
Vacation rentals with a pool in Charlottesville
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Charlottesville
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Charlottesville rentals with a pool
House rentals with a pool

Cozy 5-bedroom home for large gatherings.

Peacefield - Blue Ridge views near Culpeper

Epic Sunrise Views • 2 Decks • Game + Billiards Rm

Luxury Retreat~Hot Tub~Sauna~Game Rm~2 King Suites

Top-Rated Fall Stay! Hike Shenandoah | JMU Games

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

Bear's Mountain Escape

Mt. RelaxCATION~on resort~hottub~pool table~arcade
Condo rentals with a pool

The Modern Mountain Condo

Five Minute Walk to Everything!

Ski-In Ski-Out ~ Mtn Views ~ King Suite

Eight Minute Walk to Everything

Panoramic Peak: Wintergreen Condo with Views

New Construction! 1 Bed/2 Bath, pet friendly

Tips Up: Cozy Slopeside Retreat w/ Fireplace

Ski-in/Ski-out Wintergreen Highlands Condo -Views!
Other vacation rentals with a pool

3Bdrm | Hot tub, Firepit, Wineries | 9miles to UVA

Suite August- Charlottesville

The Red Cabin at Estouteville Farm

Spacious carriage house on 1780’s farm

Sunset Farm: Pool & Hot Tub, Views, UVA & Wineries

The Franklin Estate - Suite E- Private Apt-KingBed

Fall Deals|Views|HotTub|Theater|RecRoom|Sauna|Fun!

Your Favorite Getaway. EV charger- Walk to trails
Quick stats about vacation rentals with a pool in Charlottesville
Total rentals
50 properties
Nightly prices starting at
$55 CAD before taxes and fees
Total number of reviews
950 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- House rentals Charlottesville
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- Rentals with pools Albemarle County
- Rentals with pools Virginia
- Rentals with pools United States
- Massanutten Resort
- Luray Caverns
- Early Mountain Winery
- Ash Lawn-Highland
- Lake Anna State Park
- Chisholm Vineyards at Adventure Farm
- Hermitage Country Club
- Frontier Culture Museum
- Prince Michel Winery
- Massanutten Ski Resort
- The Foundry Golf Club
- The Plunge Snow Tubing Park
- Car and Carriage Caravan Museum
- Wintergreen Resort
- Spring Creek Golf Club
- Blenheim Vineyards
- Cardinal Point Winery
- Meriwether Springs Vineyard and Brewery
- Glass House Winery
- Farmington Country Club
- Birdwood Golf Course
- Burnley Vineyards
- Little Washington Winery