Vacation Rentals with Pool in Cape Windsor, DE: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Delaware

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  6.  Cape Windsor

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3618 Best Vacation Rentals with Pool in Cape Windsor (Starting from $132)

Fire Pit and Views Canal-Front Fenwick Island Home
Fire Pit and Views Canal-Front Fenwick Island Home
House
Selbyville, DE, USA
0.3k from Cape Windsor center

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

3 Bedrooms10 Guests
New to Booking
$383
Average price / night
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Cozy Bay View Condo in Ocean City MD
Cozy Bay View Condo in Ocean City MD
Condo
Ocean City, MD, 21842, United States
0.7k from Cape Windsor center

AC, Dryer, Free Parking, Heater, Laundry, Microwave, No Smoking, Pool, TV

3 Bedrooms8 Guests
New to Booking
$239
Average price / night
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Near Beaches and Shops Canal-Front Selbyville Home
Near Beaches and Shops Canal-Front Selbyville Home
House
Selbyville, DE, USA
0.4k from Cape Windsor center

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

3 Bedrooms6 Guests
New to Booking
$592
Average price / night
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MADISON BAY BEACH GETAWAY-PRIVATE POOL-HOT TUB- FIRE PIT- WEEKLY STAY DISCOUNT
MADISON BAY BEACH GETAWAY-PRIVATE POOL-HOT TUB- FIRE PIT- WEEKLY STAY DISCOUNT
House
Ocean City, MD, 21842, United States
0.7k from Cape Windsor center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms12 Guests
10.0

Exceptional

12 reviews

$1201
Average price / night
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Verandah Bay - 38900 Verandah Bay Drive
Verandah Bay - 38900 Verandah Bay Drive
House
Selbyville, DE, USA
0.6k from Cape Windsor center

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

6 Bedrooms12 Guests
New to Booking
$1006
Average price / night
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Best in show at the beach
Best in show at the beach
House
Ocean City, MD, 21842, United States
0.7k from Cape Windsor center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Patio, Pool, Washer

4 Bedrooms10 Guests
New to Booking
$1588
Average price / night
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Bay Breeze - 38875 Madison Ave Unit #1 Lighthouse Cove
Bay Breeze - 38875 Madison Ave Unit #1 Lighthouse Cove
House
Selbyville, DE, USA
0.8k from Cape Windsor center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$348
Average price / night
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Town House on the Bay with Water Views and Pool!
Town House on the Bay with Water Views and Pool!
House
Ocean City, MD, 21842, United States
0.8k from Cape Windsor center

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

3 Bedrooms6 Guests
9.8

Exceptional

29 reviews

$274
Average price / night
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East of the Sun - 39620 E Sun Dr #717
East of the Sun - 39620 E Sun Dr #717
Apartment
Fenwick Island, DE, USA
1.2k from Cape Windsor center

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

1 Bedroom8 Guests
New to Booking
$282
Average price / night
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Waterfront Fenwick Island Pool, Dock, Kayaks, King Bed 3 Balconies Min to Beach
Waterfront Fenwick Island Pool, Dock, Kayaks, King Bed 3 Balconies Min to Beach
House
Selbyville, DE, 19975, United States
0.8k from Cape Windsor center

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

4 Bedrooms7 Guests
10.0

Exceptional

40 reviews

$425
Average price / night
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East of the Sun - 39620 East Sun Drive #726
East of the Sun - 39620 East Sun Drive #726
Apartment
Fenwick Island, USA
1.2k from Cape Windsor center

Apartments, Accommodations, Pools, Lodgings, Places to stay

3 Bedrooms7 Guests
4.5

Review score

2 reviews

$148
Average price / night
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Fenwick Paradise Beach Villa-<br>Beautiful Bayfront  Condo .9<br>Miles From The Beach<br>
Fenwick Paradise Beach Villa-<br>Beautiful Bayfront Condo .9<br>Miles From The Beach<br>
Condo
Selbyville, DE, 19975, United States
0.9k from Cape Windsor center

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

3 Bedrooms7 Guests
9.8

Exceptional

34 reviews

$514
Average price / night
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East of the Sun - 40026 E Sun Dr Unit 611
East of the Sun - 40026 E Sun Dr Unit 611
Apartment
Cape Windsor, Selbyville, Delaware, USA
1.2k from Cape Windsor center

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

3 Bedrooms6 Guests
9.4

Superb

8 reviews

$132
Average price / night
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Ocean City Escape, Waterfront,  Pool,  Dock, Beach, Walk to Restaurants
Ocean City Escape, Waterfront, Pool, Dock, Beach, Walk to Restaurants
House
Ocean City, MD, 21842, United States
1.0k from Cape Windsor center

