Holiday rentals with a patio in Shelter Island Heights

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Popular amenities for rentals with patio in Shelter Island Heights

Flat rentals with a patio

Top guest favourite
Flat in Milford
4.95 out of 5 average rating, 161 reviews

The Boathouse, private downtown Harborside suite

ZoeRating, 5 stars1 week ago
⭐️⭐️⭐️⭐️⭐️ Clean, Comfortable, and Thoughtfully Prepared! We had a great stay! The place was spotless, quiet, and exactly what we needed for a few nights of good sleep and hot showers. It was clear that the host put thought into making guests feel welcome—there was a mini chocolate bar and a bottle of water waiting for each of us when we arrived, which was such a kind touch after a long day of travel. Check-in was smooth, the bed was comfortable, and everything worked perfectly. While we didn’t spend much time there beyond resting, it was the perfect place to recharge. Highly recommend for anyone looking for a clean, convenient, and cozy spot!
Guest favourite
Flat in Stonington
4.97 out of 5 average rating, 121 reviews

The Mystic Surfside Getaway 1-BD Apt

JoanneRating, 5 stars2 weeks ago
Jennifer’s place was perfect. Great location. Walking distance to shops and restaurants. Very new and spotlessly clean. Will definitely return.
Guest favourite
Flat in Mystic
4.87 out of 5 average rating, 123 reviews

Downtown Mystic, Private Deluxe 2BR + Parking - 4B

JordanRating, 5 stars3 weeks ago
The location is amazing! It’s just a quick walk from downtown Mystic but also far enough that it still feels private and very quiet. The apartment was also super clean. The furniture wasn’t the most comfortable and the bathroom is small, but we didn’t spend much time there as there was so much to do in town. Highly recommend this place if you plan on exploring. Huge benefit that it is also pet friendly!
Guest favourite
Flat in Shirley
4.94 out of 5 average rating, 107 reviews

Boho Beach Vibez Retreat! Private entrance

Jennifer,MRating, 5 stars2 weeks ago
this was my 4th time staying at this air b and b and as usual I dodnt want to leave!!. Sarah and Phil where amazing. I love going to this air b and b becouse its so peaceful and calm and its like be at home. I will be back again. if you looking for an awsome place to stay look no futher!!! this is thr place to go!! this family is wonderfully and beautiful people. I will be booking again. thank you again for being such an amazing host.. its like staying with family...thank you 😀😀😀..
Guest favourite
Flat in East Shore
4.92 out of 5 average rating, 181 reviews

Tranquil Apartment with Waterview, Walk to Beach!

CindyRating, 5 stars1 week ago
I love this place. Perfect but what we were looking for. Walking distance to access beach. Overlooking the pier. Very clean and check in with.
Top guest favourite
Flat in Deep River
4.93 out of 5 average rating, 147 reviews

Lovely Garden-Level Apartment in Heart of Town

ElizabethRating, 5 stars2 weeks ago
Lovely town and environment. Very spacious and fully equipped apartment. The two bedrooms are separated from each other by the big kitchen, a little reading room and the living room…so good privacy. Two TVs. Comfy beds! The small town is an easy and pleasant walk. It’s a ground floor apartment under the owners house, so be prepared for the patter of little dog feet above. We did not see the owners but communication was terrific. Great place to stay in the vicinity.
Superhost
Flat in Westerly
4.88 out of 5 average rating, 126 reviews

Downtown Getaway Oasis 1 bedroom, 1 bath sleeps 4

MelanieRating, 5 stars1 month ago
No complaints! Easy check-in and check-out. Really awesome location. We walked everywhere for the duration of our stay because it is so close to the entire downtown area!
Top guest favourite
Flat in Milford
4.98 out of 5 average rating, 104 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

JudyRating, 5 stars2 weeks ago
Dawn and Bob’s place is one of the top Airbnb’s we have stayed in! Top notch in every way. It was spotless, comfortable and had everything we needed. And on top of that Dawn and Bob were the most friendly hosts we have met! I would recommend this Airbnb without reservation and will be back whenever we are back in CT!

House rentals with a patio

Top guest favourite
Home in North Fork
5 out of 5 average rating, 19 reviews

Modern Farmhouse Oasis in GP Village

CathyRating, 5 stars2 weeks ago
Luigi was an excellent host, super responsive and a pleasure to interact with. The house is beautiful, super clean and well appointed. The beds were very comfortable and created the perfect sleep environment. Close walking distance to all the Greenport activities. I would absolutely stay here again and highly recommend staying here.
Guest favourite
Home in North Fork
4.89 out of 5 average rating, 9 reviews

Quaint Chalet w/Salt-heated Pool

VaughnRating, 5 stars8 months ago
Wonderful weekend stay. Charming.
Guest favourite
Home in South End
5 out of 5 average rating, 38 reviews

