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Darien vacation rentals

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Top-rated vacation rentals in Darien

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

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A serene beach view features soft sandy shores leading to calm waters. A small wooden bench is positioned in the foreground, while a sailboat glides gracefully on the horizon. Gentle waves can be seen lapping at the shoreline under a clear blue sky.

Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

FayeRating, 5 stars20 months ago

Mougeh's place is a lovely home with ample space, toys, books, games for entire family, within walking distance to the beach, and four mile drive to all shopping needs. The reason for the three star rating given in the "clean house" question was because when we arrived we noticed dog hair in the living area. We contacted the host and immediately the next day the cleaning service arrived and cleaned it. We were refunded the cleaning fee. Mougeh is very caring and responsive to her guests's needs.

Top guest favorite

A charming studio cottage is nestled among trees, with a covered porch adorned by an American flag. Steps lead up to the entrance, and a wooden railing provides safety. Seasonal foliage in warm colors surrounds the area, complementing the rustic setting.

Cottage in Cortlandt

4.99 out of 5 average rating, 190 reviews

The Little Cottage in the Woods

AmandaRating, 5 stars1 week ago

Joanne and Rick's place was even more lovely than expected. The cottage is surprisingly spacious for a tiny home and has everything you need. The property is stunning, tucked away off a long driveway, and I loved having a quiet cup of coffee on the porch in the morning. It is an easy ride to and from the Peekskill station and nearby places. I had travel issues and didn't arrive until after 9 p.m., but Joanne and Rick were great communicators, and Rick came out once I arrived to make sure I had everything I needed. My biggest regret is that I didn't have enough time to explore the property -- I was staying for a wedding that dominated all of my time. Luckily, I have friends in Peekskill, so when I have the opportunity to come back, I'll hopefully get to stay again!

A cozy living area features a large sectional sofa with decorative cushions, complemented by a plush armchair. Natural light is invited through two front windows, while a coffee table sits at the center, surrounded by green plants and framed art on the walls.

Home in Baldwin

4.85 out of 5 average rating, 133 reviews

Clarissa's Paradise

JamalRating, 5 stars2 months ago

First of all I would like to thank Carmen for letting me stay at her beautiful home. I enjoyed the time I spent at the air bnb even though it was a very busy weekend for me. Carmen home was clean and comfortable, also a very convenient location close to so many places. The home is also pretty spacious I was able to have a nice family dinner and gathering there. I would definitely recommend staying at this beautiful air bnb, Carmen was a great host Thankyou again.

A lakeside retreat is nestled among lush greenery, featuring a spacious deck with blue seating. A gentle slope leads to the water's edge, where a small area is provided for relaxing. A large tree casts shade over the grassy yard, enhancing the natural setting.

Home in Putnam Valley

4.97 out of 5 average rating, 59 reviews

Waterfront Lake House

EricRating, 5 stars3 days ago

Brian was such a great host, extremely responsive to any questions, and his place is amazing. Views of the lake are scenic, and the house was immaculate and well equipped with everything you would need. Would highly recommend - my wife and I (and our corgi) had a great time.

Home in New Fairfield

4.92 out of 5 average rating, 116 reviews

Beautiful Lakefront Retreat with Private Dock

GeriRating, 5 stars3 weeks ago

It was our first experience with Airbnb. We were there to tour the World Headquarters for Jehovah’s Witnesses and this proved to be our evening haven. The house was well stocked as others had commented. We enjoyed relaxing and spent much time in living room with the beautiful view. It was perfect for our stay. Our thanks to our Host.

Top guest favorite

A well-lit wooden deck features comfortable seating arrangements with padded chairs, perfect for relaxation. Soft lights illuminate the space, creating a welcoming atmosphere. A protective railing borders the deck, with a view of a privacy fence in the background.

Home in Milford

5 out of 5 average rating, 101 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

PatrickRating, 5 stars2 months ago

Rented this for six weeks while working in the area, was perfect. I enjoyed it very much. Lots of space everything you could possibly need even down to the toothpaste and brushes, you could seriously just show up completely unprepared and you would have an excellent stay. If I am back in the area for long term again this will be my first search.

Vacation rentals for every style

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Hotels

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Darien vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Darien's top sights

West Beach16 locals recommend

Rowayton Market15 locals recommend

The Restaurant at Rowayton Seafood15 locals recommend

Cafe Silvium14 locals recommend

Waveny Park12 locals recommend

Sails American Grill11 locals recommend

Other great vacation rentals in Darien

An expansive outdoor area showcases a heated pool surrounded by wooden decking. Sun loungers and umbrellas are arranged around the pool, with colorful seating accents visible. Pathways meander through lush greenery, integrating seating and recreational spaces within the tranquil courtyard.

