Holiday rentals in Santa Cruz Mountains

4.95 out of 5 average rating, 264 reviews

Farm stay in Felton

Romantic Suite on farm, walk to Henry Cowell Park

Romantic Farm Stay. Santa Cruz Vacation rental Permit #221352 TOT Certificate #AB00736. Beautiful suite with king size bed, fireplace, huge bathtub, coffee maker, (frig, freezer, microwave, (no kitchen), Stargate WIFI, Smart TV, movie library, seating and coffee table. Private patio area, fire pit, (BYO wood) patio furniture and dining table. The suite is completely private with its own entry. 2 Person Occupancy. Short walk to Henry Cowell Park and old growth redwoods right outside your door!

4.9 out of 5 average rating, 452 reviews

Cabin in Los Gatos

The Coach House

The Coach House is located on our mountain top horse and lavender farm. We offer youth summer camps so are set up for fun outdoor adventures and activities. Have fun with our horses, goats, and chickens! You can take a 10 min walk over to Nonno's Restaurant for wine/pizza/BBQ and bacchi ball, or take an 8 min drive into Los Gatos, or 15 min to Santa Cruz for the beach and some of the best restaurants and spas around!. Good for couples, solo adventurers, business travelers, kids, & behaved dogs!

4.99 out of 5 average rating, 924 reviews

Cabin in Los Gatos

Private Guest-House in the Redwoods

Our custom built guesthouse was completed in 2016. It is situated on 5 redwood-covered acres, 10 minutes south of Los Gatos and 20 minutes from Santa Cruz. We have easy access to hiking and biking trails, world-class wine-tasting, microbreweries, shops, amazing dining, and more! There is something for everyone in our area! We are surrounded by a 35 acre tree farm, so it's very private, yet close to the silicon valley! Our property has a standby generator so we are not affected by power outages.

4.92 out of 5 average rating, 735 reviews

Treehouse in San Jose

Treehouse , San Jose

250 sq ft treehouse with stairs leading to 2 lofts with beds overlooking the most gorgeous view of the Silicon Valley. The treehouse opens to a deck 14 foot high nestled in between 3 sycamore trees.Custom made stained glass window and spiral staircase leads up into the tree. Includes full functioning bathroom , kitchenette w sink , cooking stove, mini fridge . Sleeps 4 people. ( 1 queen bed in each open loft) You are living with a live tree in nature so think glamping - an amazing experience .

5 out of 5 average rating, 140 reviews

Home in Felton

Peaceful Redwood Retreat in the heart of town

This beautifully renovated home is set in a peaceful location, just a short walk from Henry Cowell Redwoods State Park, Roaring Camp Railroad, Felton Music Hall, the Farmers' Market, yoga studios, a local brewery, restaurants, wedding venues, and a natural foods market. Enjoy nearby hiking and biking trails, with Santa Cruz a 10-minute drive away and San Jose just 30 minutes. Ideally situated in the heart of town, this family-friendly retreat offers all the essentials for a relaxing vacation.

5 out of 5 average rating, 115 reviews

Cabin in Felton

Whiskey Creek: Roaring Camp+Redwoods+Dogs+UCSC

Whiskey Creek (Permit #231409) is the newest property brought to you by the folks who created Whiskey Hollow, featured in Condé Nast Traveler's "30 Cozy A-Frame Cabins for Cold-Weather Getaways" in 2023! This cozy cabin sits on 1/2 acre and includes: - covered spa - indoor wood burning stove - outdoor fire pit - two decks - A/C Felton Music Hall, Roaring Camp, Henry Cowell, world-class mountain biking and the beach are minutes away. Well-behaved dogs (up to 2) are welcome. You'll love it!

4.91 out of 5 average rating, 215 reviews

Guest suite in San Jose

Entire Guest Suite Private Entrance Kitchen & Bath

Whether you’re here for a business trip, traveling for pleasure, visiting your friends/relatives, or looking for a short term rental, our fully furnished unit can offer everything you need! What you’ll get from staying at our converted garage: * Separate entrance with self check-in (keyless entry) * Workspace with high-speed wifi * TV with Netflix * Fully stocked & equipped kitchen * Private bedroom with queen bed, wall closet, high ceiling * Private bathroom * Free parking on premise

4.85 out of 5 average rating, 119 reviews

Cabin in Los Gatos

Tranquil creek mountain house

The main house is 1 bedroom, 1 full bathrooms upstairs with vaulted ceilings throughout, stainless steel appliances, custom cabinets, hardwood floors, stained glass accent windows, and numerous skylights throughout. A tranquil creek runs through the property adding to the peaceful nature, a large wraparound redwood deck offers the perfect space to entertain. Make this inviting property your home and experience the perfect work life balance! Let your heart sing with the nature.

4.86 out of 5 average rating, 241 reviews

Guest house in Felton

Studio with redwoods in backyard, infrared sauna

Deer Run sanctuary nestled in the redwoods, with bubbling brook nearby. private and secluded yet walking distance to felton's town center restaurants and shoppings. Five minute walk to Henry Cowell State Park and a short 6 mile drive to Santa Cruz's beaches and downtown. The studio has a private entrance, kitchenette, bathroom and gas fireplace. Deck surrounded by redwoods, with outdoor grill, is partitioned for privacy. Studio is good for couples and solo travelers.

