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Dewey Beach House Rentals & Vacation Rentals with Swimming Pool - 134 Rentals Available.

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134 Vacation rentals

Filters applied: Swimming pool

1 / 18

Dewey Beach Condo

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$100.00

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from $100.00 / night

1 / 13

Dewey Beach House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$115.00

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from $115.00 / night

1 / 14

Dewey Beach Condo

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$115.00

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from $115.00 / night

1 / 33

Dewey Beach Townhouse

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,400.00

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from $2,400.00 / night

1 / 18

Dewey Beach Townhouse

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$258.00

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from $258.00 / night

1 / 15

Dewey Beach Condo

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$100.00

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from $100.00 / night

Your search has been expanded 19.9 miles to include more rentals

(1)

1 / 42

Bethany Beach House - 9.4 miles away

  • 7
  • 26
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$916.00

Excellent (1 reviews)

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from $916.00 / night

(36)

1 / 21

Rehoboth Beach Condo - 1.8 miles away

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Wonderful, peaceful location. Convenient to boardwalk, restaurants and beach. We only drove our car a few times during our 10 day stay. Home was very comfortable, loved the balcony and the view of the pool. The spiral stairs to the bedroom just...”
- Review left on 09/24/2016

$180.00

Excellent (36 reviews)

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from $180.00 / night

1 / 15

Fenwick Island Townhouse - 16.4 miles away

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$393.00

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from $393.00 / night

(37)

1 / 14

Ocean City Condo - 18.8 miles away

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“beautiful condo...owner has taken great pride in remodel...very clean, totally accommodating and "OH" the view. definitely would recommend and will absolutely stay again at this one...”
- Review left on 09/26/2016

$172.00

Excellent (37 reviews)

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from $172.00 / night

(36)

1 / 19

Rehoboth Beach Townhouse - 1.7 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 3 hours 6 minutes

“This home is exactly as advertised...Clean, spacious, and in a quite, WELL Located, community! You will not be disappointed. Everything you need is there and first class. We had 4 adults and two children and more room then we needed!! The pools...”
- Review left on 08/29/2016

$286.00

Excellent (36 reviews)

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from $286.00 / night

(3)

1 / 31

Bethany Beach House - 7 miles away

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

$985.00

Excellent (3 reviews)

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from $985.00 / night

1 / 89

Rehoboth Beach House - 2.9 miles away

  • 6
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,000.00

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from $1,000.00 / night

1 / 24

Rehoboth Beach Townhouse - 1.3 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$200.00

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from $200.00 / night

(13)

1 / 14

Ocean City Condo - 19.9 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.001 mi
  • Swimming pool

Responds fast! Avg. 2 hours 4 minutes

“The wife and I had the pleasure of staying a week in August '17. We were busy each day sometimes at the beach, sometimes at the boardwalk, sometimes fishing. I was able to catch my 1st Tuna and Flounder with the condo owners connections and guidance...”
- Review left on 02/09/2018

$323.00

Very Good (13 reviews)

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from $323.00 / night

(4)

1 / 26

Ocean City Apartment - 19.4 miles away

  • 1
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 29 minutes

$172.00

Excellent (4 reviews)

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from $172.00 / night

(51)

1 / 31

Ocean City Condo - 18.6 miles away

  • 2
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 31 minutes

“We decided to stay at the unit 2005 at The Carousel because all of the reviews were wonderful. Previous guests did not exaggerate. The place is fabulous! Everything you could possibly want is there. You can see the ocean while you're working in...”
- Review left on 09/18/2017

$144.00

Very Good (51 reviews)

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from $144.00 / night

(3)

1 / 20

Bethany Beach Townhouse - 11.3 miles away

  • 3
  • 10
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 9 minutes

$229.00

Very Good (3 reviews)

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from $229.00 / night

(9)

1 / 38

Ocean City Apartment - 19.5 miles away

  • 2
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 29 minutes

$189.00

Excellent (9 reviews)

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from $189.00 / night

(17)

1 / 47

Ocean City Apartment - 19.4 miles away

  • 2
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 29 minutes

$229.00

Excellent (17 reviews)

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from $229.00 / night

(4)

1 / 28

Ocean City Apartment - 19.5 miles away

  • 1
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 29 minutes

$201.00

Excellent (4 reviews)

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from $201.00 / night

(5)

1 / 24

Bethany Beach Townhouse - 9 miles away

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 40 minutes

$258.00

Excellent (5 reviews)

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from $258.00 / night

1 / 29

West Cape May House - 18.6 miles away

  • 5
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$350.00

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from $350.00 / night

1 / 27

West Cape May House - 18.7 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$400.00

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from $400.00 / night

1 / 12

Cape May Apartment - 18.3 miles away

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$300.00

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from $300.00 / night

(2)

1 / 32

Cape May House - 19.8 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Owners are very much involved with how clean and well kept the property is. Pool is perfect to be away from the beach crowd. The overall farm feel is quite lovely compared to craziness in town and beach crowd. More reason to bike around and enjoy...”
- Review left on 08/30/2020

$550.00

Excellent (2 reviews)

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from $550.00 / night

1 / 34

Cape May Cottage - 19.8 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$650.00

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from $650.00 / night

1 / 21

Cape May Apartment - 18.4 miles away

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$250.00

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from $250.00 / night

1 / 23

Cape May Apartment - 19.7 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$400.00

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from $400.00 / night

1 / 10

Cape May Apartment - 19.5 miles away

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$72.00

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from $72.00 / night

1 / 19

Cape May Condo - 18.4 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$286.00

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from $286.00 / night

1 / 25

Cape May House - 19.3 miles away

  • 5
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$650.00

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from $650.00 / night

1 / 22

Cape May House - 19.5 miles away

  • 5
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$715.00

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from $715.00 / night

1 / 19

Cape May Apartment - 18.3 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$272.00

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from $272.00 / night

(1)

1 / 29

Cape May Apartment - 19.3 miles away

  • 4
  • 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$458.00

Very Good (1 reviews)

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from $458.00 / night

(1)

1 / 14

Cape May Apartment - 19.5 miles away

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$168.00

Excellent (1 reviews)

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from $168.00 / night

1 / 18

Cape May Condo - 19.5 miles away

  • 1
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$186.00

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from $186.00 / night

1 / 11

Cape May Condo - 19.5 miles away

  • 1
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$79.00

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from $79.00 / night

1 / 14

Cape May House - 19.5 miles away

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$279.00

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from $279.00 / night

1 / 31

Cape May Studio - 18.9 miles away

  • -1
  • 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$386.00

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from $386.00 / night