
Holiday rentals in Shelter Island Heights
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Top-rated holiday rentals in Shelter Island Heights
Guests agree: these stays are highly rated for location, cleanliness and more.

Hamptons Oceanfront Oasis
Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Lovely 1st floor of farmhouse, wineries/downtown
Lovely Victorian home with private entrance, porch, & patio. Floor to ceiling windows in light filled large bedroom with king sized bed & ensuite bathroom. Cozy den has a beautiful bay window and a queen-size pull-out sofa bed for additional guests. Sunny sitting room just off of the kitchen for reading or games. Full kitchen, washer dryer, high speed internet, and new flat screen TV can be found in the unit. Restaurants, wineries, beaches are nearby. Enjoy all the North Fork as to offer!

2 BR Waterfront Escape in Wine Country
Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Shelter Island family getaway steps from beaches
Just 2 blocks from Hay Beach, our family & pet-friendly 3BR home offers space to relax & play. Enjoy a large yard w/ fire pits, beach gear, games, & toddler toys. Inside: open living area, fireplace, full kitchen, 2 baths, playroom, workout space, & extra sleeping options. Quiet neighborhood, perfect for families. Winter stays: cozy up by the fire & enjoy $0 cleaning fee Nov–Mar. Host lives next door for quick support. For the littles there is a full sized crib high chair and bathtub.

Harbor Heights
Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Gorgeous home with saltwater pool. Steps to beach!
Built in 1928, this gorgeous home is fully equipped to host your getaway. You're within easy walking distance of Horton's Lighthouse, where lovely beach walks and stunning sunsets await you. The local wineries are all within short drives of this lovely retreat. Enjoy the new heated gunnite pool with plenty of poolside seating. The family friendly layout features plenty of seating inside and out. You're just 100 yards north of a public beach, come enjoy the sunsets!

3 Min Walk to Beach|Close to Town| Fam-Friendly
<b>The Greenport Beach Cottage</b> Rated 5.0 ⭐️by 50+ Reviews | Top 5% of All Airbnbs ✔️ Newly renovated 800 sq ft coastal cottage ✔️ 3 minute walk to beach, 4 minute drive to town ✔️ Sleeps up to 5 guests ✔️ Family- & Dog-Friendly ✔️ Backyard with 2 fire pits, charcoal & gas grill, outdoor shower ✔️ Garage with 4 beach cruiser bikes, Foosball table & small gym area Book your coastal getaway now- summer dates are booking up! IG: @thegreenportbeachcottage

Recharge at our Renovated ocean front unit
Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

Junior 1-BR in the heart of Greenport Village
Beautiful junior one bedroom in the heart of Greenport Village. Located in the historical district, our basement apartment is walking distance (2-Blocks) to downtown Greenport. Perfect for a couples weekend, girls trip, or for a small family. Our apartment includes one queen bed and a twin day bed with trundle underneath. (Sleeps 4 total) TV with streaming service and WiFi are included. W/D are available upon request.

Renovated Townhouse, Walk to All
Discover the North Fork from our stylishly renovated 100-year-old townhouse! Perfectly located, you can walk to town, beaches, and a local brewery. This bright, airy home features a new kitchen, central AC, and a private patio with a grill. Comfortably sleeping up to 8 guests, it's the ideal base for families or groups exploring Long Island's wine country. Park your car and enjoy a walkable getaway!

Hamptons - Shelter Island Farmhouse
Kid friendly! Perfect two family split! Come enjoy our island retreat. Relax with the whole family at this peaceful pad. You will be 2 min on bike from Wades Beach. You can also walk to the best BBQ/seafood in Shelter, Commander Codys. Features a large open kitchen/dining room plus also a spacious living room. 4 bedrooms with new mattresses, huge outdoor patio for family BBQs. No dogs please.

North Fork Waterfront Escape · Sunset Views
Enjoy spectacular views of Hashamomuck Inlet off Shelter Bay from the living room, kitchen, deck, garden, and private dock of this newly renovated 3-bedroom home. With 90 feet of waterfront and a small sandy beach, it's ideal for kayaking, clamming, and swimming — perfect for families with young children. Relax with sunsets, barbecues, and local North Fork wine. The perfect family getaway!
Popular amenities for Shelter Island Heights holiday rentals
Other great holiday rentals in Shelter Island Heights

Waterfront Treehouse with Pool as seen on HBO

Family Friendly Island Home

Huge Island Getaway Pool HotTub Walk To Beach

Cosy North Fork Cottage with large backyard

Two bedroom bungalow

Stylish Studio Suite on Shelter Island

Shelter Island home with pool

Waterfront Condo C-204 at The Cliffside Resort
When is the best time to visit Shelter Island Heights?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £261 | £270 | £279 | £279 | £335 | £382 | £442 | £447 | £375 | £320 | £286 | £270 |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Shelter Island Heights?
Shelter Island Heights has more than 350 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Shelter Island Heights?
Experience the best of Shelter Island Heights with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Shelter Island Heights?
Four-legged friends are welcome in Shelter Island Heights. Choose from more than 140 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Shelter Island Heights?
Yes! Work meets play with ease at over 210 vacation rentals in Shelter Island Heights featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Shelter Island Heights condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 condo rentals with pools in Shelter Island Heights, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Shelter Island Heights?
Make yourself at home in Shelter Island Heights by choosing from our most frequently booked neighborhoods. We have over 1,630 vacation rentals in Shelter Island, over 990 vacation rentals in Shelter Island Heights, and over 510 vacation rentals in Greenport.
Do house rentals in Shelter Island Heights have air conditioning?
Absolutely! We offer over 280 house rentals with air conditioning in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Shelter Island Heights have a kitchen?
Absolutely! We offer over 30 apartment rentals with a kitchen in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shelter Island Heights have wifi?
Absolutely! We offer over 280 house rentals with wifi in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Shelter Island Heights have free parking?
Absolutely! We offer over 10 bed and breakfast rentals with free parking in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Shelter Island Heights

Total holiday rentals
Explore 430 holiday rentals in Shelter Island Heights

Nightly prices starting at
Shelter Island Heights holiday rentals start at £60 per night before taxes and fees

Verified guest reviews
Over 16,450 verified reviews to help you choose

Family-friendly holiday rentals
350 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 140 rentals that welcome pets

Holiday rentals with a pool
160 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wifi availability
410 of Shelter Island Heights holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shelter Island Heights rentals

4.9 Average rating
Shelter Island Heights stays are highly rated by guests – averaging 4.9 out of 5!
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