Pet-friendly holiday rentals in East Highland Park

4.95 out of 5 average rating, 194 reviews

Urban Farmhouse w/ Swings, FirePit & Putting Green

Welcome to your charming Richmond retreat 🏡💛! 🌳 Just a short walk to James River Park & Floodwall Park for nature lovers 🍺 Steps away from Bolos Rooftop Bar & Legend Brewery 🍩 Walking distance to Sharolina's Cakes, Croaker's Spot & Brewer’s Café 🚗 2 min drive to Downtown Richmond, I-95 & I-195 The highlight? A fenced backyard oasis with a dreamy pergola, cozy fire pit🪵🔥, playful swings, and even a mini golf putting green ⛳ — perfect for sipping, chatting, and making memories outdoors.

4.96 out of 5 average rating, 275 reviews

Private Garden Home w/ Large Fenced Yard + Gazebo

Experience Casa Terra, a one-of-a-kind historic home in the urban heart of Richmond, Virginia. Tucked away on a sprawling 1/3 acre property just ten minutes from downtown, this thoughtfully restored 1928 Craftsman bungalow blends timeless character with natural calm. Designed for couples, small families and furry companions, Casa Terra features a 6ft fully fenced backyard where dogs can play beneath the branches of a 100-year-old willow oak while guests unwind in the gazebo or around the fire.

A well-lit bedroom features a spacious bed adorned with a blue and white floral quilt. Light streams through large windows framed by gray curtains. A fan hangs from the ceiling, while a decorative plant sits in the corner, adding a touch of greenery.

4.96 out of 5 average rating, 595 reviews

4 beds/3 Private parking/2 mins to I-64 & I-95

Your family will be close to everything when you stay at this centrally-located place with a 92 walk score. 3 minutes to VCU, 7 minutes to Scott’s Addition Historical District and 2 minutes to I-64/95. New house built in 2016. Hosts up to 8-9 people comfortably Dripping coffee & Keurige coffee machine and coffee pods are provided! Pet friendly! Crib& high chair and kids dishes are provided for kids! This place is great for families with kids,couples,solo adventures,business travelers.

A cozy living room features a wood-burning fireplace surrounded by a stylish white mantel. Comfortable seating includes a brown leather chair and an accented blue sofa. A coffee table sits elegantly in the center, with soft lighting from overhead fixtures enhancing the space's warmth.

4.94 out of 5 average rating, 401 reviews

Eclectic Designer Retreat Near UofR + Peloton Bike

Modern design, impeccable lighting, and high-end finishes with a cozy wood burning fireplace. PELOTON exercise bike here, bring your cycling shoes! This charming private home is nestled in the heart of Westhampton just one mile from the University of Richmond and Libbie and Grove AVE. Surrounded by some of Richmond’s best shopping and dining and designed specifically for Airbnb guests to have a comfortable stay. Westhampton is one of Richmond’s most sought after neighborhoods. Welcome home!

4.93 out of 5 average rating, 136 reviews

Home in Quinton

Kelly's Comfortable Quinton Home

Welcome to Kelly’s Cottage, a charming retreat nestled among century-old oaks in a peaceful neighborhood. This cozy, mid-20th-century brick rancher offers a warmth and comfort you won’t find in modern homes. Enjoy a cup of cocoa by the bonfire in spring or fall, or explore nearby attractions, including local wineries, restaurants, microbreweries, and Civil War battlegrounds. Pet-friendly with a spacious backyard, Kelly’s Cottage is the perfect spot to unwind and enjoy the area’s beauty!

