Pleasure Point Vacations from $448

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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.
Sonesta San Jose - Milpitas

Sonesta San Jose - Milpitas

Save 100% on your flight
$448
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
8.8/10 Excellent! (1,069 reviews)
Aqua Breeze Inn

Aqua Breeze Inn

Westside Santa Cruz
Save 100% on your flight
$456
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
8.2/10 Very Good! (1,008 reviews)
Great location to spend the day at the boardwalk!

Reviewed on Aug 30, 2026

Marbella Lane - 3BR Designer Near Valley Fair

Marbella Lane - 3BR Designer Near Valley Fair

Save 100% on your flight
$1,412
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Seattle (SEA) to San Jose (SJC)
No reviews
@ Marbella Lane - SJ Designer Home 3BR Ldry+p

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

Save 100% on your flight
$1,768
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Seattle (SEA) to San Jose (SJC)
No reviews
@ Marbella Lane - 4BR Siliconvalley Gempool House

@ Marbella Lane - 4BR Siliconvalley Gempool House

Berryessa
Save 100% on your flight
$2,174
per person
Nov 1 - Nov 7
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
A coastal cityscape with a beach, pier, and amusement park.

Westside Santa Cruz

6 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 Santa Cruz Main Beach are two attractions nearby that you can check out.

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.

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.

Pleasure Point Hotel Deals

La Bahia Hotel and Spa

La Bahia Hotel and Spa

215 Beach Street Santa Cruz CA
Fully refundableReserve now, pay when you stay
$353 nightly
$396 total
Sep 1 - Sep 2
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
$70 nightly
$81 total
Sep 30 - Oct 1
Total with taxes and fees
8.2/10 Very Good! (1,105 reviews)
"The staff was very nice and it was very quiet at night but the hotel is very run down. Unfortunately would not stay again. The pillows were flat and cheap."

Reviewed on Aug 30, 2026

Seaside Inn & Suites
Marea Sol Hotel

Marea Sol Hotel

301 Beach St Santa Cruz CA
Fully refundableReserve now, pay when you stay
$129 nightly
$149 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,608 reviews)
"Extremely family-friendly and clean/maintained property. The staff was friendly and engaging and there was always someone available to assist with questions and requests. Super close to the beach and boardwalk with an added bonus of having a cute cafe there!"

Reviewed on Aug 28, 2026

Marea Sol Hotel
See all 1,264 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.
See properties

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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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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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
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
Rock Climbing 2 - Beyond the Basics

Outdoor Rock Climbing - Level 2

$119
per adult
Outdoor Rock Climbing - Level 2
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.