Family-friendly vacation rentals in Lakeside

The Maplewood Retreat | Luxurious European Living

Rejuvenate in a delightful king bed, soak up the sun on the giant living room sofa, or unwind by the fire on the patio out back. Satisfy your hunger with dinner at Hobnob, a regional favorite only a block away. Walk two more blocks to get a drink at Final Gravity or breakfast at the original location of Lakeside LoveShack. You'll leave inspired and refreshed from your stay in this spacious home nestled in the family-friendly Lakeside neighborhood with easy access to downtown, and attractions.

Kitchen · Indoor spaces · Value

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!

Kitchen · Family · Hospitality

Perfect Location, Classic Style & Yard with Patio

Ideal location, comfortable home and fenced yard on one of Richmond's most idyllic Near West End streets. Two queen bedrooms plus a convertible twin bedroom upstairs and an additional full pull-out sleeper in the finished basement. Separate office for dedicated work space. Fully fenced backyard with a furnished patio makes this family- and pet-friendly retreat ideal for enjoying the outdoors. Living room, separate dining room and basement den. Walking distance to Mary Munford. STR-149573-2025

Indoor spaces · Family · Getting around

Peaceful, private, upscale apartment near U of R

1 mile from UofR & a 2 min. walk to Three Chopt & Patterson Publix/restaurants, you’ll find a home-away-from-home in this impeccable 700sf one-bedroom apt. The private tree-house-like space includes large comfy couch, queen bed, full kitchen (granite, stainless), washer-dryer, fast wifi, & 2 smart TVs. The apt is above a detached garage not used for cars, which ensures quiet/privacy + off-street parallel parking (in front of them in the alley). Access does require climbing exterior stairs.

Indoor spaces · Family · Value

Spacious, pet-friendly nature retreat | The Bohive

Escape to The Bohive off I-95, a charming 1200 sq ft studio, conveniently located just off the interstate & minutes from downtown. On a private “nature reserve”, this is the perfect place to unwind & recharge. Inside, you'll find a comfortable king bed & kitchenette (no stove). The cozy living area has a smart TV, great for relaxing after a long day of exploring. Enjoy coffee on the private deck or immerse yourself in nature before heading out. Great spot for road trippers! STR2024-00002

Indoor spaces · Family · Amenities

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

Kitchen · Family · Backyard

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!

Kitchen · Family · Getting around

Glen Allen Mid-Century Modern Casita

Welcome to the Mid-Century Modern Casita located on the border of Henrico County and Richmond City; Situated in a safe and welcoming neighborhood with easy access to the best Richmond has to offer. Every detail has been carefully considered. This home is fully equip with a washer/dryer, cookware, fast internet, smart TVs, river towels and much more to make for an accommodating stay. Conveniently located to Virginia's top attractions, we are the perfect stopping ground for your next trip!

Indoor spaces · Family · Hospitality

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.

Indoor spaces · Family · Bathroom

Dear John, Suite 1

Hospitality has been our life’s work. . The suites by Dear John LLC are executed with the same keen attention to detail as our award winning restaurants. We feature Casper Pillows, Tuft & Needles luxury mattresses and 700 thread count sheets. From black out shades to white noise & everything in between, we’ve got you covered for a restful retreat. A soaking tub & sauna are just a few of the surprises at DJ. Enjoy our chef’s kitchen or pop into one of the fan’s many great eateries.

Kitchen · Family · Sleep quality

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

Kitchen · Family · Getting around

The Home Stretch

Welcome to "The Home Stretch", a beautiful quiet place in the country just a few miles from Short Pump (which has great restaurants, Golf Courses, Drive Shack, wineries, Breweries. Our second floor apartment features a private entrance with all the things you may need while you are away from home. It has a spacious living area, eat in kitchen, queen bed and 2 trundle-like twin beds. We are on the premises but not in your space at all. Available day and night should you need anything.

Kitchen · Indoor spaces · TV