Vacation rentals with a pool in Virginia

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Virginia

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Guest favorite
Cottage in Hamilton
*Cottage @ Firefly Cellars* VA Wine Country escape
The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!
Dec 21 – 28
$230 per night
4.94 out of 5 average rating, 299 reviews
Guest favorite
Condo in Moneta
Fun Lake Getaway with Breathtaking Views
Fantastic getaway on beautiful Smith Mountain Lake! Enjoy stunning views on two sides of this top-floor, corner condo with a wrap-around deck and natural shade. It is perfect for a relaxing break or an adventure! Activities include boating (with guest docks), swimming (indoor and outdoor), pickle ball, working out, and relaxing in the hot tub, steam room or sauna! If you are working remotely, this quiet space includes a desk and high-speed wireless. The individual HVAC unit also has a UV light.
Feb 16 – 23
$90 per night
4.98 out of 5 average rating, 183 reviews
Guest favorite
Apartment in Madison
The Studio at Dark Run Retreat
Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*
Jun 15 – 22
$71 per night
4.9 out of 5 average rating, 225 reviews

Popular amenities for Virginia rentals with a pool

House rentals with a pool

Guest favorite
Home in Cobbs Creek
Millionaire $ Views No Xtra Charge! Hot Tub! POOL!
Sep 26 – Oct 3
$202 per night
4.9 out of 5 average rating, 110 reviews
Guest favorite
Home in Charlottesville
Pine Lake Lodge
Aug 14 – 21
$495 per night
4.94 out of 5 average rating, 197 reviews
Guest favorite
Home in Montross
Beach Please! River cottage w/private beach & dock
Oct 31 – Nov 7
$359 per night
5.0 out of 5 average rating, 115 reviews
Guest favorite
Home in Montross
The Glebe
Dec 24 – 31
$224 per night
4.93 out of 5 average rating, 160 reviews
Guest favorite
Home in Brightwood
Hilltop Haven Luxury lodging in Wine country
Dec 16 – 23
$127 per night
4.99 out of 5 average rating, 290 reviews
Guest favorite
Home in Stanardsville
Charming Carrie's Cottage at Fairhill Farm
Dec 16 – 23
$187 per night
4.98 out of 5 average rating, 134 reviews
Guest favorite
Home in Norfolk
Private Pool 🏊‍♂️ Hot Tub, Fire Pit🔥 Close to Beach 🐠
Nov 26 – Dec 3
$179 per night
4.93 out of 5 average rating, 122 reviews
Guest favorite
Home in Cobbs Creek
Blue Heron WaterSide
Feb 14 – 21
$300 per night
4.99 out of 5 average rating, 131 reviews
Guest favorite
Home in Martinsville
Vaca Oasis, Pool, Fire-Pit, Grill, Nature, Relax!
Oct 11 – 18
$196 per night
4.95 out of 5 average rating, 160 reviews
Guest favorite
Home in Boston
Peacefield - Blue Ridge views near Culpeper
Jul 10 – 17
$405 per night
4.96 out of 5 average rating, 113 reviews
Guest favorite
Home in Accomac
Heartsong Farmhouse , a nature lover's retreat.
Sep 17 – 24
$136 per night
4.98 out of 5 average rating, 214 reviews
Guest favorite
Home in Lovingston
Secluded Mountain Cabin w/ Pool, Trails & Winery ❤️
Dec 22 – 29
$542 per night
4.85 out of 5 average rating, 277 reviews

Condo rentals with a pool

Guest favorite
Condo in Moneta
Dock Holiday at Bernard's Landing
Mar 8 – 15
$98 per night
4.91 out of 5 average rating, 182 reviews
Guest favorite
Condo in Wintergreen Resort
A True Mountain Getaway! Ski in/Ski out!
Oct 7 – 14
$93 per night
4.91 out of 5 average rating, 176 reviews
Guest favorite
Condo in Moneta
Bernard's Landing Bliss! Breathtaking Views
Nov 16 – 23
$109 per night
4.95 out of 5 average rating, 122 reviews
Guest favorite
Condo in Wintergreen Resort
Point of View | Wake in the Clouds
Mar 6 – 13
$125 per night
4.94 out of 5 average rating, 143 reviews
Guest favorite
Condo in Moneta
Lake Lover's Paradise
Sep 2 – 9
$170 per night
4.99 out of 5 average rating, 275 reviews
Guest favorite
Condo in Wintergreen Resort
Eight Minute Walk to Everything
May 29 – Jun 5
$90 per night
4.95 out of 5 average rating, 194 reviews
Guest favorite
Condo in Wintergreen Resort
Light Filled Awe-Inspiring Views from Every Window
Mar 14 – 21
$178 per night
4.89 out of 5 average rating, 188 reviews
Guest favorite
Condo in Moneta
Lake Escape - Smith Mountain Lake Condo
Feb 3 – 10
$110 per night
4.88 out of 5 average rating, 142 reviews
Guest favorite
Condo in Virginia Beach
Oceanfront Gem VaB Studio 5 day Winter Special!
May 18 – 25
$273 per night
4.9 out of 5 average rating, 168 reviews
Guest favorite
Condo in Wintergreen Resort
New Construction! 1 Bed/2 Bath, pet friendly
Jul 28 – Aug 4
$112 per night
4.95 out of 5 average rating, 172 reviews
Guest favorite
Condo in Wintergreen Resort
Five Minute Walk to Everything!
Oct 17 – 24
$111 per night
4.96 out of 5 average rating, 228 reviews
Guest favorite
Condo in Moneta
BEST Views @Bernards Landing Indoor Pool Open
Oct 19 – 26
$163 per night
4.84 out of 5 average rating, 172 reviews

Destinations to explore