Holiday rentals with a pool in Chesterfield County

An Experience; MovieNite; 2kingbeds; GarageParking

Such a beautiful, warm and intimate experience, not just a place to stay! This stylish 2 bedroom 2 full bath apartment features 2 comfortable king beds, 2 sofa beds & a balcony you can either dine or relax on a swing chair. At night, enjoy a movie on the 110in projector screen with complimentary pop corn & wakeup to a hot cup of coffee. The building is centrally located & has easy access to the entire city. Building has a gym, sky lounge, pool, 2outdoor area,co-working, Garage parking for 1 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.

2 Story Penthouse 2 Balconies, Skyline View, Pool

This stunning penthouse offers luxury and comfort for traveling nurses, professionals, solo travelers, or couples. The fully equipped kitchen includes an air fryer, crockpot, coffee bar, and Bartesian machine for a true home-away-from-home experience. Enjoy views from the Rooftop Terrace, relax in two courtyards, or take a dip in the pool. The complex features a yoga room, fitness center, modern co-working space, and private underground parking. The perfect place for an unforgettable stay!

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 rec room. 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.

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 | Garage Parking | Accessible

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.

Richmond Condo heart of Downtown w/ Parking 2Bath

Enjoy a relaxing time in this bright and airy condo, situated in Richmond's walkable Art's District downtown neighborhood. Walk to restaurants, theaters, concert venues, Capitol building, or belle isle. Stay in, and enjoy a spacious condo with or visit the building's pool, hot tub, fitness center, club lounge or attached bars or restaurants.