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

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

  4.  Delaware

  5.  Rehoboth Beach
  6.  Pilot Point

Refine your search

Price per night

Amenity Filter

Rating

666 Best Vacation Rentals with Pool in Pilot Point (Starting from $185)

Cape Shores 520 East Cape Shores Dr
Cape Shores 520 East Cape Shores Dr
House
Lewes, DE, USA
1.7k from Pilot Point center

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

5 Bedrooms12 Guests
New to Booking
$1008
Average price / night
Check Availability
STEPS To The Beach, In Sought After Cape Shores With Private Pier
STEPS To The Beach, In Sought After Cape Shores With Private Pier
House
Lewes, DE, 19958, United States
0.9k from Pilot Point center

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

5 Bedrooms10 Guests
10.0

Exceptional

91 reviews

$545
Average price / night
Check Availability
Town of Lewes - 132 New Rd.
Town of Lewes - 132 New Rd.
House
DE, USA
2.8k from Pilot Point center

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

6 Bedrooms14 Guests
New to Booking
$1067
Average price / night
Check Availability
3 bedroom, 2.5 bath unit - Ocean, bay and pool all in a day!
3 bedroom, 2.5 bath unit - Ocean, bay and pool all in a day!
House
Lewes, DE, 19958, United States
1.0k from Pilot Point center

AC, Barbecue, Free Parking, Internet, Kitchen, Microwave, No Smoking, Patio, Pool

3 Bedrooms8 Guests
9.4

Superb

25 reviews

$338
Average price / night
Check Availability
Pool, Game Room Luxe Lewes Family Beach House!
Pool, Game Room Luxe Lewes Family Beach House!
House
Lewes, DE, USA
3.3k from Pilot Point center

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

3 Bedrooms8 Guests
5.1

Review score

10 reviews

$575
Average price / night
Check Availability
NEW 7-bed with PRIVATE HEATED POOL! Lewes Beach Hideaway, steps to beach & town!
NEW 7-bed with PRIVATE HEATED POOL! Lewes Beach Hideaway, steps to beach & town!
House
Lewes, DE, 19958, United States
1.2k from Pilot Point center

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

7 Bedrooms18 Guests
New to Booking
$1225
Average price / night
Check Availability
Villas at Bay Crossing - 34682 Villa Circle Unit #4308
Villas at Bay Crossing - 34682 Villa Circle Unit #4308
Apartment
Lewes, DE, USA
4.7k from Pilot Point center

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

2 Bedrooms6 Guests
New to Booking
$507
Average price / night
Check Availability
3-bedroom townhome in Lewes, walk to beach and town
3-bedroom townhome in Lewes, walk to beach and town
House
Lewes, DE, 19958, United States
1.2k from Pilot Point center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$327
Average price / night
Check Availability
Villas at Bay Crossing - 34682 Villa Cir, Unit #4105
Villas at Bay Crossing - 34682 Villa Cir, Unit #4105
Apartment
Lewes, DE, USA
4.8k from Pilot Point center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
9.5

Superb

16 reviews

$502
Average price / night
Check Availability
Cape Shores: Lewes Bay beach, pool, fishing pier, tennis/ pickleball courts
Cape Shores: Lewes Bay beach, pool, fishing pier, tennis/ pickleball courts
House
Lewes, DE, 19958, United States
1.3k from Pilot Point center

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

4 Bedrooms10 Guests
10.0

Exceptional

94 reviews

$797
Average price / night
Check Availability
Villas at Bay Crossing - 34670 Villa Cir, Unit 2207
Villas at Bay Crossing - 34670 Villa Cir, Unit 2207
Apartment
Lewes, DE, USA
4.8k from Pilot Point center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
8.9

Fabulous

12 reviews

$540
Average price / night
Check Availability
Cape Shores Luxury - Brand NEW 2024 Pool, Beach, Private Fishing Pier, Park!
Cape Shores Luxury - Brand NEW 2024 Pool, Beach, Private Fishing Pier, Park!
House
Lewes, DE, 19958, United States
1.3k from Pilot Point center