4.97 out of 5 average rating, 973 reviews

Guest house in Los Gatos

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

4.91 out of 5 average rating, 787 reviews

Yurt in Watsonville

Mountain Top Yurt in the Redwoods

Peaceful, clean, spacious, beautifully decorated and quiet 24' Yurt completely surrounded by Redwoods on top of the Santa Cruz Mountains. Spend a couple days meditating, reading or writing the next chapter of your memoir. Walking distance to Mount Madonna Retreat Center (open now through reservation only). County Park hiking and horseback riding trails located within 3 miles. Ideal place for photography and mountain/road biking.

Campervan/Motorhome in Half Moon Bay

4.98 out of 5 average rating, 128 reviews

Airstream Beach View (Dream) - New Listing

On 9 private acres overlooking the stunning Beach and Ocean from a breathtaking cliff top view. Stunning sunsets. Surf views with large windows. Fully loaded with all the amenities to make your glamping experience perfect. Fire pit, outside BBQ, outside griddle, Heat, A/C and fully stocked kitchen. Full bathroom with shower. If this one is booked, there are three other equally similar Airstreams on the property.

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Other great holiday rentals in Santa Cruz Mountains

4.94 out of 5 average rating, 90 reviews

Cabin in Santa Cruz

Robin’s Nest in the Redwoods

LaurenneRating, 5 stars2 weeks ago

Robin’s Nest was such a beautiful getaway! Settled in the peaceful redwood forest above Santa Cruz (I rode my bike into town, which was fun!), it was a great place to escape the bustle, but close enough to enjoy some of the city’s amenities, food and culture. The bed was comfortable, kitchen was stocked, and the front deck/yard was such a lovely place for breakfast and morning coffee. I definitely plan on coming back when I need another escape!

5 out of 5 average rating, 57 reviews

Guest house in Aptos

Casa de Rowan

KateRating, 5 stars2 weeks ago

This place is absolutely incredible! It’s located in the mountains but not too far from town, it feels so peaceful when you are at the property and especially at Louie’s lookout. We stayed there for a week for our honeymoon, it’s within driving distance to so many special spots. Chris was awesome as well.

4.94 out of 5 average rating, 94 reviews

Cabin in Boulder Creek

King Suite Cabin | Santa Cruz Mountains

BryanRating, 5 stars1 week ago

Very nice place, very comfortable and had everything we needed. Host was very nice, quick to respond and took care of everything we needed. Very beautiful area surrounded by redwoods and very private. Would definitely stay again.

4.98 out of 5 average rating, 88 reviews

Treehouse in Felton

Redwood Ridge Tree Fort VRP#181501

AbigailRating, 5 stars4 days ago

We had a wonderful 2 night stay, highly recommend! We’ve haven’t had the best experiences with Airbnb in the past, but Bethany’s tree fort was amazing. This retreat was peaceful and had impressive little touches - like a hair towel wrap (I forgot mine), snacks, and s’mores station. We’ve already sent the ig/link to many family and friends. Thanks for the great getaway!

4.73 out of 5 average rating, 112 reviews

Dome in Watsonville

Apple view dome - stargazing galore!

HaroldRating, 5 stars3 weeks ago

This was a great getaway in a beautiful countryside. If you're looking for something somewhat off-the-grid, I would wholeheartedly recommend this memorable little dome. Waking up to see and hear all the birds in the morning was lovely.

5 out of 5 average rating, 14 reviews

Cabin in Bonny Doon

Eclectic Escape

MasonRating, 5 stars1 week ago

Staying at this cabin nestled in the heart of a redwood grove in the Santa Cruz mountains was truly magical. From the moment we arrived, it was clear that this wasn't just a place to stay — it was a carefully curated experience. The host has thought of everything to make guests feel at home and beyond comfortable. The attention to detail was incredible: high-quality toiletries, a well-stocked pantry with essentials (and then some!), soft, luxurious bedding, and even thoughtfully placed candles that added a cozy, relaxing atmosphere. Every touch felt intentional and generous. What truly set this stay apart, though, was the host. Incredibly accommodating, kind, and flexible — they went out of their way to ensure every one of our needs was met with care and promptness. It’s rare to come across someone so committed to hospitality. Waking up surrounded by towering redwoods, with birdsong filtering through the trees, was unforgettable.

4.94 out of 5 average rating, 95 reviews

Farm stay in Felton

Vineyard Retreat with Expansive Mountain View

MorganRating, 5 stars2 months ago

My husband used this spot to get ready for our wedding. While it was hard to get to, the instructions made it possible. The space was gorgeous inside and out and would have made a fantastic getaway. I would suggest getting there in daytime with lots of snacks so you don’t have to worry about leaving and coming back. This is a beautiful place to hunker down. She was thoughtful as well and left us champagne and chocolate!