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.
Shashi Hotel Mountain View Palo Alto
CA $1,684
per person
Sep 30 - Oct 4
found 12 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Jose (SJC)
9.4/10 Exceptional! (1,402 reviews)
Staff rocked our stay and made it a 10! All staff were excellent . Restaurant manager top shelf!
Reviewed on Aug 24, 2026
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
Westside Santa Cruz
6 out of top 10 points of interest in this area
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.
Eastside Santa Cruz
1 out of top 10 points of interest in this area
Eastside Santa Cruz is known for its beaches, and you can plan a trip to Monterey Bay and Twin Lakes State Beach while you're in town.
Beach Hill - Beach Flats
Beach Hill - Beach Flats might not have many top sights, but Santa Cruz Beach Boardwalk and Monterey Bay National Marine Sanctuary Exploration Center are two attractions nearby that you can check out.
Upper Seabright
When in Upper Seabright, you can plan a visit to Santa Cruz Beach Boardwalk and Santa Cruz Harbor, some noteworthy sights in the nearby area.
Downtown Santa Cruz
Unique features of Downtown Santa Cruz include the beaches and restaurants. Make a stop by Pacific Avenue or Pacific Garden Mall while you're exploring the area.
Pleasure Point Hotel Deals
Chaminade Resort & Spa
1 Chaminade Ln Santa Cruz CA
Fully refundableReserve now, pay when you stay
CA $174
CA $264 total
Sep 7 - Sep 8
includes taxes & fees
La Bahia Hotel and Spa
215 Beach Street Santa Cruz CA
Fully refundableReserve now, pay when you stay
CA $471
CA $606 total
Aug 30 - Aug 31
includes taxes & fees
Seaside Inn & Suites
525 Ocean St Santa Cruz CA
Fully refundableReserve now, pay when you stay
CA $84
CA $120 total
Aug 27 - Aug 28
includes taxes & fees
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.
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 $885. 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.
Stay near popular Pleasure Point attractions
Pleasure Point Park
8.2/10 (37 reviews)
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.
The Hook
10.0/10 (1 review)
If a restful vacation is part of your travel plans, The Hook might be the perfect place to seek out during your trip to Santa Cruz.
38th Avenue Beach Access
Why not spend a lazy afternoon at 38th Avenue Beach Access during your trip to Santa Cruz?
Moran Lake Beach
Why not spend a lazy afternoon at Moran Lake Beach during your trip to Santa Cruz? While you're in the area, stroll along the beautiful beaches.
Things to do
Beach Hill to Historic Downtown Santa Cruz Loop
CA $63
per adult
Santa Cruz Walking Tour: Discover Downtown & Mission Hill
CA $63
per adult
Capitola Friday Night Food Tour
CA $181
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.