House vacation rentals in Darien

Find and book unique houses on Airbnb

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Popular amenities for Darien house rentals

House rentals with a pool

Guest favorite
A well-maintained backyard features a circular swimming pool surrounded by a wooden deck. The pool is filled with clear blue water, and steps lead into it. A deck railing provides safety while offering views of the surrounding greenery and the house in the background.
Home in Massapequa
4.93 out of 5 average rating, 123 reviews

Great Family Times in this 5 Bedroom House

JorgeRating, 5 stars3 weeks ago
My family and I had a beautiful stay and I couldn’t have asked for a better rental. The Airbnb was huge with more than enough room for everyone and the backyard was large and spacious enough to have everyone eat comfortably. If I ever need another large rental you can bet I’m gonna check here first.
Top guest favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars3 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Guest favorite
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh
4.88 out of 5 average rating, 80 reviews

Entire Home (private pool), Event Friendly

ChannyRating, 5 stars1 week ago
Faisal was extremely responsive throughout our stay. we loved the indoor pool and the game tables. there was a nice selection. The rooms were nice. It was great that the bedrooms were on the same floor as the living room, dining room and kitchen. We came with an elderly person and they were able to make their way around the house. my son asked if he can use the fire pit out in back and he was able to. he collected wood from the side of the house. nice location. we really enjoyed our stay.
Top guest favorite
The outdoor area features a large in-ground pool surrounded by a fence, with lounge chairs and shaded umbrellas. A spacious wooden deck is visible, along with seating and a small shed. The lush greenery of the backyard complements the serene setting.
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars1 month ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Top guest favorite
A single-story house is depicted, featuring a light exterior complemented by solar panels on the roof. The front yard showcases well-maintained greenery, with blooming shrubs adding bursts of color. A clear blue sky serves as a backdrop, enhancing the home's inviting appearance.
Home in Shirley
5 out of 5 average rating, 16 reviews

Hope Haven

HilarioRating, 5 stars8 months ago
I was in Dion’s place with my family we really enjoyed the time we spent there,everything was perfect the pool was something that my kids enjoyed a lot, and hopefully we will come back again, for sure I totally recommend his house if you want to go and have a couple days of fun and relax thank you again Dion.
Superhost
An outdoor area features a blue swimming pool surrounded by greenery. A patio area includes a grill and a table, inviting guests to enjoy meals al fresco. Sunlight creates a bright atmosphere, while tall trees provide a sense of privacy.
Home in Fairfield
4.71 out of 5 average rating, 7 reviews

Modern Beach Area Vacation Home With Pool

VRating, 5 stars17 months ago
We were all very happy with the check-in/check-out. Instructions were clear and host left helpful information. Beds were quite comfortable. More than enough space for all. Laundry room was a plus. Easy to access town & beach. Lovely place - quiet - clean. Would definitely book again.
Guest favorite
A calm waterfront scene features a vibrant sailboat gliding across the bay, surrounded by green marshland. A wooden dock leads into the water, with several colorful chairs positioned for relaxation. Soft hills and houses line the distant shore under a gentle mist.
Home in Mastic Beach
4.93 out of 5 average rating, 121 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

EricRating, 5 stars3 months ago
Five stars doesn't feel like enough, if anything I'd say everything was better than we'd expected based on the pictures and the reviews! First, as others have mentioned John was an incredible host, the place was well stocked and had all sorts of snacks and drinks (and a nice bottle of wine); he also bought us dinner and was very good about keeping in touch the whole time we were there. The house was amazing top to bottom, but I have to specifically call out the pool, which was jaw-droppingly beautiful and the perfect temperature despite cold weather outside. We loved the neighborhood and yard to walk our dogs, and the kitchen was great to cook in (made me miss having a gas stovetop). We'll definitely be visiting again, it was the kind of stay that sets a new bar for what to look for in a vacation!
Guest favorite
Home in Englewood
4.93 out of 5 average rating, 153 reviews

Englewood NJ Country Carriage House (15 min NYC)

VirginiaRating, 5 stars4 days ago
This was such a nice space and Lisa was a nice and accommodating host. This place is full character and wonder. Very artistic color energy in this place. We started my daughter’s 18th birthday celebration here with what is her last sleepover with friends. The hot tub, steam room and sauna were the first things and last things used. They enjoyed it so much! Thanks for your hospitality Lisa. If we ever need something like this again. We will be sure to look you up! Blessings

