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Beachfront holiday rentals in Chesapeake

Find and book unique beachfront homes on Airbnb

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Popular amenities for beachfront rentals in Chesapeake

Pet-friendly beachfront home rentals

Guest favourite
Home in Chic's Beach
4.96 out of 5 average rating, 131 reviews

Water Oaks at Chic's Beach

NewRating, 5 stars1 month ago
We stayed here over spring break with our young kids. Tommy and Janet were very friendly and responsive. The location is great! Literally right across the street from the beach, and close to our all time favorite brewery :) we'd love to come back again in the summer months!
Top guest favourite
Cottage in Bayview
4.97 out of 5 average rating, 248 reviews

Villa Positano

Emily RobbinsRating, 5 stars1 week ago
Wow! We had such a wonderful time at Mr. Roger’s place! The house was just beautiful and clean. The weather caused us not to be able to enjoy the pool and beach, but thats no fault of Mr. Roger! We will definitely book here again. Thanks again!
Guest favourite
Flat in Norfolk
4.86 out of 5 average rating, 35 reviews

Quaint Apartment By the Sea

AlexRating, 5 stars3 months ago
Clean, safe, easy to get to. Did the job we needed it to for the weekend.
Guest favourite
Home in East Ocean View
4.89 out of 5 average rating, 142 reviews

Modern. Spacious. Pets Yes! 2Min Walk to Beach

VimarisRating, 5 stars2 weeks ago
The house as advertised! Clean and very supplied. The beach was small and the area does not have much options to eat. Neighborhood was ok.
Guest favourite
Flat in Bayview
5 out of 5 average rating, 7 reviews

LiveEOV: Beachcomber Two

PamRating, 5 stars2 weeks ago
The place was great it had everything that we needed it was walking distance to the beach
Superhost
Home in Virginia Beach
4.87 out of 5 average rating, 103 reviews

The Happy Place-Quiet, North End 1 block to ocean!

HaroldRating, 5 stars1 day ago
Our stay was fantastic! The location couldn't be better, just a stone's throw from the beach. The property itself was clean and well-stocked with everything we needed. Mary was prompt and helpful in addressing the one minor issue that came up. We highly recommend this spot for a worry-free beach getaway!
Top guest favourite
Home in East Ocean View
4.98 out of 5 average rating, 54 reviews

The Seaglass Cottage

LandrumRating, 5 stars3 days ago
Nancy was super kind and friendly during our stay! She gave a great seafood restaurant recommendation that was both delicious, affordable, and right down the road. The cottage is quaint and a charming place to stay for a young couple. We had plenty of space, and the cottage was accurately represented by the photos available. We would definitely stay here again if we are in the area!
Superhost
Home in Bayview
4.76 out of 5 average rating, 93 reviews

Ocean Bungalo-WiFi, fire pit, beach, pet friendly

TamaraRating, 5 starstoday
Overall stay was nice parking was. Little difficult because of the one way road but area was very peaceful

Beachfront home rentals with a pool

Superhost
Home in Virginia Beach
4.83 out of 5 average rating, 127 reviews

THE OLD BEACON 1 | Beach Living

HollyRating, 5 stars3 weeks ago
Beautiful home within walking distance to everything you need, especially the beach and restaurants. Clean home with cozy feel. My son never wanted to leave the beautiful pool at the property. Would recommended to families!!
Superhost
Apartment in Sandbridge
4.92 out of 5 average rating, 130 reviews

Ocean & Bay Views - Local Family Owned & Operated

AnnaRating, 5 stars2 weeks ago
Had an amazing time with my family which was made very easy with the hosts! Lots of recs for things to do and places to eat. Had kid friendly items in the house which was great. Very clean and in a beautiful location. Would definitely like to return in the future!
Guest favourite
Apartment in Virginia Beach
4.9 out of 5 average rating, 221 reviews

Oceanfront Gem VaB Studio Exceptional Views

GingerRating, 5 stars3 days ago
This was our second time staying at one of Rebecca and Sean’s VA Beach condos — and the experience did not disappoint! This is just a perfect location, at the very end of the Boardwalk, with a private grassy lawn and outdoor seating just for the condo residents. Lots of restaurants in the surrounding blocks. Our favorite thing is the view — you look right out onto the ocean from the patio, and you can see the beach and the sunrise from the comfortable bed each morning. We spent unhurried hours sitting on the patio in the evenings enjoying the sound of lapping waves and the night sky. This cozy studio was just right for the two of us. Highly recommend. I’ve no doubt we’ll stay there again in the future!
Guest favourite
Flat in Virginia Beach
4.87 out of 5 average rating, 152 reviews

VA Beach Oceanfront Studio, Beach, Boardwalk, Pool

KanishaRating, 5 stars5 days ago
Great location, right on the beach. The place was clean and had everything I needed for my stay. Josh and Maegan were very detailed in their instruction I didn’t have to reach out to them for anything.
Guest favourite
Apartment in Virginia Beach
4.86 out of 5 average rating, 137 reviews

