Beachfront vacation rentals in Westport

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Popular amenities for Westport beachfront rentals

Beachfront home rentals with a pool

Superhost
An outdoor seating area is positioned on a stone patio, featuring a yellow and white striped sofa with matching chairs and a glass-top table. A swimming pool is visible in the background, surrounded by lounge chairs and lush greenery.
Apartment in Black Rock
4.89 out of 5 average rating, 65 reviews

Victorian apartment

LeeRating, 5 stars4 months ago
The place matched the description perfectly and much more spacious than what one usually finds for a single bed/bath apartment. I enjoyed the stay and would return again. For me it was a perfect place to accommodate overflow thanksgiving guests over the holiday.
Superhost
An in-ground pool is surrounded by a white picket fence, featuring a clean, inviting blue surface. Lush green trees and colorful foliage can be seen in the background, while a small shed is positioned to one side. Sunlight brightens the entire scene under a clear sky.
Home in Woodmont
4.85 out of 5 average rating, 85 reviews

Spacious 4 bedroom, oasis with ocean views galore

ClaireRating, 5 stars3 days ago
We had such a great time staying at this Milford house! It was even better in person than the pictures show, more spacious than expected. The balconies overlooking the water were great to wake up to, and the small touches that the host added (towels set up and stacked in each bedroom, full coffee bar) made everything that much better! Allana was incredibly kind and responsive, being proactive about check in and check out and making sure we had everything we needed. We will definitely be repeat stayers at this house!
Guest favorite
A sleeping area features a wooden bed frame with a white bedding set and a framed landscape artwork above the headboard. A small desk and chair are positioned beside the bed, accompanied by a bedside table with a lamp. Natural light filters through dark curtains.
Hotel room in Locust Valley
5 out of 5 average rating, 17 reviews

888 - Room with one double bed

JohnRating, 5 stars3 weeks ago
Good price and clean area
A private pool area features an inviting turquoise pool surrounded by lounge chairs in a vibrant blue hue. A shaded seating area is seen nearby, providing a comfortable space for relaxation. Lush greenery is present in the backdrop, enhancing the outdoor living space.
Home in New Haven
4.57 out of 5 average rating, 21 reviews

New Haven Gem w/ Private Pool, Walk to Beach!

MaxineRating, 5 stars8 months ago
I enjoyed myself throughly!! My sisters and I had such an amazing time!! We weren’t ready to leave. My sister enjoyed her birthday getaway so much!! She fell in love with the home and the pool!! The showers felt tropical.
Guest favorite
A large swimming pool is surrounded by a spacious deck, featuring lounge chairs and umbrellas. Lush greenery provides a backdrop, with flowering plants along the fenced perimeter. The clear water reflects the sky, inviting relaxation and enjoyment.
Home in Woodmont
5 out of 5 average rating, 10 reviews

Huge Family House w/Waterviews

SheilaRating, 5 stars2 months ago
The neighborhood was beautiful. We walked out to an island that was only accessible at low tide. Great shared spaces with fun rooms and lovely bedrooms.
Guest favorite
Private room in Milford
5 out of 5 average rating, 5 reviews

Best Home in Milford for Getaway-Room(s) Available

LindaRating, 5 stars6 months ago
The location was great, so close to the beach. Everything was comfortable and clean. David gave us great information and instructions. Would definitely stay here again.

Pet-friendly beachfront home rentals

Superhost
A charming two-story house is featured with light green siding and a welcoming front porch. The entrance is framed by white railings, and landscaped gravel pathways lead to the doorstep. Nearby, other colorful houses are visible, creating a pleasant neighborhood atmosphere.
Home in Milford
5 out of 5 average rating, 3 reviews

Beach House

KatieRating, 5 stars3 months ago
So glad I came across this home! The space is great with a beautiful view. Joe was a wonderful host and always responsive and helpful. It was a peaceful getaway to begin the new year. Thanks for everything, looking forward to staying again!
Guest favorite
An aerial view showcases a coastal neighborhood featuring a series of residences surrounded by greenery. The shoreline is visible, revealing a sandy beach with gentle waves lapping at the shore. The area is framed by trees and distant water, indicating a tranquil environment.
Home in Branford
4.89 out of 5 average rating, 53 reviews

