Pleasure Point Vacations

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Your Pleasure Point Vacation

Book a Pleasure Point vacation package and immerse yourself in the way of life and rhythm of this unique neighborhood. With all your travel plans worked out, the only thing you need to concentrate on here is having a good time. Some top nearby attractions to check out during your trip to Pleasure Point include Santa Cruz Beach Boardwalk, Main Beach and Seacliff State Beach. Don't just imagine it — make it happen! Reserve your ideal Pleasure Point vacation with Expedia and travel your way.

The Latest Pleasure Point Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Marbella Lane Triplex San Jose

Marbella Lane Triplex San Jose

3.5 out of 5
Northside
Save 100% on your flight
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to San Jose (SJC)
7.2/10 Good! (32 reviews)
It was a very nice little room , perfect for a few days .

Reviewed on May 24, 2024

Marbella Lane Duplex San Jose

Marbella Lane Duplex San Jose

3.5 out of 5
Willow Glen
Save 100% on your flight
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to San Jose (SJC)
8/10 Very Good! (12 reviews)
This place is awesome because right across the street is a convenience store and a taco stand!

Reviewed on Jan 3, 2024

Homewood Suites By Hilton San Jose North

Homewood Suites By Hilton San Jose North

3 out of 5
North San Jose
Save 100% on your flight
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to San Jose (SJC)
9.2/10 Wonderful! (744 reviews)
Enjoyed our stay. Good facility

Reviewed on Jun 8, 2024

DoubleTree by Hilton San Jose

DoubleTree by Hilton San Jose

4 out of 5
Rosemary
Save 100% on your flight
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to San Jose (SJC)
7/10 Good! (1,000 reviews)
Wife and kids loved it! Our view from our room to the pool and the entire experience was great

Reviewed on Jun 14, 2024

Hampton Inn San Jose Cherry Ave

Hampton Inn San Jose Cherry Ave

3 out of 5
South San Jose
Save 100% on your flight
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to San Jose (SJC)
8.6/10 Excellent! (253 reviews)
For today's standards, the room was fine. Phone in room did not work the entirer time we were there. Was only a problem beause we had very noisy people above us and could not locate a local number to call,

Reviewed on Jun 10, 2024

Where to stay in Pleasure Point

Find the best Pleasure Point areas and neighborhoods for the activities you enjoy most. Learn more about Pleasure Point
Santa Cruz which includes watersports

Westside Santa Cruz

7 out of top 10 points of interest in this area
4/5(2,586 area reviews)

Westside Santa Cruz is known for its stunning beaches, and with sights like Santa Cruz Beach Boardwalk and Monterey Bay, you won't get bored spending a day wandering around this part of Santa Cruz.

Find hotel + flight trips in Westside Santa Cruz

Pleasure Point Hotel Deals

Courtyard by Marriott Santa Cruz
Courtyard by Marriott Santa Cruz
3 out of 5
313 Riverside Avenue, Santa Cruz, CA
Fully refundableReserve now, pay when you stay
The price is $189 per night from Jun 16 to Jun 17
$189
$214 total
includes taxes & fees
Jun 16 - Jun 17
8.2/10 Very Good! (445 reviews)
"Friendly place. Desk clerk, very helpful. The bar tenders,very friendly"

Reviewed on Jun 10, 2024

Courtyard by Marriott Santa Cruz
Hilton Santa Cruz/Scotts Valley
Hilton Santa Cruz/Scotts Valley
3.5 out of 5
6001 La Madrona Drive, Santa Cruz, CA
Fully refundableReserve now, pay when you stay
The price is $153 per night from Jun 23 to Jun 24
$153
$174 total
includes taxes & fees
Jun 23 - Jun 24
8/10 Very Good! (1,058 reviews)
"Very clean at a good price."

