Vacation Rentals with Private Pool in Pilot Point, DE: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Delaware

  5.  Rehoboth Beach
  6.  Pilot Point

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175 Best Vacation Rentals with Private Pool in Pilot Point (Starting from $128)

Kinsale Glen - 12 Kenmare Way
Kinsale Glen - 12 Kenmare Way
House
Rehoboth Beach, DE, USA
8.3k from Pilot Point center

Internet, Air Conditioner, Tv, Child Friendly, Laundry, Pool, Parking

4 Bedrooms10 Guests
New to Booking
$663
Average price / night
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111 Rodaline Avenue - in-town Lewes with a private pool!
111 Rodaline Avenue - in-town Lewes with a private pool!
House
Lewes, DE, 19958, United States
1.4k from Pilot Point center

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

4 Bedrooms10 Guests
New to Booking
$659
Average price / night
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Coastal Club --- 33718 Freeport Dr.
Coastal Club --- 33718 Freeport Dr.
House
Lewes, DE, USA
8.5k from Pilot Point center

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

3 Bedrooms8 Guests
New to Booking
$351
Average price / night
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JUST RELEASED...SPECTACULAR SUNSETS- WATERFRONT 2- BED/ 2- BATH CONDO\nPOOL/WIFI
JUST RELEASED...SPECTACULAR SUNSETS- WATERFRONT 2- BED/ 2- BATH CONDO\nPOOL/WIFI
Condo
Lewes, DE, 19958, United States
1.4k from Pilot Point center

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

2 Bedrooms5 Guests
9.4

Superb

24 reviews

$372
Average price / night
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LEWES BEACH-WATERFRONT GETAWAY...WONDERFUL 2-BED/2-BA...POOL-WIFI- LARGE BALCONY
LEWES BEACH-WATERFRONT GETAWAY...WONDERFUL 2-BED/2-BA...POOL-WIFI- LARGE BALCONY
Condo
Lewes, DE, 19958, United States
1.4k from Pilot Point center

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

2 Bedrooms5 Guests
9.6

Exceptional

19 reviews

$367
Average price / night
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NEW! CASA BLANCO  A Modern Sanctuary @ Lewes Beach + Canal + Historic Downtown \n
NEW! CASA BLANCO A Modern Sanctuary @ Lewes Beach + Canal + Historic Downtown \n
House
Lewes, DE, 19958, United States
1.5k from Pilot Point center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$847
Average price / night
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Beautiful, Spacious 4BR,Steps to the Beach,Pool & State Park
Beautiful, Spacious 4BR,Steps to the Beach,Pool & State Park
House
Lewes, DE, 19958, United States
1.5k from Pilot Point center

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

4 Bedrooms10 Guests
9.8

Exceptional

36 reviews

$1047
Average price / night
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Pure Elegance in Historic, Downtown Lewes
Pure Elegance in Historic, Downtown Lewes
House
Lewes, DE, 19958, United States
1.7k from Pilot Point center

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

6 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$1002
Average price / night
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340 Market - in town Lewes with Private Pool!
340 Market - in town Lewes with Private Pool!
House
Lewes, DE, 19958, United States
1.9k from Pilot Point center

AC, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms10 Guests
7.4

Good

3 reviews

$764
Average price / night
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Private Oasis in Downtown Lewes
Private Oasis in Downtown Lewes
House
Lewes, DE, 19958, United States
1.9k from Pilot Point center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Heater, Hot Tub, Internet, Laundry

6 Bedrooms12 Guests
10.0

Exceptional

3 reviews

$1169
Average price / night
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409 Paynter Avenue - In town Lewes with a private pool!
409 Paynter Avenue - In town Lewes with a private pool!
House
Lewes, DE, 19958, United States
2.1k from Pilot Point center

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

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$543
Average price / night
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UPDATED KITCHEN COMING SPRING 2026 Private Heated Pool, Game Room, and Pet Friendly
UPDATED KITCHEN COMING SPRING 2026 Private Heated Pool, Game Room, and Pet Friendly
House
Lewes, DE, 19958, United States
2.3k from Pilot Point center

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

4 Bedrooms14 Guests
8.2

Very Good

34 reviews

$579
Average price / night
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New Construction in-town Lewes with private pool!
New Construction in-town Lewes with private pool!
House
Lewes, DE, 19958, United States
2.4k from Pilot Point center

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

5 Bedrooms12 Guests
9.8

Exceptional

8 reviews

$1203
Average price / night
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Town of Lewes home with private pool, patio and balcony
Town of Lewes home with private pool, patio and balcony
House
Lewes, DE, 19958, United States
2.8k from Pilot Point center

