for a place to relax and recharge, look no further. Enjoy this spectacular direct waterfront home while still very close to the city. Yale and downtown New Haven are 15 minutes away. Step out of the glass doors to the patio and walk on the sandy beach! Relax, walk on the sand or swim in Long Island Sound. Stunning water views await you every day.

Guest favorite

A view from the spacious porch showcases well-maintained gardens filled with colorful flowers and lush greenery. The beach is visible in the distance, with people strolling along the coastline. A gentle breeze rustles through the leaves, creating a serene atmosphere.

Home in Woodmont

4.89 out of 5 average rating, 140 reviews

The Beach House!

Enjoy the Beach, Walks, Swimming, Kayak, Paddle Board and Local Restaurants within walking distance! The space is the entire first floor of a three family beach house. Easy in and out with beautiful views! The New York Times says "Woodmont Beach unspools like a ribbon for more than a mile around jetties, points and coves!"

Top guest favorite

A row of striped beach chairs is positioned on sandy shores, under blue umbrellas. The calm water reflects the sky and the horizon blends with distant craft, providing a tranquil beach setting.

Guesthouse in Southport

4.96 out of 5 average rating, 189 reviews

Southport, CT across from BEACH

Located at Southport beach on Westport Line, this renovated 1 bedroom apartment totally private located above the garage and includes a full kitchen with new appliance and d/w and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.