Holiday rentals with outdoor seating in Chesapeake

5 out of 5 average rating, 103 reviews

A modern kitchen features light cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator, oven, and dishwasher, are visible. Soft lighting highlights the spacious layout, which is complemented by tiled flooring and a seamless flow into the adjacent dining area.

Home in Portsmouth

Hidden Gem.4/bedroom cozy home fenced in yard

Make yourself at home!Hidden Gem offers a clean welcoming space for guests, located in a quiet established neighborhood. Guests should expect a clean and comfortable stay. Conveniently located near parks,shopping, and dining options. Attractions aren’t too far away Rivers casino.2.9. Virginia Beach Ocean Front.23miles. Waterside district Norfolk 8.5 miles. Town center 17.miles. Busch Gardens 40 miles. Old Dominion University 9.8 miles. Norfolk State University 8.8 miles.Hampton University23miles

4.94 out of 5 average rating, 133 reviews

A couple relaxes on the deck of the sailboat, enjoying drinks against a vibrant sunset backdrop of pink and purple hues. Soft blankets and a cozy atmosphere are present, with the marina and boats gently reflected in the calm water.

Boat in Norfolk

Romantic Sailboat Experience + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.

4.96 out of 5 average rating, 134 reviews

THE POINT! Private waterfront Oasis!

Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

Guest suite in Portsmouth

A comfortable living room area is featured, showcasing a light-colored sectional sofa with dark blue accent pillows. A dark coffee table is set in front of the sofa. A vibrant world map painting adorns the wall, and natural light streams through a nearby window.

4.96 out of 5 average rating, 117 reviews

Historic Hideaway Private Apartment/Suite

You will be comfortable in this spacious, one bedroom suite. You have your own kitchen, washer/dryer, and living room space with large tvs in the bedroom and the living room. To wind down from your day step into your large beautiful shower that has endless hot water. Try living room sofa pulls out to a sleeper lay down while watching tv, or to use as an extra bed. Enter/exit thru a private entrance. Only you will have access to your space. Clean and inviting. Stay a day, or stay a while!

4.99 out of 5 average rating, 186 reviews

Apartment in Chesapeake

Modern Luxury Peace & Quiet.

Covered parking with EV Charger. With one acre fenced in yard. 1000+ sq ft Modern Second Floor Guest House apartment with separate private entrance attached to a 10,000+ sq ft Mansion on 3 acres in a very safe, quiet and private neighborhood. Free private parking. Minutes from restaurants, shopping centers, and a beautiful 30 minute drive to oceanfront. Free Netflix, High Speed WiFi, washer, dryer, full kitchen. With Keurig. Brand new Heat and Air Condition! Plus 2 dedicated parking spots.

4.94 out of 5 average rating, 399 reviews

A house with a blue and white exterior is situated on the edge of the water, reflecting in the calm surface. Lily pads float nearby, while flags adorn the porch railing, indicating a welcoming environment. Greenery surrounds the area, enhancing the serene landscape.

Home in Moyock

Sportsman's Paradise ( Hunting & Fishing )

Sportsman's Paradise is just minutes away from the Currituck Sound which is famous for it's duck hunting and fishing. It overlooks Tull's Bay and Tull's Creek and is surrounded by the Northwest River Marsh Game Lands. The kitchen and living room have 9 windows so you can look out three sides of the house at the water. The walls are old rough cut boards and the ceilings are plywood. The living room and bedrooms are carpeted and the bathrooms and kitchen are laminate wood floor.

4.85 out of 5 average rating, 114 reviews

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!

4.96 out of 5 average rating, 138 reviews

A cozy bedroom features a four-poster bed adorned with soft linens and decorative pillows. A vintage armchair is positioned nearby, while a window dressed with light blue curtains allows natural light to brighten the space. Subtle wall stripes in calming colors add character.

Home in Chesapeake

Cook's Country Escape - Cozy Retreat

Escape the everyday and enjoy this cozy countryside retreat! Nestled halfway between Virginia Beach and the Outer Banks, this home offers the charm of a cabin with the comforts of a full house. Perfect for families or friends, it’s a peaceful getaway from city life yet close to beaches, parks, and attractions. From the moment you arrive, you’ll feel the warmth and relaxation of a true country home. It’s been a great rental with great ratings.

Guest suite in Chesapeake

The Purple Room features a spacious bed with white linens and purple accents. A cozy seating area is visible beside large windows with light filtering through sheer curtains. Decorative elements, including wall art and a soft purple rug, enhance the vibrant atmosphere.

