Vacation rentals with a pool in Ashland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ashland

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

Guest favorite
Guest suite in Jacksonville
Slow season discount! Hot tub and vineyard views
This is a scenic stopover between PDX and SF and a destination unto itself. As one guest put it: " Her home seems to have a magic of its own." The place is simple with elegant touches (like a hot tub!) and a great base for wine-tasters, paraglider pilots, or roadtrippers. If a house surrounded by nature, vineyards, paragliders, creativity and occasional other travelers sounds interesting, you'll love it here. As a local tourism coordinator, I can direct you to the top attractions.
May 16 – 23
$77 per night
4.84 out of 5 average rating, 216 reviews
Guest favorite
Guesthouse in Gold Hill
Octagon Studio / Beautiful Rogue River property
Park-like setting; Rogue River premier property. Use the Octagon Studio to enjoy the luxuries of the property or as a home base for the many amenities in the Rogue Valley. Relax by the pool or soak in the hot tub, lounge on the rivers beach, watch the river go by from the floating dock(seasonal) swing between two large pine trees, have an evening fire in the fire pit, catch trout for a morning breakfast, watch the abundant wildlife. Relaxing, romantic, fun, resort quality....enjoy
Sep 12 – 19
$125 per night
4.92 out of 5 average rating, 162 reviews
Guest favorite
Yurt in Grants Pass
Sunset View Yurt of Applegate Valley with HOT TUB!
NO CLEANING FEE! Large 24 ft yurt located on our 5 acre horse property. Gorgeous views to the west. Includes a king size bed, and queen sofa bed. Located in Applegate Valley. Many fabulous wineries nearby. We're 6 miles south of downtown Grants Pass, and 2 miles north of Murphy. Enjoy the hot tub under the stars, or catch a spectacular sunset. It's all good! Please note: ONLY well-behaved children are welcome. If your kids are destructive or abusive, you will be asked to leave.
Jan 17 – 24
$88 per night
4.97 out of 5 average rating, 641 reviews

Popular amenities for Ashland rentals with a pool

House rentals with a pool

Superhost
Home in Medford
Family & Work Crew Haven, Relaxing Quiet Foothills
Apr 7 – 14
$243 per night
4.87 out of 5 average rating, 167 reviews
Superhost
Home in Medford
Cute 3 king with 85" 4k TV, near huge park
Aug 11 – 18
$203 per night
4.77 out of 5 average rating, 121 reviews
Guest favorite
Home in Ashland
The Aloha House - Hot Tub - Pool
Sep 21 – 28
$403 per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Home in Medford
Red Hawk Hideaway
Sep 1 – 8
$203 per night
4.96 out of 5 average rating, 23 reviews
Guest favorite
Home in Medford
No Fees! Pool -Deck Open Light Bright Cul-de-sac
Oct 30 – Nov 6
$189 per night
4.9 out of 5 average rating, 67 reviews
Guest favorite
Home in Medford
Large 4 bedroom house with pool in bamboo forest!
Apr 3 – 10
$464 per night
4.89 out of 5 average rating, 35 reviews
Guest favorite
Home in Ashland
Perfect Getaway: Pool, Hot Tub, Sauna Bliss
Apr 15 – 22
$370 per night
4.86 out of 5 average rating, 22 reviews
Guest favorite
Home in Gold Hill
Magnificent Hilltop House - Luxury, Beauty & Peace
Nov 7 – 14
$216 per night
4.87 out of 5 average rating, 23 reviews
Guest favorite
Home in Grants Pass
Pool/Hot Tub/75 inch TV/1000mbps/Brand New
Apr 20 – 27
$180 per night
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Eagle Point
Serene Shasta Hilltop Escape w/private jacuzzi!
Nov 11 – 18
$379 per night
4.76 out of 5 average rating, 17 reviews
Guest favorite
Home in Medford
657 S. Holly St. Medford, OR
Sep 27 – Oct 4
$250 per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Home in Jacksonville
Mountain Retreat!
Nov 15 – 22
$591 per night
4.83 out of 5 average rating, 48 reviews

Quick stats about vacation rentals with a pool in Ashland

Total rentals

20 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

1.5K reviews

Nightly prices starting at

$60 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Jackson County
  5. Ashland
  6. Rentals with pools