Pleasure Point Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Dori Vogel Cirrincione
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Pleasure Point

Price found within the past 48 hours. Click for updated prices.
Shashi Hotel Mountain View Palo Alto

Shashi Hotel Mountain View Palo Alto

5 out of 5
per person
Aug. 30 - Sep. 2
found 11 hours ago
Roundtrip flight included
Vancouver (YVR) to San Jose (SJC)
9.4/10 Exceptional! (572 reviews)
Road work and building construction around, thus noisy. The room is pretty small. No breakfast provided.

Reviewed on Jun. 2, 2024

Chaminade Resort & Spa

Chaminade Resort & Spa

4 out of 5
Save 100% on your flight
per person
Aug. 16 - Aug. 20
found 13 hours ago
Roundtrip flight included
Kelowna (YLW) to San Jose (SJC)
7.8/10 Good! (1,004 reviews)
Amenities for kids with multiple pools and weekend poolside movies are great. Restaurant is underwhelming except for it’s convenience. First floor rooms have patios but choose the view that you want.

Reviewed on Jun. 2, 2024

Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
per person
Aug. 16 - Aug. 20
found 13 hours ago
Roundtrip flight included
Kelowna (YLW) to San Jose (SJC)
7.6/10 Good! (1,003 reviews)
I love that the employee gave me the option for beach view.

Reviewed on May 25, 2024

Holiday Inn Express Hotel & Suites Santa Cruz, an IHG Hotel

Holiday Inn Express Hotel & Suites Santa Cruz, an IHG Hotel

2.5 out of 5
Westside Santa Cruz
Save 100% on your flight
per person
Aug. 16 - Aug. 20
found 13 hours ago
Roundtrip flight included
Kelowna (YLW) to San Jose (SJC)
8/10 Very Good! (1,006 reviews)
Was good for an overnight.

Reviewed on Jun. 5, 2024

The Ameswell Hotel

The Ameswell Hotel

4.5 out of 5
per person
Aug. 29 - Sep. 3
found 17 hours ago
Roundtrip flight included
Vancouver (YVR) to San Jose (SJC)
9.4/10 Exceptional! (662 reviews)
Lovely, beautiful, convenient. Very thoughtful amenities within the hotel considering that there is no conveniences that are walkable. Pool, fire pit, workout room, lawn area- nearby Stevens Creek Trail and Freeway access- amazing. I happened to arrive on a Friday when the staff was clearly tired from the business travelers all week- 3:45pm is too late to get decent food at the Starbucks style coffee shop and too early to get anything at the bar. Front desk staff had the same lack of energy. But the property is amazing and very convenient.

Reviewed on Jun. 6, 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(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 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 CA $199 per night from Jun. 9 to Jun. 10
CA $199
CA $226 total
includes taxes & fees
Jun 9 - Jun 10
8.2/10 Very Good! (427 reviews)
Getaway
"Had a very enjoyable stay, from the front desk to the lounge for dinner and drinks, total customer obsession, Thank You"

Reviewed on Jun. 4, 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
The price is CA $196 per night from Jun. 23 to Jun. 24
CA $196
CA $223 total
includes taxes & fees
Jun 23 - Jun 24
8/10 Very Good! (1,056 reviews)
"Hotel front desk is friendly"

Reviewed on Jun. 6, 2024

Hilton Santa Cruz/Scotts Valley
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 CA $231 per night from Jun. 9 to Jun. 10
CA $231
CA $267 total
includes taxes & fees
Jun 9 - Jun 10
8.4/10 Very Good! (1,009 reviews)
"The location was great, super friendly staff and delicious breakfast! Highly recommend"

Reviewed on Jun. 3, 2024

Hotel Paradox, Autograph Collection
See all 1,174 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

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 $696. 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(69 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

4.5/5(11 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

CA $1,760
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

CA $542
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

CA $115
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.