Family-Friendly Vacation Rentals in Villages of Five Points, DE: Compare 10+ Sites & Save

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770 Best Family Vacation Rentals in Villages of Five Points (Starting from $136)

Village of Five Points - 33322 E Chesapeake St UNIT 46
Village of Five Points - 33322 E Chesapeake St UNIT 46
Apartment
Lewes, DE, USA
0.1k from Villages of Five Points center

Apartments, Accommodations, Pools, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$533
Average price / night
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4 Mi to Beaches: Luxe Coastal Resort Condo
4 Mi to Beaches: Luxe Coastal Resort Condo
Condo
Lewes, DE, 19958, United States
0.1k from Villages of Five Points center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.6

Exceptional

35 reviews

$294
Average price / night
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Village of Five Points - 17046 N Brandt St
Village of Five Points - 17046 N Brandt St
Apartment
Lewes, DE, USA
0.1k from Villages of Five Points center

Apartments, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$265
Average price / night
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Rehoboth/Lewes Condo-Many Amenities(Dog Friendly)
Rehoboth/Lewes Condo-Many Amenities(Dog Friendly)
Condo
Lewes, DE, 19958, United States
0.1k from Villages of Five Points center

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

2 Bedrooms4 Guests
9.8

Exceptional

46 reviews

$280
Average price / night
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Village of Five Points - 17059 S Brandt St Unit 3108
Village of Five Points - 17059 S Brandt St Unit 3108
Apartment
Lewes, DE, USA
0.1k from Villages of Five Points center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay

2 Bedrooms4 Guests
8.0

Good

2 reviews

$541
Average price / night
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Porch & Community Perks: Walkable Lewes Condo
Porch & Community Perks: Walkable Lewes Condo
Condo
Lewes, DE, 19958, United States
0.1k from Villages of Five Points center

AC, Balcony, Crib, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.2

Superb

43 reviews

$264
Average price / night
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The Villages of Five Points - 17059 S Brandt St. Unit 3306
The Villages of Five Points - 17059 S Brandt St. Unit 3306
Apartment
Lewes, DE, USA
0.1k from Villages of Five Points center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$221
Average price / night
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Awesome 3 BR Condo in Village of 5 Points! POOL,TENNIS CTS,BIKE TRL,
Awesome 3 BR Condo in Village of 5 Points! POOL,TENNIS CTS,BIKE TRL,
Condo
Lewes, DE, 19958, United States
0.2k from Villages of Five Points center

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

3 Bedrooms6 Guests
10.0

Exceptional

42 reviews

$289
Average price / night
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Villages of Five Points Townhouse, Now Renting for 2026!
Villages of Five Points Townhouse, Now Renting for 2026!
House
Lewes, DE, 19958, United States
0.2k from Villages of Five Points center

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

3 Bedrooms8 Guests
10.0

Exceptional

55 reviews

$187
Average price / night
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Porch and Community Perks Walkable Lewes Condo
Porch and Community Perks Walkable Lewes Condo
Apartment
Lewes, DE, USA
0.1k from Villages of Five Points center

Apartments, Cheap, Accommodations, Pools, Parking, Spa, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
6.5

Good

2 reviews

$393
Average price / night
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Pet Friendly Pond view condo close to the beach and historic downtown Lewes
Pet Friendly Pond view condo close to the beach and historic downtown Lewes
Condo
Lewes, DE, 19958, United States
0.3k from Villages of Five Points center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$136
Average price / night
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Villages of Five Points - 17279 N Village Main Blvd.
Villages of Five Points - 17279 N Village Main Blvd.
House
Lewes, DE, USA
0.2k from Villages of Five Points center

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

3 Bedrooms7 Guests
New to Booking
$437
Average price / night
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Minutes to Lewes Beach
Minutes to Lewes Beach
Condo
Lewes, DE, 19958, United States
0.3k from Villages of Five Points center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

14 reviews

$217
Average price / night
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4 Mi to Beaches Pet-Friendly Lewes Condo!
4 Mi to Beaches Pet-Friendly Lewes Condo!
Apartment
Lewes, DE, USA
0.2k from Villages of Five Points center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms5 Guests
9.7

Exceptional

4 reviews

$189
Average price / night
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1st Floor Beach-town Condo. We are Pet Friendly!
1st Floor Beach-town Condo. We are Pet Friendly!
Condo
Lewes, DE, 19958, United States
0.3k from Villages of Five Points center

