Shelter Island vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Shelter Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

Mar 26 – Apr 2

R14,122 ZAR per night
Guest favorite

Home in Shelter Island

4.97 out of 5 average rating, 189 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.

Jan 27 – Feb 3

R21,654 ZAR per night
Guest favorite

Guest suite in Sag Harbor

4.88 out of 5 average rating, 308 reviews

Artists Sag Harbor Village Retreat

January special -book second night for $125! This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

Nov 29 – Dec 6

R4,621 ZAR per night

Popular amenities for Shelter Island vacation rentals

Stay near Shelter Island's top sights

SALT Waterfront Bar & Grill34 locals recommend
Mashomack Preserve70 locals recommend
Ram's Head Inn19 locals recommend
Marie Eiffel Market41 locals recommend
South Ferry Inc.6 locals recommend
The Islander10 locals recommend

Shelter Island house rentals

Guest favorite

Home in Sag Harbor

4.97 out of 5 average rating, 123 reviews

Relax into Coastal Life at a Sun-Drenched Sag Harbor Home

Sep 14 – 21

R11,704 ZAR per night
Guest favorite

Home in Sag Harbor

4.95 out of 5 average rating, 129 reviews

Luxury Private King Suite + 2 Floor Living Space

Apr 9 – 16

R8,114 ZAR per night
Guest favorite

Home in East Hampton

4.96 out of 5 average rating, 187 reviews

Ritz-East Hampton Cottage- 5 stars

Sep 13 – 20

R11,476 ZAR per night
Guest favorite

Home in East Hampton

4.93 out of 5 average rating, 138 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Feb 24 – Mar 3

R6,568 ZAR per night
Guest favorite

Home in East Marion

4.98 out of 5 average rating, 107 reviews

Stylish Farmhouse in North Fork

Jan 30 – Feb 6

R13,747 ZAR per night
Guest favorite

Home in Shelter Island

5.0 out of 5 average rating, 50 reviews

CASA GYPSEA - a chic and peaceful 3 bedroom house

May 12 – 19

R7,707 ZAR per night
Guest favorite

Home in Shelter Island

4.92 out of 5 average rating, 52 reviews

Beautiful beach home with pool & water views!

Jan 24 – 31

R12,300 ZAR per night
Guest favorite

Home in Shelter Island

4.92 out of 5 average rating, 73 reviews

Family Friendly Island Home

Oct 25 – Nov 1

R13,079 ZAR per night
Guest favorite

Home in Shelter Island

5.0 out of 5 average rating, 10 reviews

Spacious house with pool.

Dec 5 – 12

R17,642 ZAR per night
Guest favorite

Home in Shelter Island

5.0 out of 5 average rating, 16 reviews

Family Friendly Oasis Steps to Water - Heated Pool

Nov 4 – 11

R21,782 ZAR per night
Guest favorite

Home in Shelter Island

4.97 out of 5 average rating, 76 reviews

Modern, spacious SI home with pool

Mar 9 – 16

R17,649 ZAR per night
Superhost

Home in Shelter Island

4.88 out of 5 average rating, 68 reviews

Charming 4BR Cottage on Shelter Island

May 27 – Jun 3

R11,673 ZAR per night

Other great vacation rentals in Shelter Island

Guest favorite

Apartment in Greenport

4.97 out of 5 average rating, 194 reviews

Greenport Village View - Walkable 2BR Stay

Feb 7 – 14

R5,984 ZAR per night
Superhost

Guesthouse in Sag Harbor

4.84 out of 5 average rating, 115 reviews

Sag Harbor Cottage in historic district

Oct 26 – Nov 2

R3,128 ZAR per night
Guest favorite

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

May 12 – 19

R4,480 ZAR per night
Guest favorite

Apartment in Sag Harbor

4.99 out of 5 average rating, 128 reviews

Updated apartment in historic village home

May 10 – 17

R5,451 ZAR per night
Guest favorite

Guest suite in Shelter Island

4.89 out of 5 average rating, 28 reviews

Private two-bedroom stay on Shelter Island

Jun 5 – 12

R6,570 ZAR per night
Guest favorite

Guesthouse in Shelter Island

5.0 out of 5 average rating, 50 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Jul 22 – 29

R7,631 ZAR per night
Guest favorite

Guesthouse in Shelter Island

4.95 out of 5 average rating, 22 reviews

Lovely Island Cottage

Nov 26 – Dec 3

R8,143 ZAR per night
Guest favorite

Cottage in Shelter Island

4.96 out of 5 average rating, 90 reviews

3 Bedroom Cottage Gem

Jun 18 – 25

R13,548 ZAR per night
Guest favorite

Cottage in Shelter Island

4.88 out of 5 average rating, 16 reviews

Waterfront Getaway on Shelter Island

Oct 18 – 25

R15,647 ZAR per night
Guest favorite

Cottage in Sag Harbor

5.0 out of 5 average rating, 27 reviews

Luxury Gem At The Heart of Sag Harbor Village

May 10 – 17

R12,486 ZAR per night
Guest favorite

Home in Greenport

5.0 out of 5 average rating, 32 reviews

Beachfront Greenport Villa

Nov 7 – 14

R14,728 ZAR per night
Guest favorite

Cottage in Sag Harbor

4.94 out of 5 average rating, 51 reviews

Steps to the Beach - Designer Cove House Cottage

May 6 – 13

R9,835 ZAR per night

Quick stats about vacation rentals in Shelter Island

Total rentals

140 properties

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

100 properties are a good fit for families

Total number of reviews

3K reviews

Nightly prices starting at

R2,275 ZAR before taxes and fees

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Shelter Island?

    Four-legged friends are welcome in Shelter Island. Choose from more than 50 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Shelter Island?

    Yes! Work meets play with ease at over 60 vacation rentals in Shelter Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Shelter Island have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Shelter Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Shelter Island have air conditioning?

    Absolutely! We offer over 90 house rentals with air conditioning in Shelter Island. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Shelter Island?

    Experience the best of Shelter Island with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly house rentals in Shelter Island?

    Shelter Island has more than 90 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Shelter Island have a bbq area?

    Absolutely! We offer over 70 house rentals with a bbq area in Shelter Island. Enjoy a tailored experience with all the comforts you desire.

  • Are there Shelter Island house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 house rentals with pools in Shelter Island, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Shelter Island have wifi?

    Absolutely! We offer over 100 house rentals with wifi in Shelter Island. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Shelter Island?

    Enhance your stay in our House Rentals with the most popular amenities: over 90 homes with air conditioning, over 10 homes with a gym, over 70 homes with a bbq area, over 100 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore