Family-Friendly Vacation Rentals in 2nd Time Designs, DE: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Family Vacation Rentals
  3.  USA

  4.  Delaware

  5.  Rehoboth Beach
  6.  2nd Time Designs

Refine your search

Price per night

Amenity Filter

Rating

146 Best Family Vacation Rentals in 2nd Time Designs (Starting from $177)

The Peninsula - 22198 Dune Cir
The Peninsula - 22198 Dune Cir
House
Millsboro, DE, USA
2.2k from 2nd Time Designs center

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

4 Bedrooms8 Guests
New to Booking
$425
Average price / night
Check Availability
Cozy 3-bedroom house in enjoyable Long Neck Delaware, By the Indian River bay
Cozy 3-bedroom house in enjoyable Long Neck Delaware, By the Indian River bay
House
Millsboro, DE, 19966, United States
1.3k from 2nd Time Designs center

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

3 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$275
Average price / night
Check Availability
The Peninsula - 22310 Dune Cir #73
The Peninsula - 22310 Dune Cir #73
House
Millsboro, DE, USA
2.2k from 2nd Time Designs center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

4 Bedrooms10 Guests
New to Booking
$383
Average price / night
Check Availability
Resort Retreat * Trails * Free Bikes * Peninsula Club
Resort Retreat * Trails * Free Bikes * Peninsula Club
House
Millsboro, DE, 19966, United States
1.9k from 2nd Time Designs center

AC, Arcade, Balcony, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$415
Average price / night
Check Availability
The Peninsula - 22308 Dune Cir 74
The Peninsula - 22308 Dune Cir 74
Apartment
Millsboro, DE, USA
2.2k from 2nd Time Designs center

Apartments, Accommodations, Pools, Lodgings, Hot tubs, Places to stay

4 Bedrooms10 Guests
New to Booking
$423
Average price / night
Check Availability
Plover Point New 4 Bedroom Home 20 minutes from area beaches
Plover Point New 4 Bedroom Home 20 minutes from area beaches
House
Millsboro, DE, 19966, United States
2.4k from 2nd Time Designs center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms10 Guests
New to Booking
$424
Average price / night
Check Availability
The Peninsula - 24647 Navigators Walk
The Peninsula - 24647 Navigators Walk
House
Millsboro, DE, USA
2.3k from 2nd Time Designs center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

5 Bedrooms10 Guests
New to Booking
$408
Average price / night
Check Availability
RANCH WITH CACTUSES
RANCH WITH CACTUSES
House
Millsboro, DE, 19966, United States
2.6k from 2nd Time Designs center

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

4 Bedrooms6 Guests
9.8

Exceptional

14 reviews

$220
Average price / night
Check Availability
The Peninsula - 33129 Serenity Circle #87
The Peninsula - 33129 Serenity Circle #87
House
Millsboro, DE, USA
2.5k from 2nd Time Designs center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

4 Bedrooms14 Guests
New to Booking
$624
Average price / night
Check Availability
Our Shorebird Way-Brand New Family-Friendly, 4 bedroom Home by the Shore
Our Shorebird Way-Brand New Family-Friendly, 4 bedroom Home by the Shore
House
Millsboro, DE, 19966, United States
2.6k from 2nd Time Designs center

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

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$401
Average price / night
Check Availability
The Peninsula - 27606 S Nicklaus Ave
The Peninsula - 27606 S Nicklaus Ave
House
Millsboro, DE, USA
2.5k from 2nd Time Designs center

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

5 Bedrooms14 Guests
New to Booking
$638
Average price / night
Check Availability
3-bedroom house in tranquil Long Neck with Pool
3-bedroom house in tranquil Long Neck with Pool
House
Long Neck, DE, 19966, United States
2.6k from 2nd Time Designs center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

4 Bedrooms10 Guests
New to Booking
$316
Average price / night
Check Availability
Fabulous on the Fairway!
Fabulous on the Fairway!
Apartment
Millsboro, DE, USA
3.2k from 2nd Time Designs center

Parking, Restaurant, Fireplace/Heating, Child Friendly, Oceanfront, Wellness Facilities, Wheelchair Accessible

3 Bedrooms6 Guests
New to Booking
$246
Average price / night
Check Availability
Welcome to the most well-appointed rental in The Peninsula five star resort!
Welcome to the most well-appointed rental in The Peninsula five star resort!
House
Millsboro, DE, 19966, United States
2.6k from 2nd Time Designs center

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

3 Bedrooms8 Guests
10.0

Exceptional

119 reviews

$301
Average price / night
Check Availability
Deck and Indian River Bay Views Coastal Cottage
Deck and Indian River Bay Views Coastal Cottage
House
Millsboro, DE, USA
3.8k from 2nd Time Designs center

