Holiday 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.
Holiday 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
Home in Stanardsville
4.98 out of 5 average rating, 135 reviewsCharming Carrie's Cottage at Fairhill Farm
1–8 Jan
Home in Lovingston
4.95 out of 5 average rating, 175 reviewsCottage on The Knoll *heated pool open May 17*
12–19 Sep
Home in Robertson
4.92 out of 5 average rating, 182 reviewsOne Of A Kind Home in VA Wine Country on 50 acres
20–27 Feb
Home in Afton
4.94 out of 5 average rating, 133 reviewsFarmhouse on Working Vineyard
18–25 Mar
Home in Boston
4.97 out of 5 average rating, 117 reviewsPeacefield - Blue Ridge views near Culpeper
31 May – 7 Jun
Home in Lovingston
4.85 out of 5 average rating, 280 reviewsSecluded Mountain Cabin w/ Pool, Trails & Winery ❤️
15–22 Jan
Home in Lyndhurst
4.97 out of 5 average rating, 99 reviewsOak Tree Cottage - beautiful farm, mountain views.
20–27 Jan
Home in Wintergreen Resort
4.97 out of 5 average rating, 153 reviewsSki-In/Ski-Out Renovated Chalet on Lower Tyro
4–11 Nov
Apartment rentals with a pool
Apartment in Wintergreen Resort
4.94 out of 5 average rating, 225 reviewsCozy, clean mountain condo- King bed, dog friendly
19–26 Apr
Apartment in Wintergreen Resort
4.91 out of 5 average rating, 179 reviewsA True Mountain Getaway! Ski in/Ski out!
16–23 Sep
Apartment in Wintergreen Resort
4.99 out of 5 average rating, 175 reviewsCozy getaway w/ heated floors, dog friendly
20–27 Aug
Apartment in Wintergreen Resort
4.96 out of 5 average rating, 153 reviewsThe Modern Mountain Condo
19–26 May
Apartment in Wintergreen Resort
4.95 out of 5 average rating, 173 reviewsNew Construction! 1 Bed/2 Bath, pet friendly
13–20 Sep
Apartment in Wintergreen Resort
5.0 out of 5 average rating, 165 reviewsWintergreen: Mountain View for Miles Sunset Vista
8–15 Aug
Apartment in Wintergreen Resort
4.91 out of 5 average rating, 100 reviewsTips Up: Cozy Slopeside Retreat w/ Fireplace
12–19 Jul
Apartment in Wintergreen Resort
4.9 out of 5 average rating, 191 reviewsLight Filled Awe-Inspiring Views from Every Window
24 Sep – 1 Oct
Quick stats about holiday rentals with a pool in Charlottesville
Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
780 reviews
Nightly prices starting at
€ 37 before taxes and fees
Destinations to explore
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