AC, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry, No Smoking

3 Bedrooms10 Guests
9.0

Fabulous

2 reviews

$392
Average price / night
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Laguna Bay - 37292 Lighthouse #201
Laguna Bay - 37292 Lighthouse #201
Apartment
Selbyville, DE, USA
1.2k from Cape Windsor center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay, Accessible hotels

3 Bedrooms6 Guests
8.0

Good

2 reviews

$497
Average price / night
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Fenwick Island DE or Ocean City MD Charming Coastal Comfort at the Beach
Fenwick Island DE or Ocean City MD Charming Coastal Comfort at the Beach
Condo
Fenwick Island, DE, 19944, United States
1.1k from Cape Windsor center

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

2 Bedrooms6 Guests
New to Booking
$213
Average price / night
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East of the Sun - 39620 E Sun Drive #715
East of the Sun - 39620 E Sun Drive #715
Apartment
Fenwick Island, DE, USA
1.2k from Cape Windsor center

Balcony/Terrace, Restaurant, Air Conditioner, Sports/Activities, Laundry, Pool, Fireplace/Heating

2 Bedrooms6 Guests
4.0

Review score

1 reviews

$196
Average price / night
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Calm, water-view bayfront condo w/ cathedral ceilings, balconies, & private dock
Calm, water-view bayfront condo w/ cathedral ceilings, balconies, & private dock
Condo
Selbyville, DE, 19975, United States
1.2k from Cape Windsor center

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

4 Bedrooms9 Guests
9.8

Exceptional

10 reviews

$394
Average price / night
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Montego Bay Bliss
Montego Bay Bliss
House
MD, USA
1.3k from Cape Windsor center

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

3 Bedrooms6 Guests
New to Booking
$356
Average price / night
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Serenity Now - Enjoy a relaxing vacation poolside in North Ocean City MD
Serenity Now - Enjoy a relaxing vacation poolside in North Ocean City MD
Condo
Ocean City, MD, 21842, United States
1.2k from Cape Windsor center

AC, Dryer, Free Parking, Heater, Laundry, Microwave, No Smoking, Pool, TV

2 Bedrooms6 Guests
New to Booking
$263
Average price / night
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Laguna Bay --- 37286 Lighthouse #207
Laguna Bay --- 37286 Lighthouse #207
Apartment
Cape Windsor, Selbyville, Delaware, USA
1.3k from Cape Windsor center

Apartments, Accommodations, Pools, Parking, Lodgings, Flats, Places to stay, Family

3 Bedrooms6 Guests
New to Booking
$452
Average price / night
Check Availability
Fenwick Island Getaway Unit 728
Fenwick Island Getaway Unit 728
Condo
Selbyville, DE, 19975, United States
1.2k from Cape Windsor center

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

3 Bedrooms8 Guests
9.6

Exceptional

32 reviews

$245
Average price / night
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BAY FRONT HOME WITH AMAZING VIEWS.  MINUTES TO THE BEACH AND STEPS TO THE POOL
BAY FRONT HOME WITH AMAZING VIEWS. MINUTES TO THE BEACH AND STEPS TO THE POOL
House
Fenwick Island, DE, 19944, United States
1.4k from Cape Windsor center

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

5 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$669
Average price / night
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Luxurious Townhouse with water views and access in Fenwick Island.  Sleeps 8-10
Luxurious Townhouse with water views and access in Fenwick Island. Sleeps 8-10
House
Fenwick Island, DE, 19944, United States
1.4k from Cape Windsor center

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

4 Bedrooms10 Guests
9.8

Exceptional

21 reviews

$565
Average price / night
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2BR 2BA Quiet North OCMD Condo+Hot Tub+Beach+Pool
2BR 2BA Quiet North OCMD Condo+Hot Tub+Beach+Pool
Condo
Ocean City, MD, 21842, United States
1.5k from Cape Windsor center

AC, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$354
Average price / night
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Keen-Wik on the Bay bay front home w/private pool & hot tub
Keen-Wik on the Bay bay front home w/private pool & hot tub
House
Selbyville, DE, 19975, United States
1.5k from Cape Windsor center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Kitchen

5 Bedrooms10 Guests
New to Booking
$704
Average price / night
Check Availability
Bayside Resort * New Listing * Breathtaking Luxury Beach House w 6BR, 4.5 Baths,
Bayside Resort * New Listing * Breathtaking Luxury Beach House w 6BR, 4.5 Baths,
House
Selbyville, DE, 19975, United States
1.5k from Cape Windsor center

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

7 Bedrooms14 Guests
New to Booking
$705
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 Cape Windsor.

Where to stay in Cape Windsor? Best neighborhoods & areas

Cape Windsor Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 3618 verified vacation rentals with a pool in Cape Windsor. 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 Cape Windsor vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $132 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Cape Windsor 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 Cape Windsor welcome pets. Currently, 11 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 Cape Windsor 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 Cape Windsor 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.