Holiday 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.

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Guest favourite

Apartment

4.86 out of 5 average rating, 229 reviews

Ocean Escape

Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Community pool area, complete with Jacuzzi tub, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

Superhost

Home

4.82 out of 5 average rating, 22 reviews

The VIBE House with POOL!

This amazing home located in the happening VIBE district with your personal in ground pool has it all. Walking distance to the Virginia Beach Convention Center and Sports center. Also, on 6 blocks off all the action at the Virginia Beach boardwalk and oceanfront. Amazing restaurants, beautiful beach and waves, and all the local hot spots for shopping are all walkable from this home. A farmers market located on 19th street is steps away from the home. Enjoy this event every Saturday from 9:00 AM

Guest favourite

Apartment

4.85 out of 5 average rating, 127 reviews

Oceanfront, beachfront, boardwalk, fun, dolphins

Fantastic condo on the beach. Floor to ceiling windows in living-room, bedrooms. Watching waves, sunrise, dolphins. Enjoy the ocean, boardwalk, beach gym, playground right at downstairs. Extra-large end-unit with fully equipped kitchen, saves you $$$ on meals. One free parking. Walking distance to restaurants, bars, stores, beach concerts, activities, art shows, performance. New 65” QLED TV, new sofa and dining set. Ask for extended stay discount! Up to 45% off Winter Special Deals. Book now!

Guest favourite

Apartment

4.93 out of 5 average rating, 59 reviews

VA Beach Retreat! Quiet and perfect for families!

Relax with the whole family at this peaceful place to stay. This property is ON the beach (unit itself is not facing the ocean) with access to 3 pools, a gym, local restaurants and much more! As you can see, guests LOVE my place! I frequently travel for work, spending a lot of time in hotel rooms. I know the NECESSITIES! ** I am currently replacing furniture! Pics may not match exactly but it is for the better. Expect brand new: King and queen mattresses. Bedding. Living room furniture.

Guest favourite

Guest suite

4.95 out of 5 average rating, 544 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

Guest favourite

Flat

4.87 out of 5 average rating, 145 reviews

VA Beach Oceanfront Studio, Beach, Boardwalk, Pool

This studio condo is located at the north end of Virginia Beach's famous boardwalk, just steps to the beach with an Atlantic Ocean view. Walking distance to area attractions, restaurants, and shopping. Ideal for couples with access to the salt water pool, lawn on the beach with lounge chairs and tables, and a reserved parking space. If you are visiting for a quiet getaway or for an event, you will love the boutique feel in an ideal location of this clean, newly renovated condo

Superhost

Holiday home

4.91 out of 5 average rating, 35 reviews

VB Paradise / Private Pool, Hot Tub

Outdoor living is king at “A Secret Spot”, a lovely cottage located at the north end of Sandbridge. Offering a beautiful outdoor pool area, fenced yard for children, covered hot tub, and plenty of decks and space to spread out or gather together! Under the house offers an outdoor living room with seating, a ping pong table, and picnic table. Imagine steamed crabs and drinks while relaxing with family by the pool. ! Inside there are more games for everyone to enjoy.

Guest favourite

Home

4.84 out of 5 average rating, 82 reviews

Perfect Getaway!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

Guest favourite

Home

4.95 out of 5 average rating, 22 reviews

Sandbridge- Great Escape Saltwater Pool &Boat Ramp

Stunning panoramic water views! Enjoy this classic cozy coastal home with an open floor plan, fully stocked kitchen & lagoon style saltwater pool. Lots of covered deck space, including a screened-in porch for relaxing after a day in the sun. 3 bedrooms, 2 full baths, an enclosed outdoor shower. Located on quiet neighborhood street with easy walk to the beach. Bring your water toys for this is a waterfront home with private boat ramp and pool. Sunday check-in.

Guest favourite

Apartment

4.89 out of 5 average rating, 208 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

Guest favourite

Cottage

4.97 out of 5 average rating, 236 reviews

Villa Positano

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

Guest favourite

Home

4.96 out of 5 average rating, 188 reviews

Exit del Sol, North End Beach

The beach AND privacy! Wide open residential beaches, with plenty of "distancing space"! Best kept secret at the beach! Fully stocked, fully furnished, immaculate Vacation rental on Va Beach North End. 5 star rating says it all. Atlantic Ocean across the street. Public beach access. 3 flat screen TVs, Wifi, cable, beach cart, chairs &'umbrella. Outdoor grill. Private parking. 2025 Pool Season... May 23–September 7. NO HAIR DYE!