The Oaks Holiday Rentals

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Holiday Rentals in The Oaks

Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.
9.8 out of 10, Exceptional, 303 reviews
"Lovely place! Great place for 2 couples!"
Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
8.6 out of 10, Excellent, 13 reviews
"Great"
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
Panoramic Ocean Views, Hot Tub Under The Stars
9.8 out of 10, Exceptional, 67 reviews
"Beautiful and very comfortable accommodations with everything you need. We enjoyed a week here and the location was perfect- about the middle of Sea Ranch- for easy walking and driving access to the coastal trail and beaches and to nearby towns for food and groceries. The night sky is absolutely incredible and we marveled at the stars and Milky Way while enjoying a glass of wine in the hot tub. Peaceful and stunning. Would love to book again!"
Panoramic Ocean Views, Hot Tub Under The Stars
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Hillside tree house in redwoods with ocean views & pool access - dog-friendly
8.8 out of 10, Excellent, 38 reviews
"Really enjoyed our time in Sea Ranch. It was a chilly, rainy weekend and we spent lots of time reading by the wood fireplace, reading on the couch, and cooking in the kitchen. The kitchen would benefit from a few more supplies - but ended up having everything we needed for the weekend."
Hillside tree house in redwoods with ocean views & pool access - dog-friendly
Oceanfront Home with Private Hot Tub & Deck, Beach Access & Shared Pools/Tennis
9.6 out of 10, Exceptional, 83 reviews
"Great location overlooking the ocean. Comfy beds and the living room is spacious with large couches and window seats. We really enjoyed our stay!"
Oceanfront Home with Private Hot Tub & Deck, Beach Access & Shared Pools/Tennis
Architecturally Stunning Ocean View Home featured in Coastal Living Magazine
10.0 out of 10, Exceptional, 177 reviews
"Wonderful home in the middle of a wildlife meadow and in the sound of the Pacific surf."
Architecturally Stunning Ocean View Home featured in Coastal Living Magazine
Newly Renovated Home with Ocean Views, Private Hot Tub - One Dog OK
9.4 out of 10, Exceptional, 111 reviews
"Furniture needs to be updated, but overall I would rent it again."
Newly Renovated Home with Ocean Views, Private Hot Tub - One Dog OK
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach
9.0 out of 10, Wonderful, 38 reviews
"The property is set on a picturesque spot in SeaRanch. Beautiful ocean views. The home itself has lots of nice and unexpected touches (amazing water pressure, oyster knife, dog blankets). It also had a few cost reducing pieces that ranked it down a notch for me (one ply toilet paper and paper towels, super thin cloth towels). We did have an issue with wet towels upon arrival and the property management remedied it within the first 24 hours of our stay. The outdoor space was very useful and...
Gorgeous Esherick home with ocean views, hot tub, and trail to Black Point Beach
Sunny Home w/ Private Hot Tub & Deck, Pools & Saunas - Two Dogs Welcome
9.0 out of 10, Wonderful, 52 reviews
"We spent four nights in this great home. It's in a nice location on a very quiet cul-de-sac. Close to day hiking trails and Gualala for restaurants. Home was very well equiped - we cooked several meals without finding any missing household items. Hot tub works great...which is sometimes a rarity in rental homes. We would definitely stay here again."
Sunny Home w/ Private Hot Tub & Deck, Pools & Saunas - Two Dogs Welcome
Enchanting cabin with hot tub, full kitchen, & washer/dryer - dog-friendly
8.6 out of 10, Excellent, 19 reviews
"This property is in a secluded, safe, and quiet location tucked away in the redwoods. It’s a few minutes driving from all the restaurants Gualala has to offer. The hot tub was a huge plus and hit the spot on a chilly night. The kitchen is great with everything you need to cook a simple meal. House was very clean. Beds were comfortable and good fit for a few couples or group of friends. Keep in mind quiet house are at 9pm so not a good place for parties or loud groups. Overall, would definitely...
Enchanting cabin with hot tub, full kitchen, & washer/dryer - dog-friendly
Ocean-View Getaway w/Shared Pools, Tennis & Saunas - Two Dogs Welcome
8.0 out of 10, Very good, 60 reviews
"Overall, very relazi"
Ocean-View Getaway w/Shared Pools, Tennis & Saunas - Two Dogs Welcome
Sunny home with Ocean Views, Private Hot Tub, High-Speed WiFi, Washer/Dryer
8.6 out of 10, Excellent, 30 reviews
"We enjoyed our stay at this home - it was cozy, easy to find, and comfy for us and the dog. There were two small enclosed spots outside which was helpful for the dog, and the beds and bathrooms were clean and comfortable. The kids and adults alike LOVED the retro Nintendo game console and we had a blast playing Technobowl, Kirby, Bubble Bobble together. A few small things to keep in mind: because of its proximity to Highway 1, there was some traffic noise in the mornings. The bottom floor was...
Sunny home with Ocean Views, Private Hot Tub, High-Speed WiFi, Washer/Dryer
Cloud 9 | Ocean views & new ownership!
9.0 out of 10, Wonderful, 17 reviews
