
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

Corova Beaches 5BR w/Heated Pool & Hot Tub!

Aloha Beaches OBX

The Sandbridge Jewel

York River Vacation Home

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

Walk to Beach! Dogs OK, Backyard, Hot Tub, Pool

Private Pool at the Oceanfront in a Spacious Home

Salida del Sol, North End Beach
Condo rentals with a pool

Beach Luxury Beachfront

NEW Updated Oceanfront 2bd 2bth / Beachfront /Pool

2BD2BA Condo w/Pool2Blocks2Beach

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Paradise at the Beach

OBC - 2BR/2BA Suite - City View

Back Bay Breeze
Other vacation rentals with a pool

Coastal Retreat @ Coliseum| Bonus Room, Gazebo

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

The Green Bean Bungalow

Stunning Views | Kayaks | Pet-Friendly | Sunsets

POOL, Pool House, Hot Tub, Grill, 2 bedroom

Saltwater Seaclusion- Corolla-Walk to Everything!

Unit 1005-Modern Oceanfront Retreat w/Serene Views

Beautiful 1BR at Williamsburg + Amenities
Quick stats about vacation rentals with a pool in Chesapeake
Total rentals
130 properties
Nightly prices starting at
€ 26 before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Destinations to explore
- New York Vacation rentals
- Washington Vacation rentals
- Myrtle Beach Vacation rentals
- Philadelphia Vacation rentals
- Jersey Shore Vacation rentals
- Outer Banks Vacation rentals
- Ocean City Vacation rentals
- Charlotte Vacation rentals
- South Jersey Vacation rentals
- Virginia Beach Vacation rentals
- Jersey City Vacation rentals
- North Myrtle Beach Vacation rentals
- Family-friendly rentals Chesapeake
- Townhouse rentals Chesapeake
- Beach house rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with a washer and dryer Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- House rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with lake access Chesapeake
- Condo rentals Chesapeake
- Rentals with beach access Chesapeake
- Cottage rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Smoking-friendly rentals Chesapeake
- Waterfront rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Beachfront rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a kayak Chesapeake
- Apartment rentals Chesapeake
- Guesthouse rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with pools Virginia
- Rentals with pools United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Kingsmill Resort
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Wilkins Beach
- James River Country Club
- Little Creek Beach