AC, Crib, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.8

Exceptional

35 reviews

$290
Average price / night
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The Villages of Five Points - 17405 N Village Main Blvd
The Villages of Five Points - 17405 N Village Main Blvd
House
Lewes, DE, USA
0.2k from Villages of Five Points center

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

3 Bedrooms8 Guests
New to Booking
$404
Average price / night
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Welcome to The Savannah Suite!  Renovated 3 bedroom apartment in charming Lewes.
Welcome to The Savannah Suite! Renovated 3 bedroom apartment in charming Lewes.
Apartment
Lewes, DE, 19958, United States
0.6k from Villages of Five Points center

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

3 Bedrooms8 Guests
New to Booking
$303
Average price / night
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The Villages of Five Points - 17228 Chatham St
The Villages of Five Points - 17228 Chatham St
Apartment
Lewes, DE, USA
0.3k from Villages of Five Points center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$403
Average price / night
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🏖️ Reservations for Spring and Summer 2026 are now open!
🏖️ Reservations for Spring and Summer 2026 are now open!
House
Lewes, DE, 19958, United States
1.0k from Villages of Five Points center

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

4 Bedrooms10 Guests
9.8

Exceptional

46 reviews

$186
Average price / night
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Crow's Nest - Private Guest Apt Near Bike Trail/3.7 mi to Beach
Crow's Nest - Private Guest Apt Near Bike Trail/3.7 mi to Beach
Apartment
Lewes, DE, USA
0.8k from Villages of Five Points center

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

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$297
Average price / night
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Spacious Oasis in Lewes minutes from the Beach, State Park, and Trail
Spacious Oasis in Lewes minutes from the Beach, State Park, and Trail
House
Lewes, DE, 19958, United States
1.0k from Villages of Five Points center

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

3 Bedrooms10 Guests
10.0

Exceptional

24 reviews

$254
Average price / night
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Fenced yard, game room, community pool & close to Rehoboth/Lewes attractions!
Fenced yard, game room, community pool & close to Rehoboth/Lewes attractions!
House
Lewes, DE, 19958, United States
1.1k from Villages of Five Points center

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

3 Bedrooms7 Guests
10.0

Exceptional

19 reviews

$403
Average price / night
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Bay-n-Beach! Comfy Coastal Condo in Lewes!
Bay-n-Beach! Comfy Coastal Condo in Lewes!
Condo
Lewes, DE, 19958, United States
1.2k from Villages of Five Points center

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

3 Bedrooms8 Guests
New to Booking
$366
Average price / night
Check Availability
Newly furnished, large, bright, beach house in the heart of it all!
Newly furnished, large, bright, beach house in the heart of it all!
House
Lewes, DE, 19958, United States
1.2k from Villages of Five Points center

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

3 Bedrooms10 Guests
9.6

Exceptional

35 reviews

$364
Average price / night
Check Availability
Renovated & Spacious Retreat on East Rt 1 – Pool, Bike Trails, Rehoboth Parking!
Renovated & Spacious Retreat on East Rt 1 – Pool, Bike Trails, Rehoboth Parking!
House
Lewes, DE, 19958, United States
1.2k from Villages of Five Points center

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

3 Bedrooms7 Guests
10.0

Exceptional

33 reviews

$329
Average price / night
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Coastal retreat close to beaches, bike trails and historic downtown Lewes
Coastal retreat close to beaches, bike trails and historic downtown Lewes
House
Lewes, DE, 19958, United States
1.2k from Villages of Five Points center

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

3 Bedrooms6 Guests
10.0

Exceptional

66 reviews

$252
Average price / night
Check Availability
3 Mi to Savannah Beach: Lewes Condo w/ Pool Access
3 Mi to Savannah Beach: Lewes Condo w/ Pool Access
Condo
Lewes, DE, 19958, United States
1.3k from Villages of Five Points center

AC, Crib, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms5 Guests
10.0

Exceptional

8 reviews

$236
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 Villages of Five Points.

Stay Near Villages of Five Points's Top Attractions

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Villages of Five Points Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 770 verified family-friendly vacation rentals in Villages of Five Points. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Villages of Five Points vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $136 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Villages of Five Points 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 Villages of Five Points 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 Villages of Five Points 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.