Oceanfront, beachfront, boardwalk, fun, dolphins

AnitaRating, 5 stars1 month 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.
Superhost
Home in Sandbridge
4.84 out of 5 average rating, 126 reviews

Stunning Views of Back Bay & Seconds to the Beach

TrenellRating, 5 stars1 month ago
Jade & Nathan were great host. Their home was beautiful and exactly what we needed for our trip. My only recommendation is to come with your own cookware if you’re into cooking. They had plenty of kitchen items that I just had to make work. Other than that the neighborhood was peaceful. The kids enjoyed the pool area it was actually warm temperature and the view behind the house was one of the most amazing parts. I will definitely be back.
Top guest favourite
Home in Virginia Beach
4.97 out of 5 average rating, 201 reviews

Salida del Sol, North End Beach

BeatriceRating, 5 stars1 week ago
The best spot. Super nice amenities and very clean, great location, right across the street from beach access.
Top guest favourite
Apartment in Sandbridge
5 out of 5 average rating, 7 reviews

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym

ChristopherRating, 5 stars2 weeks ago
If there was such thing as a super-duper host, Cheryl hits the mark. Her condo was meticulous and clean. She was lucid with her communications and quick to respond. This condo has an awesome view and the balcony had plenty of seating to enjoy with others. We want to thank Cheryl for making our stay a very memorable one. She is a ROCK STAR!!!

Private beachfront home rentals

Top guest favourite
Home in Buckroe Beach
5 out of 5 average rating, 63 reviews

The Canary Island … Keep Calm and Fish On

TimothyRating, 5 stars1 month ago
We made wonderful memories at this beautiful place. Would definitely recommend!
Guest favourite
Apartment in Ocean View
4.86 out of 5 average rating, 58 reviews

Beachside Condo | 2BR/2BA | Cross street to beach!

HildaRating, 5 stars1 week ago
Clean and Spacious for Four people. Great kitchen Space. But could use a better couch Seating in living room. Bedrooms. And beds were great. Would rent again.
Guest favourite
Apartment in Virginia Beach
4.86 out of 5 average rating, 85 reviews

Cozy 1 Bd condo, 1 block from the beach!

BladimirRating, 5 stars5 months ago
Charles was very kind and a great host , always answered our messages quickly. The airbnb was very clean and very nice, We loved our stay here !
Guest favourite
Home in Virginia Beach
4.89 out of 5 average rating, 85 reviews

Paradise On Pacific

PhillipRating, 5 stars2 days ago
The location was convent, comforting and clean. Susan responded in an appropriate time frame to my questions and went above and beyond to make sure my stay was what I paid for. I’d visit again.
Top guest favourite
Flat in Virginia Beach
4.96 out of 5 average rating, 79 reviews

North End Beach Cottage Apt - One Block from Beach

MasonRating, 5 stars3 weeks ago
My girlfriend and I stayed at Ritamarie’s to explore VA Beach. This was by far our favorite beach air bnb we’ve been to so far. The location is great just in between Norfolk and the oceanfront. The space was very clean and quiet, simple check in and check out. 10/10 would come back again!
Superhost
Home in Chic's Beach
4.89 out of 5 average rating, 74 reviews

Beach Front Views ~ Chics Beach Gem + Garage!

LaurenRating, 5 stars3 weeks ago
Great location! Kitchen well stocked for cooking meals. Plenty of starter necessities, such as soap, shampoo, garbage bags, etc. Quiet beach area.
Top guest favourite
Guest suite in Virginia Beach
4.94 out of 5 average rating, 35 reviews

Croatan Beach Suite Retreat

AdelineRating, 5 stars9 months ago
Had a wonderful stay! The neighborhood / property is beautiful and peaceful. Just a short walk to the beach with mostly private neighborhood access. Hosts were extremely friendly and helpful but also respected our privacy. Everything was as described or better and we'd love to stay here again!
Guest favourite
Apartment in Virginia Beach
4.94 out of 5 average rating, 84 reviews

Oceanfront Loft: Free Parking & 1 Block from Beach

NicholasRating, 5 stars3 weeks ago
My girlfriend and I recently stayed at this property and we had a great time! We were looking for a nice little getaway from the everyday grind of NY and we found it. A short walk to the strip, two blocks away from the beach, the location is great. Access to shops, restaurants and all manner of night life. The property was as described and more. We were welcomed by a note with a fun little fortune telling activity, which was a nice way to start our romantic getaway. The unit has beach supplies which is very convenient (chairs, umbrella, towels, and even floaties!) and a top of the line Keurig model (k-cups, beans and grinder included!). There were even shower steamers and self care items stocked in the bathroom! The host put in work to prepare a binder with information about the area and you can tell it was carefully curated to help you make the best of your stay. All in all one of our best Airbnb experiences, highly recommend!

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