Family-Friendly Vacation Rentals in Orleans, MA: Compare 10+ Sites & Save

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  4.  Massachusetts

  5.  Orleans

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447 Best Family Vacation Rentals in Orleans (Starting from $223)

Sailor Sanctuary
Sailor Sanctuary
House
Orleans, MA, USA
0.5k from Orleans center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms6 Guests
New to Booking
$963
Average price / night
Check Availability
Salt River Retreat - Easy Walk to Scenic Kent's Point - Pet Friendly!
Salt River Retreat - Easy Walk to Scenic Kent's Point - Pet Friendly!
House
Orleans, MA, 02653, United States
0.4k from Orleans center

AC, Barbecue, Crib, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
New to Booking
$338
Average price / night
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Perfectly private location w deeded beach access
Perfectly private location w deeded beach access
House
Orleans, MA, USA
0.6k from Orleans center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$526
Average price / night
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Enchanting Waterfront Summer Escape on Pleasant Bay
Enchanting Waterfront Summer Escape on Pleasant Bay
House
Orleans, MA, 02653, United States
0.5k from Orleans center

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

4 Bedrooms6 Guests
9.6

Exceptional

28 reviews

$1602
Average price / night
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Great White Cape Escape
Great White Cape Escape
House
Orleans, MA, USA
0.7k from Orleans center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms9 Guests
New to Booking
$357
Average price / night
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Private Estate, heated pool, outdoor Livingroom, kitchen, 11 bedrooms, sleeps 20
Private Estate, heated pool, outdoor Livingroom, kitchen, 11 bedrooms, sleeps 20
House
East Orleans, MA, 02653, United States
0.9k from Orleans center

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

11 Bedrooms20 Guests
10.0

Exceptional

21 reviews

$2460
Average price / night
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2 Miles to Nauset Beach and convenient to town
2 Miles to Nauset Beach and convenient to town
House
Orleans, MA, USA
1.0k from Orleans center

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

3 Bedrooms8 Guests
New to Booking
$943
Average price / night
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Waterfront retreat, private yet minutes to town and beach. Sleeps 7, 3 bedrooms
Waterfront retreat, private yet minutes to town and beach. Sleeps 7, 3 bedrooms
House
Orleans, MA, 02653, United States
0.9k from Orleans center

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

3 Bedrooms7 Guests
10.0

Exceptional

28 reviews

$1163
Average price / night
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Coastal Comfort Near Orleans Adventures
Coastal Comfort Near Orleans Adventures
House
Orleans, MA, USA
1.0k from Orleans center

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

3 Bedrooms6 Guests
New to Booking
$223
Average price / night
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Peaceful Cape Cod retreat, 1.5mi to National Seashore
Peaceful Cape Cod retreat, 1.5mi to National Seashore
House
Orleans, MA, 02653, United States
0.9k from Orleans center

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

4 Bedrooms8 Guests
10.0

Exceptional

20 reviews

$650
Average price / night
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Close to Barley Neck Landing
Close to Barley Neck Landing
House
Orleans, MA, USA
1.1k from Orleans center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms10 Guests
New to Booking
$374
Average price / night
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Recently reno’ed private & spacious E. Orleans 3B/2B. Close to Orleans beaches
Recently reno’ed private & spacious E. Orleans 3B/2B. Close to Orleans beaches
House
Orleans, MA, 02653, United States
1.0k from Orleans center

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

3 Bedrooms8 Guests
10.0

Exceptional

51 reviews

$457
Average price / night
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Spacious Home with Sprawling Yard
Spacious Home with Sprawling Yard
House
Orleans, MA, USA
1.1k from Orleans center

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

4 Bedrooms8 Guests
8.0

Good

1 reviews

$400
Average price / night
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Charming, Renovated 1870s Home with Private Beach
Charming, Renovated 1870s Home with Private Beach
House
Orleans, MA, 02653, United States
1.0k from Orleans center

