Vacation Rentals with Pool in Dewey Beach

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

Filtering by: Swimming pool

637 vacation rentals

(2) Excellent 

22

Dewey Beach Condo - with Beach and Pool Views. Life is Good!

Delaware / Dewey Beach

Dewey Beach condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$150

Price per night from

$150

(3) Very Good 

6

4 BR Oceanblock with Pool & Multiple Decks w/ View

Delaware / Dewey Beach

Dewey Beach townhouse

4 11 2 nights min

  • 4 bedrooms
  • sleeps 11
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$200

Price per night from

$200

(1) Excellent 

32

Luxury Penthouse Rental, Bay & Ocean Views, Rooftop Pool, Linens Included, Xbox

Delaware / Dewey Beach

Dewey Beach condo

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$645

Responds fast!
avg. 2 hours 37 minutes

Price per night from

$645

(3) Very Good 

23

26 Collins

Delaware / Dewey Beach

Dewey Beach house

7 18 7 nights min

  • 7 bedrooms
  • sleeps 18
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Wonderful Memories in a Gorgeous House” Our extended family of 14 people (10 adults and 4 kids) thoroughly enjoyed our stay at this house. It was a quick walk to the uncrowded, quiet beach and we enjoyed lounging in the private pool or soaking in the
…see more

Price per night from

$400

Price per night from

$400

50

Only 3 nt. Min. Family friendly. Luxury, Location, Convenience with Comm. Pool

Delaware / Dewey Beach

Dewey Beach apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$150

Responds fast!
avg. 2 hours 53 minutes

Price per night from

$150

(5) Very Good 

36

Ocean Block Town Home with Two Pools, Tennis and Free Activities Inc. Golf, Wate

Delaware / Dewey Beach

Dewey Beach house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Seaside Delight!” We were so happy and relaxed during our stay at Seagate. The home was steps to the beach which was a must for us. There were also 2 beautiful pools, tennis courts,and a community game room. Gorgeous landscaping everywhere which lent
…see more

Price per night from

$44

Responds fast!
avg. 5 minutes

Price per night from

$44

11

Res. Lighthouse Cove 416

Delaware / Dewey Beach

Dewey Beach house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$100

Price per night from

$100

14

Res. Lighthouse Cove 411

Delaware / Dewey Beach

Dewey Beach house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$100

Price per night from

$100

43

10 Chicago

Delaware / Dewey Beach

Dewey Beach house

10 22 7 nights min

  • 10 bedrooms
  • sleeps 22
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$857

Price per night from

$857

Great rentals within 20 miles that match your search

Distance approx 11.64 km from Dewey Beach

(8) Excellent 

Certificate of Excellence

40

Spacious Bethany Beach Retreat

Delaware / Bethany Beach

Bethany Beach condo

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

Certificate of Excellence

Price per night from

$98

Responds fast!
avg. 54 minutes

Price per night from

$98

Distance approx 17.97 km from Dewey Beach

(6) Excellent 

Certificate of Excellence

25

Lorelei II, Unit 210/3Bdr/ Bayside Condo

Maryland / Ocean City

Ocean City condo

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Amazing place” I must say from the booking,communication, and the let talk about the place, it was perrrffect. It was clean, it had everything we needed and more, felt like home away from home, i definitely recommend this place! No doubt especially t
…see more

Certificate of Excellence

Price per night from

$149

Responds fast!
avg. 1 hour 16 minutes

Price per night from

$149

Distance approx 11.37 km from Dewey Beach

(2) Very Good 

9

Sea Colony West- 3 Blocks to Beach!

Delaware / Bethany Beach

Bethany Beach townhouse

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$239

Price per night from

$239

Distance approx 11.11 km from Dewey Beach

7

Bethany Beach - Sea Colony West - quiet and peaceful

Delaware / Bethany Beach

Bethany Beach condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$137

Price per night from

$137

Distance approx 2.15 km from Dewey Beach

(2) Excellent 

16

Spacious & Spectacular, Community Pool &Tennis,Family Friendly. Amazing location

Delaware / Rehoboth Beach

Rehoboth Beach house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$296

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$296

Distance approx 10.47 km from Dewey Beach

(1) Excellent 

34

Memorial Day $100 off! Spacious Beach & Golf Home near Beach w/ New Pool!

Delaware / Ocean View

Ocean View house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

Price per night from

$335

Price per night from

$335

Distance approx 19.25 km from Dewey Beach

(1) Very Good 

22

CENTURY 1: 2 BR 2 BA, North Ocean City, DIRECT Oceanfront, FABULOUS Views!!

Maryland / Ocean City

Ocean City condo

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$173

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$173

Distance approx 19.46 km from Dewey Beach

17

Ocean City Beach Front High Rise 2 BR/2BA Condo

Maryland / Ocean City

Ocean City condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$198

Price per night from

$198

Distance approx 19.19 km from Dewey Beach

13

Marigot Beach 209

Maryland / Ocean City

Ocean City apartment

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$137

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$137

Distance approx 4.43 km from Dewey Beach

25

NEW! 3BR Home w/ Pool near Rehoboth Beach & Lewes!