Superhost

4.93 out of 5 average rating, 244 reviews

Rally & Rest: Pickleball & Designer Home

Welcome to our modern-retro 1925 brick house 🏡 — where historic charm meets bold, designer style. Perfect for groups, families, or friends who want comfort, creativity, and FUN. 📍 Steps from Scott’s Addition breweries + restaurants 🍻 🎬 Outdoor movie projector theater under the stars 🌌 🏓 Regulation-size pickleball court for epic matches 🧘 Private yoga + fitness studio with mats, blocks, and free weights 🔥 Backyard fire pit + swings for cozy nights 🚗 Parking for up to 6–8 cars

4.99 out of 5 average rating, 219 reviews

Tiny home in Richmond

The Barkin’ B & B

Just five minutes from the airport and downtown, this cozy tiny home offers rustic charm and modern comfort. Fully equipped with kitchen essentials, books, games, and even coloring books, it’s perfect for relaxing. Pet-friendly, it comes stocked with dog treats, chews, toys, and a large fenced-in backyard for furry companions to enjoy. Conveniently located for travelers, it provides a peaceful retreat while keeping you close to city attractions. A perfect home away from home!

4.96 out of 5 average rating, 693 reviews

The kitchen area features wooden cabinetry and a spacious white refrigerator. A dining table with four wooden chairs is set to one side, while the living area, equipped with a cozy blue couch, is visible in the background. Natural light illuminates the space.

Guesthouse in Ashland

2 Bdrms★Pet Friendly★4K Theater★Fire Pit★Fast Wifi

Minutes from I-95 "The Cottage" is a great stop along your journey just 15 minutes to Kings Dominion or Meadow Event Park. Surf high speed internet, catch up on laundry, dine in Ashland or have a cookout and share stories around the campfire. You’ll love the Cottage because of the clean accommodations, complete kitchen, quiet neighborhood, home theater, comfy beds & pet friendly! The Cottage is great for Families, Couples, Business Travelers & Fun Seekers!

4.94 out of 5 average rating, 159 reviews

The spacious living area features a green couch, a reclining chair, and a wooden coffee table, arranged on a soft area rug. Light streams in from the high ceiling, highlighting framed plant artwork on the wall and a glimpse of the kitchen in the background.

Apartment in Richmond

Spacious unit in Arts District

Tucked away in the heart of The Arts District, you'll be able to walk to all the best restaurants and activities the city has to offer. A few blocks away from The National and a few minutes away from Cary Town, The Fan, Shockoe Bottom, Manchester, and Scott's Addition, you'll have easy access to anything the city has to offer! Just blocks away from the convention center, this unit is perfect for Richmond guests who are in town for work related events.

The interior space features a distinctive floating staircase adorned with lush green plants. A bookshelf filled with various titles stands nearby, while a cozy guitar is positioned on the floor. A glimpse of a bedroom is visible through the archway.

4.92 out of 5 average rating, 132 reviews

Maymont Boho Bungalow

Located right beside Maymont Park, the James River at Texas Beach, the picturesque lakes of Byrd Park, The Fan & Carytown! Easy access to the city, too! This stylish space had loads of character, two comfortable bedrooms, a cozy living room with a unique floating staircase, and fully outfitted kitchen and eating area. Perfect for anyone who loves to be outside with all of the parks within walking distance and the private back deck with string lights!

The living room features a comfortable couch with a pull-out queen bed and decorative pillows. A round coffee table sits on a patterned rug, surrounded by a cozy armchair and natural light from adjacent windows. A ceiling fan offers ventilation, enhancing the welcoming ambiance.

4.9 out of 5 average rating, 310 reviews

The Sweet Retreat RVA • Fenced Yard • Fire Pit • P

Welcome to The Sweet Retreat RVA, your perfect home away from home in Richmond! This beautifully maintained, family-friendly home is just minutes from downtown and offers everything you need for a comfortable and relaxing stay. Enjoy a private fenced backyard, fire pit, free parking, and a fully equipped kitchen. Ideal for families, small groups, and travel professionals, this home comfortably accommodates up to 8 guests.

A well-equipped kitchen features white cabinetry and stainless steel appliances. A gas stove and microwave are present, along with a spacious island that includes two wooden bar stools. Natural light fills the space, highlighting the warm wooden flooring and contemporary design elements.