Family-Friendly Vacation Rentals in East of Maui, DE: Compare 10+ Sites & Save

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780 Best Family Vacation Rentals in East of Maui (Starting from $251)

Dewey Beach - Rehoboth By The Sea - 102 Chicago St
Dewey Beach - Rehoboth By The Sea - 102 Chicago St
House
Dewey Beach, DE, USA
0.1k from East of Maui center

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

3 Bedrooms6 Guests
New to Booking
$505
Average price / night
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Spectacular pet friendly house walk to beach w/ocean views, private pool
Spectacular pet friendly house walk to beach w/ocean views, private pool
House
Dewey Beach, DE, 19971, United States
0.1k from East of Maui center

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

6 Bedrooms14 Guests
10.0

Exceptional

4 reviews

$1058
Average price / night
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Houston street 109
Houston street 109
House
Dewey Beach, DE, USA
0.1k from East of Maui center

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

3 Bedrooms8 Guests
New to Booking
$548
Average price / night
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6.27-7.4 & 7.25-8.1 FREE BONFIRE & CHEF, BCH CHRS & UMBRELLAS INCLUDED!  BOGO!
6.27-7.4 & 7.25-8.1 FREE BONFIRE & CHEF, BCH CHRS & UMBRELLAS INCLUDED! BOGO!
House
Dewey Beach, DE, 19971, United States
0.1k from East of Maui center

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

15 Bedrooms32 Guests
10.0

Exceptional

121 reviews

$2294
Average price / night
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Town of Dewey Beach - 17 Saint Louis St
Town of Dewey Beach - 17 Saint Louis St
House
Dewey Beach, DE, USA
0.1k from East of Maui center

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

1 Bedroom14 Guests
New to Booking
$1576
Average price / night
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Exceptional Dewey Beach Stay Central Location Near Ocean & Bay
Exceptional Dewey Beach Stay Central Location Near Ocean & Bay
Cottage
Dewey Beach, DE, 19971, United States
0.2k from East of Maui center

AC, Barbecue, Free Parking, Heater, Internet, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms9 Guests
New to Booking
$488
Average price / night
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Town of Dewey Beach - 303 Wilson Dunes
Town of Dewey Beach - 303 Wilson Dunes
Apartment
Dewey Beach, DE, USA
0.2k from East of Maui center

Oceanfront, Guest Services, Air Conditioner, Accessibility, View, Laundry, Fireplace/Heating

3 Bedrooms8 Guests
New to Booking
$547
Average price / night
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Large Luxurious Dewey Beach House Just Steps to the Beach - Pet Friendly!
Large Luxurious Dewey Beach House Just Steps to the Beach - Pet Friendly!
House
Dewey Beach, DE, 19971, United States
0.2k from East of Maui center

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

7 Bedrooms16 Guests
9.6

Exceptional

32 reviews

$1211
Average price / night
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St louis street 10
St louis street 10
House
Dewey Beach, DE, USA
0.2k from East of Maui center

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

5 Bedrooms10 Guests
New to Booking
$523
Average price / night
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Beautiful California Style House 2 Blocks to the Beach. Walk to Dewey & Rehoboth
Beautiful California Style House 2 Blocks to the Beach. Walk to Dewey & Rehoboth
House
Rehoboth Beach, DE, 19971, United States
0.2k from East of Maui center

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

4 Bedrooms10 Guests
10.0

Exceptional

118 reviews

$906
Average price / night
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Clayton street 17a
Clayton street 17a
House
Dewey Beach, DE, USA
0.2k from East of Maui center

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

1 Bedroom16 Guests
New to Booking
$916
Average price / night
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Steps to Beach!  California Vibe - Families, Groups, Reunions - Fun Property!
Steps to Beach! California Vibe - Families, Groups, Reunions - Fun Property!
House
Rehoboth Beach, DE, 19971, United States
0.2k from East of Maui center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet

8 Bedrooms26 Guests
10.0

Exceptional

50 reviews

$2895
Average price / night
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Clayton street 9
Clayton street 9
House
Dewey Beach, DE, USA
0.2k from East of Maui center

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

5 Bedrooms11 Guests
New to Booking
$1027
Average price / night
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DEWEY BEACH! NEW LISTING in \"Rehoboth by the Sea,\" 5 min walk to beach 4BDR/3BA
DEWEY BEACH! NEW LISTING in \"Rehoboth by the Sea,\" 5 min walk to beach 4BDR/3BA
House
Dewey Beach, DE, 19971, United States
0.2k from East of Maui center

