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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Superhost

Home in Virginia Beach

4.79 out of 5 average rating, 24 reviews

The VIBE House with POOL!

This amazing home located in the happening ViBe district of the Virginia Beach Oceanfront has it all! Personal in-ground pool and backyard dining table! 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 h

Top guest favourite

Home in Gloucester Point

4.99 out of 5 average rating, 178 reviews

York River Vacation Home

This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

Guest favourite

Apartment in Sandbridge

4.87 out of 5 average rating, 233 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.

Guest favourite

Apartment in Virginia Beach

4.89 out of 5 average rating, 211 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Nestled in the heart of the coastal city of Virginia Beach where all of the area’s greatest attractions will be right at your fingertips. This coastal beach studio offers a space-maximizing layout which includes kitchenette with full size appliances. All on the desirable north end of the Virginia Beach boardwalk. This small oceanfront complex is one of a kind, a great place for couples or a small family. Enjoy an early morning cup of coffee while enjoying beautiful views of the Atlantic Ocean.

Guest favourite

Home in Sandbridge

4.99 out of 5 average rating, 70 reviews

The Golden Hour Pool is Open!

The Golden Hour is a third row beach house with a private beach access just off the pool deck! 5BR/3.5BA completely remodeled beach house in the heart of Sandbridge with a 16x32 pool AND baby pool! Custom kitchen and baths with personalized touches throughout. Lots of outdoor spaces to go and enjoy the Sandbridge Beach lifestyle! Pool opens May 2nd and closes October 15th! Pets on a case by case basis. Some breed restrictions for insurance purposes. Must provide docs after booking

Guest favourite

Home in Corolla

4.91 out of 5 average rating, 22 reviews

LUX Oceanview•Heated Pool•2-Min Walk to Beach

🏖 Upscale oceanview retreat in Corolla—just 2 mins walk to the beach! • Private heated pool & hot tub (Pool open Apr 1 - Oct 31, no heat fee) • Breathtaking ocean views from balconies & living spaces • Outdoor spaces: 10-seat dining, modern patio furniture, pergola, swings and more • EV charger on-site—free Level 2 charging • Entertainment: Ping pong, Xbox, Smart TVs, & streaming • Pet-friendly! Bring your furry friends • Prime location near Currituck Lighthouse & wild horse beaches

Guest favourite

Home in Suffolk

4.84 out of 5 average rating, 90 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

Apartment in Sandbridge

4.94 out of 5 average rating, 63 reviews

Cher's Place @ The Beach

Relax with the whole family at this peaceful place to stay in Sandbridge! 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 and bedding so pics may not match perfectly. Need more room?? See my other property!

Top guest favourite

Home in Sandbridge

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.

Top guest favourite

Cottage in Norfolk

4.97 out of 5 average rating, 242 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.

Top guest favourite

Home in Virginia Beach

4.96 out of 5 average rating, 197 reviews

Salida 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!

Superhost

Holiday home in Sandbridge

4.89 out of 5 average rating, 38 reviews

VB Paradise / Private Pool, Hot Tub

A Secret Spot – 6BR/4BA Family Oasis with Pool, Hot Tub & Game Lounge | 4-Min Walk to Beach Discover your dream coastal getaway at “A Secret Spot,” a stunningly appointed 6-bedroom, 4-bathroom home tucked into the peaceful north end of Sandbridge Beach. Just 750 feet from the ocean, this spacious home blends laid-back beach charm with resort-style outdoor living and non-stop entertainment for the whole family.