
Holiday rentals with a pool in Chesapeake Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chesapeake Beach
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Chesapeake Beach rentals with a pool
House rentals with a pool
Guest favourite

Home in Portsmouth
4.94 out of 5 average rating, 108 reviewsWooded Wonderland Miniature Golf Hot tub Pool
JustinRating, 5 stars2 weeks ago
We rented this property to visit the Virginia Tattoo and the beach and had a great trip!
Superhost

Home in Virginia Beach
4.83 out of 5 average rating, 125 reviewsTHE OLD BEACON 1 | Beach Living
VernaRating, 5 stars6 days ago
Old Beacon is a cozy beach spot. The property consists of 4 units - two in front and two in back. The shared pool is a great place to relax on a windy afternoon and be out of the wind and featured plenty of seating and tables with umbrellas. Bedrooms are cozy and welcoming and the beds were comfortable. Bathrooms were clean and bright! Great place for a weekend or week long getaway! Matt is very responsive and gives clear instructions on how to park at the property and when you can access the house. Hope to be back soon!
Top Guest favourite

Home in Virginia Beach
4.94 out of 5 average rating, 107 reviewsCountry Comfort Close to the Beaches
MaryJaneRating, 5 stars1 week ago
I can't say enough positive things about Alice and her home. She was incredibly welcoming, and made my entire weekend a delight. Her home is beautiful, and it was a very comfortable stay. But Alice's kindness and generosity really went above and beyond. Thank you again!
Guest favourite

Home in Virginia Beach
4.86 out of 5 average rating, 29 reviewsStar of Sandbridge
AnthonyRating, 5 stars1 week ago
Loved this house. Hated to have to leave !!
Superhost

Home in Portsmouth
4.84 out of 5 average rating, 31 reviewsElegance Escape on Saunders Dr
TshepoRating, 5 stars3 weeks ago
Clean Place with thoughtful touches from the host. Place has a pool and mini cinema. Would definitely book this place again when am next in Virginia
Guest favourite

Home in Norfolk
4.95 out of 5 average rating, 99 reviewsGorgeous Vacation House
VeronicaRating, 5 stars2 weeks ago
We were very pleased with the house. Just be careful w little ones, all vent covers were not secured to the floor properly and that could be safety hazard. One disappointment we had -although the beach was very close (5 minutes walk) there were runoff pipes all along the beach. Public beach a 5 minute drive. We ended up driving to Virginia Beach and had much better time there, 40 minute drive.
Superhost

Home in Virginia Beach
4.84 out of 5 average rating, 125 reviewsStunning Views of Back Bay & Seconds to the Beach
SigridRating, 5 stars1 month ago
Great place for families walking distance from the beach. I’ll love to visit in the summer when we can enjoy the beach and everything Virginia Beach has to offer.
Superhost

Home in Cape Charles
4.88 out of 5 average rating, 25 reviewsSunshine Baydream Cape Charles
LorrieRating, 5 stars1 month ago
We were in town for our son’s wedding and enjoyed our stay very much. Jason responded quickly to the few questions we had. We would definitely stay again.
Condo rentals with a pool
Guest favourite

Condo in Virginia Beach
4.9 out of 5 average rating, 52 reviewsBeach Luxury Beachfront
LuciaRating, 5 stars1 month ago
Amazing place. Recommended.
Superhost

Condo in Williamsburg
5 out of 5 average rating, 3 reviewsRelax in Style: 2BR Condo w/ Balcony at Wyndham GG
JamesRating, 5 stars2 months ago
We were very pleased with our stay. Check-In was very easy with plenty of text notifications. Check out was easy as well. We were greeted by Club Wyndham timeshare staff and invited to attend a presentation, but the offer was very friendly and not pushy at all. It was a very good experience, and we would love to stay again. We visit our Aunt who lives in Ford's Colony and found this location we'll suited for all of Williamsburg.
Top Guest favourite

Condo in Virginia Beach
5 out of 5 average rating, 51 reviewsSandbridge Beach - DeepSeaSide Retreat
AnneRating, 5 stars8 months ago
We loved our stay here in sandbridge! Bill and Anne were great hosts, with a lovely home that had everything we needed. Highly recommend!
Guest favourite

Condo in Virginia Beach
4.92 out of 5 average rating, 12 reviews2BD2BA Condo w/Pool2Blocks2Beach
KrystleRating, 5 stars2 months ago
Came with my girls for a conference at the Beach. Salt and Serenity was super peaceful, felt private and quiet. Beds were super comfy and the water pressure in the showers was awesome. We had everything we needed in the kitchen and all amenities were as described. Susan was a great, responsive host and made accommodations for our early check-in. And all the restaurant suggestions were a hit! Would definitely come again!
Guest favourite

Condo in Virginia Beach
4.87 out of 5 average rating, 85 reviewsGood Vibes at the Beach
MarceeRating, 5 stars7 months ago
A great find. Everything we needed, including a grocery store, was walkable and convenient. Loved being 2 blocks from the ocean and boardwalk. Excellent space and very comfortable. Colin is an excellent host. Always addressed our questions and needs in a timely fashion. We will be back!
Guest favourite

Condo in Williamsburg
5 out of 5 average rating, 11 reviewsWyndham Governor's Green (3 BD Deluxe)
GlennRating, 5 stars5 months ago
Great location, private and peaceful. Staff was very helpful and friendly.
Superhost

Condo in Williamsburg
4.9 out of 5 average rating, 10 reviewsUpscale condo with Golf Course views
MaryRating, 5 stars8 months ago
The condo is well appointed with everything I needed. Kingsmill is a special place. Rodica was very quick to reply when I had a few different questions. Very comfortable bed and reading chairs. Top notch.
Guest favourite

Condo in Virginia Beach
4.86 out of 5 average rating, 137 reviewsOceanfront, beachfront, boardwalk, fun, dolphins
AnitaRating, 5 stars3 weeks ago
We enjoyed staying at Kelly's place in VB. Its an ideal location for anyone who wants to stay right at the boardwalk. We witnessed amazing sunrises and moonrises. The ocean was right in front of us and from the 6th floor, the view was expansive. A lot of restaurants were also nearby. Kelly was always very communicative, polite and professional. The apartment was clean with the kitchen well stocked with utensils The bedrooms were of a pretty large size. And parking was on the premises. Overall, it was a wonderful experience and holiday for us. We strongly recommend Kelly's place.
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- Virginia Beach Oceanfront
- Carova Beach
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