Dewey Beach Rentals with Pools

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223 house rentals in Dewey Beach with pools

Ocean Block Town Home with Two Pools with 2021 Renovations and Free Activities.

Dewey Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 7 minutes

Match: Swimming pool

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Price per night from

$585

Dewey Beach Condo at Opal with pool!!

Dewey Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 29 minutes

Match: Swimming pool

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Price per night from

$487

Great rentals within 20 miles that match your search

Beach Rental Condo

Bethany Beach condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$279

Magnificent Ocean Front Unit

Ocean City apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Ocean City, MD” Our family had a great time! Plenty to do with young adults. Beautiful view of the beach. Owner is pleasant and answers immediately.

Match: Swimming pool

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Price per night from

$287

Sea Watch 1319

Ocean City apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 3 minutes

Match: Swimming pool

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Price per night from

$158

“Beautiful condo on the ocean!” This ocean front, 16 story high, condo not only has a great view, but is so beautifully decorated on the inside as well! The location is perfect because on 99th street, you are just outside of the noisy part of Ocean City and the beaches aren't as crowded as the lower numbered streets, but you're still close enough to hop on the bus or drive to the boardwalk. The building was never crowded and it felt more like a home than a vacation destination. Besides the condo itself, the owner, Wendy, is so beyond nice and helpful with very quick communication before, during, and after the trip. I highly recommend choosing this location for a really spectacular beach trip!

Responds fast! avg. 2 hours 22 minutes

Match: Swimming pool

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Price per night from

$287

Gorgeous Direct Oceanfront Condo, 3BR/2 BA !!!

Ocean City condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 4 minutes

Match: Swimming pool

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Price per night from

$458

Sally's Sandcastle 4 Blocks To Bethany Beach!

Bethany Beach townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$229

LORELEI II Beach & Bay

Ocean City condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Lorelei II Ocean City MD condo” We would like to thank you for allowing us to rent your Ocean City condo. The drive can be hectic, but we arrived to comfortable, clean and well-appointed living spaces. It was a beautiful and spacious; plenty of room for our family to all gather together or relax in their own bedroom spaces. The kitchen had everything we needed for our stay; complete with the “little things" like salt and pepper, pizza cutter, etc. The unit also had the convenience of getting some much needed laundry done, especially after a few "salty" days at the beach or a dip in the pool. The televisions and WiFi came in handy for that one rainy ‘do activities indoors’ day. The unit is true to the photos and video you have online. Again, we had a wonderful time in Ocean City and your home was an excellent place to stay. We look forward to renting from you again in the future.

Match: Swimming pool

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Price per night from

$360

Victorian Beach House. 300ft to the beach.

Cape May house

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 22

Match: Swimming pool

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Price per night from

$2,862

Sea Colony West- 3 Blocks to Beach!

Bethany Beach townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$344

Contemporary upgraded sophisticated beach condo

Ocean City condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 44 minutes

Match: Swimming pool

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Price per night from

$474

Quiet Family Getaway Only a Few Blocks from Beach with Pool

Ocean City condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$212

Ocean City Maryland One Bedroom Condo - Sleeps 4

Ocean City condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Clean and quiet” This is a Very Nice one bedroom condo a short walk to the beach and even shorter walk to the pool. Clean and quiet... enjoyed staying there.

Match: Swimming pool

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Price per night from

$149

Endless Summer- Spacious Canal Beauty /w POOL/ Golf Cart - #Beach/Dock/Kayaks

Rehoboth Beach house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Swimming pool

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Price per night from

$859

Large, Luxury 7 BR, 5 BA House, Indoor/Outdoor Pools, Tennis, Golf, Near Beach

Bethany Beach house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 26

Match: Swimming pool

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Price per night from

$1,031

Clean Spacious Townhome in quiet community

Rehoboth Beach townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“A perfect getaway!” This is a beautiful home. It is clean, comfortable, spacious and the kitchen is very well equipped. Within minutes of shopping, beach, boardwalk and numerous restaurants. Three swimming pools and tennis courts are also available. Had a wonderful time and will definetly be back!

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Price per night from

$314

Match: Swimming pool

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Price per night from

$287

5 Bedroom Beach House with Pool

Rehoboth Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 13

Match: Swimming pool

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Price per night from

$344

King Bed En Suite, free parking&pool closet to beach

Frankford house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$910

Bayside Resort back to the water house

Fenwick Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$630

Cozy Home in Salt Pond Golf Community - Only 2 Miles from the Beach!

Bethany Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$225

Beach Condo - Pet Friendly - Outlet Central - VERY CLEAN

Rehoboth Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 33 minutes

Match: Swimming pool

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Price per night from

$252

Marigot Beach 303

Ocean City condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 3 minutes

Match: Swimming pool

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Price per night from

$173

Groups - Events - Weddings - Family Reunions - Canalside Inn - Pool - Hot Tub

Rehoboth Beach villa

  • 13 bedrooms
  • 14 bathrooms
  • sleeps 35

Match: Swimming pool

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Price per night from

$2,288

Turtles Nest in Rehoboth Beach, walk to beach and downtown

Rehoboth Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Swimming pool

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Price per night from

$1,488

Spectacular Bay Forest Villa near Bethany Beach

Ocean View villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$132

Beautiful Ocean Front 3BR/2BA Condo

Ocean City condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 4 minutes

Match: Swimming pool

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Price per night from

$458

Family Beach Home w/Pool near Outlets, Lewes, & Rehoboth beaches | 30 Days+

Rehoboth Beach townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$77

Irene 506

Ocean City condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 48 minutes

Match: Swimming pool

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Price per night from

$242

oceanfront 3 bedroom Carousel

Ocean City apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$171

Beachfront with Bay and Ocean views, sleeps 8

Ocean City condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 44 minutes

Match: Swimming pool

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Price per night from

$515

Rare Bayfront VIlla - Bayside at Bethany Lakes 56

Bethany Beach townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 28 minutes

Match: Swimming pool

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Price per night from

$258

Summer 2023 Booking Now

Rehoboth Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 52 minutes

Match: Swimming pool

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Price per night from

$226

Capri 1908

Ocean City apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 36 minutes

Match: Swimming pool

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Price per night from

$167

“All Superlatives!” Clean. Comfortable. Quiet. Well-supplied. Wonderful ocean view from balcony and bedroom. Easy access to beach. Smooth "registration" system. Convenient to restaurants, shops, entertainment. We loved it!

Match: Swimming pool

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Price per night from

$147

Marigot Beach 207

Ocean City condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 36 minutes

Match: Swimming pool

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Price per night from

$138

Mad Men Beach House* Fashionably Family Friendly* 6min walk to Sea *Disney+

Fenwick Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$631

Viewing 38 of 223
rentals in Dewey Beach

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