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Glenwood Holiday Rentals

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Our top choices for Glenwood holiday rentals

Fern River Resort

Fern River Resort
3.0 star property
Felton
9.2 out of 10, Wonderful, (513 reviews)
"Lovely Cabin, my son had an amazing experience. We will definitely come back"
United States
Iris
The price is NZ$321
includes taxes & fees
15 July - 16 July
Fern River Resort

Mays Luxury Farm Stays

Mays Luxury Farm Stays
3.0 star property
Los Gatos
8.2 out of 10, Very good, (18 reviews)
"A great place to stay in the Santa Cruz mountains. A little tricky to find and get to with winding mountain roads and no signs but that is part of getting away from everything and hanging with the chicks and ducks and geese all a-clucking. Fully stocked bar and kitchen made it so easy to just have fun. The dozens of huge koi fish will practically climb out of the pond when you start feeding them, and the chickens seemed to like Fritos. Watching the sun setting beyond the trees and hills while...
United States
James
The price is NZ$387
includes taxes & fees
9 Aug - 10 Aug
Mays Luxury Farm Stays

Bella Notte

Bella Notte
4.0 star property
Eastside Santa Cruz
9.6 out of 10, Exceptional, (4 reviews)
"Great spot. Love the keyless, personless checkin!"
United States
Andrew
The price is NZ$484
includes taxes & fees
30 July - 31 July
Bella Notte

LOVELY HOUSE IN SAN JOSE

LOVELY HOUSE IN SAN JOSE
South San Jose
9.0 out of 10, Wonderful, (49 reviews)
"Place was clean and spacious"
United States
Angelaya L.
The price is NZ$721
includes taxes & fees
27 July - 28 July
LOVELY HOUSE IN SAN JOSE

WOW! Better Than A Hotel! SPACIOUS 4BR in SAN JOSE

WOW! Better Than A Hotel! SPACIOUS 4BR in SAN JOSE
South San Jose
9.8 out of 10, Exceptional, (48 reviews)
"Clean house, communicative host. Some of the electrical outlets didn't work but otherwise everything was great."
United States
Kyle
The price is NZ$904
includes taxes & fees
13 July - 14 July
WOW! Better Than A Hotel! SPACIOUS 4BR in SAN JOSE

Oceanfront Watsonville Condo w/ Beach Access!

Oceanfront Watsonville Condo w/ Beach Access!
3.5 star property
Watsonville
10.0 out of 10, Exceptional, (1 review)
"Nice family trip to the beach. The condo was spacious and the primary bedroom was fantastic. The other two bedrooms were small, but were still accommodating. The property is very well maintained. There’s paths to walk on for a nature walk and the beach has some hard sand that makes long walks on the beach very easy to do. There were 6 of us that went and there was plenty of space. Great stay!"
United States
Sarah
Oceanfront Watsonville Condo w/ Beach Access!

Luxury stay near Oakridge Mall for vacation/work

Luxury stay near Oakridge Mall for vacation/work
South San Jose
9.8 out of 10, Exceptional, (84 reviews)
"Very clean unit, comfortable beds, AC working fine, well equipped kitchen. Good shower water pressure. Only downside is that wall are thin so we could hear neighbors conversations and walking upstairs. Overall very recommendable"
United States
Gabriel
The price is NZ$455
includes taxes & fees
27 July - 28 July
Luxury stay near Oakridge Mall for vacation/work

Pleasure Point Getaway with hot tub, dog friendly!

Pleasure Point Getaway with hot tub, dog friendly!
Pleasure Point
9.8 out of 10, Exceptional, (27 reviews)
"Great place for a family. Excellent location for surfing, shopping, and small bites! "
United States
Kelda G.
The price is NZ$2,506
includes taxes & fees
26 July - 27 July
Pleasure Point Getaway with hot tub, dog friendly!

Luxurious & cozy Large 4 BR 2BA Home with Swimming POOL- San Jose Cambrian area

Luxurious & cozy Large 4 BR 2BA Home with Swimming POOL- San Jose Cambrian area
South San Jose
9.6 out of 10, Exceptional, (66 reviews)
"Enjoyed the pool, house was great, has everything we needed"
United States
James L.
The price is NZ$1,099
includes taxes & fees
15 July - 16 July
Luxurious & cozy Large 4 BR 2BA Home with Swimming POOL- San Jose Cambrian area

Mountain cabin w/king suite in the Redwoods of the Santa Cruz Mountains

Mountain cabin w/king suite in the Redwoods of the Santa Cruz Mountains
Boulder Creek
9.8 out of 10, Exceptional, (60 reviews)
"Great place and Great communication from hosts."
United States
Tom P.
The price is NZ$1,158
includes taxes & fees
16 July - 17 July
Mountain cabin w/king suite in the Redwoods of the Santa Cruz Mountains

