Vacation rentals with a pool in Chesapeake Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Chesapeake Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.

Home in Portsmouth

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!

4.92 out of 5 average rating, 173 reviews

Top guest favorite

A modern kitchen area is visible, featuring stainless steel appliances and a granite countertop with bar seating. Two stylish light fixtures hang above, while the space is illuminated by natural light from large windows covered with light curtains. A seating arrangement includes sleek black bar stools.

Home in North Virginia Beach

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!

4.97 out of 5 average rating, 247 reviews

Top guest favorite

A private pool area features comfortable lounge chairs with floral cushions, surrounded by a clean concrete patio. A screened-in porch is visible in the background, with two inviting chairs for relaxing. The fenced yard offers additional privacy and space for outdoor enjoyment.

Home in Virginia Beach

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!

4.96 out of 5 average rating, 129 reviews

Guest favorite

A two-story house featuring a welcoming porch with white railings and steps leading to the front door. The exterior is clad in light siding, complemented by well-kept landscaping and a driveway leading to a garage on the right. Trees provide a natural backdrop.

Home in Suffolk

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!

4.84 out of 5 average rating, 116 reviews

Guest favorite

A welcoming living area features a tan leather sofa and two light-colored armchairs arranged around a wooden coffee table. A textured area rug covers the floor, and large windows provide natural light. The open kitchen is visible in the background, enhancing the spacious feel.

Home in North Virginia Beach

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!

4.97 out of 5 average rating, 100 reviews

Guest favorite

Cottage in Norfolk

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.

4.96 out of 5 average rating, 299 reviews

Top guest favorite

Condo in Virginia Beach

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.

4.97 out of 5 average rating, 153 reviews

Guest favorite

A welcoming living area features a large orange sofa adorned with white cushions, paired with two light-colored armchairs. A round wooden table sits at the center, complemented by a beige area rug. The open kitchen behind includes modern bar stools and stylish pendant lighting.

Home in Sandbridge

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.

4.95 out of 5 average rating, 132 reviews

Superhost

A charming coastal cottage exterior is depicted, featuring a white clapboard façade and a shingled roof. The blue front door is framed by decorative shutters, with a welcoming wreath displayed. An American flag hangs proudly, completing the inviting entrance.

Home in Virginia Beach

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.

4.81 out of 5 average rating, 167 reviews

Guest favorite

Home in Hampton

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!!!

4.91 out of 5 average rating, 138 reviews

Top guest favorite

The exterior of a two-story brick apartment building is shown, featuring a staircase leading to the entrance. Lush green shrubs and trees frame the entrance, while a driveway accommodates two blue recycling bins. A neighboring structure is visible to the left.

Guesthouse in Chesapeake

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.

4.98 out of 5 average rating, 262 reviews

Guest favorite

The exterior of a private attached suite is shown, featuring a welcoming entrance with white steps and a small porch. Lush greenery and colorful flowers frame the walkway, leading to a paved driveway. A wooden fence provides privacy, while a well-maintained lawn enhances the setting.

Guest suite in Chesapeake

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. NOTE: Pool is open from Memorial Day to Labor Day. 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.

4.94 out of 5 average rating, 681 reviews