Holiday rentals with a pool in Chesterfield County

Modern Gem; Amenities Galore;Cinema;Garage parking

Fall in love with this stylish Gem minutes from the city! This spacious 2bed 2bath features 2 king beds, a queen sofa bed & other sleeping options for larger groups. Enjoy a full-well stocked kitchen, pool table & a 150in projector screen for a relaxing movie-nite along with a complimentary pop corn & coffee stations. Unit is located in a new & luxury building with tons of amenities like gym, pool, 2 outdoor patios, lounge and coworking space (based on availability) & garage parking (1 car only)

Value · Location · Quiet

“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.

Value · Family · View

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.

Location · Value · Comfort

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!

Value · Family · Hospitality

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.

Value · Location · Bathroom

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.

Family · Location · Pool

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.

Location · Family · Indoor spaces

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.

Location · Value · Comfort

Entire Home • Central Richmond • Free Parking

This house has everything you need for your home away from home. It’s walking distance from VCU, the Fan, several parks, and free access to the community pool. It’s less than a 10 minutes from Downtown RVA, Carytown, Allianz Amphitheater, The Altria Theater, and the Richmond Convention Center. The nearest park is a 5 minute walk away with open tennis courts, basketball courts, community garden, playground, and fitness area.

Family · Location · Hospitality

Pet-Friendly Home w/ Private Pool

Bring the whole family—including your furry friends—and enjoy a relaxing stay in our spacious, pet-friendly home. Featuring a private pool, comfortable bedrooms, inviting living spaces, and a large yard to play and unwind, it’s the perfect place to make lasting memories. Whether you’re looking to relax, explore the area, or spend quality time together, you’ll find everything you need to feel right at home.

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.

Family · Location · Walkability

Luxe King Bd W Resort Amenities, Moseley, VA

Enjoy a stylish experience at this centrally-located place on the 1st floor. Enjoy everything from swimming and tennis to championship golf. Just 20 minutes from downtown Richmond, near plenty of shopping, entertainment, nearby beaches, mountains, parks and Richmond International Airport.

Value · Location · Nearby