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

3 Bedrooms6 Guests
10.0

Exceptional

19 reviews

$394
Average price / night
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The Perfect Beach Getaway
The Perfect Beach Getaway
House
Orleans, MA, USA
1.1k from Orleans center

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

3 Bedrooms6 Guests
8.5

Very Good

2 reviews

$541
Average price / night
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New Saltwater Heated Pool & Hot Tub -Less than 5 Minutes from Nauset Beach!
New Saltwater Heated Pool & Hot Tub -Less than 5 Minutes from Nauset Beach!
House
Orleans, MA, 02653, United States
1.1k from Orleans center

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

4 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$1526
Average price / night
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Barley Breeze
Barley Breeze
House
Orleans, Massachusetts, USA
1.1k from Orleans center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

3 Bedrooms8 Guests
9.3

Superb

3 reviews

$250
Average price / night
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New Listing 2024 Eastwind Estate - Luxury Home on Barley Neck in East Orleans
New Listing 2024 Eastwind Estate - Luxury Home on Barley Neck in East Orleans
House
Orleans, MA, 02653, United States
1.3k from Orleans center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Heater, Hot Tub, Internet, Kitchen

6 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$1589
Average price / night
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10 ft from Crystal Lake New renovation
10 ft from Crystal Lake New renovation
House
Orleans, MA, USA
1.2k from Orleans center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1303
Average price / night
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Modern Cape Escape, 3BR, Fire Pit, Central AC, 8 Min to Nauset Beach, Sleeps 8
Modern Cape Escape, 3BR, Fire Pit, Central AC, 8 Min to Nauset Beach, Sleeps 8
House
Orleans, MA, 02653, United States
1.3k from Orleans center

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

3 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$632
Average price / night
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Adorable home in the heart of East Orleans!
Adorable home in the heart of East Orleans!
House
Orleans, MA, 02653, United States
1.5k from Orleans center

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

2 Bedrooms5 Guests
9.8

Exceptional

28 reviews

$310
Average price / night
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Spacious, Brand New Home - 5 bedroom 6 bath!
Spacious, Brand New Home - 5 bedroom 6 bath!
House
Orleans, MA, 02653, United States
1.5k from Orleans center

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

5 Bedrooms12 Guests
10.0

Exceptional

14 reviews

$1716
Average price / night
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Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches
Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches
Condo
Orleans, MA, 02653, United States
1.5k from Orleans center

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

2 Bedrooms6 Guests
10.0

Exceptional

11 reviews

$297
Average price / night
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Coastal Chic sunny and private in East Orleans \"center\" w  bed/bath rebuild 2024
Coastal Chic sunny and private in East Orleans \"center\" w bed/bath rebuild 2024
House
Orleans, MA, 02653, United States
1.6k from Orleans center

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

3 Bedrooms6 Guests
9.8

Exceptional

30 reviews

$560
Average price / night
Check Availability
Walk to Beach, Home with Central A/C.  Private Acre+ Lot
Walk to Beach, Home with Central A/C. Private Acre+ Lot
House
Orleans, MA, 02653, United States
1.8k from Orleans center

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

4 Bedrooms12 Guests
10.0

Exceptional

11 reviews

$423
Average price / night
Check Availability
Custom Cape Home Near Pleasant Bay & PahWah Pond (1580)
Custom Cape Home Near Pleasant Bay & PahWah Pond (1580)
House
Orleans, MA, 02653, United States
1.8k from Orleans center

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

4 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$972
Average price / night
Check Availability
Under 1  Mile to Nauset Beach (2245)
Under 1 Mile to Nauset Beach (2245)
House
Orleans, MA, 02653, United States
2.0k from Orleans center

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

3 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$585
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 Orleans.

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Orleans Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 447 verified family-friendly vacation rentals in Orleans. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Orleans vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $223 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Orleans 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 Orleans 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 Orleans often include amenities such as Child Friendly, View, and Fireplace/Heating. 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.