Spacious Modern Beach House

BeckyRating, 5 stars2 weeks ago
We were gathered from around the country for my Mother s Memorial. It was such a pleasure to stay in such a peaceful environment, as emotions were high. It was healing. Beautiful home, and all directions were clear. If it had been a little later in the Spring and the weather warmer, it would have been even better. I highly encourage anyone to stay and enjoy what the area has to offer in Gregory's beautiful home. You will have a wonderful vacation!
Top guest favorite
The living area features a high ceiling with large windows, allowing natural light to brighten the space. A comfortable sofa adorned with colorful pillows sits opposite two red armchairs. A wooden coffee table holds various books and a decorative tray, creating an inviting gathering spot.
Apartment in Branford
4.97 out of 5 average rating, 105 reviews

Ridgeview Suite at Stony Creek Depot

HunterRating, 5 stars5 months ago
The photos don't do it justice—this charming place is even more spacious than it looks online. The vintage decor added a cozy touch that made us feel right at home. Highly recommend!
Top guest favorite
Guesthouse in Mahopac
4.95 out of 5 average rating, 223 reviews

Lakeview Guesthouse with Sauna

CatherineRating, 5 stars5 days ago
This is a gorgeous guest house with a lovely view of the lake. Didn’t get to try the sauna but appreciated that it was available all hours. Shower and bed were nice! We traveled here on bike while going from Poughkeepsie to NYC on the Empire State Trail. The house is close to the trail and they gave us good bike directions. Great place to stop to split up the 100 mile journey - right in the middle!
Guest favorite
A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.
Cottage in Milford
4.95 out of 5 average rating, 315 reviews

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly

AnnRating, 5 stars1 week ago
We had nice weekend at the cozy cottage. We loved that it was pet friendly and a short walk to the beach. Cameron was very friendly and responsive. She offered great suggestions for food and activities.
Superhost
Cottage in Branford
4.75 out of 5 average rating, 4 reviews

Beachside Branford- walk t0 Beach, Grill, Fire Pit

NickRating, 5 stars1 month ago
Amazing, quaint beach house just seconds from the water. Hosts were great, answered any questions I had immediately. We are from town and stayed while work was being done at our home but will definitely be recommending this property to friends and family who come to visit.
Guest favorite
A spacious outdoor deck features a wooden dining table surrounded by six woven chairs, with cushions for added comfort. The serene harbor view is visible in the background, framed by lush greenery and distant houses.
Home in Centerport
5 out of 5 average rating, 13 reviews

Charming waterview house

PatriciaRating, 5 stars2 weeks ago
This is a charming house with a wonderful view. Very comfortable and has everything you may need for your stay. William was very solicitous that everything was to our satisfaction – which it was. We totally enjoyed our stay.
Guest favorite
A serene lakeside scene is depicted with a figure leaping from a wooden dock into calm waters, accompanied by a dog. The sun casts a gentle glow on the surface of the lake, while a wooded hillside frames the background.
Home in Putnam Valley
4.87 out of 5 average rating, 287 reviews

The Pudding Pad Lake House

LindsayRating, 5 stars1 week ago
Our Spring Break stay at the Pudding Pad was great. I was there solo with an 8 year old and our dog, and we loved the huge yard that sloped down to the lake, the movie room, and the proximity to Fahnestock State Park (literally 8 minutes away). Basquali and Michelle have decorated the cozy space with a lot of fun details and vintage furniture - a favorite moment was our first day when the afternoon sunshine came in at just the right angle to hit a disco ball flower pot. It added a lot of surprise and delight. While we weren't brave enough to jump in the lake in April, we'd love to return in the warmer months to take advantage of the canoes and floats.

Private beachfront home rentals

Superhost
An aerial view captures a stretch of sandy beach bordered by several residential houses. Beach chairs are arranged in groups along the shoreline, while the calm waters of Long Island Sound glisten under a clear sky. Subtle autumn colors can be seen in the background.
Home in Milford
4.82 out of 5 average rating, 97 reviews

Beachfront house on Long Island Sound

DominiqueRating, 5 stars1 week ago
We loved our stay! The private beach was perfect for our kiddos - far enough away from the water that they could play independently in the sand while we sat on the beautiful deck. The kitchen had all the items we needed (we even took a virtual cooking class while there). Dmitry was super responsive and helpful. The master bedroom was a beautiful place to watch the sunrise/sunset.
Guest favorite
Apartment in Milford
4.9 out of 5 average rating, 10 reviews

The Sun is strong & The days are getting long!