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

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$697
Average price / night
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Clayton street 17b
Clayton street 17b
House
Dewey Beach, DE, USA
0.2k from East of Maui center

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

1 Bedroom16 Guests
New to Booking
$787
Average price / night
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ONE BLOCK TO BEACH-PET FRIENDLY-FREE BEACH BONFIRE FOR WEEKS OF 5/30-6/13!!
ONE BLOCK TO BEACH-PET FRIENDLY-FREE BEACH BONFIRE FOR WEEKS OF 5/30-6/13!!
House
Dewey Beach, DE, 19971, United States
0.2k from East of Maui center

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

4 Bedrooms10 Guests
10.0

Exceptional

39 reviews

$583
Average price / night
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Bayard avenue 1603
Bayard avenue 1603
House
Dewey Beach, DE, USA
0.2k from East of Maui center

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

3 Bedrooms10 Guests
New to Booking
$251
Average price / night
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Location, Location, Location! Immaculately Kept!
Location, Location, Location! Immaculately Kept!
House
Dewey Beach, DE, 19971, United States
0.3k from East of Maui center

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

8 Bedrooms20 Guests
9.8

Exceptional

43 reviews

$1314
Average price / night
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Ann Acres 21039 Elizabeth Ave
Ann Acres 21039 Elizabeth Ave
House
Rehoboth Beach, DE, USA
0.2k from East of Maui center

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

3 Bedrooms6 Guests
9.0

Fabulous

4 reviews

$679
Average price / night
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Cozy, renovated, coastal cottage in the middle of Dewey Beach! Prime location!
Cozy, renovated, coastal cottage in the middle of Dewey Beach! Prime location!
Condo
Dewey Beach, DE, 19971, United States
0.3k from East of Maui center

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

3 Bedrooms10 Guests
9.6

Exceptional

61 reviews

$573
Average price / night
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Great Location and Rents as a 3 Night Weekend on Saulsbury St.
Great Location and Rents as a 3 Night Weekend on Saulsbury St.
Condo
Dewey Beach, DE, 19971, United States
0.3k from East of Maui center

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

2 Bedrooms8 Guests
8.8

Fabulous

42 reviews

$417
Average price / night
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Prime location on  Saulsbury St in Dewey!
Prime location on Saulsbury St in Dewey!
Condo
Dewey Beach, DE, 19971, United States
0.3k from East of Maui center

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

4 Bedrooms10 Guests
10.0

Exceptional

43 reviews

$1072
Average price / night
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Be the Envy of those walking by! Prime location in the middle of Dewey Beach!
Be the Envy of those walking by! Prime location in the middle of Dewey Beach!
Apartment
Dewey Beach, DE, 19971, United States
0.3k from East of Maui center

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

4 Bedrooms10 Guests
10.0

Exceptional

42 reviews

$1160
Average price / night
Check Availability
Fantastic Location on Saulsbury St with a 3-night weekend option
Fantastic Location on Saulsbury St with a 3-night weekend option
House
Dewey Beach, DE, 19971, United States
0.3k from East of Maui center

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

4 Bedrooms14 Guests
9.8

Exceptional

66 reviews

$638
Average price / night
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Iconic A-Frame - Beach Block Dewey! Sleeps up to16! Walk Everywhere!
Iconic A-Frame - Beach Block Dewey! Sleeps up to16! Walk Everywhere!
House
Dewey Beach, DE, 19971, United States
0.3k from East of Maui center

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

7 Bedrooms16 Guests
10.0

Exceptional

33 reviews

$902
Average price / night
Check Availability
Spacious Family Retreat: 7 Bedrooms, Large Yard, Deck & Loft for All Ages!
Spacious Family Retreat: 7 Bedrooms, Large Yard, Deck & Loft for All Ages!
House
Dewey Beach, DE, 19971, United States
0.4k from East of Maui center

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

7 Bedrooms14 Guests
New to Booking
$519
Average price / night
Check Availability
Surfrider F — 70 Steps to the Sand • 3BR/2BA • 2 Balconies • Sleeps 8
Surfrider F — 70 Steps to the Sand • 3BR/2BA • 2 Balconies • Sleeps 8
Condo
Dewey Beach, DE, 19971, United States
0.4k from East of Maui center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms8 Guests
New to Booking
$837
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 East of Maui.

Where to stay in East of Maui? Best neighborhoods & areas

East of Maui Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 780 verified family-friendly vacation rentals in East of Maui. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in East of Maui vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $251 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in East of Maui 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 East of Maui 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 East of Maui often include amenities such as Laundry, Child Friendly, 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.