
Vacation rentals with a pool in Chesapeake Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chesapeake 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 Chesapeake Beach rentals with a pool
House rentals with a pool

Oceanfront | 7BR | Pool | Hot Tub | Sleeps 20

Ocean Front Studio on Boardwalk

Elegance Escape on Saunders Dr

1-bedroom home in Suffolk

Coral Point - Updated Cozy 4 bedroom w/ Salt Water

4BD home w/ game room & pool near Langley & PTC!

Half house w/pool & new patio all to yourself

The VIBE House with POOL!
Condo rentals with a pool

2BD2BA Condo w/Pool2Blocks2Beach

Good Vibes at the Beach

Oceanfront Queen Suite in Virginia Beach

Paradise at the Beach

Beach Studio - Oceanside, Pool, Boardwalk, Bikes

Paradise Cove

Seas The Day of Virginia Beach

Ocean Escape
Other vacation rentals with a pool

Coastal Retreat @ Coliseum| Bonus Room, Gazebo

The Green Bean Bungalow

Unit 901 - Luxury Living on the Oceanfront

Ava’s Estuary

Nates Nook on Back Bay

North End Home with pool, beach & state park.

Oceanfront Building Boardwalk Pool Beach 3 Beds

Waterfront On Back Bay In Sandbridge.
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- Chesapeake Bay
- Virginia Beach Oceanfront
- Carova Beach
- Busch Gardens Williamsburg
- Corolla Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- James River Country Club
- Wilkins Beach