Vacation rentals with a pool in Chesterfield County

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Popular amenities for Chesterfield County rentals with a pool

House rentals with a pool

A single-story house features a welcoming front porch with a railing and staircase. Light-colored siding and a gabled roof are visible, complemented by windows with green shutters. A fenced yard surrounds the property, with trees in the background and a gentle dusk sky casting a soft hue.
Home in Richmond
4.81 out of 5 average rating, 450 reviews

Pool/Hot tub/Entire House 2100 Sq ft

EricaRating, 5 stars2 weeks ago
Beautiful and well matained
Top guest favorite
A serene outdoor pool area is surrounded by lush greenery and features a spacious pool deck with lounge chairs. The house stands in the background, framed by trees and a well-maintained yard, offering a tranquil setting for relaxation.
Home in Richmond
5 out of 5 average rating, 23 reviews

Historic Blanton Getaway

KatherineRating, 5 stars3 weeks ago
Gorgeous period house with beautiful yard and pool! Elegant yet comfortable with terrific amenities. Loved having the space to work, cook, relax and celebrate UR college graduation with family! Super fun game room with Pac Man and pinball machine, piano in dining room, and large TV in living room. Fully outfitted kitchen for gourmet cooking. Perfect amount of space for 6 people. Lovely neighborhood adjacent to parkland and centrally located/convenient to everything in Richmond. Always available parking on street. Richard & Julia were super friendly/helpful, proactive with comms and always quick to respond. Staying @ 900 Blanton made our special weekend even more memorable!
Guest favorite
A two-story home features a muted exterior with light grey siding and black shutters. The front porch is accessible via a set of white steps, flanked by neatly trimmed shrubs. A driveway leads to a dark garage, surrounded by a grassy lawn and mature trees.
Home in Midlothian
5 out of 5 average rating, 9 reviews

A house you wish you called home

RebeccaRating, 5 stars11 months ago
Good communication, great value, and flexible with a small adjustment that was needed. I would definitely stay there again.
A welcoming living space is highlighted by a ceiling fan and a cozy fireplace. Two comfortable sofas are arranged around a glass coffee table on an area rug with geometric patterns. Natural light pours in through nearby windows, enhancing the relaxed atmosphere.
Home in Sandston
4.86 out of 5 average rating, 14 reviews

Sandston Home w/ Private Pool ~ 9 Mi to Richmond!

WarrenRating, 5 stars6 months ago
As described and exactly what we needed.
An expansive resort-style home features a lush backyard with a natural stone pool surrounded by greenery. Comfortable seating areas are visible near the water, with large windows highlighting the elegant architecture of the home in the background.
Home in Chesterfield
4.82 out of 5 average rating, 34 reviews

Lakefront Resort

JamesRating, 5 stars2 months ago
This house is awesome. It's huge and priced very competitively. It did have issues, but they didn't bother us too much. If you're expecting perfection from a home this size, at this location at this price, you're not being reasonable. For our needs, it was PERFECT.
A comfortable living area features plush seating, including a mustard-colored sofa and reclining chair. A glass coffee table with decorative items sits at the center. Light streams in through a set of double doors leading to a bright entryway.
Home in Chester

Chester Virginia Fully furnished Apt

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