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Pet-friendly vacation rentals in Chesapeake

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Vacation rentals for every style

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Popular amenities for Chesapeake pet-friendly home rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Pet-friendly home rentals with a pool

Guest favorite
A three-story beach house is shown during sunset, with soft orange and pink hues in the sky. The exterior features multiple balconies and large staircases. A private pool is illuminated within a fenced area, surrounded by outdoor seating for relaxation.
Home in Corolla
4.9 out of 5 average rating, 21 reviews

LUX Oceanview•Heated Pool•2-Min Walk to Beach

Guest favorite
A spacious pool area is presented, featuring a large, inviting blue swimming pool with a built-in hot tub. Several lounge chairs and umbrellas provide shaded seating around the pool, while sliding glass doors lead to the interior of the house.
Guesthouse in Virginia Beach
4.72 out of 5 average rating, 115 reviews

POOL, Pool House, Hot Tub, Grill, 2 bedroom

Guest favorite
A well-appointed backyard patio features a dining table accompanied by several chairs. A swimming pool is situated nearby, surrounded by a wooden fence and trees. Sunlight illuminates the area, creating a bright and inviting outdoor space.
Home in Norfolk
4.95 out of 5 average rating, 97 reviews

Gorgeous Vacation House

Superhost
A private pool with a curvy shape is surrounded by a sun patio featuring several lounge chairs. A red umbrella provides shade over a dining area nearby, accompanied by a concrete surface and blue siding of the home in the background.
Home in Corolla
4.83 out of 5 average rating, 35 reviews

N-2-Wishn, Corolla Light, NC- 5BR, 6BA,Water Views

Guest favorite
An outdoor deck area is visible, featuring a wooden table surrounded by six chairs, a grill nearby, and two lounge chairs positioned for relaxation. The space is enclosed by a wooden fence, with greenery providing a natural backdrop.
Place to stay in Virginia Beach
4.93 out of 5 average rating, 76 reviews

North End Home with pool, beach & state park.

Guest favorite
A spacious backyard features a saltwater inground pool surrounded by manicured grass. A two-level deck is visible with patio furniture, offering comfortable seating options. The exterior of the two-story house is seen in the background, under a partly cloudy sky.
Home in Suffolk
4.84 out of 5 average rating, 87 reviews

Perfect Getaway!

Superhost
Home in Virginia Beach
4.89 out of 5 average rating, 132 reviews

Beach Home, Upscale Croatan Resort + Private Pool

Guest favorite
The open-concept living space is shown, featuring a comfortable seating area with a queen sleeper sofa and two armchairs. A wood-burning fireplace is adjacent to the large TV, while a dining table is set for six. Wall-to-wall glass doors provide views of the outdoors.
Condo in Williamsburg
4.95 out of 5 average rating, 122 reviews

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

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Pet-friendly home rentals with a hot tub

Guest favorite
A charming blue beach house features a multi-level design with large windows that invite natural light. A spacious deck offers unobstructed views of the surrounding sandy landscape. Steps lead up to the entrance, enhancing accessibility to the home. Wild grasses frame the property.
Cottage in Corolla
4.88 out of 5 average rating, 145 reviews

Horses-Views-Dog Friendly-4WD Area

Guest favorite
Aerial view of the property showcasing a fenced backyard with a sparkling blue pool surrounded by concrete. A seating area with lounge chairs and various floatation devices is visible beside the pool. Lush greenery from surrounding trees frames the scene, providing a sense of privacy.
Home in Portsmouth
4.94 out of 5 average rating, 107 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Superhost
A multi-level house is set against a clear blue sky, featuring a light-colored exterior with multiple windows. A paved pathway leads to the entrance, lined with greenery, while a sandy area extends alongside, reflecting the property's coastal location.
Home in Corolla
4.83 out of 5 average rating, 48 reviews

The Moor House

Guest favorite
A private hot tub is enclosed within a screened area, featuring steps for easy access. A plastic chair is located nearby, and the walls are finished in soft yellow, providing a bright and airy atmosphere. Natural light filters through the surrounding screens, enhancing the space.
Townhouse in Corolla
4.87 out of 5 average rating, 30 reviews

