Pleasure Point Vacations from $390

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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.
DoubleTree by Hilton San Jose

DoubleTree by Hilton San Jose

4 out of 5
Rosemary
Save 100% on your flight
Price was $565, price is now $390 per person
$390
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Seattle (SEA) to San Jose (SJC)
7.2/10 Good! (1,004 reviews)
The lobby area, restaurant, gym, and pool were all fantastic spaces. Our family spent a lot of time in the pool and had a great time. The staff was helpful and the place was clean. The rooms and hallway (3rd floor) were pretty outdated with some pretty visible carpet stains but as I said, it didn't seem dirty just old. The halls and rooms could use a remodel but this was still a fine place to stay close to the airport.

Reviewed on Sep 25, 2025

Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
Price was $2,948, price is now $1,373 per person
$1,373
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to San Jose (SJC)
8/10 Very Good! (1,002 reviews)
Was very close to the boardwalk and beach,but the inn itself was not in the best condition, the room was musty smelling and tight to get around ,there was no pool,but they did allow pets,the staff was friendly.

Reviewed on Sep 27, 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 $1,651, price is now $1,114 per person
$1,114
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to San Jose (SJC)
5.8/10 (545 reviews)
Basic motel. Door was difficult to open due to damage to frame. No bulbs in bedside lamp. Smoke alarm smashed Reported but nothing done in a week. Lots of homeless in the area

Reviewed on Sep 20, 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 $1,060, price is now $716 per person
$716
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to San Jose (SJC)
10/10 Exceptional! (4 reviews)
As a local, we watched this prime Santa Cruz lot sit unused for many years. It's finally developed and they did an amazing job. This is a huge upgrade for Santa Cruz. There's nothing in town that competes. It's upscale without being tacky or pretentious. We stayed in their most basic room and it was still impressive. The pool area is sublime. It's a great addition to Santa Cruz!

Reviewed on Sep 22, 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

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
$109 nightly
The price is $126 total per night from Oct 26 to Oct 27
$126 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (1,052 reviews)
"Super cute hotel, comfortable, good amenities, decent spot to stay in Santa Cruz :)"

Reviewed on Sep 25, 2025

Hotel Paradox, Autograph Collection
Marea Sol Hotel

Marea Sol Hotel

2 out of 5
301 Beach St, Santa Cruz, CA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $108 total per night from Sep 29 to Sep 30
$108 total
Sep 29 - Sep 30
Total with taxes and fees
9/10 Wonderful! (1,183 reviews)
"Love that this hotel is right across the street from the main beach, boardwalk arcade and much more. Our room had the best view! The street infront is noisy during the night and restaurants around are cooking so you cant really leave your balcony open it will stink up the room. The first night our ..."

Reviewed on Sep 24, 2025

Marea Sol Hotel
Dream Inn Santa Cruz

Dream Inn Santa Cruz

4 out of 5
175 W Cliff Dr, Santa Cruz, CA
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $295 total per night from Oct 13 to Oct 14
$295 total
Oct 13 - Oct 14
Total with taxes and fees
9.2/10 Wonderful! (1,015 reviews)
"Great. No issues."

Reviewed on Sep 24, 2025

Dream Inn Santa Cruz
See all 1,193 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.