Apartment in Downtown Stamford

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

JoanRating, 5 stars3 months ago

Clean , modern apt. Very easy to navigate with the technology. Staff very friendly and helpful. A bit noisy on street outside with traffic. Will definitely rent again with URBY, but request a courtyard side unit

Large windows allow natural light to fill the open living space, showcasing the stunning view of the Great South Bay. A comfortable sofa with decorative pillows faces the water, complemented by a dining area nearby. Warm wood tones enhance the cozy atmosphere of the room.

Cabin in Shirley

4.87 out of 5 average rating, 153 reviews

A-Frame cabin with private beach & epic sunsets

JenniferRating, 5 stars2 weeks ago

Amber’s place was immaculate and stunning. This was my 2nd time staying and it was just as magical! The place had plenty of space for a family of 3 and the washer/dryer was very convenient. We had a great time and would stay here again!

The spacious kitchenette features modern appliances, including a refrigerator and a stove, set against rustic wooden beams and a brick fireplace. Natural light filters through the wooden windows, illuminating the inviting wood flooring and enhancing the open layout.

Cottage in Norwalk

4.94 out of 5 average rating, 68 reviews

Seaside Serenity: 2B 1B, Patio,Near Beach

AdamRating, 5 stars1 week ago

We had a wonderful stay at the cabin. It was a perfect size for our family and our son had a great time playing in the yard and the playground right next door. Our hosts were super responsive the couple of times we needed something. We'll definitely be back!

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and an oven. Gray cabinetry contrasts with a mosaic backsplash. A sink is positioned beneath a window, while a clean mat lies on the floor near the countertop.

Apartment in Brentwood

4.84 out of 5 average rating, 32 reviews

Home away your home

GeraldineRating, 5 stars6 days ago

Nice place exactly what the pictures show .. Super nice host.. but if you are looking for a quiet place. This place is definitely not it. You can hear every move and every sound from the people that live upstairs last night we spent a good few hours hearing a baby cry. Also they have the children’s toys such as a trampoline up against the window of the unityou do park on the street and the owner or tenants whoever lives upstairs parks in the driveways. it’s a very tight walk in between cars in the driveway because they do park a lot of cars in the driveway side-by-side.

A spacious master suite features two king beds and a full bed, all on a neutral tile floor. A ceiling fan provides airflow, while a large TV is mounted on the wall. The room is illuminated by recessed lighting, creating a bright atmosphere.

Home in Bayonne

4.74 out of 5 average rating, 19 reviews

The Rainforest I|Sleeps 12|20m to NYC|Free Parking

GuadalupeRating, 5 stars3 months ago

Natalia‘s place was so great for our huge family even though it is a house divided into it is very roomy. The basement is big enough for the whole family and overall it’s just a great place you feel right at home. Highly recommend everything is walkable

A modern bathroom features a dual sink vanity with sleek fixtures and a large mirror above. Neutral-toned tile lines the walls and floor. Natural light filters through a window, and two white towels are neatly arranged on a towel rack beside the toilet.

Home in East Patchogue

4.79 out of 5 average rating, 150 reviews

Bay's Edge Vacation Get a Way

BillRating, 5 stars2 weeks ago

Earl, was great to work with. We were only there for few hours. However I would recommend highly and will look to stay here again should work bring me back out that way.

A serene waterfall cascades over rocky terrain, surrounded by lush greenery. Tall trees and vibrant foliage frame the scene, enhancing the natural beauty of the area. Gentle movements of the water create a calming effect, reflecting sunlight in the peaceful setting.

Apartment in Beacon

4.85 out of 5 average rating, 105 reviews

Lovely 2 bed, 2 full bath. & private yard getaway

TylerRating, 5 stars3 days ago

Plenty of space, great for traveling with dog, really close to some great trails, and Beacon is a great little city.

A shoreline is depicted with a mixture of smooth, round pebbles covering the sand. Gentle waves are seen rolling onto the beach, and a colorful sunset fills the sky, casting reflections over the water's surface.

Cabin in Rocky Point

4.89 out of 5 average rating, 485 reviews

Great little place just for a couple

PaulRating, 5 stars3 days ago

The property was cozy and clean with great graden sitting are and almost everything you could need. Only qualm was that the property was advertised to have a fence but there isn’t one, there is a hedge but not a gate to make an enclosed space for a dog. This isn’t a huge deal because the beach is so close and great for walks just a minor disappoint other than that the place is incredibly cozy and we would be happy to stay here again

Quick stats about vacation rentals in Darien

Total rentals
50 properties
Total number of reviews
1.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Frequently Asked Questions

Where should I stay in Darien?
Make yourself at home in Darien by choosing from our most frequently booked neighborhoods. We have over 300 vacation rentals in Noroton, over 300 vacation rentals in The Cove, and over 430 vacation rentals in Tokeneke.
Are there vacation rentals with a dedicated workspace in Darien?
Yes! Work meets play with ease at over 30 vacation rentals in Darien featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Darien?
Four-legged friends are welcome in Darien. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there Darien vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Darien, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Darien have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Darien. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Darien have wifi?
Absolutely! We offer over 30 house rentals with wifi in Darien. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Darien?
Darien has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Darien?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore