Family-Friendly Vacation Rentals in Little Bay, NY: Compare 10+ Sites & Save

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  5.  Little Bay

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41 Best Family Vacation Rentals in Little Bay (Starting from $118)

BayFront Cottage
BayFront Cottage
Villa
Orient, NY, USA
4.3k from Little Bay center

Parking, Air Conditioner, Ocean View, View, Internet, Child Friendly

3 Bedrooms6 Guests
New to Booking
$306
Average price / night
Check Availability
Serene East End Oasis
Serene East End Oasis
House
Orient, NY, 11957, United States
1.6k from Little Bay center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

4 Bedrooms8 Guests
New to Booking
$710
Average price / night
Check Availability
Lagoon Lodge: North Fork,Charming 3Br, Waterfront
Lagoon Lodge: North Fork,Charming 3Br, Waterfront
House
East Marion, NY, USA
7.4k from Little Bay center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

3 Bedrooms8 Guests
New to Booking
$550
Average price / night
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Orient Point Vacation Home Saltwater Pool and Five Bedrooms Book Summer Now
Orient Point Vacation Home Saltwater Pool and Five Bedrooms Book Summer Now
House
Orient Point, NY, 11957, United States
1.7k from Little Bay center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
9.6

Exceptional

5 reviews

$1370
Average price / night
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Shelter Island Retreat with Outdoor Pool!
Shelter Island Retreat with Outdoor Pool!
House
Shelter Island, NY, USA
7.6k from Little Bay center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings

5 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1119
Average price / night
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1.5 Acre Luxury Escape - Saltwater Pool with Water Views
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Villa
Orient, NY, 11957, United States
1.7k from Little Bay center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$1127
Average price / night
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Lavender Bay Breezes - Private Bay Beach Community
Lavender Bay Breezes - Private Bay Beach Community
House
Little Bay, Orient, New York, USA
8.2k from Little Bay center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay, Accessible hotels

4 Bedrooms8 Guests
New to Booking
$312
Average price / night
Check Availability
Beachfront vacation Dream house in Long Island Sound.
Beachfront vacation Dream house in Long Island Sound.
House
Orient, NY, 11957, United States
1.9k from Little Bay center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms8 Guests
9.8

Exceptional

61 reviews

$859
Average price / night
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Charming Greenport Gem 1, 1 Mile to Ferry!
Charming Greenport Gem 1, 1 Mile to Ferry!
Apartment
Greenport, NY, USA
9.8k from Little Bay center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$118
Average price / night
Check Availability
The Lane House | Private Beach Escape
The Lane House | Private Beach Escape
House
Orient, NY, 11957, United States
2.0k from Little Bay center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
9.8

Exceptional

20 reviews

$626
Average price / night
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Gorgeous North Fork Farmhouse with Private Beach Rights
Gorgeous North Fork Farmhouse with Private Beach Rights
House
Orient, NY, 11957, United States
2.1k from Little Bay center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1475
Average price / night
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Private Vineyard Estate in Orient Village w Pool / AC / Walk to Beach & Town
Private Vineyard Estate in Orient Village w Pool / AC / Walk to Beach & Town
House
Orient, NY, 11957, United States
3.6k from Little Bay center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms6 Guests
New to Booking
$1909
Average price / night
Check Availability
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
House
Orient, NY, 11957, United States
4.0k from Little Bay center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.4

Superb

10 reviews

$2299
Average price / night
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Waterfront Bungalow w/ Private Beach on Peconic Bay
Waterfront Bungalow w/ Private Beach on Peconic Bay
House
East Marion, NY, 11939, United States
7.2k from Little Bay center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
9.8

Exceptional

7 reviews

$335
Average price / night
Check Availability
Quiet 3BR home in East Marion. Private beach access 3 min walk away.
Quiet 3BR home in East Marion. Private beach access 3 min walk away.
House
East Marion, NY, 11939, United States
7.4k from Little Bay center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$649
Average price / night
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4-bed 3.5-bath house with fenced heated pool and hot tub, fire pit, kids swings
4-bed 3.5-bath house with fenced heated pool and hot tub, fire pit, kids swings
House
East Marion, NY, 11939, United States
7.4k from Little Bay center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
8.0

Good

1 reviews

$834
Average price / night
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Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home
Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home
House
East Marion, NY, 11939, United States
7.4k from Little Bay center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$642
Average price / night
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Shelter Island Retreat w/ Outdoor Pool!
Shelter Island Retreat w/ Outdoor Pool!
House
Shelter Island, NY, 11964, United States
7.6k from Little Bay center

AC, Arcade, Balcony, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$1227
Average price / night
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Heavenly Craftsman  Just minutes to beaches, vineyards, ferries and Greenport!
Heavenly Craftsman Just minutes to beaches, vineyards, ferries and Greenport!
House
East Marion, NY, 11939, United States
7.7k from Little Bay center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$542
Average price / night
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Bright and Spacious Summer Home Steps from the Beach
Bright and Spacious Summer Home Steps from the Beach
House
Shelter Island, NY, 11965, United States
7.7k from Little Bay center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet

4 Bedrooms10 Guests
9.0

Fabulous

41 reviews

$814
Average price / night
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House by the Bay with Large In-ground Pool, Steps from Beach
House by the Bay with Large In-ground Pool, Steps from Beach
House
East Marion, NY, 11939, United States
7.7k from Little Bay center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

27 reviews

$741
Average price / night
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Elegant Treetop Modern Steps from Hay Beach, Heated Gunite Pool
Elegant Treetop Modern Steps from Hay Beach, Heated Gunite Pool
House
Shelter Island, NY, 11965, United States
7.7k from Little Bay center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms5 Guests
9.8

Exceptional

7 reviews

$1087
Average price / night
Check Availability
North Fork Paradise
North Fork Paradise
House
East Marion, NY, 11939, United States
7.7k from Little Bay center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$951
Average price / night
Check Availability
Quiet Oasis Near Greenport with Views of Lavendar Farm walk to Beach
Quiet Oasis Near Greenport with Views of Lavendar Farm walk to Beach
House
East Marion, NY, 11939, United States
7.7k from Little Bay center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.4

Superb

3 reviews

$408
Average price / night
Check Availability
Bohemian Old Life Saving Station with Beach & Pool
Bohemian Old Life Saving Station with Beach & Pool
House
East Marion, NY, 11939, United States
7.9k from Little Bay center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

6 Bedrooms13 Guests
10.0

Exceptional

33 reviews

$1371
Average price / night
Check Availability
Family friendly home near beach with wonderful deck!
Family friendly home near beach with wonderful deck!
House
Shelter Island, NY, 11964, United States
7.9k from Little Bay center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.8

Exceptional

16 reviews

$677
Average price / night
Check Availability
NEW RENTAL:  MAGICAL SHELTER ISLAND RETREAT
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
House
Shelter Island, NY, 11964, United States
7.9k from Little Bay center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms12 Guests
10.0

Exceptional

5 reviews

$2378
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Little Bay.

Where to stay in Little Bay? Best neighborhoods & areas

Little Bay Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 41 verified family-friendly vacation rentals in Little Bay. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Little Bay vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $118 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Little Bay offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Little Bay are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Little Bay often include amenities such as Child Friendly, Ocean View, and View. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.