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

6 Bedrooms14 Guests
10.0

Exceptional

10 reviews

$880
Average price / night
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12 Canary Dr- Lewes vacation rental with private pool and outdoor entertaining1
12 Canary Dr- Lewes vacation rental with private pool and outdoor entertaining1
House
Lewes, DE, 19958, United States
2.9k from Pilot Point center

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

4 Bedrooms8 Guests
New to Booking
$454
Average price / night
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Private Oasis Midway Between Historic Lewes And Rehoboth Beach
Private Oasis Midway Between Historic Lewes And Rehoboth Beach
House
Rehoboth Beach, DE, 19971, United States
4.4k from Pilot Point center

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

4 Bedrooms10 Guests
9.6

Exceptional

18 reviews

$426
Average price / night
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Newly Renovated Rancher Close to Restaurants and Midway Park
Newly Renovated Rancher Close to Restaurants and Midway Park
House
Rehoboth Beach, DE, 19971, United States
5.1k from Pilot Point center

AC, Barbecue, Dryer, Free Parking, Internet, Laundry, Microwave, No Smoking, Pool

3 Bedrooms6 Guests
8.0

Good

2 reviews

$382
Average price / night
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Family Home w/ Private Pool & Hot Tub in Lewes
Family Home w/ Private Pool & Hot Tub in Lewes
House
Lewes, DE, 19958, United States
5.1k from Pilot Point center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Kitchen, Laundry, Microwave

3 Bedrooms9 Guests
7.6

Good

5 reviews

$399
Average price / night
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4 Bed Townhome in Lewes/Rehoboth with Community Pool\n
4 Bed Townhome in Lewes/Rehoboth with Community Pool\n
House
Lewes, DE, 19958, United States
5.2k from Pilot Point center

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

4 Bedrooms10 Guests
10.0

Exceptional

98 reviews

$352
Average price / night
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Designer Lewes Beach Home w/ Private Pool - New Luxury
Designer Lewes Beach Home w/ Private Pool - New Luxury
House
Sussex County, DE, 19958, United States
5.2k from Pilot Point center

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

5 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$822
Average price / night
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Lots Of Room--Main House And Cottage With Pool (Sleeps 12)
Lots Of Room--Main House And Cottage With Pool (Sleeps 12)
House
Rehoboth Beach, DE, 19971, United States
5.4k from Pilot Point center

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

6 Bedrooms12 Guests
10.0

Exceptional

87 reviews

$523
Average price / night
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Spacious Coastal Home! Large game room, private pool, 5 minutes to beach!
Spacious Coastal Home! Large game room, private pool, 5 minutes to beach!
House
Lewes, DE, 19958, United States
5.6k from Pilot Point center

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

5 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$1015
Average price / night
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Spacious & Cozy 3BR/2.5BA in Rehoboth/Lewes Townhouse! Summer 2025 OPEN!
Spacious & Cozy 3BR/2.5BA in Rehoboth/Lewes Townhouse! Summer 2025 OPEN!
House
Lewes, DE, 19971, United States
5.7k from Pilot Point center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.6

Exceptional

4 reviews

$302
Average price / night
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Stunning Canal-Front Home in North Shores with Private Pool & Elevator!
Stunning Canal-Front Home in North Shores with Private Pool & Elevator!
House
Rehoboth Beach, DE, 19971, United States
5.8k from Pilot Point center

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

5 Bedrooms10 Guests
New to Booking
$1737
Average price / night
Check Availability
5BR, Private Pool, Off Bike Trail, 4 miles to Beach
5BR, Private Pool, Off Bike Trail, 4 miles to Beach
House
Lewes, DE, 19958, United States
5.9k from Pilot Point center

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

5 Bedrooms8 Guests
9.8

Exceptional

26 reviews

$693
Average price / night
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Let the fun begin 🏖🏊‍♀️😁<br>Located between both beaches
Let the fun begin 🏖🏊‍♀️😁<br>Located between both beaches
Condo
Rehoboth, DE, 19971, United States
6.0k from Pilot Point center

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

2 Bedrooms5 Guests
9.8

Exceptional

10 reviews

$128
Average price / night
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Luxury Beachside Escape w/ Private Pool, Elevator, & Ocean Views!
Luxury Beachside Escape w/ Private Pool, Elevator, & Ocean Views!
Cottage
Rehoboth Beach, DE, 19971, United States
6.1k from Pilot Point center

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

7 Bedrooms19 Guests
New to Booking
$2970
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 Vacation Rentals with Private Pool in Pilot Point.

Stay Near Pilot Point's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Pilot Point Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 175 verified vacation rentals with a private pool in Pilot Point. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Pilot Point vary depending on the property size, location, and travel season. Rates typically start from around $128 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Pilot Point also welcome pets. Currently, 11 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Pilot Point often include additional features such as Pool, Private Pool, and Laundry. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Pilot Point include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.