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House vacation rentals in Shelter Island Heights

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Top-rated house rentals in Shelter Island Heights

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Home in Greenport

4.83 out of 5 average rating, 190 reviews

The Greenport Townhouse - Amazing Location & Large Backyard

The house is located on a .35 acre lot with plenty of outdoor dining space and a huge grass area with a firepit & hammock. There are 2 floors. The first floor has an open floor plan with a connecting kitchen, dining room, and living room. The kitchen is well equipped with a dish washer, electric stove/oven, refrigerator, and coffee bar. There is also a bedroom on the 1st floor with 2 full-sized beds. The 2nd floor has 3 bedrooms and a loft/den area. The three bedrooms on this floor have 1 queen bed+futon, 2 full-sized beds, and 2 twin beds (which can be made together to form a king upon request), respectively. All rooms have AC. There are 2 full bathrooms (1 on each floor) and a washer/dryer. Guests have access to the entire house and backyard area. We respect your privacy, but we are accessible if you have questions or need anything throughout your stay. Greenport was voted one of the prettiest towns in America by Forbes magazine. It has a vibrant and relaxing culture, offering access to beaches, wine tasting, and wonderful restaurants. The Shelter Island Ferry and Hampton Jitney stops are nearby. We are just a few short blocks from the Hampton Jitney stop, the LIRR station, and the Shelter Island Ferry. No car necessary - you can walk wherever you need!

Apr 6 – 13

ﺩ.ﺇ1,898 per night

Home in Greenport

4.92 out of 5 average rating, 121 reviews

Beautiful Cottage Home W/ Beach & Dock Access

Beautiful, spacious beach side home situated within a block of a private beach. This cozy home is walking distance to Kontokosta Winery, Island's End Golf & Country Club, Lavender By the Bay and a five minute drive to the Village of Greenport. Replete with natural light and an open backyard perfect for outdoor dining and barbecues, this home is perfect for your stay in Greenport. Netflix/Hulu/Disney+ / ESPN+ / HBO MAX. Please note, 4 Bikes/1 Paddle Board/1 Kayak & Life Jackets provided May-Sept.

Sep 19 – 26

ﺩ.ﺇ3,213 per night

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (open 04/19 - additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool, shoot hoops, or take a 15 minute walk to the private (and empty) bay beach where you can use my paddle board. Or drive to the famous Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg 22-1590 Local taxes included

Oct 23 – 30

ﺩ.ﺇ2,537 per night

Home in Sag Harbor

4.89 out of 5 average rating, 166 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence for pool area. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

May 8 – 15

ﺩ.ﺇ1,946 per night

Home in Sag Harbor

4.94 out of 5 average rating, 102 reviews

Sag Harbor Village Cottage with Pool

Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

May 26 – Jun 2

ﺩ.ﺇ3,738 per night

Home in Greenport

4.94 out of 5 average rating, 136 reviews

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).

Mar 2 – 9

ﺩ.ﺇ430 per night

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway.

Nov 4 – 11

ﺩ.ﺇ3,349 per night

Home in Sag Harbor

4.95 out of 5 average rating, 129 reviews

Luxury Private King Suite + 2 Floor Living Space

Your modern, spacious, sparkling clean guest home has 2 private floors and a private entrance. The bedroom provides luxury and calm as light from the green trees filters in. Watch movies & chill in your living room complete with kitchenette, wine cooler, powder room and adjoining dining space. You’re in a peaceful neighborhood facing a land forest preserve, 5 minutes from bay beaches and the plethora of farm fresh, organic Sag Harbor eateries.

Oct 10 – 17

ﺩ.ﺇ1,609 per night

Home in Greenport

4.97 out of 5 average rating, 223 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

Jun 9 – 14

ﺩ.ﺇ1,669 per night

Home in Shelter Island

4.89 out of 5 average rating, 106 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Monday-Thursday stays February through June no cleaning fees!!!

