
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

Aug specials, Firepit, pool/hottub, ocean view

Atlantic Sunrise - Bright Renovated 9BR | Private

Pool River House

Private Pool at the Oceanfront in a Spacious Home

Splash of Lime Carova 4x4 Beach Cottage

6BR Sandbridge Family Retreat w/ Pool

Beach Haven House

Spotless Treehouse | Pool | HotTub | Pickle | Pets
Condo rentals with a pool

Beautiful Beachfront Condo

Beach Luxury Beachfront

2BD2BA Condo w/Pool2Blocks2Beach

Oceanfront Queen Suite in Virginia Beach

Back Bay Breeze

Walk to Corolla Village and the Beach!

Modern Oceanfront Condo + Pool near Top Dining

Ocean Escape
Other vacation rentals with a pool

Cozy Corolla Cottage, <10min walk to beach, petsOK

LA Bella Beach House (2 BR)

Great last minute deals! Message me! 8bdrm, 6bath

Saltwater Seaclusion- Corolla-Walk to Everything!

The Seaglass Cottage

Newly built Contemporary Coastal Villa

Waterfront On Back Bay In Sandbridge.

Oceanfront Views! 2 BR, 2 BATH!
Quick stats about vacation rentals with a pool in Chesapeake
Total rentals
140 properties
Nightly prices starting at
ﺩ.ﺇ110 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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- Rentals with pools Virginia
- Rentals with pools United States
- Virginia Beach Oceanfront
- Carova Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Kingsmill Resort
- Buckroe Beach and Park
- Haven Beach
- Bethel Beach
- Grandview Beach
- Kiptopeke Beach
- Jamestown Settlement
- Outlook Beach
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Golden Horseshoe Golf Club
- Cape Charles Beachfront
- Chrysler Museum of Art
- Sarah Constant Beach Park
- James River Country Club
- Red Wing Lake Golf Course