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Beachfront vacation rentals in Chesapeake

Find and book unique beachfront homes on Airbnb

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Popular amenities for Chesapeake beachfront rentals

Beachfront home rentals with a pool

Top guest favorite
A private saltwater pool is depicted, surrounded by a spacious patio area. The pool's clear blue water is inviting, with a ladder providing easy access. Lush greenery and a white fence frame the background, enhancing the serene ambiance near the Chesapeake Bay.
Cottage in Norfolk
4.97 out of 5 average rating, 240 reviews

Positano Villa

DanicaRating, 5 stars3 days ago
Roger’s beach house was charming. It was an older-style home with many modern updates. Quick and easy walking path to the beach. The pool in the backyard was lovely. It was a little dirty upon arriving and Roger came right over and got it all cleaned up for us during our stay. The neighborhood was a little rough we did have a few uncomfortable encounters with homeless people being two girls alone it was a little unsettling. Overall, I would definitely come back again. The weather was absolutely beautiful for our stay.
Superhost
Condo in Sandbridge
5 out of 5 average rating, 3 reviews

NEW! Oceanfront / Sunset Bay, 3 Bd / Pool

SonyaRating, 5 stars2 weeks ago
What a great getaway! I brought two other moms. We had three children under 12 and the beaches are pristine. Home was exactly as described and very clean and it was just a lovely time. I highly recommend this unit and the location.
Top guest favorite
A private in-ground pool glistens under clear blue skies, surrounded by a wooden fence. An umbrella provides shade next to a lounge area. In the background, a cabana is visible along with outdoor seating, enhancing the inviting space for relaxation.
Home in Sandbridge
4.99 out of 5 average rating, 81 reviews

Breathtaking Ocean views at Pinch Me, 8bdrm, 6bath

NicholasRating, 5 stars2 weeks ago
Beautiful home in a wonderful location. Tanya was very friendly and communicative throughout the process.
Top guest favorite
The outdoor pool area features a well-maintained pool surrounded by lounge chairs. A clear blue sky is noted above, with clouds adding texture. Nearby greenery and structures contribute to the atmosphere, allowing for a relaxing outdoor experience.
Condo in Virginia Beach
4.98 out of 5 average rating, 88 reviews

Paradise at the Beach

JoanieRating, 5 stars3 weeks ago
Great location for walking to the beach and many restaurant options. The beds are comfy and the living room has good seating options (unlike rentals that have only one couch). Kat was very responsive and attentive to our requests. She was great. FYI, Chicos has good pizza and fun atmosphere, Pocahontas Pancakes has great breakfast options and seems to be very popular there. The Shack is a cool outdoor bar. The Irish Pub had live music and fun atmosphere. We would rent again from Kat.
Superhost
A clear, inviting pool is surrounded by lounge chairs and a shaded gazebo. Lush palm trees are visible, enhancing the outdoor area. In the background, a serene body of water stretches towards a lush green landscape under a bright blue sky dotted with fluffy clouds.
Home in Sandbridge
4.84 out of 5 average rating, 124 reviews

Stunning Views of Back Bay & Seconds to the Beach

FrancescaRating, 5 stars2 months ago
What a beautiful and serene space for a women’s retreat! It is very obvious that the home is very well loved as well as very special. We all discussed coming back again because we enjoyed the space, the comfort and the scenery very much. We thoroughly enjoyed the great blue heron right outside the window each day as well as breathtaking sunsets. It was hard to get back to the grind after such a beautiful sanctuary weekend away.
Superhost
A refreshing pool is surrounded by five lounge chairs, positioned on a large deck overlooking the serene bay. Lush greenery lines the water's edge, with kayaks resting on the sandy bank. The clear blue sky reflects on the tranquil water, enhancing the peaceful setting.
Home in Sandbridge
4.68 out of 5 average rating, 74 reviews