Delaware / Rehoboth Beach

Rehoboth Beach house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$149

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$149

Distance approx 8.91 km from Dewey Beach

29

Relaxing Bay Forest Villa near Bethany Beach

Delaware / Ocean View

Ocean View villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$148

Responds fast!
avg. 2 hours 18 minutes

Price per night from

$148

Distance approx 9.94 km from Dewey Beach

24

Condo w/ Pool Access - 2 Miles to Bethany Beach!

Delaware / Millville

Millville apartment

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$159

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$159

Distance approx 16.67 km from Dewey Beach

(1) Very Good 

14

Paradise in north ocean city - 25 years of age and above

Maryland / Ocean City

Ocean City condo

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$198

Responds fast!
avg. 3 hours 33 minutes

Price per night from

$198

Distance approx 1.71 km from Dewey Beach

(1) Excellent 

13

5BR,4BA Villa 1mile to ocean & 3 pools in resort

Delaware / Rehoboth Beach

Rehoboth Beach villa

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$395

Price per night from

$395

Distance approx 7.9 km from Dewey Beach

(1) Average 

24

Bethany Beach House- 1000 Feet from the Ocean!

Delaware / Bethany Beach

Bethany Beach house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$422

Responds fast!
avg. 9 minutes

Price per night from

$422

Distance approx 19.05 km from Dewey Beach

(5) Excellent 

19

Ocean City MD - Penthouse Suite, Great Oceanfront Building

Maryland / Ocean City

Ocean City condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Very nice place” My husband, daughter, and I stayed for four nights. The condo is updated and very clean. It is a 2-story condo with an elevator. Ed was wonderful. He gave us a tour of the facilities on arrival. It's right on the beach which was perfe
…see more

Price per night from

$110

Price per night from

$110

Distance approx 19.74 km from Dewey Beach

(8) Very Good 

10

4 BR, 3.5 Bath Newer Townhouse w/pool in Cape May

Cape May County / Cape May

Cape May apartment

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
“Family time in Cape May” Good location, plenty of room to sleep 8-10. Amentities were plentiful. Condo just needs some TLC and a good cleaning. Other than that it was great.
…see more

Price per night from

$424

Price per night from

$424

Distance approx 16.11 km from Dewey Beach

39

NEW! Gorgeous Home Steps from Fenwick Island Beach

Delaware / Fenwick Island

Fenwick Island house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$680

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$680

Distance approx 11.18 km from Dewey Beach

1

Beach Rental Condo

Delaware / Bethany Beach

Bethany Beach condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

Price per night from

$240

Price per night from

$240

Distance approx 17.36 km from Dewey Beach

10

Bluewater East 803S

Maryland / Ocean City

Ocean City apartment

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$203

Responds fast!
avg. 1 hour 52 minutes

Price per night from

$203

Distance approx 18.61 km from Dewey Beach

15

Fountainhead Towers 1208

Maryland / Ocean City

Ocean City apartment

1 6 3 nights min

  • 1 bedroom
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$276

Responds fast!
avg. 1 hour 42 minutes

Price per night from

$276

Distance approx 18.18 km from Dewey Beach

9

2-Story Uptown Condo on the Bayside with Outdoor Pool

Maryland / Ocean City

Ocean City condo

1 6 3 nights min

  • 1 bedroom
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$249

Price per night from

$249

Distance approx 18.63 km from Dewey Beach

(49) Very Good 

Certificate of Excellence

24

OCEANFRONT

Maryland / Ocean City

Ocean City condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Certificate of Excellence

Price per night from

$69

Price per night from

$69

Distance approx 4.29 km from Dewey Beach

(7) Very Good 

20

Rehoboth Beach House & Pool w/ optional Cottage

Delaware / Rehoboth Beach

Rehoboth Beach house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$170

Price per night from

$170

Distance approx 1.71 km from Dewey Beach

(32) Excellent 

19

Clean Spacious Townhome in quiet community

Delaware / Rehoboth Beach

Rehoboth Beach townhouse

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“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.
…see more

Price per night from

$277

Price per night from

$277

Distance approx 2.12 km from Dewey Beach

(16) Excellent 

30

Chic and affordable 4 bedroom home, bike to beach!

Delaware / Rehoboth Beach

Rehoboth Beach townhouse

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$272

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$272

Distance approx 18.96 km from Dewey Beach

(20) Very Good 

54

Golden Sands Premier Direct Ocean Front Resort!

Maryland / Ocean City

Ocean City condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children

Price per night from

$143

Price per night from

$143

Distance approx 18.68 km from Dewey Beach

14

Direct Ocean Front Condo W/ Pool! 2 Large Decks, Panoramic 7th floor views

Maryland / Ocean City

Ocean City condo

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$298

Price per night from

$298

Distance approx 2.49 km from Dewey Beach

(27) Excellent 

32

Brand New Townhome with beautiful views!

Delaware / Rehoboth Beach

Rehoboth Beach townhouse

3 8 120 nights min

  • 3 bedrooms
  • sleeps 8
  • 120 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$60

Price per night from

$60