Weekly house rentals

Top guest favorite
A wooden exterior house is surrounded by trees displaying autumn foliage. A pathway of stones leads to the entrance, where a deck with white railings is visible. Lush shrubs and decorative rocks enhance the natural landscaping.
Home in Philipstown
4.93 out of 5 average rating, 128 reviews

Cozy 3 bedroom house on quiet private road

ScottRating, 5 stars1 month ago
Having a current child / Cadet at West Point and also another child / graduate of West Point , we always make it a point to stay at different Airbnbs in small towns around the USMA on both sides of the Hudson River . Melanie ‘s place was wonderful. Plenty of rooms/ beds for our Parent Weekend visit. Peaceful and safe location , yet a short 20 minute drive to the Academy . We felt right at home and look forward to staying at Melanie’s place again . The house was very clean and we had no issues at all !! Thank you
Superhost
A spacious bedroom features a queen bed with striped bedding and a decorative red pillow. A large mirror is positioned against one wall, while minimalist decor includes vertical branches and wall-mounted leaves. Soft carpet covers the floor, creating a comfortable environment.
Home in Mineola
4.79 out of 5 average rating, 118 reviews

Home for Your Holiday!

AaronRating, 5 stars3 weeks ago
Clean, quiet, easy. Close to where I was going for work. Would absolutely stay again.
Superhost
A comfortable living room features an orange sofa accompanied by decorative pillows. A wall-mounted electric fireplace adds warmth, while a stylish clock is displayed above. Light wooden flooring complements the vibrant area rug, and a small beverage cart is visible in the background near a door.
Home in White Plains
4.88 out of 5 average rating, 8 reviews

Indigo Inn III -A Retro Modern Cove White Plains

ShannonRating, 5 stars6 months ago
Great space. Wonderful communication with host regarding any questions we had. Host was quick to respond. Very happy with the stay, would rent again.
Superhost
The exterior of a cottage is presented, featuring a gravel driveway and a single garage. Surrounding trees showcase autumn foliage while a small wooden deck is visible above the garage. The mountains can be seen in the distance beneath a partly cloudy sky.
Home in Philipstown
4.86 out of 5 average rating, 128 reviews

Bear Mtn Haus near hiking trails

EtiRating, 5 stars3 months ago
I am very excited because of I found this wonderful , cozy and comfortable house! The view from here was amazing 😻 this home is very close from NY city, you need about one hour to get there. 15 minutes away from shopping center. Angie is the great host! Thank you! Me and my family have wonderful memories 🥰🥰 I will always stay here for the future ✨
Top guest favorite
The rustic cabin is nestled among trees, with a stone foundation and wooden siding. A screened-in porch extends from the front, surrounded by natural greenery. A stone pathway leads towards the entrance, emphasizing the cabin's serene and secluded setting.
Home in Cold Spring
4.89 out of 5 average rating, 45 reviews

Cabin with a View

TerriRating, 5 stars1 week ago
Ellen’s place was beautiful and cozy. The kitchen worked perfectly and even though it was April it was still a bit chilly so the wood stove was a welcome amenity. The shower was great and there was a soaking tub. It was quiet and beautiful. We like all the art and it was very homey.
Guest favorite
The front exterior of the home features a charming porch with white pillars and a welcoming door adorned with a circular wreath. Bright yellow flowers and vibrant plants are arranged in decorative pots, complementing the manicured lawn and lush greenery.
Home in Syosset
4.9 out of 5 average rating, 51 reviews

Elegant, resort style, clean, north shore home

FredRating, 5 stars9 months ago
The inside and outside areas were meticulously maintained. The weather was great, so we were able to really enjoy the pool and deck. Michelle was extremely responsive and did a great job with instructions, recommendations, and communications. One member of our party needed to work a few days, and the office space in the basement was perfect.
Top guest favorite
Home in Cos Cob
5 out of 5 average rating, 16 reviews

GREENWICH HOUSE WITH NYC FLAIR/CLOSE TO BEACH /NYC

AnishRating, 5 stars1 month ago
This is our 2nd review Victoria’s properties and we just want to reiterate how special of a landlord Victoria is. The best. I cannot recommend her properties enough if you are in need of a Greenwich rental like we were.
Guest favorite
A spacious two-story home features a white exterior with red accents and a red roof. Original architectural details are visible, including dormer windows. Lush greenery surrounds the entrance, along with manicured bushes and a small tree in the front yard, creating a serene outdoor setting.
Home in Highland Falls
4.97 out of 5 average rating, 61 reviews

West Point Hudson Valley Getaway

TimRating, 5 stars4 months ago
We stayed at Patrick’s place to attend an Army football game. Everything was perfect and easy. It’s really close to campus/post. It’s a nice little town and close to Cold Spring where we had lunch on Friday. Thanks for a great weekend.

