
Pet-friendly holiday rentals in Shelter Island Heights
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Top-rated pet-friendly home rentals in Shelter Island Heights
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Pet-friendly house rentals

The Gait House at High Gait Farm
Lori was an amazing host. She coordinated with me on everything prior to checking in. I explained that I would be using her home for a small surprise birthday party and she even offered to do some decorations or help out any way she could. Way above and beyond her responsibilities as a host. On top of that she set up a fire pit with firewood and even left a s’mores kit for us. The most amazing thing was she left a birthday card and gift for my girlfriend. It was completely unexpected and we were so appreciative. The home was very clean, cozy, and had everything that we were looking for.

3BR Gem, 10 min to Yale, walk to Tweed
Very nice place, welcoming and accommodating. Owner quick to respond. Would recommend to others .

PICTURE PERFECT SOUTHAMPTON HOME-
Lovely, quiet home, with well-appointed furnishings, and comfortable beds.

Relaxing 2BR Stay | Fast Wi-Fi & Full Kitchen
Ritestay was a great place. We didn’t spend much time there because we were there to see our daughter. Would be perfect in the summer!!

Sag Harbor House for rent.
Ed was great at communicating, house was everything we could have asked for. Would definitely book again!

Three Bedroom Cape Near Ocean Beach Park
Everything was wonderful! So peaceful, clean, and comfortable! The neighborhood was quiet and safe feeling. I personally loved that it wasn’t over cluttered with decorations! Plenty of room to put your stuff down and get to your vacation. Felt right at home!

Southampton Winter Rental, 3 bed, 2 bath
We were so excited to find this house available again. We were here a few years ago and always wanted to return. It was just as wonderful as we remembered. Iris is a great host. She meets every request with prompt enthusiasm. We highly recommend her and this beautiful home.

Cozy Farmhouse Retreat in North Fork, NY
We came back to stay for a second time and hope to be back for many more! The place is exactly as advertised, beautiful, and an easy walk into town. Marianne and Stephen were super flexible with a few requests we had around the stay and so easy to communicate with. Greenport is the best and this home is amazing - you won’t regret booking here!
Pet-friendly home rentals with a pool

Bailey House
It was a lovely stay. Great location. House felt like a home and had great vibes.

Stylish Beach Getaway: pool & walking location
Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

Bright Zen Beach Cottage, Pool Access, EV Charger
Simply put - A perfect stay! Jami’s home is peaceful and beautiful and in an ideal location in Easy Hampton. We felt very welcomed and ‘at home’ for our entire stay. Jami is also an excellent communicator. Thank you very much much for sharing your home with us, Jami. We will be back :)!

The Hideaway
Dorina’s home was the calm, peaceful reprieve from the city we were looking for. Her home was so comfortable and she went above and beyond to make sure we had everything we needed. The backyard was a little oasis with a large pool (with floats!), several (6 I think) lounger chairs, two 6 top tables in different areas and a functioning grill. We spent most of our time here! Dorina was fast to respond, helpful with recommendations and overall what you hope to have in a host. We would definitely come back to Dorina’s home!

"NORTH APT." Renovated 1 Br Apt. In Great Location
Had an absolutely wonderful stay! Location is perfect and Jaime was incredibly friendly throughout!! He let me know that they had everything we would need.. but as a self-described obsessive packer I didnt listen. He wasn't kiding! They had beach chairs, umbrellas, and everything else you need for the perfect beach day. I brought an entire wagon of stuff and used one bag. It really is an awesome little find!!

Spacious Village Fringe East Hampton Home W/ Pool
Amazing host and great property! Had an amazing time - thank you Daniel!!
Walk to Water. Stunning Home with Gorgeous Pool & Grounds.
House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.

POOL in APRIL! Waterview, Free For Dogs! Kayaks
The stay was fantastic, we wanted a quick getaway for the weekend, and their home was the perfect spot. We enjoyed the space by the fire and the cleanliness of the spaces. We would love to come back for a longer stay.
Private, pet-friendly home rentals

Total Privacy in Springs.
The place is roomy and clean. The bed is comfy and the shower is great. There were juices and sodas and water in the mini fridge, a coffee maker with coffee and some wrapped snacks. A comfortable place to stay in a very pricy part of Long Island if you prefer a home over a hotel. We were only there for the 2 nights of our stay since we were out all day and for that it was perfect.

Zion's Light Beach Cottage
We had a great stay at this cottage- it was a perfect size for our family and was extremely clean, warm and comfortable. We especially enjoyed the quick walk to the beach, and proximity to town. Hosts were very friendly and responsive but never intrusive. Would highly recommend.

Ho Hum Holiday In Bellport with Pool
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.

1940s Fisherman’s Cottage close to beach.
Madelaine’s cottage was the perfect location for our weekend in Water Mill! The house was cozy with a spacious and private backyard. The location is centrally located, and we were even able to walk to and from breakfast and the farmers market. I would recommend the cottage and would absolutely stay again!

Southold- Adorable 1 Bedroom Cottage
Marta & Pete were great hosts. Left helpful instructions and a list of places in the area. The Cottage was definitely a great place to celebrate our anniversary. We wish we could have tried some of their oysters, but look forward to going back during the beach season when they're probably plentiful.

Secluded Farmhouse - Studio Apartment Style Unit
We had a great stay at Jess and Zack’s place for my birthday weekend on the North Fork! They provided clear directions ahead of time on how to find their place and how to check in. We were greeted by the sweetest pup. The space was spotless and very comfortable. We had a fire in the fire pit one night and that was excellent. It’s super close to lots of great restaurants and wineries! I would recommend their place to anyone looking for a quiet and peaceful getaway!

Chic Beach Bungalow - Amazing Sunsets!
Lovely stay! The hosts were incredibly helpful and responsive, and the view was AMAZING! It must be absolutely gorgeous in the summer! Thank you again! :)

Amagansett Dunes Gem
Judy’s place is super lovely and in a fantastic location! Easy walk to the beach or quick ride into town. Easy to communicate with as well. Highly recommend!
Quick stats about holiday rentals that are pet-friendly in Shelter Island Heights
Total rentals
100 properties
Nightly prices starting at
$302 AUD before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
100 properties are a good fit for families
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Destinations to explore
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Cooper's Beach, Southampton
- Clinton Town Beach
- Woodmont Beach
- Shennecossett Beach
- Connetquot River State Park Preserve
- Walnut Public Beach
- Seaside Beach
- Shoreham Beach
- Shinnecock Hills Golf Club
- Horton Lane Beach
- Burlingame State Park
- Mystic Seaport Museum
- South Pine Creek Beach
- Sunken Meadow State Park
- Fire Island National Seashore
- Overlook Beach
- Jennings Beach
- Sasco Hill Beach