Pleasure Point Vacations from $735

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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

$735
per person
Nov 14 - Nov 17
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
9.4/10 Exceptional! (1,458 reviews)
Overall, we had a decent stay and really liked the concept of Shashi Hotel. The hotel feels very modern and technology-focused, and we loved how much could be personalized through the app — lighting, sleep music, relaxing tea at a specific time, uploading your own photos to the TV, and other small details. It definitely makes the stay feel more unique than a typical hotel. Unfortunately, the room itself did not feel very cozy or inviting. The wardrobe/cabinet was heavily scratched and covered with strange drawings and shapes scratched into the surface by previous guests. It was honestly not something you want to see first thing in the morning when you open your eyes, and it really took away from the feel of the room. The jacuzzi was another disappointment. The chlorine smell was extremely strong, and after a short time our eyes were burning and we started feeling lightheaded, so we could not really enjoy it. I think the hotel should definitely check the chemical levels. Overall, there is a lot to like about Shashi, especially the modern concept and personalization options, but the room atmosphere, damaged furniture, and jacuzzi experience kept the stay from feeling as comfortable and polished as we expected.

Reviewed on Oct 13, 2026

Marbella Lane Triplex San Jose

Marbella Lane Triplex San Jose

Northside
Save 100% on your flight
$751
per person
Dec 31 - Jan 3
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
7.2/10 Good! (45 reviews)
Just only 4 pm can check in. 😞

Reviewed on Apr 28, 2026

@ Marbella Lane - SJ Designer Home 3BR Ldry+p

@ Marbella Lane - SJ Designer Home 3BR Ldry+p

Save 100% on your flight
$1,650
per person
Dec 31 - Jan 3
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
No reviews
@ Marbella Lane - 4BR Siliconvalley Gempool House

@ Marbella Lane - 4BR Siliconvalley Gempool House

Berryessa
Save 100% on your flight
$2,130
per person
Dec 31 - Jan 3
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
No reviews
@ Marbella Lane - Immaculate & Cozy 3BR Home

@ Marbella Lane - Immaculate & Cozy 3BR Home

Save 100% on your flight
$1,099
per person
Dec 31 - Jan 3
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) 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
A natural rock arch formation on a beach with waves crashing below.

Westside Santa Cruz

7 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.

A rocky coastline with waves crashing against the rocks.

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.

A street with a clock tower, a tram, and a building with a sign.

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.

A historic building with a distinctive corner turret, surrounded by autumn-colored trees and a clear street.

Downtown Santa Cruz

Unique features of Downtown Santa Cruz include the beaches and restaurants. Make a stop by Pacific Avenue or Santa Cruz Museum of Art and History while you're exploring the area.

A beach with people playing and walking.

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.

Pleasure Point Hotel Deals

La Bahia Hotel and Spa

La Bahia Hotel and Spa

215 Beach Street Santa Cruz CA
$399 nightly
$448 total
Oct 19 - Oct 20
Total with taxes and fees
La Bahia Hotel and Spa
Seaside Inn & Suites

Seaside Inn & Suites

525 Ocean St Santa Cruz CA
Fully refundableReserve now, pay when you stay
$69 nightly
$79 total
Nov 1 - Nov 2
Total with taxes and fees
8.2/10 Very Good! (1,151 reviews)
"Me and my family decided to have a last minute beach visit we had no idea we were going to want to stay the night and once we figured we would I called everywhere (it was 7pm) and only this hotel answered there was always someone to help at the desk and it was fast and easy to book and it was a great ..."

Reviewed on Oct 13, 2026

Seaside Inn & Suites
Marea Sol Hotel

Marea Sol Hotel

301 Beach St Santa Cruz CA
$129 nightly
$149 total
Oct 27 - Oct 28
Total with taxes and fees
9/10 Wonderful! (1,633 reviews)
"We had a view of the beach, which we paid extra for. But the rest of the rooms look at nothing, and parking is really bad there. You have to park in another lot around the corner, and I’m not sure how safe it is. Unless you’re lucky enough to get the parking spots outside the lobby. The hotel is ..."

Reviewed on Oct 14, 2026

Marea Sol Hotel
See all 1,236 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.

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.
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38th Avenue Beach Access

Why not spend a lazy afternoon at 38th Avenue Beach Access during your trip to Santa Cruz?
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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.
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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.
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Things to do

Santa Cruz Beach Hill to Mission Hill Loop Via Downtown

Beach Hill to Historic Downtown Santa Cruz Loop

$45
per adult
Beach Hill to Historic Downtown Santa Cruz Loop
Capitola Friday Night Food Tour

Capitola Friday Night Food Tour

$129
per adult
100% of travellers recommend
Capitola Friday Night Food Tour
Santa Cruz Walking Tour: Discover Downtown & Mission Hill

Santa Cruz Walking Tour: Discover Downtown & Mission Hill

$45
per adult
Santa Cruz Walking Tour: Discover Downtown & Mission Hill
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.