Private house rentals

Guest favorite
The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars2 weeks ago
It was wonderful stay and I’d go back anytime
Superhost
A living area is shown featuring a black shelving unit with decorative items. A television is positioned on the shelf, displaying an animated show. A potted plant adds greenery beside the shelf, while a patterned rug covers the hardwood floor.
Home in Amityville
4.72 out of 5 average rating, 74 reviews

Cheerful 2-Bedroom Home With On Premises Parking

SharozRating, 5 stars5 months ago
Very respectable, responsive and courteous couple! Proactive in solving your issues. Felt like home
Guest favorite
A charming beachside home is showcased, featuring a wrap-around porch with seating. The sandy beachfront extends along the water's edge, and a clear blue sky overhead enhances the coastal atmosphere. Nearby houses are visible, offering a sense of community along the shore.
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars3 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Superhost
A rustic log cabin is showcased, featuring a wraparound porch and a stone foundation. The structure is surrounded by greenery, with tall trees providing shade. A wooden fence borders the property, and gravel leads up to the entrance.
Home in Ridgefield
4.81 out of 5 average rating, 21 reviews

Log House, sits on 3acres. A retired mini farm.

TaylorRating, 5 stars1 week ago
Great stay! Tough to heat the downstairs if it’s cold, but a great cozy space nonetheless. Would definitely recommend :)
Top guest favorite
The exterior of the house is surrounded by trees, featuring large windows that invite natural light. A stone patio includes outdoor seating and a grill, with an umbrella providing shade. The property is enveloped by greenery, offering a serene atmosphere.
Home in Philipstown
5 out of 5 average rating, 26 reviews

Charming Retreat 3B/3B Garrison, 2 Fireplaces

BibiRating, 5 stars4 months ago
There were 5 of us, with another 6 staying in another nearby air bnb. We had Thanksgiving in our house and found everything we needed to cook. Seating was a bit challenging, but we made it work and it was very comfortable. The location is in the woods with lots of boulders and rocks, which we all loved. We found the place easily using GPS. Everyone’s bed was comfy. Close enough to what we wanted, just far enough away to make it an adventure. Because it was so cold and grey, we didn’t hike, but saw plenty of opportunities (maybe next time?!)
Guest favorite
Home in Mastic
4.95 out of 5 average rating, 140 reviews

Paradise Citadel hottub, Htd pool golf basketball

RyanRating, 5 stars2 weeks ago
This place is excellent for groups. There is plenty to do around the house and lots of room to just sit and chat. We had a great time with 4 different family groups. You had space to spend time together, and space to be on your own if you wanted ;)
Top guest favorite
A charming beach cottage is showcased, featuring a light-colored exterior and a welcoming front porch adorned with potted plants. Large windows allow natural light to flood the interior. The surrounding area includes a gravel driveway and mature trees with autumn foliage.
Home in Woodmont
4.92 out of 5 average rating, 254 reviews

Bright and Breezy Cottage by the Sea

LucinaeRating, 5 stars4 days ago
Anne was an amazing host! The house was beautiful and very roomy! The backyard was amazing as well! 10/10 experience
Guest favorite
A mid-century modern house is nestled among vibrant autumn trees, showcasing a private pond in the foreground. A spacious deck extends from the house, offering a connection to nature with colorful foliage surrounding the property. Bright blue skies provide a contrasting backdrop.
Home in Norwalk
4.89 out of 5 average rating, 37 reviews

Entire House on Scenic Estate with Private Pond

KristyRating, 5 stars1 month ago
We had a lovely stay. JP was extremely responsive and accommodating. The house was exactly as stated in the listing. We would stay there again if in the area.

Quick stats about house rentals in Darien

  • Total rentals

    30 properties

  • Total number of reviews

    650 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Fairfield County
  5. Darien
  6. House rentals