Vacation rentals with a pool in Chesapeake Beach

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.

Oceanfront Building Boardwalk Pool Beach 3 Beds

Welcome to the Cozy Crab – updated, comfort-focused & steps from the sand! Located in a quiet corner of a beachfront building on the Virginia Beach boardwalk with a seasonal pool (open mid-May–mid-Oct). Sleeps 4 with 3 real beds: one queen and two singles, all with real mattresses. Features a large, updated bathroom with full vanity and a kitchen. Just a few steps up—no elevator needed. No chore checkout, pro cleaning, fresh linens/towels, WiFi. 2nd-floor grills. Eat! restaurant is downstairs!

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!

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.

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!

THE OLD BEACON 3 I Beach Living

The Old Beacon unit 3 is a two story unit with living space on the first floor and bedrooms on the second floor. It’s one of the units of the back cottage on the property. Adorable, cozy interior with access to the amazing outdoor common area - pool, cornhole, porch swings, outdoor dining area, and outdoor shower for when you return from the beach! Kick back and relax in this calm, stylish space that’s two blocks to the beach and Virginia Beach boardwalk!

Oceanfront Studio: Boardwalk, Beach, & Pool Views

Atlantic Ocean views from the comfort of an Oceanfront studio, perfect for beach-loving travelers. Reserved parking space just steps from the beach, indulge in the sand & surf without having to cross a street. Park your car, & let your toes sink into the sand for a truly relaxing stay. Equipped with Wi-Fi & Roku TV, you can stay connected throughout your visit. Take a refreshing dip in the saltwater pool or lounge on the lawn just steps from the beach.

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen

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

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.

Sunrise, North End Beach

The beach AND privacy! Wide open residential beaches, with plenty of 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. 2026 Pool Season... May 22-September 7. NO HAIR DYE!

Beautiful and Chic Studio Apartment

Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.