Pleasure Point Vacations from $528

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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.
Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
Save 100% on your flight
Price was $1,018, price is now $528 per person
$528
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to San Jose (SJC)
8/10 Very Good! (1,008 reviews)
Booked the double room with kitchenette. Was more like a small 1 bedroom apartment. Kitchenette came with full size refrigerator and gas stove. Perfect for small family. Older hotel right in front of Boardwalk parking lot so it made getting to boardwalk very easy and convenient. We needed an ADA room, but they were sold out (my fault i forgot to request when booking) but they were very accommodating to what we needed. I also appreciate that they called to confirm our check-in eta since we were running late and they waited for us..with a welcoming smile. Thank you

Reviewed on Nov 11, 2025

@ Marbella Lane - 3BR Designer Near Valley Fair

@ Marbella Lane - 3BR Designer Near Valley Fair

3 out of 5
Price was $4,377, price is now $2,464 per person
$2,464
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip flight included
Seattle (SEA) to San Jose (SJC)
No reviews
Marbella Lane Triplex San Jose

Marbella Lane Triplex San Jose

3.5 out of 5
Northside
Price was $3,731, price is now $2,109 per person
$2,109
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip flight included
Seattle (SEA) to San Jose (SJC)
7.4/10 Good! (42 reviews)
It is very nice of a place. I just didnt get a kitchen to cook in. So the pictures lied and i couldnt get in just yet. Other then that great place, location and nice community.

Reviewed on Nov 11, 2025

@ Marbella Lane - Stylish Cozy4br in Siliconvalley

@ Marbella Lane - Stylish Cozy4br in Siliconvalley

3 out of 5
Save 100% on your flight
Price was $5,645, price is now $3,431 per person
$3,431
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip flight included
Seattle (SEA) to San Jose (SJC)
No reviews
@ Marbella Lane - Elegant Home in SJ

@ Marbella Lane - Elegant Home in SJ

3 out of 5
Willow Glen
Save 100% on your flight
Price was $4,235, price is now $2,584 per person
$2,584
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip flight included
Seattle (SEA) 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 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

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
$119 nightly
The price is $138 total per night from Nov 30 to Dec 1
$138 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (1,102 reviews)
gorgeous inside, amenities were perfect from the water fill stations to the lawn games at the pool. rooms were spacious and adorable. we had a great stay

Reviewed on Nov 8, 2025

Hotel Paradox, Autograph Collection
Holiday Inn Express Hotel & Suites Santa Cruz by IHG

Holiday Inn Express Hotel & Suites Santa Cruz by IHG

2.5 out of 5
1410 Ocean Street, Santa Cruz, CA
Fully refundable
$115 nightly
The price is $133 total per night from Nov 16 to Nov 17
$133 total
Nov 16 - Nov 17
Total with taxes and fees
8.4/10 Very Good! (1,161 reviews)
Ongoing business trips

Reviewed on Nov 7, 2025

Holiday Inn Express Hotel & Suites Santa Cruz by IHG
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
$101 nightly
The price is $118 total per night from Nov 16 to Nov 17
$118 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (1,243 reviews)
Great location. Room was spacious and had a balcony. Room was very clean and had enough towels. Staff was friendly and helpful. Breakfast was great! Had everything that we wanted for breakfast. We will stay again when we come back.

Reviewed on Oct 31, 2025

La Quinta Inn & Suites by Wyndham Santa Cruz
See all 1,196 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

4.5/5(2,013 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
The place where you can't stay straight.

Mystery Spot

4/5(639 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

Rock Climbing 2 - Beyond the Basics

Outdoor Rock Climbing - Level 2

$119
per adult
Outdoor Rock Climbing - Level 2
Santa Cruz Redwoods Forest Therapy

Redwoods Forest Bathing

$89
per adult
Redwoods Forest Bathing
Beginner Surf Lesson in Santa Cruz

Beginner Surf Lesson in Santa Cruz

$129
per adult
Beginner Surf Lesson in Santa Cruz
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.