4.97 out of 5 average rating, 387 reviews

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!

Welcome to The Purple Room, where every guest is made to feel like royalty. More than an Airbnb, it’s a one-of-a-kind boutique retreat intentionally designed to create unforgettable memories. From the peaceful atmosphere and thoughtful touches to your private entrance and relaxing escape, every detail has been curated to help you unwind, recharge, and experience something truly special. Come discover The Purple Room experience. 💜

A charming two-story home is seen from the street, featuring a welcoming front porch with white railing. Large windows allow natural light to fill the space. The yard is well-maintained and bordered by a sidewalk, surrounded by trees that provide shade.

4.99 out of 5 average rating, 156 reviews

Ghent on the Corner: Cozy 3 bed 2.5 bath home

My cozy, 3 bed / 2.5 bath Norfolk home has a spacious 1st floor primary suite with a full bathroom, 2 bedrooms upstairs along with a 2nd full bathroom. No cleaning fee or checkout instructions. Pet-friendly! Free Wi-Fi, parking for 4 cars, grill & gazebo. Distances: CHKD - 5 min EVMS - 5 min Sentara Norfolk General - 5 min Waterside / Downtown - 10 min Ocean View - 20 min VB Oceanfront - 25 min

The living room features a cozy seating arrangement, including an orange couch and a blue armchair. A round coffee table sits in the center, adorned with books. A mounted TV can be seen on a light-colored wall, contributing to a welcoming atmosphere.

4.89 out of 5 average rating, 133 reviews

10 min to Ocean View Beach: 20% Off Aug

Welcome to our charming 3-bedroom retreat nestled near the lake and Ocean View beach, just a short 10-minute drive away. Our property has an outdoor patio with firepit and balcony deck for alfresco dining area. Our Volleyball net in the large backyard is also available for use. This cozy haven is designed for comfort and entertainment, with thoughtful touches to make your stay truly memorable.

Guest suite in Chesapeake

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.

4.95 out of 5 average rating, 663 reviews

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.

Popular amenities for Chesapeake outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.92 out of 5 average rating, 169 reviews

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

4.96 out of 5 average rating, 123 reviews

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

The living room features a welcoming layout with plush blue couches and two light-colored round ottomans. A ceiling fan hangs above, and natural light streams in through multiple windows. The front door is painted in a vibrant teal, adding a cheerful touch.

4.9 out of 5 average rating, 101 reviews

Cozy 3BD Beachfront | Foosball & Yard Games w/ BBQ

4.83 out of 5 average rating, 134 reviews

Walk to Beach! Fully Updated + Hot tub!

The exterior of the three-story vacation home features a light-colored facade with pink door accents. A welcoming porch with multiple white railings is visible, alongside neatly arranged landscaping. The surrounding area includes multiple parked vehicles and trees, creating a pleasant setting.

4.92 out of 5 average rating, 206 reviews

Coastal Family Retreat • Fire Pit • Walk To Beach

4.99 out of 5 average rating, 229 reviews

A sandy beach stretches into the distance, bordered by gentle dunes and green grasses. A wooden walkway leads to the shore, where several figures can be seen walking. The calm ocean reflects the blue sky, dotted with fluffy white clouds.

Home in Virginia Beach

Play by the Bay 1 MIN TO WATER

A bright kitchen is highlighted by light-colored cabinetry and natural wood flooring. The countertop displays a cutting board, and the sink is complemented by a stylish faucet. Large windows allow natural light to fill the space, enhancing the tile backsplash's subtle patterns.

4.82 out of 5 average rating, 380 reviews

Charming Home by the Sea, a block from the beach!

A cozy living area features two armchairs and a leather sofa, arranged around a circular coffee table on a patterned rug. A fireplace is situated against the wall, complemented by a television mounted above. Natural light is allowed in through the window with white blinds.

4.85 out of 5 average rating, 167 reviews

Beach Hideaway 2 bdr/2bth- Pet friendly!

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 31 reviews

A light-filled living space features a comfortable leather sofa and a modern dining table. A TV is mounted on the wall, and a large window allows natural light to illuminate the room. A small indoor plant adds a touch of greenery, enhancing the airy ambiance.

Apartment in Chesapeake

Serene Tree House Retreat | Spacious 1br/1bth Home

Apartment in Buckroe Beach

A spacious bedroom is depicted, featuring a large bed with a light-colored blanket. A ceiling fan is installed above, and large windows are dressed with dark curtains. A couch and a small table with a chair are positioned to the side, contributing to the room's layout.