4 bedroom T/H, Hot tub, short walk to beach

Superhost
A private hot tub is situated on a shaded deck, featuring a protective cover. Adjacent seating is provided by two light-colored chairs, allowing for relaxation. Lush greenery can be seen in the background, enhancing the tranquil environment.
Home in Sandbridge
4.95 out of 5 average rating, 20 reviews

Beach Dreams Sandbridge

Guest favorite
A wide, sandy beach is outlined by spacious condos in soft pastel colors against a clear blue sky. Fishing rods are positioned in the sand near beach carts, indicating a relaxed atmosphere. Waves gently lap at the shoreline, creating a tranquil coastal setting.
Condo in Sandbridge
4.87 out of 5 average rating, 232 reviews

Ocean Escape

Guest favorite
Cabin in Smithfield
4.88 out of 5 average rating, 139 reviews

Wickline Cabin on Moon Creek

Guest favorite
A new six-person hot tub is featured, equipped with 48 jets and two pumps. Water is illuminated, and a cover is positioned nearby. A wooden fence provides privacy around the hot tub, creating a secluded outdoor space for relaxation.
Cottage in Norfolk
4.91 out of 5 average rating, 108 reviews

Cozy Cottage - NEW hot tub, dogs OK, fenced yard

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Pet-friendly house rentals

Guest favorite
An aerial view captures the surrounding area, featuring a mix of residential homes and lush greenery with sandy beach access visible. The Chesapeake Bay Bridge-Tunnel stretches toward the horizon over calm waters, providing a scenic backdrop to the coastal neighborhood.
Home in Chic's Beach
4.96 out of 5 average rating, 130 reviews

Water Oaks at Chic's Beach

Top guest favorite
A cozy living space features a green armchair with a patterned cushion, along with a small dining table and four chairs. The kitchen area is visible, showcasing wooden cabinetry and modern appliances. Natural light floods in through blinds on the windows, enhancing the inviting atmosphere.
Home in Virginia Beach
4.93 out of 5 average rating, 42 reviews

Cozy and Modern Beach House

Top guest favorite
A panoramic view showcases a serene riverfront setting with lush green grass and a fenced backyard. A fire pit with seating is positioned in the foreground, while docks and a pier extend into the calm water, framed by trees and grasses along the shore.
Home in Portsmouth
4.96 out of 5 average rating, 109 reviews

The Captains Cottage KAYAK/FISH on Elizabeth River

Guest favorite
A living area features a dark sectional sofa with a decorative pillow and a coffee table with a patterned surface. A soft area rug covers the hardwood floor. Light flows in through glass doors that lead to an outdoor space, while ceiling fans provide additional comfort.
Home in East Ocean View
4.91 out of 5 average rating, 188 reviews

@Whit’s End? Come in and Relax

Top guest favorite
Home in Corolla
4.98 out of 5 average rating, 40 reviews

2min Walk to beach! Dogs ok! Fully Loaded!

Guest favorite
The covered porch features a seating area with two white chairs and a small table, surrounded by hanging flower baskets. The front door is framed by large windows, allowing natural light into the space. Lush trees are visible in the background.
Home in Moyock
4.86 out of 5 average rating, 113 reviews

Cozy Country Cottage

Guest favorite
A spacious outdoor patio area is visible, featuring a combination of stone paving and green grass. Two turquoise chairs and a white table provide seating options. A wooden fence surrounds the area, offering privacy, while various plants add natural beauty to the setting.
Home in Norfolk
4.84 out of 5 average rating, 153 reviews

Picture Worthy Spanish Style Casita! 2 BR/ 2BA

Guest favorite
A dining area is set with a round table surrounded by eight upholstered chairs. The walls are painted in a calming blue, and large windows allow natural light to fill the space. In the background, a kitchen can be seen, featuring a modern layout.
Home in Williamsburg
4.87 out of 5 average rating, 251 reviews

Bamboo Bungalo Duplex Near Busch Gardens

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Quick stats about vacation rentals that are pet-friendly in Chesapeake

  • Total rentals

    280 properties

  • Total number of reviews

    9.4K reviews

  • Family-friendly rentals

    160 properties are a good fit for families

  • Rentals with a pool

    40 properties have a pool

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wifi availability

    270 properties include access to wifi

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