A pebble beach with people sunbathing and swimming, a white building with a red roof, and a rocky coastline with houses on a hillside in the background.

Santa Cruz Vacations from $385

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The Latest Santa Cruz Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 20 - Sep 22

    Pestana Royal All Inclusive Ocean & Spa Resort + Flight

    Funchal
    2 nights
    5.0 star property
    8.2/10 - Very Good (141 reviews)
    "Pestana Royal is a very outdated hotel. If you are looking for clean modern look that is not the place for you. If you are looking for a place with high quality food that is not the right place. Food quality is very poor. It is a very mediocre place with clean rooms and very mediocre food."
    Reviewed June 19, 2026
    Roundtrip Lisbon (LIS) - Madeira Island (FNC)
    LIS - FNCNonstop FNC - LISNonstop
    Save 100% on your flight
    $682
    $385
    per traveler
    found 22 hours ago
    Pestana Royal All Inclusive Ocean & Spa Resort
  • Sep 16 - Sep 21

    Pestana Quinta Perestrello + Flight

    Funchal
    4 nights
    4.0 star property
    9.8/10 - Exceptional (46 reviews)
    "Clean room, nice garden view, very good breakfast"
    Reviewed July 26, 2026
    Roundtrip Boston (BOS) - Madeira Island (FNC)
    BOS - FNC1 stop FNC - BOS1 stop
    $1,730
    $1,229
    per traveler
    found 1 day ago
    Pestana Quinta Perestrello
  • Oct 8 - Oct 14

    Pestana Casino Park Ocean and SPA Hotel + Flight

    Funchal
    5 nights
    5.0 star property
    8.6/10 - Excellent (1,001 reviews)
    "This location was beautiful. Staff amazing! Breakfast buffet the best, I’ve ever had. The lobby and surrounding grounds amazing. Great room! Highly recommend."
    Reviewed June 30, 2026
    Roundtrip Boston (BOS) - Madeira Island (FNC)
    BOS - FNC1 stop FNC - BOS1 stop
    $1,943
    $1,425
    per traveler
    found 1 day ago
    Pestana Casino Park Ocean and SPA Hotel
  • Oct 20 - Oct 25

    Pestana Promenade Ocean Resort Hotel + Flight

    Funchal
    4 nights
    4.0 star property
    9.2/10 - Wonderful (691 reviews)
    "Good "
    Reviewed May 15, 2026
    Roundtrip New York (NYC) - Madeira Island (FNC)
    EWR - FNC1 stop FNC - EWR1 stop
    $1,618
    $1,210
    per traveler
    found 1 day ago
    Pestana Promenade Ocean Resort Hotel
  • Oct 20 - Oct 25

    Pestana Carlton Madeira Ocean Resort Hotel + Flight

    Funchal
    4 nights
    5.0 star property
    8.8/10 - Excellent (1,001 reviews)
    "We had an ocean view suite just gorgeous! The gym is small. Food isn’t great."
    Reviewed July 22, 2026
    Roundtrip New York (NYC) - Madeira Island (FNC)
    EWR - FNC1 stop FNC - EWR1 stop
    $1,442
    $1,104
    per traveler
    found 1 day ago
    Pestana Carlton Madeira Ocean Resort Hotel

Discover the most popular places to visit in Santa Cruz

What to do in Santa Cruz

Santa Cruz Hotel Deals

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

How much does a Santa Cruz vacation package cost?

You'll find cheap prices from $385 on Expedia for your Santa Cruz getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Santa Cruz costs.

What are the cheapest months to go to Santa Cruz?

May, November and December are the best times to search for cheap Santa Cruz vacation packages. Traveling in less busy periods means you can typically find lower prices on flights and accommodations.

How many days is enough for Santa Cruz?

To get the most out of your Santa Cruz vacation, we suggest staying for 5 days. Split your time between visiting Palheiro Golfe, Ponta da Oliveira and other must-see attractions, on top of experiencing neighborhoods like Palheiro Ferreiro and Sao Goncalo. If you've got some time to spare, add a day trip to your Santa Cruz vacation itinerary.

Is it worth booking a vacation package to Santa Cruz?

Santa Cruz has everything you need for a memorable trip — hiking, fishing and coastal beaches are just the start. Whether you'd like to visit sights like Palmeiras Beach and Santo da Serra Market, or take the path less traveled, there's plenty to experience on your Santa Cruz vacation.

How to find the best Santa Cruz package deals?

Use Expedia's handy filters to find some great Santa Cruz package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Santa Cruz package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.

Is it cheaper to book a Santa Cruz vacation as a package?

You can enjoy significant savings on your Santa Cruz retreat by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Santa Cruz?

If you're considering a spur-of-the-moment Santa Cruz vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score terrific deals on your flights and hotels by booking well in advance.

How to plan a trip to Santa Cruz?

  1. Choose when to go: Check your calendar and get packing. Your favorite time of year and the type of activities on offer will also help you decide when to escape to Santa Cruz.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you should consider other expenses. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Santa Cruz.
  3. Use our trip planning tool to explore Santa Cruz: Research every aspect of your trip to Santa Cruz with this comprehensive planner. Invite friends or family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Decide how long to go for: Now that you know more about Santa Cruz, you can work out the ideal length of your break. Pull together a draft plan and give yourself enough time for all the things you want to do.
  5. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, lock in the perfect Santa Cruz vacation package for you.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to do and see. Explore some of the incredible things to do in Santa Cruz and book your tickets early to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Santa Cruz vacation packages?

Your Santa Cruz break is meant to be an escape from your busy life, not a source of money-related stress. So to give you more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.