Beach House with breathtaking sunsets

MattRating, 5 stars2 weeks ago
Rodica’s house was as advertised and a great place to spend a long weekend. I would love to come back in the summer when it’s a little warmer and enjoy the pool. We loved sitting in the back deck watching the sunsets and had great weather.
Top guest favorite
A lagoon-style saltwater pool is framed by a spacious deck, featuring multiple lounge chairs. Beyond the pool, serene water views are observed, and lush greenery adds a natural touch to the setting.
Home in Sandbridge
4.95 out of 5 average rating, 22 reviews

Sandbridge- Great Escape Saltwater Pool &Boat Ramp

LaurenRating, 5 stars8 months ago
We enjoyed our stay at The Great Escape! Most of our time was spent in the private pool and fishing from the yard into the canal. The walk to the beach was quick and easy. We loved how quiet and safe the neighborhood was. The house had all the amenities we needed- it felt like a home away from home. Kim was a great host supplying us with lots of recommendations and was quick to resolve any problems. We hope to visit again in the future!
Guest favorite
Home in Sandbridge
5 out of 5 average rating, 24 reviews

Pool, hot tub, walk to beach, family friendly home

JeromyRating, 5 stars3 weeks ago
The place had plenty of sleeping spaces which is what we needed it was a great stay. Communication went well and there was plenty to entertain everyone

Beachfront home rentals with a hot tub

Superhost
A hot tub with bubbling water is positioned under a wooden pergola. Surrounding the tub are two wooden Adirondack chairs and potted plants, creating a serene space. Dense greenery and a wooden fence provide privacy, enhancing the tranquil outdoor atmosphere.
Home in Virginia Beach
4.83 out of 5 average rating, 36 reviews

Tranquility with Hot Tub! 5 min walk to beach

TomRating, 5 stars1 month ago
We thoroughly enjoyed our stay Jan 29-Mar2 at Tranquility with Hot Tub. It was so bright and airy. Everything was super clean and there were plenty of towels and hangers. The king size bed was so comfortable and since we were there a month we washed the sheets & put them back on when we did laundry. Soaps were provided for the washer, dishwasher, and kitchen sink. Dimitri was very thoughtful in running an extremely long extension cord out to the parking area since he knew we had an EV! He also had the walk/steps & drivers side of the car shoveled after the 10.5” snow storm & salt applied. Due to the cold weather we didn’t make use of the deck but that would be a lovely place to have morning coffee or grill out although not private from the neighbors view. We highly recommend staying here & will definitely rent here again when visiting our daughter’s family!
Guest favorite
An aerial view displays the beach house and its surrounding neighborhood, with a clear path leading to the nearby beach. The vibrant shoreline is visible in the background, emphasizing the proximity to beach access, just 1.5 blocks away.
Home in Norfolk
5 out of 5 average rating, 59 reviews

Stylish Beach House, Hot Tub, Pet Friendly

BrittanyRating, 5 stars2 weeks ago
The walk to the beach was so quick and easy. We traveled with two kids 5 and 8 and the walk back and forth had zero complaints :). Kids loved the hot tub and the super cool shower on the first floor. The decor of the home was beautiful. The beach had a magical low tide for kids to play in and the locals were supper friendly. The house is right up on the highway so at night it’s pretty noisy. We just cranked up our white noise machines and on the second night no one noticed. Thank you for opening up your home and letting us create some more great memories.
Superhost
An aerial view captures the Boardwalk Resort & Villas situated directly on the Virginia Beach Boardwalk. The building features a distinctive green roof and is surrounded by sandy beach and the Atlantic Ocean. The nearby Fishing Pier and parking area are also visible.
Condo in Virginia Beach
5 out of 5 average rating, 4 reviews

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!

