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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
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MjgwNzk3NDU%3D/original/6eac7425-7d29-4b56-8b15-86e797aea1b4.jpeg?im_w=720)
Home in Norfolk
4.76 out of 5 average rating, 121 reviewsBEACH/ POOL HOUS, 1 min walk to the beach Norfolk
![](https://a0.muscache.com/im/pictures/35e76522-b4c5-4287-8137-ee041b99f1b4.jpg?im_w=720)
Home in Virginia Beach
4.89 out of 5 average rating, 122 reviewsHalf house w/pool & new patio all to yourself
![](https://a0.muscache.com/im/pictures/miso/Hosting-608784272918190588/original/7bd04295-545e-4f28-8eda-50e245c9c6f8.jpeg?im_w=720)
Home in Virginia Beach
4.91 out of 5 average rating, 80 reviewsTHE OLD BEACON 3 I Beach Living
![](https://a0.muscache.com/im/pictures/898c9a34-9df0-40b7-8c19-6f7abab95147.jpg?im_w=720)
Home in East Ocean View
4.98 out of 5 average rating, 40 reviewsThe Seaglass Cottage
![](https://a0.muscache.com/im/pictures/miso/Hosting-1122325163770871927/original/696f98b8-6d97-4fcc-b884-6e73362b603d.jpeg?im_w=720)
Home in Corolla
5 out of 5 average rating, 10 reviewsAloha Beaches OBX
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Home in Sandbridge
4.95 out of 5 average rating, 19 reviewsDesigner 7BR w/ Pool and Hot Tub. Pets welcome!
![](https://a0.muscache.com/im/pictures/miso/Hosting-52367408/original/f735b2b5-c0d0-4fc9-93d2-d02cefc05b8e.jpeg?im_w=720)
Home in Sandbridge
4.95 out of 5 average rating, 19 reviewsSandbridge- Great Escape Saltwater Pool &Boat Ramp
![](https://a0.muscache.com/im/pictures/miso/Hosting-663081555407478435/original/06f55713-5d50-41bd-b4b6-c4d10a194f90.jpeg?im_w=720)
Home in Sandbridge
4.91 out of 5 average rating, 35 reviewsSilver Strand-Renovated 2022, Sandbridge/Bayfront
Condo rentals with a pool
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Condo in Virginia Beach
4.83 out of 5 average rating, 250 reviewsBeautiful Beachfront Condo
![](https://a0.muscache.com/im/pictures/miso/Hosting-906656432202785378/original/c92292e1-f101-43c0-aa7b-aaaf07298b12.jpeg?im_w=720)
Condo in Virginia Beach
4.98 out of 5 average rating, 57 reviewsOceanfront Studio: Boardwalk, Beach, & Pool Views
![](https://a0.muscache.com/im/pictures/miso/Hosting-53664843/original/d9b2690e-8735-468c-9314-cf74023d977e.jpeg?im_w=720)
Condo in Virginia Beach
4.81 out of 5 average rating, 32 reviewsLovely Beachfront 3-Bedroom Condo
![](https://a0.muscache.com/im/pictures/miso/Hosting-48508290/original/81f296ff-2446-47c3-8646-ba98f9917bbc.jpeg?im_w=720)
Condo in Virginia Beach
4.91 out of 5 average rating, 47 reviewsOceanfront Condo with Spectacular Beach View
![](https://a0.muscache.com/im/pictures/019119ce-c5bb-4d6d-8073-098b9156a7fd.jpg?im_w=720)
Condo in Virginia Beach
4.83 out of 5 average rating, 52 reviewsSeas The Day of Virginia Beach
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Condo in Sandbridge
5 out of 5 average rating, 9 reviewsSojourn Southern Dunes Sleeps 6
![](https://a0.muscache.com/im/pictures/miso/Hosting-43452480/original/2b37c5b4-f7ff-4e0b-9b27-6d2c24b8e158.jpeg?im_w=720)
Condo in Virginia Beach
4.93 out of 5 average rating, 74 reviewsOceanfront/Boardwalk Complex, Beach, Pool, Balcony
![](https://a0.muscache.com/im/pictures/miso/Hosting-581308499861195188/original/e275a73b-bd25-42b3-a37c-f256664d3e7d.jpeg?im_w=720)
Condo in Virginia Beach
4.88 out of 5 average rating, 43 reviewsOcean front best beach, boardwalk, dolphins!
Quick stats about vacation rentals with a pool in Chesapeake
Total rentals
200 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
4.5K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Destinations to explore
- Outer Banks Vacation rentals
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- Rentals with pools United States
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