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

4 Bedrooms10 Guests
10.0

Exceptional

27 reviews

$1013
Average price / night
Check Availability
Community Pool and Private Balcony Chic Lewes Gem
Community Pool and Private Balcony Chic Lewes Gem
Apartment
Lewes, DE, USA
4.8k from Pilot Point center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay, Condos

2 Bedrooms4 Guests
6.4

Good

5 reviews

$376
Average price / night
Check Availability
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
Check Availability
Villas at Bay Crossing - 34670 Villa Circle #2206
Villas at Bay Crossing - 34670 Villa Circle #2206
Apartment
Lewes, DE, USA
4.8k from Pilot Point center

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

2 Bedrooms5 Guests
9.8

Exceptional

4 reviews

$185
Average price / night
Check Availability
Waterfront, walkable to beach and downtown Lewes attractions
Waterfront, walkable to beach and downtown Lewes attractions
Condo
Lewes Beach, DE, 19958, United States
1.4k from Pilot Point center

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

2 Bedrooms6 Guests
9.8

Exceptional

185 reviews

$312
Average price / night
Check Availability
Charming Lewes-Rehoboth Retreat, Pet Friendly
Charming Lewes-Rehoboth Retreat, Pet Friendly
House
Lewes, DE, USA
4.8k from Pilot Point center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$250
Average price / night
Check Availability
Relax & Unwind - Charming 2 Bedroom/2 Bath Condo with Screened in Porch
Relax & Unwind - Charming 2 Bedroom/2 Bath Condo with Screened in Porch
Condo
Lewes, DE, 19958, United States
1.4k from Pilot Point center

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

2 Bedrooms7 Guests
9.8

Exceptional

52 reviews

$241
Average price / night
Check Availability
4 Mi to Beach Lewes Townhome with Ping-Pong Table
4 Mi to Beach Lewes Townhome with Ping-Pong Table
House
Lewes, DE, USA
4.8k from Pilot Point center

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

3 Bedrooms7 Guests
New to Booking
$427
Average price / night
Check Availability
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
Check Availability
Villas at Bay Crossing - 34670 Villa Circle Unit #2304
Villas at Bay Crossing - 34670 Villa Circle Unit #2304
Apartment
Lewes, USA
4.8k from Pilot Point center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay, Family

2 Bedrooms7 Guests
9.7

Exceptional

20 reviews

$442
Average price / night
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
☀️Cozy Canalside Retreat ⚓️
☀️Cozy Canalside Retreat ⚓️
Condo
Lewes, DE, 19958, United States
1.5k from Pilot Point center

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

2 Bedrooms4 Guests
9.2

Superb

43 reviews

$211
Average price / night
Check Availability
Coastal Club * 6BR New Twin Vacation Home w 3.5 Baths, Sleeps up to 14
Coastal Club * 6BR New Twin Vacation Home w 3.5 Baths, Sleeps up to 14
House
Lewes, DE, 19958, United States
1.6k from Pilot Point center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

6 Bedrooms14 Guests
9.6

Exceptional

15 reviews

$473
Average price / night
Check Availability
COASTAL CLUB * 5BR LUXURY BEACH HOUSE w 3 Full Baths, 2 - ½  Baths   * Sleeps 12
COASTAL CLUB * 5BR LUXURY BEACH HOUSE w 3 Full Baths, 2 - ½ Baths * Sleeps 12
House
LEWES, DE, 19958, United States
1.6k from Pilot Point center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
9.8

Exceptional

18 reviews

$461
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 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 Pool on the Map

Frequently Asked Questions

You can explore 666 verified vacation rentals with a pool in Pilot Point. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Pilot Point vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $185 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Pilot Point offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Pilot Point welcome pets. Currently, 24 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Pilot Point often include additional outdoor features such as Pool, Fireplace/Heating, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Pilot Point offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.