AldoRating, 5 stars9 months ago
We stayed a week at Kerri’s place in Virginia. She went above and beyond our expectations, very communicative and organized. She offered a ton of information and insights before and during our stay. Her place offers a delightful and relaxing getaway experience. The resort's picturesque location by the ocean provides stunning views and a serene atmosphere. The rooms are spacious, well-appointed, and comfortable, ensuring a pleasant stay. The resort amenities such as the pool, spa, and on-site restaurants add to the overall wonderful experience. The staff is friendly, accommodating, and dedicated to providing top-notch service to guests. Whether you're looking to relax by the beach or explore the nearby attractions, Boardwalk Resort is a fantastic choice for a vacation in Virginia. I would definitely recommend and revisit Kerri’s place.
Guest favorite
A spacious hot tub is situated on the deck, overlooking the vast expanse of the water. The tranquil surface ripples under the cloudy sky, creating a serene ambiance. A black lounge chair is positioned nearby, inviting relaxation while enjoying the captivating views.
Home in Buckroe Beach
4.96 out of 5 average rating, 76 reviews

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

LoganRating, 5 stars1 week ago
Kiána was super responsive and very kind! So thankful she helped us out last minute too! Anything we needed she was there to help! Hail to the redskins!!
Superhost
A coastal home is positioned amidst lush greenery with a backdrop of the ocean. The house features multiple levels and balconies, highlighting its spacious design. The inviting pool area is visible in the backyard, providing an outdoor leisure space.
Home in Corolla
4.78 out of 5 average rating, 9 reviews

Milk 'N' Honey at the 4X4 Carova Beach

ElizabethRating, 5 stars7 months ago
Absolutely loved the home and the whole experience! Our only issue was in our arrival and not being aware that high tide would impact when you should attempt getting to the house. More information regarding the tide schedule and if the roads within the houses are accessible would be very helpful. Recommendation to stop at the grocery store before you each the beach access road and what types of things are not supplied at the house would be good, too. Overall we were so very pleased with our stay and Misty was great when we needed her. I would absolutely recommend this house to my friends and family and would love to visit again!
Superhost
An aerial view of a spacious bayfront home, featuring multiple decks and a private pool surrounded by lounge chairs. A grassy yard leads to the waterfront, complemented by a dock. Nearby, tree line and neighboring homes create a serene coastal environment.
Home in Sandbridge
4.88 out of 5 average rating, 26 reviews

Star of Sandbridge

PhilipRating, 5 stars1 week ago
House was perfect for our group. Plenty of space to hang out inside and out. Everything was as described and there were no issues checking in or out. Would stay again if in the area.
Superhost
A private balcony features two woven chairs with a small table, overlooking a sandy beach and calm ocean. The sky is bright with wispy clouds, providing a peaceful setting for relaxation.
Apartment in Virginia Beach
4.62 out of 5 average rating, 13 reviews

Ocean Sands Resort 1 bedroom Oceanfront Balcony!

KimRating, 5 stars11 months ago
Everything went as smooth as expected. It was clean centrally, located, and easy to find . We have already discussed going back in the future. Jessica was friendly and easy to contact when needed, and very responsive. At this location, the staff was amazing. Desmond works at the front desk and gave us an amazing suggestion for dinner and Quinn also works at the front gave me a suggestion for breakfast. Both were amazing and we ended up eating dinner at the restaurant five nights while we were there I believe it was called 21st Street Seafood Company.
Superhost
Apartment in Virginia Beach
5 out of 5 average rating, 3 reviews

Beach Quarters Resort - The Presidential Suite 2

CatherineRating, 5 stars9 months ago
We really enjoyed our stay! The accommodations were perfect for our family of 5. Gorgeous views. The staff were very helpful and responsive.

Pet-friendly beachfront home rentals

Guest favorite
An aerial view captures the two-level beach home surrounded by lush greenery, with the Chesapeake Bay visible in the background. Neighboring properties are seen, along with a pier extending into the water, enhancing the coastal setting.
Home in Chic's Beach
4.96 out of 5 average rating, 130 reviews

Water Oaks at Chic's Beach

ClaireRating, 5 stars1 month ago
I could not recommend this place and these hosts enough! The place was warm and welcoming and I absolutely love the location. A very peaceful neighborhood with easy bay access. The hosts were amazing and responsive. The house had some maintenance problems but at no fault of theirs…just typical house problems and they handled everything extremely well and we were not inconvenienced at all! Also our dog loved the place and they were stocked will all the dog necessities which was very helpful!
Guest favorite
A dog stands on sandy beach, facing the sunset over the ocean. The vibrant colors of the sky create a serene backdrop, reflecting on the water. The dog's black and white coat contrasts softly with the warm tones of the setting sun.
Home in East Ocean View
4.91 out of 5 average rating, 158 reviews

Cozy beach cottage! One block to the beach!

