Pleasure Point Vacation Packages

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Top Holiday Package Deals in Pleasure Point

Price found within the past 48 hours. Click for updated prices.
Hotel Zico, BW Signature Collection

Hotel Zico, BW Signature Collection

3 out of 5
Price was CA $929, price is now CA $670 per person
CA $670
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Calgary (YYC) to San Jose (SJC)
8.2/10 Very Good! (1,360 reviews)
Walkable pathways and a nice continental breakfast

Reviewed on Aug. 31, 2025

Holiday Inn San Jose - Silicon Valley by IHG

Holiday Inn San Jose - Silicon Valley by IHG

3 out of 5
Rosemary
Price was CA $1,017, price is now CA $754 per person
CA $754
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Calgary (YYC) to San Jose (SJC)
8.2/10 Very Good! (1,046 reviews)
The property was great but we got put in the wrong room with a pet. Merritt at the front desk was the professional you wish for when staying at a hotel and corrected the issue with a smile. The overnight lady was extremely rude and I was worried about the service I would receive the next day but Merritt was a complete 180 in terms of professionalism and service quality. Thank you Merritt

Reviewed on Sep. 3, 2025

@ Marbella Lane - 3BR Designer Near Valley Fair

@ Marbella Lane - 3BR Designer Near Valley Fair

3 out of 5
Price was CA $1,925, price is now CA $1,457 per person
CA $1,457
per person
Oct 17 - Oct 20
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Jose (SJC)
No reviews
Shashi Hotel Mountain View Palo Alto

Shashi Hotel Mountain View Palo Alto

5 out of 5
Price was CA $1,759, price is now CA $1,349 per person
CA $1,349
per person
Oct 26 - Oct 29
found 6 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to San Jose (SJC)
9.4/10 Exceptional! (1,031 reviews)
Awesome place to stay if visiting Shoreline Amphitheater

Reviewed on Sep. 5, 2025

@ Marbella Lane - Stylish Cozy4br in Siliconvalley

@ Marbella Lane - Stylish Cozy4br in Siliconvalley

3 out of 5
Price was CA $2,126, price is now CA $1,642 per person
CA $1,642
per person
Oct 17 - Oct 20
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Jose (SJC)
No reviews

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 featuring general coastal views and views as well as an individual male

Westside Santa Cruz

7 out of top 10 points of interest in this area
4/5(34 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 hotels in Westside Santa Cruz

Pleasure Point Hotel Deals

La Quinta Inn & Suites by Wyndham Santa Cruz

La Quinta Inn & Suites by Wyndham Santa Cruz

3 out of 5
550 2nd St, Santa Cruz, CA
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Sep 8 to Sep 9
CA $193
CA $223 total
Sep 8 - Sep 9
includes taxes & fees
La Quinta Inn & Suites by Wyndham Santa Cruz
Ocean Pacific Lodge

Ocean Pacific Lodge

2 out of 5
301 Pacific Avenue, Santa Cruz, CA
The price is CA $111 per night from Sep 8 to Sep 9
CA $111
CA $145 total
Sep 8 - Sep 9
includes taxes & fees
Ocean Pacific Lodge
Seacliff Inn Aptos, Tapestry Collection by Hilton

Seacliff Inn Aptos, Tapestry Collection by Hilton

3.5 out of 5
7500 Old Dominion Court, Aptos, CA
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Sep 28 to Sep 29
CA $176
CA $203 total
Sep 28 - Sep 29
includes taxes & fees
Seacliff Inn Aptos, Tapestry Collection by Hilton
See all 1,198 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family 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 CA $670. 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

Santa Cruz Beach Boardwalk

Santa Cruz Beach Boardwalk

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
Santa Cruz Harbor

Santa Cruz Harbor

Explore the waterfront in Santa Cruz with a trip to Santa Cruz Harbor. While you're in the area, stroll along the beautiful beaches.

Santa Cruz Harbor
Cowell's Beach

Cowell's Beach

Explore the waterfront of Cowell's Beach and enjoy activities such as surfing in Santa Cruz. Attend a sporting event in this walkable area, or seek out the biking trails.

Cowell's Beach

Things to do

Beginner Surf Lesson in Santa Cruz

Beginner Surf Lesson in Santa Cruz

CA $177
per adult
Beginner Surf Lesson in Santa Cruz
5-Hour Wilderness Skills & Survival Clinic

5-Hour Wilderness Skills & Survival Clinic

CA $191
per adult
5-Hour Wilderness Skills & Survival Clinic
Santa Cruz Guided E-Bike Ride & Most Fun Ebike Tour

Santa Cruz Guided eBike Ride & Most Fun Bike e-Bike Tour

CA $151
per adult
Santa Cruz Guided eBike Ride & Most Fun Bike e-Bike Tour
See all activities in Santa Cruz
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.