Salt & Sea House - Near wineries, farms, & beaches

FellRating, 5 stars4 months ago
We had a wonderful stay! The master suite is huge and the bathroom is dreamy. We didn’t really use the backyard bc it was winter but it was great for our pup! Kitchen was small but did the job (no microwave). We had issues with streaming on the “guest” accounts but we always travel with our own firestick so we were fine. The beds were super comfortable (firm memory foam type) but it was quite bright in the upstairs bedrooms in the morning bc several of the windows had no covering so if you need a blackout situation for little ones pack accordingly. We were able to put the provided pack and play in the closet which was fine for us! We would definitely recommend and return!
Superhost
Home in North Fork
4.73 out of 5 average rating, 22 reviews

Greenport Beauty 3bdr 2 bath

BrianRating, 5 stars4 months ago
House was perfect for our quick And easy family get away. Would certainly Stay again and recommend
Top guest favourite
Home in South End
5 out of 5 average rating, 11 reviews

Private Waterfront home with Dock!

MeganRating, 5 stars7 months ago
We had a lovely fall weekend stay at Paul’s place. The house and the water views are just as pictured. Convenient location allowed us a good home base to explore the north fork wine trail and local businesses. We did have one small plumbing issue during our stay however Paul was extremely responsive to ensure it did not affect our stay at all. It was a nice experience having such a responsive host. Overall our friend group had a great time and would return again.
Top guest favourite
Home in North Fork
5 out of 5 average rating, 15 reviews

Oak Street Cottage

AndrewRating, 5 stars1 week ago
This was our wedding day weekend and we were shocked just how well this Airbnb was designed, built and cared for. All of the appliances were high quality, an art TV, a gorgeous shower. My wife and I couldn't have been happier calling this cute cottage home for this special weekend. Thank you Sara!
Top guest favourite
Home in Westbrook
5 out of 5 average rating, 25 reviews

Secret Seaside Stone Cottage

SabineRating, 5 stars3 weeks ago
Our stay at the Secret Stone Cabin was truly unforgettable. The breathtaking views and thoughtful touches made it feel like a home away from home. It was a luxurious retreat, complete with extra amenities like plush bathrobes, quality toiletries, and a chef-style kitchen. We took the row boat for a short spin, and had the weather been nicer, we would have loved to enjoy the beautiful outdoor fireplace. Every detail was perfectly curated for comfort — we can’t wait to come back!
Guest favourite
Home in Guilford
5 out of 5 average rating, 13 reviews

3BR Waterfront Oasis on Joshua Cove, Private Beach

RajRating, 5 stars3 weeks ago
Wow what a gorgeous home with an even better view of Joshua Cove. We have honestly never been to a better Airbnb - it was just sublime, especially in the Connecticut sun! Loved how well equipped the home was for us.

Apartment rentals with a patio

Apartment in The Hamptons

Bright and Airy One Bedroom Apartment in the Dunes

TimRating, 5 stars21 months ago
A fantastic place to stay in the Hamptons, a special gem of a place located in the Dunes of Amagansett, will be back every year!
Top guest favourite
Apartment in The Hamptons
5 out of 5 average rating, 26 reviews

Sun N Sound Resort, Montauk, NY

DevinRating, 5 stars1 week ago
Perfect spot for a Montauk getaway. Walking distance to everything dockside has to offer, great pool and lounge chairs on the property, very simple check-in via code with the front desk. Nick was kind and communicative our whole stay. We’ll be coming back!
Superhost
Apartment in The Hamptons
4.89 out of 5 average rating, 9 reviews

Endless Summer Studio Condo w Balcony Bayview

StephenRating, 5 stars22 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.
Superhost
Apartment in Old Saybrook
4.89 out of 5 average rating, 74 reviews

Seashore getaway - CT shoreline

RussellRating, 5 stars2 weeks ago
Lisa and I enjoyed our stay at Laurens place. Felt right at home. Very clean, open space. We had the best time and did not want to leave. We will be back for sure.
Superhost
Apartment in The Hamptons
4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

StaceyRating, 5 stars9 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+
Top guest favourite
Apartment in The Hamptons
5 out of 5 average rating, 7 reviews

Condo on the Sound - Navy Beach

GabeRating, 5 stars4 days ago
Terrific condo, very communicative and friendly host, and easy check in and check out. Would recommend to everyone!
Apartment in The Hamptons
4.56 out of 5 average rating, 18 reviews

Immersed in Montauk's Mesmerizing Waterfront Bliss

BillyRating, 5 stars8 months ago
George was a wonderful host , so available and willing to help with local knowledge and suggestions. The Condo is beautiful with a stunning sea view and plenty of amenities. I would definitely recommend this place to all .
Apartment in Westbrook

Watersedge resort time share Westbrook ct

AbbieRating, 5 stars49 months ago
Andrew’s place was awesome. Just steps to a beautiful pool and the ocean! Couldn’t have asked for a better place.

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

  • Total rentals

    280 properties

  • Nightly prices starting at

    ₹10,385 before taxes and fees

  • Total number of reviews

    12K reviews

  • Family-friendly rentals

    250 properties are a good fit for families

  • Pet-friendly rentals

    100 properties allow pets

  • Rentals with a pool

    100 properties have a pool

Destinations to explore