Pleasure Point Vacations from $505

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Photo by Jennifer Radman

Your Pleasure Point Vacation

Reserving a Pleasure Point vacation package is a wonderful way to get to know this unique neighborhood. From its must-see spots to its lesser-known gems, there's a lot to delve into. Can't wait to explore the sights during your trip to Pleasure Point? Make sure you stop by nearby attractions like Santa Cruz Beach Boardwalk, Main Beach and Capitola Wharf. Expedia can help turn your dream Pleasure Point vacation into reality, no matter your budget or travel plans.

The Latest Pleasure Point Vacation Packages

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
Save 100% on your flight
Price was $748, price is now $505 per person
$505
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to San Jose (SJC)
9.4/10 Exceptional! (1,007 reviews)
We liked the style of everything. Everything was clean and minimalist but modern. The staff was polite and helpful. The AC didn't seem to be controllable. And it worked sub par. Again the scene was nice. It was perfectly located for comfortable walking distance to the Shoreline Ampiatheater. The hotel menu could use better choices. Maybe too fancy for me but mousse liver before heading out was not going to be enough 😭

Reviewed on Sep 1, 2025

Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
Price was $2,950, price is now $1,353 per person
$1,353
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to San Jose (SJC)
8/10 Very Good! (1,003 reviews)
Short walk to Boardwalk great views

Reviewed on Aug 25, 2025

Motel 6 Santa Cruz, CA

Motel 6 Santa Cruz, CA

2 out of 5
Westside Santa Cruz
Save 100% on your flight
Price was $1,631, price is now $1,094 per person
$1,094
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to San Jose (SJC)
5.8/10 (535 reviews)
This was a very clean room and they had just done improvements on the location and the room. Only thing that was bad was our room did not have shampoo or conditioner and per other guests asking at the front office they did not have any either. The one gentleman was told at 0715 am that he would have to wait til 0900 to get shampoo. I walked the couple blocks down the road and bought some at the gas station.

Reviewed on Aug 16, 2025

La Bahia Hotel and Spa

La Bahia Hotel and Spa

3.5 out of 5
Westside Santa Cruz
Save 100% on your flight
Price was $788, price is now $574 per person
$574
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Portland (PDX) to San Jose (SJC)
No reviews
Spark by Hilton San Jose Airport

Spark by Hilton San Jose Airport

3 out of 5
North San Jose
Price was $752, price is now $552 per person
$552
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to San Jose (SJC)
8.6/10 Excellent! (159 reviews)
Modern decor, helpful staff.

Reviewed on Aug 29, 2025

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 showing 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(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 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
$137 nightly
The price is $158 total per night from Oct 1 to Oct 2
$158 total
Oct 1 - Oct 2
Total with taxes and 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
$104 nightly
The price is $120 total per night from Sep 22 to Sep 23
$120 total
Sep 22 - Sep 23
Total with taxes and fees
Ocean Pacific Lodge
Chaminade Resort & Spa

Chaminade Resort & Spa

4 out of 5
1 Chaminade Ln, Santa Cruz, CA
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $250 total per night from Sep 14 to Sep 15
$250 total
Sep 14 - Sep 15
Total with taxes and fees
7.8/10 Good! (980 reviews)
"Nice, but slightly overpriced"

Reviewed on Aug 26, 2025

Chaminade Resort & Spa
See all 1,206 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Pleasure Point

"Hibiscus Tiliaceus"

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
Another beautiful sunset 🌇

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
The place where you can't stay straight.

Mystery Spot

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

Beginner Surf Lesson in Santa Cruz

Beginner Surf Lesson in Santa Cruz

$129
per adult
Beginner Surf Lesson in Santa Cruz
Santa Cruz Redwoods Forest Therapy

Santa Cruz Redwoods Forest Therapy

$85
per adult
Santa Cruz Redwoods Forest Therapy
Bay Area Rock Climbing

Beginner Outdoor Rock Climbing - Bay Area

$119
per adult
Beginner Outdoor Rock Climbing - Bay Area
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.