
Vacation rentals with a hot tub in Shelter Island Heights
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Top-rated hot tub rentals in Shelter Island Heights
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House rentals with a hot tub

Bayfront Fun - 3 BR & 3 Ensuite Bath with Hot Tub!
We loved staying here! Stayed in October but had stunning weather, quick walk to town, walked the Sunken Forrest, which was easy to get too. Quick walk to the ocean for morning sunrises and enjoyed some wildlife friends, loved the deer. Hosts were accommodating, can’t beat three master bedrooms, would absolutely stay again, my family had a wonderful time!

Your Zen Retreat
This getaway was very last minute and there was huge importance on it because I needed some time away and because I had never booked an Airbnb before. I wanted to make sure that my family and I were able to be someplace peaceful and have a really good time and Brian’s home provided just that. The stay was so much more than we expected and Brian was absolutely amazing. He’s super responsive and accommodating. Hoping to stay here again in the near future!

Hamptons Retreat | Pool, Volleyball, Jacuzzi
Our stay was fantastic, the patio and backyard were perfect for us to hang out all weekend. The rooms and house were clean and well kept. Kitchen had all the essentials for us to cook and checking out was a breeze with very lax rules. Host was very accommodating and communicative. Would absolutely return here!! Just be aware the gps will bring you around the block instead of to the actual driveway.

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy
what can i say, Daniels place was fun! there was so many things to do so many activities, Beautiful home, Very clean. Jacuzzi & hot tub was a huge plus. Kitchen had everything you would need to cook, Great appliances everything worked perfectly and we didn’t need to go anywhere. Living was absolutely comfortable! We felt right at home. With a huge TV and surround sound system we watched multiple movies <3 Game room was lots of fun! Everything was clean, if you brought your family here you would not regret it! Thank you so much for having us and we hope to see it again soon! :)

Brand new house with an all year round hot tub.
Great spacious place, enjoyed our stay!

Perfect New England Getaway has a pool/ hot tub
The home is beautiful, clean, and very comfortable. We were there for six nights celebrating our son’s graduation from the United States Coast Guard Academy, and couldn’t have found a better place. Our family enjoyed gathering and spending time together. The house had everything you could need - Tracy and Patrick clearly care about creating an inviting place for families to enjoy and were very responsive. The location was perfect with easy access to restaurants, a grocery store, New London, Mystic, Foxwoods and Point Judith.

Relax Villa ,Hot tub /New pool,7min from the beach
We stayed at this property for Memorial Day Weekend and had a great time! Due to the chilly weather, our group was unable to enjoy the beautiful swimming pool but we spent plenty of time in the hot tub and sauna! The house was clean, had everything we needed and felt very comfortable and safe!! We forgot a personal belonging at the house and Adriana was kind enough to let us know (instead of throwing it away!) and shipping it out to us! So Thankyou!!

Minutes from Beaches | Large Spa - Home Theater
This place is outstanding. The house is quaint, clean, and accommodating. Jason/Ed were always prompt in communication whenever we had questions. Amazing place to stay!
Villa rentals with a hot tub

Private Luxury Waterfront Home
We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

Year-Round Heated Pool Villa - 3 blocks from town
George was an excellent Air BnB host!!!! His responses were prompt and answered any questions we had. The location was ideal in Greenport as everything was walking distance. We had an amazing time!

Spacious large room in Yale neighborhood
Our family had a very enjoyable stay! The home and surroundings were beautiful, everything was extremely clean and organized, our host was wonderful! We absolutely loved the tea ceremony! It was very educational! We will definitely stay here again when we return to New Haven!

Luxe| Pool| GOLF Sim| HotTub| Movie|Arcade|Firepit
We had an amazing long weekend in East Hampton celebrating a birthday with a group of seven. The house and pool were fantastic, and Ann Marie was the perfect host — responsive and welcoming. Would definitely stay again !

TREETOPS! An upscale, unique 5 bdrm home with POOL
We stayed at this beautiful home for a college graduation weekend, and it was absolutely amazing! The house is incredibly spacious and comfortably accommodated all 10 members of our group. It provided the perfect setting to create lasting family memories. The open-concept kitchen, dining room, and living room were ideal for gathering and entertaining, and the wrap-around deck expanded our space even further with stunning views of the trees surrounding the property. We loved the peaceful, secluded feel of the home—it offered wonderful privacy while still being just minutes from a charming downtown with great restaurants. Dan, our host, was fantastic—friendly, responsive, and thoughtful. He added a special touch to our stay that made us feel truly welcomed. Highly recommend this property for anyone looking for a memorable and relaxing getaway!

Villa Emilio -pool/beach retreat
Quick stats about vacation rentals with a hot tub in Shelter Island Heights
Total rentals
40 properties
Nightly prices starting at
$140 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
30 properties have a pool
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- Beach
- Charlestown Beach
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- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Cooper's Beach, Southampton
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Woodmont Beach
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- Quotonset Beach
- Ocean Beach Park
- Giants Neck Beach
- Jennings Beach
- Seaside Beach
- Blue Shutters Beach
- Sunken Meadow State Park
- Silver Sands Beach
- Heckscher State Park
- Bayview Beach
- South Jamesport Beach
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