Big 6BR DT SJ Getaway + Huge Backyard

Big 6BR DT SJ Getaway + Huge Backyard
Ryland
10.0 out of 10, Exceptional, (4 reviews)
"Stayed at this property for 10 days…needed a place with ample space to accommodate members of a bridal party, and work space to finish decorations and other wedding related projects. This house fit our needs perfectly. Rooms and bathrooms were clean, beds were comfortable, location was ideal. Driveway had plenty of room for multiple rental cars (no need to search for street parking). Communication with property manager was prompt and clear. I highly recommend this property!"
United States
Christina
The price is NZ$1,325
includes taxes & fees
10 Aug - 11 Aug
Big 6BR DT SJ Getaway + Huge Backyard

Stunning Oceanfront - Sunset Magazine Home

Stunning Oceanfront - Sunset Magazine Home
Eastside Santa Cruz
9.4 out of 10, Exceptional, (27 reviews)
"Really unbelievable views and access. Excellent stay, can’t wait to go back "
United States
Michelle D.
The price is NZ$2,168
includes taxes & fees
12 Aug - 13 Aug
Stunning Oceanfront - Sunset Magazine Home

Aptos Bayview, large 1 Br.Cottage, Pets & parking. Ocean View deck, fire pit

Aptos Bayview, large 1 Br.Cottage, Pets & parking. Ocean View deck, fire pit
Aptos
9.8 out of 10, Exceptional, (67 reviews)
"The cottage was clean, comfortable, and well stocked. We enjoyed our stay in Aptos. "
United States
C B.
The price is NZ$578
includes taxes & fees
19 July - 20 July
Aptos Bayview, large 1 Br.Cottage, Pets & parking. Ocean View deck, fire pit

Santa Cruz mountain Redwoods: Sunny beautiful home: VRP#221367:

Santa Cruz mountain Redwoods: Sunny beautiful home: VRP#221367:
Corralitos
9.8 out of 10, Exceptional, (93 reviews)
"This is a remarkable house, hidden in the redwoods on a small mountain road several miles from Watsonville. It's a uniquely designed home, a great kitchen, and four bedrooms. The road and driveway up to the house are themselves quite an experience, and guests should be aware that there are quite a few stairs up to the large deck. "
United States
Roger R.
The price is NZ$1,509
includes taxes & fees
19 July - 20 July
Santa Cruz mountain Redwoods: Sunny beautiful home: VRP#221367:

7 Houses from the Ocean - Pleasure Point Surf!

7 Houses from the Ocean - Pleasure Point Surf!
Eastside Santa Cruz
9.6 out of 10, Exceptional, (52 reviews)
"We had a great time! "
United States
Mary Grace M.
The price is NZ$3,352
includes taxes & fees
24 July - 25 July
7 Houses from the Ocean - Pleasure Point Surf!

"Queens Palace" Studio Apt Business Ready - San Jose

"Queens Palace" Studio Apt Business Ready - San Jose
San Tomas
9.8 out of 10, Exceptional, (9 reviews)
"We had a good overnight rest which was our main objective."
United States
Janet S.
The price is NZ$259
includes taxes & fees
16 July - 17 July
"Queens Palace" Studio Apt Business Ready - San Jose

Midnight Modern 2BR | 5m to SAP & 1GB Fiber

Midnight Modern 2BR | 5m to SAP & 1GB Fiber
San Jose
2.0 out of 10, (1 review)
"Llevo tiempo rentando lugares para pasar en familia pero este fue una mala experiencia el dueño del apartamento dentra sin permiso a cualquier hora del día o de la noche por qué dice que él es el dueño y puede hacerlo lo otro es que deja la nevera llena de comida del uso personal de él y desorden en toda la casa muy mala experiencia sinceramente si pueden no renten este apartamento"
United States
Jorge
Midnight Modern 2BR | 5m to SAP & 1GB Fiber

Modern San Jose retreat for 6, 3-bedrooms, 2-bath.

Modern San Jose retreat for 6, 3-bedrooms, 2-bath.
Naglee
Modern San Jose retreat for 6, 3-bedrooms, 2-bath.

Spacious 4-bedroom house in enchanting San Jose with AC, WiFi, washer and dryers

Spacious 4-bedroom house in enchanting San Jose with AC, WiFi, washer and dryers
East San Jose
8.4 out of 10, Very good, (20 reviews)
"Dmize had a wonderful stay at this beautiful house. Communication with Kim was seamless!!"
United States
Chiqui R.
The price is NZ$968
includes taxes & fees
17 July - 18 July
Spacious 4-bedroom house in enchanting San Jose with AC, WiFi, washer and dryers
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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Top Glenwood Hotel Reviews

Find out more about Glenwood

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 Glenwood 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 Glenwood. 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 Glenwood. Seeing all the best attractions is bound to make you fall in love with Glenwood. 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 Glenwood short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Glenwood?

Yes, we have holiday rentals where you'll be just 10.1 mi (16.2 km) from Santa Cruz Beach Boardwalk, offering you a more remote option if you'd like a quiet spot to stay.

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

Serene Guest Suite w/ Private Bath and Kitchenette: This holiday home rental outside of Glenwood has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Glenwood?

Explore the area and family-friendly sights such as Santa Cruz Beach Boardwalk, or get out into nature at a spot like The Forest of Nisene Marks State Park. You’ll find favourite places to visit such as Winchester Mystery House and Santana Row Shopping Center in the wider area.

What are holiday rentals like in Glenwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Glenwood. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for families.