
Vacation rentals with a pool in Ocean Pines
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Ocean Pines
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 Ocean Pines 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

*Catch Me By The Sea*

Amazing 2 Bedroom home close to the beach!

OC MD trip bayside, great amenities

Beautiful Spacious 4 Bedroom Home in Ocean Pines

Close to OC, Family Friendly, Pool Access

Charming Home in a Beach Town Community!

Entire Home w King Bed in Peaceful OceanPines 🌊🌲
Condo rentals with a pool

Sea Colony Premier Family Resort

Oceanfront Family Oasis: Pool, Beach & Parking!

Luxury Bay & Oceanview Condo in the Heart of Dewey

New Updated Direct Oceanfront Condo - Pool & Wifi!

Top Rated! Beautful Sunsets! Midtown Bayside Condo

🌊Oceanfront studio w/ amazing views & amenities🏖

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool

Direct Ocean Front/Gorgeous Views/Indoor Pool
Quick stats about vacation rentals with a pool in Ocean Pines
Total rentals
140 properties
Nightly prices starting at
G$8,372 GYD before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
140 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace
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- Ocean City Beach
- Broadkill Beach
- Assateague Island National Seashore
- Cape May Beach NJ
- Mile Beach
- Higbee Beach
- Poverty Beach
- Ocean City Boardwalk
- Dewey Beach Access
- Cape Henlopen State Park
- Jolly Roger Amusement Park
- Willow Creek Winery & Farm
- Towers Beach
- Northside Park
- Assateague Beach
- Bayside Resort Golf Club
- Jolly Roger at the Pier
- Poodle Beach
- Delaware Seashore State Park
- Pearl Beach
- Wildwood Dog Park & Beach
- Peninsula Golf & Country Club
- Heritage Shores
- Killens Pond State Park