Vacation rentals with a patio in Shelter Island Heights

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Popular amenities for Shelter Island Heights accommodations with an outdoor patio

Apartment rentals with a patio

Guest favourite
Apartment in Milford
4.95 out of 5 average rating, 148 reviews

The Boathouse, private downtown Harborside suite

JoeRating, 5 stars4 days ago
Enjoyed my day and a half stay. Very unique setting. Loved the chicken coops in the backyard. Close to everything. Ilk be back!
Guest favourite
Apartment in Sag Harbor
5 out of 5 average rating, 13 reviews

Spacious Apt. Walk to Beach!

AngelaRating, 5 stars5 months ago
Lisa's apartment is exactly as depicted in the AirBnb listing. It is spacious, clean, comfortable, close to the village of Sag Harbor and down the block from a beautiful private beach. Given the cost of hotels in this area this apartment is an excellent value. While we did not speak or meet during our stay Lisa provided clear directions with regard to finding the home, parking and how to enter and left us her cell phone number in case we needed anything.
Guest favourite
Apartment in Patchogue
4.95 out of 5 average rating, 145 reviews

Spend A Few Days In This Cozy Getaway

AmyRating, 5 stars1 month ago
This was my second time staying here at Erica’s place and I will be choosing this airbnb every time I come to Long Island! It’s truly SO cozy and feels like my home away from home. Checking in is very simple and Erica will respond quickly every time you reach out. The place is always spotless, smells amazing and I always get the best sleep here! Thank you Erica for being such a great hostess and opening your home for us to enjoy our time in:)
Guest favourite
Apartment in New Haven
4.92 out of 5 average rating, 177 reviews

Tranquil Apartment with Waterview, Walk to Beach!

BriannaRating, 5 stars1 week ago
Great stay! The place was super clean and the hosts responded quickly when we reached out with a question. Would definitely return in the future!
Guest favourite
Apartment in New Haven
4.92 out of 5 average rating, 214 reviews

Edgewood Delight II

ThatoRating, 5 stars1 month ago
The apartment is spacious, the bedrooms are huge and the bathroom is an absolute delight. The shower is definitely a highlight. The area is safe and quiet but still close enough to amenities. It was a pleasure staying here, I’m sorry Sabrina for forgetting to water the plants, but I appreciate everything you did to accommodate us. We had a wonderful stay.
Guest favourite
Apartment in Clinton
4.99 out of 5 average rating, 67 reviews

Cozy Shoreline Getaway

FrederickRating, 5 stars2 months ago
Comfortable accommodation. Everything you could ask for. We we’re lucky to stay longer over the holiday. Dave and Charlene are great hosts, great communicators. We plan to stay at this location whenever we vist family in Connecticut.
Guest favourite
Apartment in Bayport
4.91 out of 5 average rating, 121 reviews

Private Studio in Lovely South Bayport

KelleyRating, 5 stars2 months ago
It was the perfect space for my husband and myself! So adorable and walkable to my daughter’s home.
Guest favourite
Apartment in Madison
4.9 out of 5 average rating, 10 reviews

One Bedroom Apt-Cristys Madison

JeffreyRating, 5 stars6 months ago
My expectations were exceeded, the apartment was exactly what we needed. It’s was very clean and neatly maintained and convenient.

House rentals with an outdoor patio

Guest favourite
Home in Hampton Bays
4.89 out of 5 average rating, 35 reviews

Hamptons 3/2 - New Gunite Pool &Bluestone Patio

MeganRating, 5 stars6 months ago
We had a wonderful stay! Clean, comfortable and easily located to all. We will deff be back soon!
Superhost
Home in Hampton Bays
4.77 out of 5 average rating, 81 reviews

Cozy 4-bedroom home close to the beach & town

AstaRating, 5 stars3 months ago
Aida was a great host! She was a great communicator.
Guest favourite
Home in Hampton Bays
5 out of 5 average rating, 63 reviews

Family Fun House by the Bay #chateaustclair

FlorentRating, 5 stars3 months ago
We loved our stay at Deborah and David's home. The house was perfect for our family, so clean and well equipped. It is even better than on the photos. And what an amazing backyard for the kids!
Guest favourite
Home in East Haven
4.89 out of 5 average rating, 98 reviews