MarkRating, 5 stars4 months ago
Great place; wonderful 2 bed place, clean, cosy and top end, one of the nicer places I've stayed. Alison was super easy to communicate with and the location was great for a Christmas break. Was very happy with everything!
Top guest favorite
An aerial view showcases the expansive Bayview Beach, where gentle waves lap against the sandy shoreline. The surrounding coastal homes and green spaces are visible, all under a clear blue sky. The lush landscape meets the ocean, creating a serene beach environment.
Cottage in Woodmont
4.98 out of 5 average rating, 89 reviews

Welcome to Ocean’s 55 !

MaqCRating, 5 stars5 months ago
We lived in Joseph’s fantastic place as a team of 4 chaperons and 7 teenagers attending the tournament of champions at Yale University. Everything about this listing is fantasy - proximity to the beach and amenities, the decor, furniture and fixings, and Joseph’s super speed in response and guidance. Every one of us was stoked and it’s a place we’d love to come back to and call home again after a while.
Guest favorite
A spacious balcony offers a view of the water, framed by trees and power lines. The railing adds a sense of openness, while the calm water reflects soft clouds in the sky, enhancing the serene atmosphere of the setting.
Home in West Haven
4.97 out of 5 average rating, 29 reviews

Beautiful, Spacious, Waterfront Home on the Bay

KevinRating, 5 stars4 months ago
Had a great stay over Christmas Holiday with family. House was big, convenient, clean and easy to get into. Great view of the ocean. Would definitely stay there again.
Superhost
Aerial view of Barefoot Bungalow's location, featuring Silver Sands Beach and the ocean in the background. The residential street is visible, along with nearby homes and open space. A glimpse of the shoreline and the calm waters creates a serene coastal setting.
Home in Milford
5 out of 5 average rating, 3 reviews

Newly renovated beachfront escape in Milford, CT!

ShanleyRating, 5 stars8 months ago
Overall a great space, right next to the ocean and silver sands State Park. Easy to find and available parking. Clean and tidy, space as pictured. Shared back yard. Quick and easy communication with owner.
Top guest favorite
Home in Milford
5 out of 5 average rating, 100 reviews

Milford Beach House - Newer Construction!

CharleneRating, 5 stars2 weeks ago
The host was extremely accommodating and communicative. This home is absolutely beautiful, the perfect place to stay! We stayed for our daughters wedding and we had all the girls getting hair & make-up done the day of the wedding, it was the perfect peaceful setting. The sound of the waves with the beach back drop is simply gorgeous! If your traveling to Milford, this is the perfect place to stay!! Thank you Victor for a wonderful weekend.
Superhost
A serene coastal view captures a vibrant sunset, where the sun dips below the horizon, casting warm hues across the sky. Gentle waves lap against dark rocks, creating a tranquil atmosphere along the shore. The scene evokes a sense of calm and natural beauty.
Cottage in North Fork
4.91 out of 5 average rating, 53 reviews

Cottage in Calverton

KaitlynRating, 5 stars8 months ago
Perfect for our weekend getaway. Very clean and relaxing and close walk to a cute little beach. We would stay here again!
Top guest favorite
A wrap-around deck is highlighted, featuring a round table and two chairs, offering a vantage point of the expansive water view. Calm waters reflect the sky, while boats are seen in the distance. Lush greenery frames the scene, enhancing the natural surroundings.
Cottage in Centerport
4.89 out of 5 average rating, 61 reviews

Waterfront beach house 1 hr from Brooklyn and NYC

KeithRating, 5 stars2 weeks ago
Astrid was a great host and the house was awesome. It has an indescribable character and charm, with amazing views to go with it. Visiting in the early Spring, we weren't fully able to enjoy the outdoor amenities, but could only imagine a stay later in the spring/summer. The home was cozy and private. Additionally, very well equipped with everything you could need, from paper towels to cooking supplies. The stairs are steep as mentioned, but we had zero issues. Would highly recommend!

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