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
Home in Portsmouth
4.94 out of 5 average rating, 85 reviewsWooded Wonderland Miniature Golf Hot tub Pool
Home in Sandbridge
4.99 out of 5 average rating, 77 reviewsBreathtaking Ocean views at Pinch Me, 8bdrm, 6bath
Home in East Ocean View
4.98 out of 5 average rating, 49 reviewsThe Seaglass Cottage
Home in Norfolk
4.95 out of 5 average rating, 81 reviewsGorgeous Vacation House
Home in Corolla
4.88 out of 5 average rating, 32 reviewsSandy Beaches OBX *New Pool and Hot Tub 2024*
Home in Corolla
4.98 out of 5 average rating, 60 reviewsCarova Beach 4x4 - OBX Getaway
Home in Hampton
4.92 out of 5 average rating, 88 reviews4BD home w/ game room & pool near Langley & PTC!
Home in Virginia Beach
4.81 out of 5 average rating, 21 reviewsThe VIBE House with POOL!
Condo rentals with a pool
Condo in Virginia Beach
4.9 out of 5 average rating, 50 reviewsOcean front best beach, boardwalk, dolphins!
Condo in Sandbridge
5 out of 5 average rating, 51 reviewsSandbridge Beach - DeepSeaSide Retreat
Condo in Virginia Beach
4.99 out of 5 average rating, 72 reviewsOceanfront Studio: Boardwalk, Beach, & Pool Views
Condo in Virginia Beach
5 out of 5 average rating, 12 reviewsParadise Cove
Condo in Virginia Beach
4.83 out of 5 average rating, 53 reviewsSeas The Day of Virginia Beach
Condo in Virginia Beach
4.89 out of 5 average rating, 9 reviewsBeachfront Oasis
Condo in Virginia Beach
4.94 out of 5 average rating, 80 reviewsOceanfront/Boardwalk Complex, Beach, Pool, Balcony
Quick stats about vacation rentals with a pool in Chesapeake
Total rentals
130 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Destinations to explore
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- Rentals with pools United States
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