Vacation rentals with a pool in Chesapeake

The Great River Escape *Hot Tub!

Welcome to the River Escape, where the sun is hot and river breezes are cool! Located on the Hampton River, on a big fenced lot, with easy river access and just a 10 minute drive to sandy toes and the sound of crashing waves, this fantastic river house is made for the best family vacations around. It is furnished to comfortably sleep 6, featuring a spacious, well-stocked kitchen, private in-ground pool, hot tuband a gas grill in the backyard! Just add family, and you've got instant vacation fun!

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

Ocean & Bay Views - Newly Renovated! Local Family!

Just steps away from the sand, "Carolina on My Mind" is a 2b/2ba oceanside condo at the exclusive Sanctuary at False Cape, the only Oceanfront complex at Sandbridge in Virginia Beach. You'll enjoy a private patio with both Ocean and Back Bay views. The condo features a large open-concept living space, and a fully equipped gourmet kitchen, and high end finishes. Free access to all condo amenities, including free parking, 3 pools, grills, and a fitness center! Your beach vacation awaits!

"Shangri-La", of Hampton, Virginia

2nd story 1200 square foot apartment with 2 BR's, Wi-Fi, microwave, fridge and bar with sink. Walk in glass enclosed shower & soaker tub. Private deck with gas grill down the spiral stairs below on ground level patio. Pool table in BnB. We share our pool with our BnB guests seasonally. Please inquire about pool availability if important to your booking. Local history, sites, nature and beaches abound. Security cameras surround the exterior of our home for our protection as well as yours!

Gorgeous Vacation House

This is is the perfect home away from home! Enjoy cozy furnishings and modern amenities in this 3bed/2.5 bath house located in the vibrant city of Norfolk oceanview. The house is renovated with top notch material and artistic touch. The kitchen, living room, and private backyard with deck/patio swimming pool make it the ideal place to relax. Shopping, restaurants, and entertainment are all within minutes; plus onsite parking and self-check-in make this an ideal destination for travelers.

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.

Jen n John's Mini Mansion.

Welcome to Surfside at Sandbridge!!! Sandbridge is the northern most portion of the OBX!!! Location location location. this tiny home is 3 years old and was previously a vacation property. This will be it's first year on airbnb. there is a queen adjustable bed in the master and two twins in the loft. There is room for a air mattress in the loft also. This unit comes fully stocked for everything you'd need for a beach vacation. Towels..chairs..beach canopy..boogie boards..ect.

Artful Retreat with a Private Pool

Take a break and unwind at your private pool! Stylish, updated interior and a spacious backyard with pool and lounge area. Rinse off at the outdoor shower after a day at the beach and enjoy your private retreat! The Rudee Inlet is less than a block away with great restaurants, fishing, and water activities. A path along the Rudee Inlet leads to the beach and shops - a quick 4 block trip with the included bikes! Outdoor seating and gas fire pit added for the cooler months!

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

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 on the balcony 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.

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!

Positano Villa

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.

Retreat with Pool, Walk to Beach

Escape to The Old Beacon, a spacious 3-bedroom first floor unit just 2 blocks from the Virginia Beach boardwalk! This 1940 vintage cottage turned modern retreat in 2021 comfortably fits your group and offers a private interior with access to a fantastic shared pool and backyard (exclusively for guests staying at The Old Beacon). Enjoy the perfect blend of beach life and poolside relaxation in a prime, walkable location.