
Holiday rentals with a pool in Ashland
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Ashland

Total holiday rentals
Explore 30 holiday rentals in Ashland

Nightly prices starting at
Ashland holiday rentals start at $67 NZD per night before taxes and fees

Verified guest reviews
Over 2,030 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Ashland holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Ashland rentals

4.9 Average rating
Ashland stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in Ashland
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Tiny Groove with plunge pool and soaking tubs
A unique off grid experience awaits you at our eco-friendly solar powered tiny home on 6 secluded acres. The home site is perfectly cut into a groove in the hillside 200 feet above the valley below allowing for beautiful Mountain views and amazing privacy with no visible neighbors other than the variety of local wildlife. Enjoy the outdoor soaking tubs, wood fired sauna and a seasonal plunge pool. Just a short 5 minute drive to the lovely town of Rogue River and access to I-5. Pet friendly too!

1940s Vintage apartment steps from the Rogue River
Welcome one and all to DunMovin'. At Riverside on the Rogue you will go to sleep with views of the stars through the skylights and wake up to the Wild and Scenic Rogue just outside your French Doors. Throw a line in and fish from the yard if you like. Lounge by the heated saline pool, feed the geese, go shopping, or head to any of our amazing local restaurants. I'm in the city limits. It's my slice of heaven and I'm sharing it with you. My other unit can be found at: 'The Cottage at DunMovin'

Beautiful Country Home next to Jacksonville!
The whole group will enjoy easy access to everything from this centrally located home! Enjoy a pool day with the family next to the serine pool. Or a fun day of wine tasting with Relik winery less than one mile away and Hummingbird less than 2 miles away! Or have a blast at a concert this summer at the Britt festival less than 2 miles away! Downtown Jacksonville is only a 3 minute drive! All queen beds have been upgraded to NEW Tempurpedic beds! King size bed is a Jennings (Very High Quality!)

Mexico Apartment at Wood Hamlet, by Downtown
The Wood Hamlet Mexico Apartment is a delightful space filled with color and culture. A short walk to town, 72-acre park & the theaters. Feel the welcoming warmth of the hand-crafted Mexican decor. Basement unit but with lots of windows and light. (4 beams at 6'1") Kitchen, with top of the line induction burner, fridge, microwave..., full bath, W/Dryer, work area... Wi-fi. Beautiful, garden with sitting areas & swimming pond. Parking. (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Cool Blue Waters-Guest Suite
Enjoy our guest suite, perfect for short stays of 26 nights max. We are a comfortable space for 3 guests. Cool Blue Waters is perfect for traveling professionals, families and dog lovers. We are centrally located in the heart of historic Grants Pass. The guest suite is attached to your Host's home and includes: Queen bed, office area, Wi-fi, TV, futon couch/folding bed, walk-in closet, kitchenette with coffee and breakfast items, Private Bathroom, toiletries, Pool and Private patio area.

The Green Arrow Loft
Situated right on the state line this studio apartment with EV charger access is nestled in its own nook of the gorgeous Colestine Valley. We're on 80 acres that adjoin the Cascade-Siskiyou National Monument to the North, perfect for a scenic hike or a casual stroll. Nature and wildlife abound, and though quiet and private the Loft is just 5 minutes off I-5 and 20 from downtown Ashland. We're pet friendly and have an outdoor pool! See the House Rules for details on EV, pet, and pool fees.

The Aloha House - Hot Tub - Pool
The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

Farm Cottage 1/2 Mile Outside Jacksonville
Private cottage with fenced yard. 1/2 mile to historic Jacksonville and the famous Britt Festival. Noted local winery Rellik is one property away and we are in the heart of the Rogue Valley wine country. Pool available in the summer and meeting our farm animals is available with advanced notice. Our place is designed to help you create lasting memories! We look forward to your visit!

Peace on the Rogue river Studio
Beautiful park like setting on the Rogue river with a jacuzzi, swim spa two decks, fishing, yard games, hammock, barbecues, kitchenette has Keurig With pods,a toaster oven, crock pot, small George Forman a portable two burner cook top , small skillet, one pot and most utensils to provide a meal. Minutes from Grants Pass, shopping, restaurants, and winery's.

Sunflower
Nestled within the serene 20-acre expanse of Wagner Creek Sanctuary, the Sunflower Cabin offers a distinctive retreat that harmoniously blends sustainable living with natural beauty. This unique straw bale structure stands as a testament to eco-conscious design, providing guests with a cozy and authentic living experience.

Dream House at Paschal Winery
Discover your dream retreat in this stunning 3-bedroom, 3.5-bath home nestled on the picturesque Paschal Winery in Talent, Oregon. Surrounded by 360 degree views of mountains, vineyards and orchards with the most romantic view of city lights from the patio. Plus we do have a two foot outdoor not heated wading pool!

Capital House - Private getaway with POOL!
Capital House is a completely renovated 1950's classic located in a private neighborhood. Just minutes from downtown Medford, Capital House is situated on a half acre of mature landscaping with a gorgeous pool. Whatever your reason for visiting, we know the whole family will feel right at home at Capital House!
Popular amenities for Ashland rentals with a pool
House rentals with a pool

Cherry Lane, Crystal Skies

Chef's Kitchen | Pool | Bright, Spacious | 4 Bed

Entertainment Home on Golf Course - Hot Tub /Pool

Red Hawk Hideaway

Pool, Hot Tub & Sauna 2 Mi to Jacksonville

Rellik Winery - The Alpaca Suite

Medford White House

The Siskiyou House
Other holiday rentals with a pool

The Gem~ Pool, Hot tub, Views

Jacksonville Cottage, Hot tub+wildlife+boutique

Treehouse at Rancho de la Paz

Luxury Ashland Mountain Escape: Pool, Hot Tub

The Cherry Cottage with built in pool & Hot Tub

King Beds/River/Hot Tub/Pool/BBQ/Full Kitchen/New!

Be Our Guest at The Sunrise Guest House

3BR near Asante | Pool Open | Fast WiFi | Pets Ok
When is the best time to visit Ashland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $166 NZD | $166 NZD | $166 NZD | $194 NZD | $216 NZD | $328 NZD | $279 NZD | $279 NZD | $279 NZD | $233 NZD | $161 NZD | $127 NZD |
| Avg. temp | 5°C | 7°C | 9°C | 12°C | 16°C | 19°C | 24°C | 24°C | 20°C | 13°C | 7°C | 4°C |
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