Pleasure Point Vacations

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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
Aerial view of the Santa Cruz beach and the amusement park in California

Westside Santa Cruz

8 out of top 10 points of interest in this area
4/5(2,615 area reviews)

Westside Santa Cruz is known for its stunning beaches, and with sights like Monterey Bay and Santa Cruz Beach Boardwalk, 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

Dream Inn Santa Cruz

Dream Inn Santa Cruz

4 out of 5
175 W Cliff Dr Santa Cruz CA
Fully refundableReserve now, pay when you stay
The price is ₩323,636 per night from May 17 to May 18
₩323,636
₩369,168 total
May 17 - May 18
includes taxes & fees
9.4/10 Exceptional! (1,027 reviews)
Five stars

Reviewed on May 11, 2026

Dream Inn Santa Cruz
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
The price is ₩272,053 per night from May 26 to May 27
₩272,053
₩311,296 total
May 26 - May 27
includes taxes & fees
9.2/10 Wonderful! (1,291 reviews)
5 stars

Reviewed on May 6, 2026

La Quinta Inn & Suites by Wyndham Santa Cruz
Hotel Paradox, Autograph Collection

Hotel Paradox, Autograph Collection

4 out of 5
611 Ocean St Santa Cruz CA
Fully refundableReserve now, pay when you stay
The price is ₩214,836 per night from May 25 to May 26
₩214,836
₩247,100 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (1,255 reviews)
Room was clean

Reviewed on May 10, 2026

Hotel Paradox, Autograph Collection
See all 1,265 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.

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 . 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

EN5XP1 Street scene in autumn with shops art galleries on Ocean Avenue Carmel Monterey County California

Ocean Street

During your visit to Santa Cruz, you can enjoy retail therapy at Ocean Street. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

Ocean Street
T4D055 Sunset, Cowell Beach, Santa Cruz, California, United States

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