Vacation rentals with a pool in Chesapeake Beach

Private Pool at the Oceanfront in a Spacious Home

Private Pool at the Oceanfront in a spacious 2600 sq ft home. 3 blocks from the Virginia Beach Boardwalk, Vibe District. 4 bedrooms in a three-story Private Home. 1st Flr: 2 bathrms, a bedrm with Full-bunk bds, kitchen, dining rm & living rm. 2nd lvl contains a lux Mstr ste with massive jacuzzi, dbl shwr and living rm . 3rd Lvl: 2+ bedrms, bathrms & prvt balconies (queen in 1 room and 2 doubles in the other). Two-car garage and driveway, NOT a duplex. Pool unheated. Modern Tvs and cable!

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!

Salida del Sol, North End Beach / Oceanfront Area

Immaculate 2 bedroom/2 private bath condo. 5 Star unit is located on the Va Beach North End across the street from the Atlantic Ocean with public beach access. The unit is fully furnished to accommodate 6 guests. Fully stocked kitchen, beach gear (cart/chairs/umbrella), outdoor grill, 2 patio areas, WIFI, 3 flat screen TV’s, 2 private parking spaces, keyless entry. 2026 Pool Season May 22-Sept 7. PLEASE NOTE. We are unable to accommodate late checkouts (AFTER 10:00AM ) May-September!

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!

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!

Condo with pool & beach access!

Our family beach condo is ready to welcome you too! All new flooring, furnishings, bedding, TVs, & decor... you're going to love it! Open kitchen and gathering space for the family to relax, just steps away from the beautiful community pool and across the street from the north end beaches! This two bedroom, two bath unit sleeps up to six guests! A 2 minute drive to the shopping and nightlife on the boardwalk! Enjoy a peaceful oasis with access to all the fun!

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

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.

Oceanfront Studio: Boardwalk, Beach, & Pool Views

Atlantic Ocean views from the comfort of a thoughtfully designed Oceanfront Studio featuring Boardwalk, Beach, and Saltwater Pool Views, perfect for a relaxing Virginia Beach getaway. A “Guest Favorite” Airbnb that offers reserved parking just steps from the sand , no streets to cross. Park your car, settle in, and enjoy a walkable oceanfront experience with restaurants, entertainment, and the beach and boardwalk right outside your door.

Designer Beach House | Pool, Hot Tub, Walk to Sand

Breaker Bay is a fully renovated 5BR, 3BA beach cottage in the heart of Sandbridge. With a private pool, hot tub, spacious deck, and open living space, it’s perfect for families or groups. Just minutes from the sand, it offers the ideal blend of comfort and coastal charm. Wake up to ocean sunrises, unwind with bay sunsets, and enjoy all that this peaceful beach community has to offer. Your perfect coastal getaway starts here.

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.

4BD home w/ game room & pool near Langley & PTC!

Welcome Home! Be the next to rent this beautifully renovated, modernized home with beautiful kitchen, amazing bathrooms and generous bedrooms and closets. Come in and relax in this centrally located neighborhood - convenient ten minute trip for shopping, restaurants and military bases. Great for families coming in town for Boo Williams tournaments! This is the one! DONT FORGET TO ASK ABOUT OUR YACHT RENTAL OPTIONS!!!