
Vacation rentals with a pool in Dewey Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Dewey Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Dewey Beach rentals with a pool
House rentals with a pool

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

Gorgeous Bayfront, Pool, Hot Tub, Linens Included

Cape Shores Luxury - NEW Pool, Beach, Pier, Park!

Dodd House Beach Home w/private pool and hot tub

Beautiful Beach House in Rehoboth

The Jungalow - Dog Friendly, Fenced in & Pool

Luxury Carriage House in Rehoboth Beach

Coastal Cottage! Walk to Beach!
Condo rentals with a pool

Romantic Beachfront Penthouse Ocean City MD

Luxury Oceanfront Getaway!

1st Floor 2BR/2BA | Pool | Quiet & Convenient

The Cozy little Condo

Direct Ocean View*Walk to Lake Gerar, Playground

1 Bedroom 1 Bath Condo on Silver Lake

Breathtaking Ocean view. Few steps to the beach

2 BR DEWEY w/pool, 1 blk to beach, 6-person limit
Other vacation rentals with a pool

Sunsets at Hidden Harbour

Lakefront condo blocks from the beach

Studio Bedroom in the Woods

Henlopen Haven (bikes & pool access)

Luxury Coastal Townhouse with Pool & Game Room

Coastal Retreat | Lakefront | Pool | Hidden Gem

Pelican's Loft Beach Retreat- (two story)

Condo at Eagles Landing
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- Ocean City Beach
- Broadkill Beach
- Assateague Island National Seashore
- Wildwood Crest Beach New Jersey
- Fortescue Beach
- Cape May Beach NJ
- Mile Beach
- Ocean City Boardwalk
- Cape Henlopen State Park
- Dewey Beach Access
- Higbee Beach
- Jolly Roger Amusement Park
- Willow Creek Winery & Farm
- Big Stone Beach
- Pearl Beach
- Poverty Beach
- Towers Beach
- Ocean City Beach
- Northside Park
- Bayside Resort Golf Club
- Poodle Beach
- Bear Trap Dunes
- Jolly Roger at the Pier
- Stone Harbor Beach