Reviewed on Jun 11, 2024

Hilton Santa Cruz/Scotts Valley
Hyatt Place Santa Cruz
Hyatt Place Santa Cruz
3 out of 5
407 Broadway, Santa Cruz, CA
Fully refundable
The price is $227 per night from Jul 10 to Jul 11
$227
$259 total
includes taxes & fees
Jul 10 - Jul 11
8.8/10 Excellent! (1,018 reviews)
"Amazing stay! Concierge was super helpful and overall very friendly."

Reviewed on Jun 10, 2024

Hyatt Place Santa Cruz
See all 1,170 properties in Pleasure Point
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Pleasure Point vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Pleasure Point from just $266. And the more you bundle, the more you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Pleasure Point?
Bundle your flights and hotels with Expedia to save on your next trip. With more than 550 air carriers and 1,000,000 hotel options worldwide, your Pleasure Point vacation package can be customized exactly to suit your budget. With all that extra cash, why not throw in a few awesome tours and activities? It’s an easy way to unlock even more bargains. The vacation you’ve always dreamed of in Pleasure Point is much closer than you thought!
Where should I stay in Pleasure Point?
A journey to Pleasure Point isn’t complete without seeing Santa Cruz Beach Boardwalk and Mystery Spot. Look for somewhere to stay right nearby and easily access these impressive sights.
What are the top hotels in Pleasure Point?
If it’s your first time in Pleasure Point, secure a room at Beach Lovers Retreat or One Of Two Oceanfront Units Right On The Beach Near Pleasure Point In Santa Cruz. Both have good amenities and are favorites with lots of travelers.
How far in advance should I book my Pleasure Point vacation?
While not all air carriers release ticket prices early, customers are usually able to start comparing international fares on Expedia up to 12 months in advance. This is the time when you’ll bag some fantastic deals. If you’re booking at the last minute, you might still be in luck. Sometimes the cheapest prices emerge only weeks prior to departure.
What does an Expedia Pleasure Point travel package include?
Flights, hotels and car rentals — we bring you the very best deals. All you’ll have to do is decide on your preferred combination. Once you’ve made your booking, you can add on the fun stuff like activities and tours. Our travel packages make it easy to put together an exciting Pleasure Point escape.
What should I know before booking a Pleasure Point travel package?
You’ll land terrific savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything in one place makes trip planning easier. So why waste your money or time? Whether you’re organizing a luxury city stay with your love or a budget family adventure, check out our vacation packages today.
If I'm not able to travel, can I cancel my Pleasure Point vacation package?
You can cancel your Pleasure Point booking if your plans have changed. Whether you’ll incur a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Pleasure Point

Image for Pleasure Point Park

Pleasure Point Park

Explore the lovely green spaces of Pleasure Point Park and enjoy the surfing in Santa Cruz. Attend a sporting event in this walkable area, or seek out the biking trails.

Pleasure Point Park
Image for Santa Cruz Beach Boardwalk

Santa Cruz Beach Boardwalk

4.5/5(2,013 reviews)

Enjoy the thrills at Santa Cruz Beach Boardwalk and find out why people love this theme park in Santa Cruz. Attend a sporting event in this walkable area, or seek out the biking trails.

Santa Cruz Beach Boardwalk
Image for Mystery Spot

Mystery Spot

4/5(639 reviews)

Find out about the history of Santa Cruz with a stop at Mystery Spot. Attend a sporting event in this walkable area, or seek out the surfing spots.

Mystery Spot

Things to do

Image for Big Sur Private Charter from San Francisco by Luxury SUV 10 hrs

Big Sur Private Charter from San Francisco by Luxury SUV 10 hrs

$1,300
Per adult
Big Sur Private Charter from San Francisco by Luxury SUV 10 hrs
Image for Whale Watching Monterey Bay semi-private limited to 6 people max

Whale Watching Monterey Bay semi-private limited to 6 people max

$400
Per adult
100% of travellers recommend
Whale Watching Monterey Bay semi-private limited to 6 people max
Image for Santa Cruz Redwoods Forest Therapy

Santa Cruz Redwoods Forest Therapy

$85
Per adult
Santa Cruz Redwoods Forest Therapy
See all activities in Santa Cruz

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.