Holiday rentals with a pool in Ashland

Guesthouse in Grants Pass

4.94 out of 5 average rating, 453 reviews

Sweet Vintage Cottage steps from Rogue River

Welcome one and all to DunMovin'. The Cottage you will be staying in may make you feel like you have stepped back in time. Don't forget your fishing pole, this property is on the banks of the Wild and Scenic Rogue River. Lounge by the pool, feed the geese, go shopping, or head to any of the amazing restaurants that are just around the corner. I'm in the city limits, so everything is a minute or two away. It's my slice of heaven. I also have a larger unit, search for 'Riverside on the Rogue'

4.89 out of 5 average rating, 88 reviews

Tiny home in Rogue River

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!

4.93 out of 5 average rating, 384 reviews

Loft in Hornbrook

The Green Arrow Loft

Situated right on the state line this studio apartment is nestled in its own little corner of the gorgeous Colestine Valley. We're located 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 five minutes off I-5 and 25 minutes from unique downtown Ashland. We're pet friendly and have an outdoor pool! See the House Rules for details on pet and pool fees.

4.96 out of 5 average rating, 105 reviews

Home in Central Point

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!)

4.97 out of 5 average rating, 244 reviews

Cabin in Grants Pass

Tiny Cottage w/Firepit/Hottub/Outdoor tubs

Enjoy the charm of staying in a Tiny Forest Cottage, surrounded by nature on the outskirts of town. This tiny cottage has all the essentials that you need for your stay. Tucked between Grants Pass & Merlin (8 mins from Merlin & 15mins from Grants Pass). The closest access to the river is only 10 mins away at Matson Park! After a day of exploring; stargaze in your cabins outdoor bath-tubs, enjoy the peaceful wooded view from the hot tub or roast smores by the fire pit. Perfect Couples getaway!

4.94 out of 5 average rating, 268 reviews

Apartment in Ashland

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

4.95 out of 5 average rating, 97 reviews

Home in Ashland

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!

Guest suite in Jacksonville

4.85 out of 5 average rating, 240 reviews

Scenic and relaxing roadtrip stop-over!

This is a scenic stop between PDX and SF and its own destination. One guest says " Her home has a magic of its own." Simple, elegant, and a great base for wine-tasters, paraglider, or roadtrippers. If a house surrounded by nature, vineyards, paraglider pilots, 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. Note: this is a self-contained unit but attached to the main house!

4.92 out of 5 average rating, 212 reviews

Guest suite 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

4.97 out of 5 average rating, 756 reviews

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.

Guesthouse in Grants Pass

4.98 out of 5 average rating, 121 reviews

Serene Upstairs Studio with Bath & Kitchenette

This upstairs studio is surrounded by beautiful trees that gives you the impression of staying in a treehouse. Located in a panoramic rural area just 5 miles from downtown Grants Pass and 5 miles from downtown Rogue River. Perfect place to be away from the hectic city lifestyle, yet close enough to restaurants, local shops, wineries, jet boat rides, hiking trails and much more... In addition, this pictured-postcard location is 8 mins walking from Pierce Riffle County Park.

4.92 out of 5 average rating, 177 reviews

Apartment in Medford

Broken Chair Ranch

Welcome to the beautiful Griffin Creek area just outside of Medford, Jacksonville, and Ashland. Our home is at the top of a hill with stunning views of the city lights as well as upper and lower Table Rock. Enjoy the hot tub and watch the sunset with the fire pit on the front porch. The house is on 40 acres and has a gorgeous view at the top with a stunning echo off the mountain Private setting one mile up a gravel road, 2wd friendly

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Popular amenities for Ashland rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.71 out of 5 average rating, 342 reviews

New kitchen! Pool rv prkg 5 beds, hot tub Private

StephanieRating, 5 stars1 day ago

It was a nice place and accommodated my families needs. Only wish was the weather was nicer to take advantage of the pool.

5 out of 5 average rating, 12 reviews

Home in Central Point

Rellik Wine Suite near Jacksonville Hot Tub/Pool

LakeiaRating, 5 stars6 months ago

We stayed here for Thanksgiving and it surely was a place to be grateful for. I love that this place is dog friendly and allows for guests. We were able to invite my sister (who we were there visiting) over to show of the beautiful grounds. There were doggy bag stations all over, which is always so appreciated! The room was very cozy and kept at a comfortable temperature, which was much appreciated during this cold month. I do recommend to any guests to make sure you either wipe your shoes off really well or just take them off inside because the gravel really sticks to your shoes and tracks inside easily. we learned this after it was too late. The property was absolutely breathtaking! We loved every second of it here and we look forward to coming back in the future to try the winery and restaurant.

4.96 out of 5 average rating, 27 reviews

Capital House - Private getaway with POOL!

MichaelRating, 5 stars2 weeks ago

We would totally recommend staying with Diane! The house is beautiful, clean and well maintained! Hope to stay with them again!

5 out of 5 average rating, 18 reviews

Home in Rogue River

In Town of Rogue River. Home with Pool and Hot tub

SarahRating, 5 stars1 week ago

The home was clean, well stocked with very comfy beds and high end supplies. The front and back yards were stunning and so perfect for relaxing and enjoying the outdoors. So many options for cooking outside and in walking distance to some great restaurants. Will definitely come again.

4.96 out of 5 average rating, 28 reviews

Fantastic Bright 4 Bedroom- Deck - Fireplaces

TamaraRating, 5 stars2 weeks ago

Absolutely beautiful!! It was a great start and would definitely come back

4.75 out of 5 average rating, 16 reviews

Home in Ashland

Siskiyou Chateau

DeborahRating, 5 stars1 month ago

Spectacular views and lots of space and grandeur. Mixed art styles, some dust and clear signs of slight neglect, but mostly very well kept! All the rooms are as pictured, downtown Ashland is a 15-20 minute drive away. Some of the amenities were out of order, hard to figure out with no instructions, and /or didn’t work. Minor complaints mostly, because this is such a lovely location and property.

4.82 out of 5 average rating, 50 reviews

Large 4 bedroom house with pool in bamboo forest!

SaraRating, 5 stars2 months ago

Beautiful home , great space to stay with friends and family… we stayed at the end of March . Wish our trip would have brought us here in the Summer months with everything in bloom . Would have loved to have used the pool !