Family-friendly holiday rentals in East Highland Park

The Farm House Retreat

Looking for a peaceful escape with easy access to the city? Welcome to the Farm House Retreat! Nestled in the country, yet only 20 minutes from downtown Richmond, 15 minutes from the airport, and just 8 minutes from local shops. Enjoy a cozy Queen-sized bed, sleeper sofa, fireplace, coffee bar, fridge, central air/heat, lightning-fast Wi-Fi, and streaming TV, all run on 100% renewable energy. Ideal for business travel, weekend getaways, or family and friends. Your perfect country retreat awaits!

Bright, quirky bungalow

Take it easy at this unique and tranquil home within 3 miles of downtown Richmond, VCU and the Fan (also close to I 95/64 exits). Located in the historic Bellevue neighborhood with restaurants and shops within walking distance, this charming Arts and Crafts bungalow has an open feel with a large family room and dining room, a kitchen with a tin-plated ceiling, a butcher block island, and breakfast nook. There are 2 Bedrooms, an office and large front and back porch perfect for morning coffee!

Trailside Treehouse - Riverside in Richmond, VA

Fulfill your childhood dream of camping in a treehouse! From this central spot, easily explore the trails and river. Then, relax on the deck and enjoy the magic of the trees. •Airbnb “Top 20 Places to Stay in VA” •"Best of Richmond" by Style Magazine •Featured in Airbnb article on hospitality •One of "8 Great Airbnbs" in the U.S. by Inside Hook •Comes with bathroom, kitchenette & lounge apartment in host house •Dog-friendly Social media: @trailside_treehouse City permit #BLDR-107741-2022

Cozy "Blue Butterfly" Cottage w/ futon

Clean & cozy 1 bedroom cottage w/ ample parking. Cottage is located in a safe and quiet neighborhood close to shopping with a plethora of restaurants. Only minutes away from the historic City of Richmond with it's rich history, museums, & beautiful views of the James River. Enjoy the nightlife with scads of restaurants & clubs or dine at Rockets Landing & watch the sun set over the river. Being centrally located makes this cottage the perfect place for traveling nurses & professionals.

Cozy 3-Bedroom Home - Minutes to Downtown Richmond

Your family and friends will love the convenience of this centrally located home, while also enjoying the cheerful and cozy space it offers. It's just minutes from Richmond International Raceway, the Convention Center, VCU campuses, and downtown Richmond, which offers an influx of wonderful restaurants and eateries...both indoor or patio dining. Don't delay...make your reservation today! Your host's top priority is YOU and making sure your stay is a comfortable and enjoyable experience!

Funky, Private Guesthouse Near Richmond Food Scene

Welcome to the Yellow Tiger’s Den, a private, tucked-away guesthouse filled with bold color, thoughtful design, and a little Richmond edge. Set above a spiral staircase for total privacy, this sunny studio blends mid-century modern style with curated yellow accents, a cozy private patio, and everything you need for a relaxed stay. Located in Richmond’s historic Battery Park neighborhood, you’re minutes from the city’s growing food scene, local attractions, and easy highway access.

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!

Great For Families | Fenced Yard | Pet Friendly

Relax with your whole group and stay close to downtown Richmond! This apartment is the upstairs side of the duplex with access to a fenced-in yard - perfect for dogs. The yard also has a fire pit, playground, and lots of room for children to run around. * 2 bedrooms plus a sleeper sofa * Renovated Bathroom - April 2024! * Fully stocked kitchen * Large front porch * Very kid-friendly! There is a crib set up in the one of the bedrooms at all times. * Free on-street parking

Quaint Studio in Oregon Hill

This quaint studio apartment lies in the heart of historic Oregon Hill. Less than two blocks from the James River nestles this space near VCU, Hollywood Cemetery, Brown's Island and Downtown Richmond. Studio on the Hill invites you to enjoy the best of Richmond with its vibrant arts scene, deep history and unbelievable food scene. Whether you're visiting Richmond for move-in day at VCU or a concert at the Allianz Amphitheatre, we're perfectly situated for your stay!

City Living in this Church Hill Gem

Located in the center of Church Hill, this apartment features new appliances and furnishings, as well as fantastic, architectural details like huge stained glass windows, exposed brick and soaring ceilings . Guests can stay in the private bedroom with 1 Qn bed, or up in the loft that overlooks the living room area. Walking distance to all the great eateries in Church Hill. The apartment is located on the second floor (no lift) with plenty of free on street parking. .

Historic Meets Hip | 5 Min to Downtown RVA

Welcome to Historic Meets Hip, your private guest suite in a beautifully restored 1920s home just 5 minutes from Downtown RVA. Thoughtfully designed for couples, weekend getaways, business travelers, and those passing through Richmond, you'll enjoy a private entrance, stylish décor, and thoughtful amenities in a quiet historic neighborhood. Relax, recharge, and experience the best of Richmond just minutes away.

Cozy Carriage House Conversion

Enjoy a quiet get away in this carriage house that has been converted to a cozy studio apartment in Church Hill. 400 sq ft of TINY living! Originally built in 1902 this space was home to one horse and hay loft above- it's not your typical hotel chain. It was updated in 2020 to become a small landing pad travelers in search of a unique place to stay.