Mar 19 – 26

ﺩ.ﺇ2,976 per night

Home in Sag Harbor

4.97 out of 5 average rating, 260 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

Sep 26 – Oct 3

ﺩ.ﺇ2,166 per night

Home in Greenport

4.98 out of 5 average rating, 145 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

May 10 – 17

ﺩ.ﺇ2,638 per night

Vacation rentals for every style

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Popular amenities for Shelter Island Heights house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Stony Brook

4.94 out of 5 average rating, 479 reviews

Spacious Studio Apartment- near SBU

Oct 26 – Nov 2

ﺩ.ﺇ380 per night

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

Dec 20 – 27

ﺩ.ﺇ2,804 per night

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Jan 15 – 22

ﺩ.ﺇ2,110 per night

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

Oct 31 – Nov 7

ﺩ.ﺇ832 per night

Home in Water Mill

4.91 out of 5 average rating, 110 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Nov 11 – 18

ﺩ.ﺇ3,581 per night

Home in Cutchogue

4.87 out of 5 average rating, 116 reviews

The Perfect North Fork Escape

Oct 15 – 22

ﺩ.ﺇ2,112 per night

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

Dec 31 – Jan 7

ﺩ.ﺇ3,049 per night

Home in Sag Harbor

4.82 out of 5 average rating, 132 reviews

New! Sag Harbor Village Pool, Hot Tub &Beach House

Nov 7 – 14

ﺩ.ﺇ2,759 per night

Weekly house rentals

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

Apr 13 – 20

ﺩ.ﺇ1,586 per night

Home in Shelter Island

4.92 out of 5 average rating, 73 reviews

Family Friendly Island Home

Jun 3 – 10

ﺩ.ﺇ3,042 per night

Home in Greenport

5.0 out of 5 average rating, 30 reviews

Historic Stunner in Heart of Village

Jan 22 – 29

ﺩ.ﺇ2,045 per night

Home in Greenport

4.99 out of 5 average rating, 72 reviews

Beach House in L.I. Wine Country

Oct 24 – 31

ﺩ.ﺇ1,765 per night

Home in Greenport

5.0 out of 5 average rating, 36 reviews

Beachfront Greenport Villa

Jan 22 – 29

ﺩ.ﺇ2,182 per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Nov 5 – 12

ﺩ.ﺇ2,402 per night

Home in Shelter Island

4.97 out of 5 average rating, 76 reviews

Modern, spacious SI home with pool

Dec 9 – 16

ﺩ.ﺇ3,418 per night

Home in Shelter Island

5.0 out of 5 average rating, 10 reviews

Spacious house with pool.

Mar 22 – 29

ﺩ.ﺇ3,417 per night

Private house rentals

Home in Shelter Island

4.92 out of 5 average rating, 52 reviews

Beautiful beach home with pool & water views!

May 10 – 17

ﺩ.ﺇ2,780 per night

Home in Shelter Island

5.0 out of 5 average rating, 16 reviews

Family Friendly Oasis Steps to Water - Heated Pool

Apr 21 – 28

ﺩ.ﺇ4,219 per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

Sep 24 – Oct 1

ﺩ.ﺇ2,133 per night

Home in East Marion

4.95 out of 5 average rating, 99 reviews

Quiet, Upscale Retreat by the Beach

Dec 15 – 22

ﺩ.ﺇ1,617 per night

Home in Greenport

5.0 out of 5 average rating, 3 reviews

Waterfront Greenport Boathouse

Jan 3 – 10

ﺩ.ﺇ2,294 per night

Home in East Marion

4.96 out of 5 average rating, 50 reviews

North Fork Paradise

May 29 – Jun 5

ﺩ.ﺇ3,794 per night

Home in Southold

5.0 out of 5 average rating, 17 reviews

Le Petit Cottage Southold NY

Feb 4 – 11

ﺩ.ﺇ810 per night

Home in Sag Harbor

5.0 out of 5 average rating, 22 reviews

Primely located Sag Harbor Village home

Jun 11 – 18

ﺩ.ﺇ2,215 per night

Quick stats about house rentals in Shelter Island Heights

Total rentals
190 properties
Rentals with a pool
70 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
180 properties are a good fit for families
Total number of reviews
5.5K reviews
Nightly prices starting at
ﺩ.ﺇ441 before taxes and fees

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