"We spent 3 nights. Long time girlfriends meeting up with our sons to just enjoy the beauty of the Sea Ranch. The house was just what we expected and the views were just as advertised. The house is nestled on the hillside with beautiful views. We also enjoyed the wildlife. Deer grazing casually and the resident turkeys that hung around. They didn’t seemed bothered by us at all and we loved watching them. We also enjoyed the coziness of the fireplace after returning home from all the amazing hikes...
Cloud 9 | Ocean views & new ownership!
Moonrise Retreat in Gualala
10.0 out of 10, Exceptional, 1 review
"How refreshing and renewing spending a week in a beautiful home surrounded by forest. The view was expansive and we were not even 10 minutes away from the ocean. The house was very comfortable and well stocked with everything I needed. Our host was responsive and very helpful. Our stay could not have been better!"
Moonrise Retreat in Gualala
Artful hexagon home with amazing views, private hot tub & pool access
9.6 out of 10, Exceptional, 86 reviews
"We absolutely loved our stay in this home. It was beautifully furnished and comfortable with stunning views of the ocean. Easy access to bluff trails and walking distance to Shell Beach. Could not ask for a better week. Thank you!"
Artful hexagon home with amazing views, private hot tub & pool access
Pipers Reach! Ocean view home, Steps to Shell beach and... dog friendly.
9.8 out of 10, Exceptional, 189 reviews
"Our favorite place to stay. Great location, comfortable beds, hot tub, everything you need!"
Pipers Reach! Ocean view home, Steps to Shell beach and... dog friendly.
Lovely Home w/a Private Hot Tub, Shared Pool, & Tennis - Dogs OK
7.0 out of 10, Good, 9 reviews
"Our stay coincided with the huge coastal waves that affected the whole California coast. Absolutely beautiful. Weather was great. But the house...it needs lots of repairs and upgrades. The heater was temperamental and would not come on at all on the first night, we froze. When it did work it only worked sporadically. The tub faucet in the downstairs bath would not shut off completely and dripped a stream of water no matter what we tried. Tub design was awkward, especially for an older person....
Lovely Home w/a Private Hot Tub, Shared Pool, & Tennis - Dogs OK
Charming Forest Lodge with Private Hot Tub, Sauna, Fireplace, & Shared Pool Access
9.4 out of 10, Exceptional, 110 reviews
"Met all of our expectations!!"
Charming Forest Lodge with Private Hot Tub, Sauna, Fireplace, & Shared Pool Access
Meadow Home with Private Hot Tub, Ocean Views, Shared pool, Tennis, & Sauna
8.8 out of 10, Excellent, 67 reviews
"We had an awesome time here. The home was perfect for this remote location, quiet and peaceful, while being centrally located to golf, hiking, and services like; restaurants groceries, shops, and gas. This home was equipped with al the essentials to cook and be self-contained in a roomy pleasant environment as well."
Meadow Home with Private Hot Tub, Ocean Views, Shared pool, Tennis, & Sauna
Coastal house near trails, beaches, & dining with firepit - dog-friendly
8.6 out of 10, Excellent, 4 reviews
"There was no heater in the house and as note in my questionnaire we were all 3 in our 80 and 70 No heat was mentioned This person that kept checking on us Vancasa knew nothing about the house. We did not have TV because there were no instructions. No information sheets about what to do upon checking out . This has never happened to me with a VRBO normally everything is typed out and very easy for our stay. Excellent clean kitchen, with everything you might need to cook with."
Coastal house near trails, beaches, & dining with firepit - dog-friendly
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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9.0 out of 10, Wonderful, 229 reviews
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7.8 out of 10, Good, 518 reviews
"Very little water pressure in sink. Otherwise, room was sufficient. "
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Cloverdale Wine Country Inn & Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our The Oaks holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up The Oaks. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in The Oaks. Seeing all the best attractions is bound to make you fall in love with The Oaks. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in The Oaks short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in The Oaks?

Yes, there are holiday rentals close to the most popular sights in The Oaks, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that The Oaks has to offer?

Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge.: This holiday home rental outside of The Oaks is located near the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, 1 hot tub and a selection of books so that you can immerse yourself in your holiday.

What’s there to see and do in The Oaks?

Explore the area and family-friendly sights such as Anderson Valley Chamber of Commerce, or get out into nature at a spot like Lake Sonoma. In the wider area, you’ll find Yorkville Cellars and Terra Savia Winery.

What’s a holiday rental in The Oaks like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in The Oaks. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family gatherings.

Recent reviews of The Oaks properties
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