Pleasure Point Vacation Packages
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Top Holiday Package Deals in Pleasure Point
Price found within the past 48 hours. Click for updated prices.
Sonesta San Jose - Milpitas
per person
Aug 24 - Aug 31
found 4 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to San Jose (SJC)
8.4/10 Very Good! (1,006 reviews)
Staff was very friendly and even went we arrived at 1am they still were very understanding and quick to get us to our room and the room was clean was spacious
Reviewed on Jul. 4, 2025
Aqua Breeze Inn
Westside Santa Cruz
per person
Sep 3 - Sep 10
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Jose (SJC)
8/10 Very Good! (1,003 reviews)
The room was perfect for a family with a separate king bedroom and two queens in the other room. This property was perfect for us as we had 17 and 15 year old grandsons and our 6 year old grandaughter with us. The boys walked to the boardwalk when ever they wanted to which was great. This property is older but well maintained and clean, the staff was great and the free on site parking was a godsend. We read alot of the negative reviews from people that were obviously expecting the Ritz Carlton which it is not but it so convenient and totally met our expectations. We were very satisfied.
Reviewed on Jul. 22, 2025
Shashi Hotel Mountain View Palo Alto
per person
Aug 24 - Aug 31
found 20 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to San Jose (SJC)
9.4/10 Exceptional! (1,009 reviews)
I loved these accommodations. The hotel is like new. The room is modern and comfortable. The bed was super comfortable. Everything is clean. The pool and bar looked great, though did not have a chance to make use of them. The hotel is located in an upscale business area so not a lot to see walking around, but the parking and access are easy and quick, and countless dining and shopping areas are nearby.
Reviewed on Jul. 19, 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
Westside Santa Cruz
7 out of top 10 points of interest in this area
4/5(34 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.
Pleasure Point Hotel Deals
La Quinta Inn & Suites by Wyndham Santa Cruz
550 2nd St, Santa Cruz, CA
Fully refundableReserve now, pay when you stay
The price is CA $299 per night from Aug 6 to Aug 7
CA $299
CA $341 total
Aug 6 - Aug 7
includes taxes & fees
9.2/10 Wonderful! (1,218 reviews)
Decent place in Santa Cruz
"We were upgraded to a larger room which was great. The room was clean and comfortable, although the carpet was a bit worn. Breakfast could have had more options."
Reviewed on Jul. 21, 2025
Seacliff Inn Aptos, Tapestry Collection by Hilton
7500 Old Dominion Court, Aptos, CA
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Aug 17 to Aug 18
CA $207
CA $238 total
Aug 17 - Aug 18
includes taxes & fees
8.4/10 Very Good! (1,074 reviews)
"Great for families! Love the balcony and pool!"
Reviewed on Jul. 21, 2025
Dream Inn Santa Cruz
175 W Cliff Dr, Santa Cruz, CA
Fully refundableReserve now, pay when you stay
The price is CA $590 per night from Aug 12 to Aug 13
CA $590
CA $667 total
Aug 12 - Aug 13
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"great location , easy walk to the wharf and boardwalk ."
Reviewed on Jul. 21, 2025
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.
Frequently asked questions
Discover the most popular places to visit in Pleasure Point
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 Harbor
Explore the waterfront in Santa Cruz with a trip to Santa Cruz Harbor. While you're in the area, stroll along the beautiful beaches.
Cowell's Beach
Explore the waterfront of Cowell's Beach and enjoy activities such as surfing in Santa Cruz. Attend a sporting event in this walkable area, or seek out the biking trails.
Things to do
Santa Cruz Guided eBike Ride & Most Fun Bike e-Bike Tour
CA $151
per adult
5-Hour Wilderness Skills & Survival Clinic
CA $190
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.