Holiday rentals with a pool in Chesterfield County

Charming 3 bedroom w/ prvt bath Apart. in Scott

Welcome to your luxurious home base in the heart of Scott’s Addition. Private bathrooms in each bedroom, a full kitchen, in-unit laundry, fast Wi-Fi, and Smart TVs in every room, plus access to a pool, gym, and secure parking. Walk to breweries, restaurants, and shops—great for families, groups, or business travelers. This is our personal apartment when not hosting, so you may notice neatly stored clothing, pantry items, or basic toiletries. The space is clean, organized, and fully guest-ready.

Adorable Studio;Movie-Night;Kingbed;Garage Parking

This adorable studio has been described as “simply Romantic.” It’s a cute space with bold features like a king bed, 135inch projector screen&complimentary popcorn station for a relaxing movie night. It has a small balcony to enjoy the breeze, kitchen, coffee station, washer&dryer. It’s very close to Shockoe bottom, James River, canal walk etc. It’s also walking distance to nearby restaurants and stores. The building has a gym, outdoor patios, pool and lounge. Complimentary garage parking-one car

“WaterView" The Pool Pavilion, waterfront property

This unique and elegant Family friendly partial wheelchair access property offers a beautiful waterfront view, a pool, a pier, 4 king rooms, and a futon. Offering a large entertainment area also with indoor games. This home with its hand-milled elegant woodwork, spiral staircase, and custom bar overlooks the beautiful swift creek reservoir. It resides on a 100-acre private estate with walking trails along the water. Enjoy our newly renovated fully stocked kitchen! Found in the Midlothian area.

Cozy 1BR | Private Balcony, Gym, Pool & Workspace

This luxury apartment is perfect for traveling nurses, professionals, solo travelers, or couples. The fully equipped kitchen features an air fryer, crockpot, coffee bar, and Bartesian machine to make you feel at home. The apartment complex offers amazing amenities, including a Rooftop Terrace , two courtyards, a pool, yoga room, on-site fitness center, and a modern co-working space. Step into this fully furnished, upscale space, where every detail has been designed with your comfort in mind.

Stay Above It All w/ Sky Lounge/Parking/WiFi/Gym

This contemporary unit in Manchester district is the ideal place to be so Kick back and relax in this calm pad *Amazing atmosphere * Hardwood Flooring* * Natural Granite Countertops * Stainless-Steel Appliances * indoor garage * Expansive Windows & Abundant Natural Light * Spectacular Views of Downtown* * Additional Storage Options * Modern, Maintenance-Free Fireplaces * Private Chef package * Washer & Dryer * Private pool * High-Speed Internet Included * Keyless entry * 42 in smart-tvs

Lovely 1 BR Apartment with Riverfront Balcony

Looking for a calm space to relax while taking in the expansive views of the wild & wonderful James River? Then, look no further! Furnished with a mix of period pieces that provide a personal touch, this bright 1 BR space with private balcony & sweeping views of the city is just for you! Amenities include: garage, fitness & yoga rooms, rooftop lounge & adjoining terraces with fire pit & barbecue. Shiplock Views sits between historic Church Hill and a riverside bike & walking trail.

The Get-Together

Welcome to our family-friendly retreat, where comfort and convenience meet. Our home is designed for families seeking to create lasting memories. With spacious rooms, a fully-equipped kitchen, and a cozy living area, there's plenty of space for everyone to enjoy. The backyard is your private oasis, featuring a swimming pool, fire pit, and comfortable seating. Just minutes away from grocery stores, dining and major highways to ensure a stress free vacation. We can’t wait to host you!

Historic Blanton Getaway

Blanton Historic Haven with Pool & Game Room A stunning retreat located in the heart of Richmond, VA. Nestled near the picturesque Byrd Park and the charming Carillon neighborhood, this historic house offers the perfect blend of vintage charm and modern amenities. Enjoy a serene stay in this beautifully preserved home featuring a spacious pool, a fun-filled game room, and a gorgeous yard perfect for relaxation. Walking distance to great restaurants, bars, and shopping in the fan.

Keystone Acres Farm *Enclosed Heated Pool*

Keystone Acres is located in Chesterfield, VA at a beautiful 1000 acre horse farm. On property we have roughly 60 horses owned by different tenants. The brick farm house in which you will be staying in overlooks one of our ponds & multiple horse barns. We have many "internal" roads here and hope you enjoy the farm views. Our 5 bedroom house is perfect for families or friends who want to have a getaway to "unplug" and experience the country life and each other's time.

Cute and Cozy

This stylish and spacious one bedroom one bath apartment is at the heart of the city, yet tucked quietly near the river. The room has a king bed with beautiful and sublet decor. It’s fun packed with a 75 inch television for an evening of relaxation in the cozy living room, fresh popping popcorn machine, a Nintendo Switch, and a fully stocked kitchen. It’s walking distance to restaurants and bars and minutes from VCU, James River, Carytown and most of Richmond.

cozy urban condo-free garage parking

Historic reuse development project transformed a beloved local department store (Miller & Rhoads- originally built in 1925) into modern condominiums and apartment spaces. Shared amenities with attached Hilton Hotel make this space unique and appealing, as well as the general location, which is highly walkable and accessible to many businesses, hospitals, learning institutions and popular local eateries, coffee shops, museums and cultural events.

A house you wish you called home

Your family will be close to everything when you stay at this centrally-located place. There’s shopping, dining, major roads, etc all nearby. Four bedroom home with one queen bed in master suite, 2 bedrooms with full beds, and another bedroom with a couch & tv/ hang out area. Fenced in yard, paths and parks in neighborhood, and multiple other amenities in the community.