House holiday 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 favourite
Home in Fairfield
4.96 out of 5 average rating, 26 reviews

Once a Pond - time and stress slow down.

ShivaRating, 5 stars1 month ago
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.
Guest favourite
Home in Patchogue
4.93 out of 5 average rating, 126 reviews

Joyful Beach House, viewing The Great South Bay

DanielRating, 5 stars2 weeks ago
Great host, great house with a bunch of fun things to do walking distance. Would definitely recommend and will 100% be booking again!
Guest favourite
Home in Stony Brook
4.93 out of 5 average rating, 535 reviews

Spacious Studio Apartment- near SBU

ElizabethRating, 5 stars2 weeks ago
Gabby’s apartment is exactly as described. It is in a great location. Very close to Stoney Brook Village. We enjoyed walking to get our morning coffee. The apartment was very well stocked and spotless. Gabby thought of everything we could have possibly needed. We hope to be back next year!
Superhost
Home in The Hamptons
4.94 out of 5 average rating, 131 reviews

Peaceful Retreat in Immaculate Architect’s House

JessikahRating, 5 stars1 month ago
Michael’s place was amazing, means a few friends stayed this weekend for my birthday. He was always willing to help and very accommodating! The house itself is so beautiful and had everything we needed! It was our first time in The Hamptons and he gave us tons of recommendations!
Top Guest favourite
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months 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!
Guest favourite
Home in Commack
4.99 out of 5 average rating, 140 reviews

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

AliceRating, 5 stars3 weeks ago
We liked how easy it was to punch the code in to get into the home. Once in the home, it was really nice to see the welcome placard. We enjoyed access to robes, skincare, slippers, towels, etc. The game room was loads of fun. The indoor and outdoor ping pong tables were fun. We enjoyed billiards, arcade games and table games. The icing on the cake were the hot tub, the four mode shower and bidet. The Smart Home technology took a little getting used to, but it was very convenient once we did. We love the quick response time whenever we had a question or concern. This place allowed for a rejuvenating relaxing atmosphere and we are so glad that we chose “The Good Vibes” home for our debut AirBNB experience. Thanks again for hosting us in your charming abode!
Guest favourite
Home in Manorville
4.98 out of 5 average rating, 255 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

SolomonRating, 5 stars1 month ago
This Home was Amazing!! Anastasia is Phenomenal, I could see why they are Super Hosts. Their home is Beautiful and very clean. It’s filled with amenities! all that are in the description. So much so we didn’t even get a chance to take advantage of them all. We were only there for two days. Next time it’ll be much longer. I love this place!
Guest favourite
Home in Greenwich
4.96 out of 5 average rating, 45 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

Rich Rating, 5 stars4 days ago
A truly Great stay in Greenwich with David, we really enjoyed our stay in the house, such an awesome place and quiet location (next to a beautiful river!) too, which we loved. The pool was a massive bonus for sure! Comms with David were great, he was very quick to respond at all times on any queries we had, much appreciated indeed. Many thanks again, Rich

Weekly house rentals

Guest favourite
Home in Glenbrook
4.98 out of 5 average rating, 54 reviews

Spacious Duplex with Private Entrance & Sun Room

MadelineRating, 5 stars2 months ago
This place is beautiful and serene. Very Zen. Loved the Sun porch! Very clean, large bathroom with a great tub! Full kitchen with everything you need. We felt very much at home. Tracy got back to us right away when we had questions. I would definitely recommend this spacious apartment!
Top Guest favourite
Home in Norwalk
5 out of 5 average rating, 54 reviews

❤️ Your Silvermine Hideaway, nestled in nature.

DennyseRating, 5 stars1 week ago
It’s obvious that Scott and Wendy have put a lot of thought and effort into making their place more than just functional. It is also comfortable and attractive. My husband and I just hope it’s available the next time we visit our grandkids!
Guest favourite
Home in Stamford
4.92 out of 5 average rating, 66 reviews

Spacious Home - Center Of Stamford

MaryRating, 5 stars1 month ago
This home was fantastic! Absolutely immaculate and it offered everything we needed. We live close by and this was a perfect place for family to stay while visiting for Easter! As a matter of fact, the host put Easter eggs all around and the children were thrilled. Such attention to detail. Would highly recommend!
Top Guest favourite
Home in Westport
5 out of 5 average rating, 55 reviews

Westport Deco HAUS /5 min to Town /10 min to Beach

AlexandraRating, 5 stars2 weeks ago
great location and loved the backyard
Guest favourite
Home in Stamford
4.98 out of 5 average rating, 61 reviews

Gameroom, backyard + pool! 7m to train + downtown

RebeccaRating, 5 stars3 weeks ago
Everything was clean, just a few glitches with dining room lights and needed more towels. Otherwise everything was great!
Guest favourite
Home in Shippan Point
4.96 out of 5 average rating, 50 reviews