Welcome To Piper's Rest

ChristinaRating, 5 stars2 months ago
We booked this last minute as we were coming to celebrate Christmas with my family. We were going to be getting in very late, so I asked if that would be ok. Also, we thought it would be easier if my parents checked us in and set up the crib and toddler bed for the kids and she was very understanding and let us make that accommodation. The rooms were all clean and set up and it was perfect for what we needed. Great location. Definitely would book here again if we are in the area
Guest favourite
Home in Mastic Beach
4.92 out of 5 average rating, 13 reviews

Gateway to the Hamptons in Mastic Beach

TomRating, 5 stars6 months ago
Really liked this house - quiet and secluded with the family. Good amenities, lovely back yard, and peaceful surroundings. About 20 mins to the beach by the time you park and walk across. A 10-15 min walk to a little dock with a playground for young kids. Thanks for the stay!
Superhost
Home in New Haven
4.76 out of 5 average rating, 99 reviews

Heavenly Home in New Haven

LeahRating, 5 stars2 weeks ago
Had a lovely visit! the house was very clean and had everything we needed. perfectly suited for our birthday weekend get together. couldn’t have asked for a better spot.
Guest favourite
Home in East Patchogue
5 out of 5 average rating, 20 reviews

Ho Hum Holiday In Bellport with Pool

GraceRating, 5 stars3 months ago
We needed a dog-friendly ranch style to home with three bedrooms and two bedrooms close to Sayville, where we would be celebrating Thanksgiving. I was lucky enough to find this rental which was clean, comfortable and ideal for our two-night stay. Adam was attentive and easily accessible via text. I would highly recommend this lovely home.
Guest favourite
Home in Milford
4.93 out of 5 average rating, 81 reviews

Charming one bedroom house in Milford, CT

JinghongRating, 5 stars1 week ago
Sue is a very nice and responsible host. Thank you for everything!

Condo rentals with a patio

Condo in Cherry Grove
5 out of 5 average rating, 3 reviews

Cherry Grove 1 bedroom condo w/heated pool!

RobertRating, 5 stars6 months ago
Great place, exactly as advertised. Terrific location near ferry dock (making arrival/check-in extremely easy and fast, which was a relief after a long trip to get to Fire Island), near the little main hub of Cherry Grove… minutes or less to the general store, restaurants, bars. 5 minute walk to the beach. Although there is some bar noise at night, the unit is well sound-insulated. Hosts extremely friendly and communicative, full of info and recommendations. They take pride in their place and in being great hosts. Cozy place with very good value for Fire Island. The pool was a nice plus - salt water pool, lit at night. Met some of the other residents in the building who were extremely friendly and fun. Bed was very comfy. We slept in a lot. Wi-Fi worked perfectly. Nice desk in the bedroom for the few times work called. Roku TV. Lots of board games Bedroom has AC which worked great. Beach chairs and towels included. Coin laundry on site worked well. Great value. Would definitely return!
Guest favourite
Condo in Montauk
5 out of 5 average rating, 20 reviews

Sun N Sound Resort, Montauk, NY

HirmilaRating, 5 stars4 months ago
We had a pleasant stay at Nick’s place. The unit was comfortable and clean. The location was perfect with a beautiful view of the water & restaurants in walking distance. Check-in was very easy and Nick was always responsive.
Condo in Old Saybrook Center
4.89 out of 5 average rating, 72 reviews

Seashore getaway - CT shoreline

JulieRating, 5 stars1 month ago
Thanks Lauren! We enjoyed your lovely place!
Superhost
Condo in Montauk
4.89 out of 5 average rating, 9 reviews

Endless Summer Studio Condo w Balcony Bayview

StephenRating, 5 stars18 months ago
We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.
Condo in Bridgehampton
4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

StaceyRating, 5 stars5 months ago
Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+
Guest favourite
Condo in Montauk
5 out of 5 average rating, 6 reviews

Condo on the Sound - Navy Beach

AshleyRating, 5 stars4 months ago
Tara’s place was a perfect for a weekend getaway! Close enough to town and great view of the sunset!
Superhost
Condo in Sag Harbor
4.89 out of 5 average rating, 73 reviews

Cute cottage apartment upstairs in Sag

MichaelRating, 5 stars1 month ago
Adam's place was amazing and perfect for the location. I would give it five stars!

Quick stats about vacation rentals with a patio in Shelter Island Heights

  • Total rentals

    180 properties

  • Nightly prices starting at

    $130 CAD before taxes and fees

  • Total number of reviews

    7.3K reviews

  • Family-friendly rentals

    160 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    70 properties have a pool

Destinations to explore