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

Pool River House

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

New! Boat Dock /Pool /HotTub/ Waterfront/ Beach

Gorgeous Views | Kayaks | Pet-Friendly | Sunsets

4BR House w 2 King BEDS,2 kitchens, POOL & SAUNA

Private Pool at the Oceanfront in a Spacious Home

Stunning Views of Back Bay & Seconds to the Beach

Splash of Lime Carova 4x4 Beach Cottage
Condo rentals with a pool

Beach Luxury Beachfront

2BD2BA Condo w/Pool2Blocks2Beach

Ocean & Bay Views - Local Family Owned & Operated

Oceanfront Studio: Boardwalk, Beach, & Pool Views

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

Walk to Corolla Village and the Beach!

Barefoot Bliss - Single Level Steps to the Beach

Ocean Escape
Other vacation rentals with a pool

Bright & Spacious Camper + Bunks+Indoor Fireplace

Ava’s Estuary

The Green Bean Bungalow

Barclay Towers Resort Oceanfront Balcony or Patio

Newly built Contemporary Coastal Villa

Waterfront On Back Bay In Sandbridge.

Coastal Cottage, heated pool, resort community

Works 4 Me: New listing
Quick stats about vacation rentals with a pool in Chesapeake
Total rentals
140 properties
Nightly prices starting at
$41 CAD before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
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- Virginia Beach Oceanfront
- Carova Beach
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- Resort Beach
- Busch Gardens Williamsburg
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- Water Country USA
- Kingsmill Resort
- First Landing State Park
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- Jamestown Settlement
- Currituck Beach Lighthouse
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- Norfolk Botanical Garden
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- Cape Charles Beachfront
- Bonito St. Public Beach Access