Seashell Bungalow | 3 Bed 1 Bath | Beach House

DorisRating, 5 stars1 week ago
Beautiful place. Pristine. Comfortable Short walk to the beach. Unfortunately because of rain we didn’t get to enjoy the lovely back yard. Owners were very good at getting back to us with any questions we had And being able to have a later check out really helped! Would definitely recommend this home and would love to find a reason to ho back again!!
Guest favourite
Home in Stamford
4.96 out of 5 average rating, 24 reviews

Modern Tranquil Home In Connecticut- 40 min to NYC

RogerRating, 5 stars1 month ago
The location and house is etremely peaceful and safe, in the middle of nature. Our stay was wonderful and extremely comfortable. We had an excellent time. This is a return stay and we would stay again. It feels like home. Phylilis is very helpful and resppnsive. Overall a great experience. 5 star.
Guest favourite
Home in South Norwalk
4.97 out of 5 average rating, 67 reviews

Chic Historic Home w/Water View

JeffRating, 5 stars1 month ago
Comfortable, quiet, clean, and well appointed, this home was the perfect day for my family for a wedding week. Highly recommend it. Kim communicated really well and was very attentive. A+

Private house rentals

Guest favourite
Home in Holmes
4.91 out of 5 average rating, 11 reviews

Enchanted Escape | POOL, LAKE, Concierge Services

AnxhelaRating, 5 stars2 weeks ago
We had such a great experience staying at this Airbnb. The house was beautiful, super clean, and the view was just perfect honestly even better than the photos. What really made our stay stand out though was the host, Sunny. He was amazing so helpful, kind, and incredibly thoughtful. As a Muslim family, we really appreciated how respectful and considerate he was. He made sure we had our privacy and went out of his way to make everything as easy and comfortable as possible for us. It honestly felt like staying at a friend’s place. We’d definitely come back and highly recommend this spot to anyone looking for a peaceful, welcoming place to stay.
Top Guest favourite
Home in Danbury
4.98 out of 5 average rating, 96 reviews

Lakeview Estate - Chef's Kitchen - NYC Getaway

AizelRating, 5 stars1 month ago
This house was wonderful as I would definitely stay there again and recommend it to family and friends. The views from the balconies and windows were amazing! The house was absolutely beautiful and super clean. The location was secluded but still near shops and restaurants. We loved our stay!
Top Guest favourite
Home in Milford
5 out of 5 average rating, 96 reviews

Oceanfront Retreat: Modern Beach House

ShannonRating, 5 stars1 week ago
We had a relaxing overnight with our two pups! The bay/sound area is so peaceful. Our dogs enjoyed swimming before the tide came in and we kayaked along the shoreline. The inside was stunning and had everything you needed and more! We door dashed lobster rolls from the Bonfire Grille nearby (10/10) and ended the night in the hot tub! Coffee on the sunny patio was a great perk, too! Thanks again!!
Superhost
Home in Westport
4.67 out of 5 average rating, 3 reviews

Boho Chic Private Home in the Heart of Westport CT

ClaudiaRating, 5 stars1 month ago
Emma and Nick were so welcoming. The entire property has an amazing vibe and peaceful surroundings. The kitchen had all the basics needed. The rooms were very comfortable. You felt like you were in the country but we were a short drive to everything. The entire area was just very charming. Emma and Nick deserve a super host rating for sure.
Top Guest favourite
Home in Putnam Valley
5 out of 5 average rating, 10 reviews

Dr. Ruth’s Serene Lake Retreat

EvanRating, 5 stars5 months ago
After using Airbnb for years now no other place was a perfect 10. The lake house was simply great. Not only the physical status but the follow up and generosity of the hosts where beyond. We didn’t want to leave.
Guest favourite
Home in Redding
4.88 out of 5 average rating, 16 reviews

Meeker Hill House - Country Escape w/ Heated Pool

RoryRating, 5 stars8 months ago
Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend
Guest favourite
Home in Redding
5 out of 5 average rating, 36 reviews

Quiet and Cozy Cottage near NYC with a Pond

LouiseRating, 5 stars3 weeks ago
We loved Erin’s style, her beautiful cottage was comfortable and welcoming from the first. We found all we needed in the kitchen and everything worked well. The home was light and bright and well thought out. The grounds around the house were heavenly, with grassy dappled pathways through the woods and a gorgeous pond beyond the garden, with a river running through. Endless bird song and deer passing by, it was charming and peaceful. I highly recommend it.
Top Guest favourite
Home in Bedford
5 out of 5 average rating, 39 reviews

Comfortable Mid-Century on Quiet Country Road

BessRating, 5 stars1 week ago
Adam provided a beautiful home with everything you could ask for to have a lovely stay. The beds were very comfortable, it was spacious and clean. He was responsive and gave clear instructions for check in/out and using the various amenities. I would definitely recommend him as a host!

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

  • Wi-Fi availability

    30 properties include access to Wi-Fi

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