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

2 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$177
Average price / night
Check Availability
Perfectly situated, great view, sleeps 10+.
Perfectly situated, great view, sleeps 10+.
House
Millsboro, DE, 19966, United States
2.8k from 2nd Time Designs center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms12 Guests
9.8

Exceptional

27 reviews

$393
Average price / night
Check Availability
Dream Cottage in Lewes
Dream Cottage in Lewes
House
DE, USA
5.3k from 2nd Time Designs center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Self-catering

4 Bedrooms9 Guests
8.0

Good

1 reviews

$318
Average price / night
Check Availability
Luxury Retreat at The Peninsula, Endless Amenities, Private Beach, Sleeps 10
Luxury Retreat at The Peninsula, Endless Amenities, Private Beach, Sleeps 10
House
Millsboro, DE, 19966, United States
3.0k from 2nd Time Designs center

AC, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
New to Booking
$538
Average price / night
Check Availability
Angola By The Bay - 23730 Elmwood Ave E
Angola By The Bay - 23730 Elmwood Ave E
House
Lewes, DE, USA
5.3k from 2nd Time Designs center

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

1 Bedroom11 Guests
New to Booking
$353
Average price / night
Check Availability
Windswept Dr  Condo in a quiet, golf course community close to Rehoboth Beach
Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach
Condo
Millsboro, DE, 19966, United States
3.2k from 2nd Time Designs center

AC, Balcony, Dryer, Fireplace, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

19 reviews

$240
Average price / night
Check Availability
Peek-a-Boo view-Angola by the bay
Peek-a-Boo view-Angola by the bay
House
Lewes, DE, USA
5.4k from 2nd Time Designs center

Parking, Sports/Activities, Oceanfront, View, Internet, Breakfast, Child Friendly

1 Bedroom15 Guests
New to Booking
$323
Average price / night
Check Availability
The Peninsula  0n the Indian river Bay, near Lewes, Rehobeth, Dewey Beach.
The Peninsula 0n the Indian river Bay, near Lewes, Rehobeth, Dewey Beach.
Condo
Milsboro, DE, 19966, United States
3.2k from 2nd Time Designs center

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

2 Bedrooms4 Guests
9.4

Superb

42 reviews

$316
Average price / night
Check Availability
Luxury 6BR Peninsula Estate - 5,000 Sqft • 6.5 Baths • EV Charger • Linen
Luxury 6BR Peninsula Estate - 5,000 Sqft • 6.5 Baths • EV Charger • Linen
House
Millsboro, DE, 19966, United States
3.4k from 2nd Time Designs center

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

6 Bedrooms14 Guests
10.0

Exceptional

15 reviews

$716
Average price / night
Check Availability
Deck & Indian River Bay Views: Coastal Cottage
Deck & Indian River Bay Views: Coastal Cottage
Cottage
Millsboro, DE, 19966, United States
3.5k from 2nd Time Designs center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Kitchen, Laundry, Microwave

2 Bedrooms7 Guests
9.0

Fabulous

14 reviews

$267
Average price / night
Check Availability
Beautiful Family Vacation Home. The Peninsula - Exclusive 5 Star Gated Community
Beautiful Family Vacation Home. The Peninsula - Exclusive 5 Star Gated Community
House
Millsboro, DE, 19966, United States
3.5k from 2nd Time Designs center

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

6 Bedrooms12 Guests
10.0

Exceptional

15 reviews

$739
Average price / night
Check Availability
New Listing!  Osocozy.  Waterfront home on the Indian River Bay.  Lovely views!
New Listing! Osocozy. Waterfront home on the Indian River Bay. Lovely views!
House
Millsboro, DE, 19966, United States
3.5k from 2nd Time Designs center

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

3 Bedrooms7 Guests
10.0

Exceptional

19 reviews

$407
Average price / night
Check Availability
Stunning-waterfront, beach, pools, family fun
Stunning-waterfront, beach, pools, family fun
House
Long Neck, DE, 19966, United States
4.1k from 2nd Time Designs center

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

4 Bedrooms10 Guests
9.6

Exceptional

12 reviews

$699
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 2nd Time Designs.

Where to stay in 2nd Time Designs? Best neighborhoods & areas

2nd Time Designs Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 146 verified family-friendly vacation rentals in 2nd Time Designs. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in 2nd Time Designs vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $177 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in 2nd Time Designs 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 2nd Time Designs 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 2nd Time Designs often include amenities such as Child Friendly, Fireplace/Heating, and Laundry. 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.