
Holiday rentals with a pool in Chesterfield County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chesterfield County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterfield County rentals with a pool
House rentals with a pool

Home in Richmond
4.81 out of 5 average rating, 456 reviewsPool/Hot tub/Entire House 2100 Sq ft
EliRating, 5 stars1 week ago
Comfortable home that was exactly what my family needed. The rooms were spacious and beds comfortable. Shower on the first floor is my favorite of any place I’ve stayed. Maria was always responsible and was flexible my with requests.
Top Guest favourite

Home in Richmond
5 out of 5 average rating, 25 reviewsHistoric Blanton Getaway
SarahRating, 5 stars3 weeks ago
This place was great! The location makes it easy to get to many places in Richmond quickly and it was a perfect location for a family wedding in nearby Maymont. The house is beautiful and the furnishings very comfortable. The pool was a special bonus - lovely and relaxing with incredible plantings. Clearly a lot of time was spent considering what guests might want. I just wish we'd had more time to enjoy it.
Guest favourite

Home in Midlothian
5 out of 5 average rating, 9 reviewsA house you wish you called home
RebeccaRating, 5 stars12 months ago
Good communication, great value, and flexible with a small adjustment that was needed. I would definitely stay there again.

Home in Sandston
4.86 out of 5 average rating, 14 reviewsSandston Home w/ Private Pool ~ 9 Mi to Richmond!
WarrenRating, 5 stars6 months ago
As described and exactly what we needed.

Home in Chesterfield
4.83 out of 5 average rating, 35 reviewsLakefront Resort
TeresaRating, 5 stars2 weeks ago
It is an incredible property, pictures and words don’t do it justice. The home, grounds and neighborhood are very well appointed with a wonderful layout. There are multiple outdoor gathering areas, we saw swans daily, the bird and frog songs were enchanting. We walked the neighborhood every day. The pool and landscaping were amazing. The master wing is exceptional. We were there for a family wedding and the “princess” dressing room was very well used. The master bath/ shower room has a steam feature that we enjoyed and the” sparkly” bath and shower were magical for our grandkids ( and the adults.). The art and collections were exotic and everyone, not just the grandchildren were enchanted. We entertained 10-25 guests comfortably each evening. As to previous reviews about cleanliness-it was fine, as per linens, everything was available, clean, folded. PS if you want the St. Regis this property has much more to offer than fluffy robes and slippers. We will be back!
Destinations to explore
- Rentals with a patio Chesterfield County
- Rentals with breakfast Chesterfield County
- Rentals with a fire pit Chesterfield County
- Smoking-friendly rentals Chesterfield County
- Rentals with a home theatre Chesterfield County
- Rentals with an EV charger Chesterfield County
- Rentals with outdoor seating Chesterfield County
- Rentals with a washing machine and dryer Chesterfield County
- House rentals Chesterfield County
- Pet-friendly rentals Chesterfield County
- Apartment rentals Chesterfield County
- Kid-friendly rentals Chesterfield County
- Rentals with a hot tub Chesterfield County
- Fitness-friendly rentals Chesterfield County
- Waterfront rentals Chesterfield County
- Rentals with a fireplace Chesterfield County
- Rentals with a kayak Chesterfield County
- Condo rentals Chesterfield County
- Rentals with lake access Chesterfield County
- Rentals with pools Virginia
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Carytown
- Kings Dominion
- Pocahontas State Park
- Brown's Island
- Jamestown Settlement
- Science Museum of Virginia
- Hollywood Cemetery
- Royal New Kent Golf Club
- Independence Golf Club
- The Country Club of Virginia - James River
- The Foundry Golf Club
- The Poe Museum
- Kinloch Golf Club
- Libby Hill Park
- Kiskiack Golf Club
- Hermitage Country Club
- Grand Prix Raceway