TaraRating, 5 stars2 weeks ago
We stayed at the cozy beach cottage for a "girls trip" for three busy moms looking for a peaceful retreat for the weekend. The house was just as described - cute, clean, and cozy. We appreciated Kenzi's attention to detail and clear instructions, as well as local restaurant recommendations. This house is one block from the ocean; an easy stroll to watch the sunset from beach. We appreciate that the house had everything we needed and required no tasks for checkout. Thank you Kenzi for allowing us a weekend of rest and relaxation!
Superhost
An open-concept living area features a cozy seating arrangement with patterned chairs and a decorative rug. Natural light fills the space, highlighting a welcoming dining area in the background. A rustic wall decor piece adds a coastal touch, while a doorway leads to the inviting kitchen.
Home in Norfolk
4.76 out of 5 average rating, 103 reviews

Beach Bungalow - 1 Block to Beach - Pets Welcome!

OliviaRating, 5 stars1 week ago
Absolutely loved this spot! The theming was adorable for a beach weekend and the location was perfect - just steps from the beach! Would definitely stay here again
Superhost
Home in Norfolk
5 out of 5 average rating, 4 reviews

Beachfront Getaway, pet friendly

JasonRating, 5 stars5 months ago
Our family enjoyed our weekend at Big Blue. It was special because it was my wife's birthday and there was plenty of family with us. We really liked how the 2nd and 3rd floor are duplicates of each other. It's like 2 different apartments , but we had access to both. The kids on the 2nd floor and the adults on the 3rd. Very clean open spaces. The host were responsive and proactive. We hope to make the Willoughby Spit area a regular vacation spot, very lovely.
Guest favorite
Home in East Ocean View
4.9 out of 5 average rating, 137 reviews

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

AshleyRating, 5 stars4 days ago
Space was perfect for us staying as a family of 6. Bedrooms were great and the home offered plenty of space throughout. Awesome backyard, although we did not really use - very close beach access. Had all the amenities we needed for a long weekend!
Top guest favorite
A modern kitchen features white cabinetry and a granite countertop, equipped with stainless steel appliances including a stove and a refrigerator. Under-cabinet lighting enhances the space, and ample storage is provided by multiple upper and lower cabinets. A sink is positioned near a window, allowing natural light.
Home in East Ocean View
5 out of 5 average rating, 113 reviews

Quiet East Beach Bungalow, 1 block to beach!

D1Rating, 5 stars1 week ago
A+++ From the front door to the sand is only a football field away! New and pristine house. Host is incredibly responsive. Peaceful and clean beach. Close to shopping and VA beach boardwalk is only 20 minutes. Highly recommended.
Top guest favorite
A charming cottage is presented with a well-maintained front yard, featuring blooming trees and vibrant flower planters. A covered porch is visible, framed by decorative railings and welcoming steps that lead from a concrete driveway. The surrounding greenery adds a peaceful ambiance.
Cottage in Norfolk
4.97 out of 5 average rating, 324 reviews

Lovely Ocean View Cottage

JeromeRating, 5 stars1 week ago
We had such an enjoyable trip staying at this perfect cottage. The location was amazing-short walk to a tranquil beach that felt like our own little escape. The landscaping and yard were beautiful! The place felt like a peaceful retreat. The cottage itself was cozy, clean, and had everything we needed even a thoughtful welcome basket. It truly was the perfect getaway and just what we needed to recharge. Highly recommend!
Superhost
A three-story house with light green siding features a welcoming front porch supported by white columns. A flag is displayed on the left side, while the driveway leads to a garage. Lush greenery surrounds the property, contributing to a tranquil atmosphere.
Home in East Ocean View
4.85 out of 5 average rating, 163 reviews

Your family beach house

JenniferRating, 5 stars19 months ago
Prefect place and everything we needed. Host couldn’t have been more helpful

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