4.89 out of 5 average rating, 146 reviews

The Cottage at Sojourn: Buckroe - one bedroom

Apartment in Virginia Beach

An open-concept living area features a blue sofa with colorful throw pillows and a light-colored rug. A pair of small woven tables is situated in front, while a well-equipped kitchen is visible in the background, featuring white cabinetry and modern appliances.

4.77 out of 5 average rating, 164 reviews

Historic 1910 Getaway Steps to Beach

4.9 out of 5 average rating, 119 reviews

An inviting living area showcases two comfortable couches arranged around a glass coffee table. A large television is mounted on the wall opposite. The dining area, featuring a modern table and chairs, can be seen in the background, enhancing the open floor plan.

Apartment in Hampton

Comfy 3 Bedroom Hideaway Minutes From H.U. & Beach

Apartment in Virginia Beach

A wooden deck is showcased, surrounded by lush greenery. The railing is made of wood with black metal accents. The space offers an inviting outdoor area, nestled in a tranquil environment with a view of trees and a fenced yard.

4.91 out of 5 average rating, 594 reviews

Private apartment only 3 blocks from the Beach

4.94 out of 5 average rating, 136 reviews

The exterior of a historic home features classic architectural details, including a covered porch with white columns. An American flag is prominently displayed, and mixed flower pots are arranged on the brick pathway. Large windows allow for natural light, showcasing the home’s inviting presence.

Apartment in Portsmouth

Best location in Olde Towne Portsmouth

Apartment in Newport News

A spacious studio apartment features a queen-size bed adorned with a colorful coral-themed quilt. Nearby, a small seating area is visible, alongside a well-equipped kitchen. Warm wood flooring enhances the inviting atmosphere, complemented by a modern ceiling fan and natural light entering through the window.

4.98 out of 5 average rating, 251 reviews

Centrally Located Sleek Studio Apartment

4.97 out of 5 average rating, 315 reviews

A fully stocked kitchen is presented, featuring a gas stove, a refrigerator, and a microwave. A dark wooden hutch displays dishes and glassware, while a Keurig coffee maker is located on the countertop. Natural light filters in through a nearby window, illuminating the tiled floor.

Apartment in Portsmouth

Cozy Ground Floor Apt in Historic Home

Condo rentals with outdoor seating

Two light blue Adirondack chairs are positioned facing the ocean, accompanied by a small table. The sandy beach stretches into the distance, meeting gentle waves under a pastel sky at dusk. A lounge chair rests nearby on the green grass.

4.89 out of 5 average rating, 245 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

4.99 out of 5 average rating, 106 reviews

A workspace with a wooden desk and a comfortable chair is situated by large windows, offering expansive views of the ocean. Natural light streams in, highlighting the tranquility of the beach outside. The windows are framed by light-colored blinds, with a small plant placed on the desk.

Condo in Norfolk

Beachfront Getaway, Pet Friendly, Mermaid Suite

A private backyard area is visible, featuring well-maintained grass and colorful flowering plants. Seating areas with chairs and umbrellas overlook the beach, which is just beyond the fence. The ocean appears calm under a clear sky, enhancing the serene atmosphere.

4.88 out of 5 average rating, 104 reviews

Oceanfront Condo with Spectacular Beach View

The living room showcases two spacious leather sofas facing a flat-screen television. Natural light floods the room through two large windows, adorned with light-colored blinds. A coffee table centers the space, complemented by decorative plants and artwork on the wall.

4.93 out of 5 average rating, 136 reviews

Spacious Captain’s Beach Suite Near Rudee Inlet

A charming private balcony offers a dining setup for two with white Adirondack chairs and a table, overlooking the beach. A stunning sunset illuminates the horizon, while the seaside view provides a serene backdrop for the table adorned with floral centerpiece and tableware.

4.88 out of 5 average rating, 264 reviews

Oceanfront Gem VaB Studio Exceptional Views

4.97 out of 5 average rating, 144 reviews

Oceanfront Studio: Boardwalk, Beach, & Pool Views

The outdoor pool area features a well-maintained pool surrounded by lounge chairs. A clear blue sky is noted above, with clouds adding texture. Nearby greenery and structures contribute to the atmosphere, allowing for a relaxing outdoor experience.

4.98 out of 5 average rating, 114 reviews

Paradise at the Beach