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Santa Cruz Vacation Packages

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Santa Cruz Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Moon & Sun Funchal

Moon & Sun Funchal

4 out of 5
Price was $1,691, price is now $1,309 per person
$1,309
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Stay at this hotel in Funchal. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Popular attractions Funchal Marina and Plaza Madeira are located nearby.
An amazing place to stay at.

Reviewed on Oct 8, 2026

Pestana Grand Premium Ocean Resort

Pestana Grand Premium Ocean Resort

5 out of 5
Price was $2,013, price is now $1,344 per person
$1,344
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Book a stay at this luxury hotel in Funchal. Enjoy free WiFi, 3 restaurants, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Funchal Marina and Centro Comercial Forum Madeira are located nearby.

Pestana Casino Park Ocean and SPA Hotel

Pestana Casino Park Ocean and SPA Hotel

5 out of 5
Price was $5,469, price is now $3,723 per person
$3,723
per person
Dec 28 - Jan 2
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Book a stay at this luxury hotel in Funchal. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Funchal Marina and Madeira Casino are located nearby.
All good

Reviewed on Sep 19, 2026

Pestana Carlton Madeira Ocean Resort Hotel

Pestana Carlton Madeira Ocean Resort Hotel

5 out of 5
Price was $1,946, price is now $1,358 per person
$1,358
per person
Nov 29 - Dec 5
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Book a stay at this luxury hotel in Funchal. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Funchal Marina and Centro Cultural da Quinta Magnólia are located nearby.

Pestana Churchill Bay

Pestana Churchill Bay

4 out of 5
Price was $4,240, price is now $3,249 per person
$3,249
per person
Dec 28 - Jan 2
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Stay at this hotel in Camara de Lobos. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Funchal Marina and Farol de Camara de Lobos are located nearby.
First-class experience all the way 😎

Reviewed on Sep 9, 2026

The Editory Ocean Way Funchal

The Editory Ocean Way Funchal

5 out of 5
Price was $4,103, price is now $3,257 per person
$3,257
per person
Dec 28 - Jan 2
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Book a stay at this luxury hotel in Funchal. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Funchal Marina and Centro Comercial Forum Madeira are located nearby.
Staff was professional and helpful. Breakfast was delicious and loved the outside pool.

Reviewed on Oct 12, 2026

Pestana Royal All Inclusive Ocean & Spa Resort

Pestana Royal All Inclusive Ocean & Spa Resort

5 out of 5
Price was $2,081, price is now $1,676 per person
$1,676
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Funchal (FNC)
Book a stay at this luxury hotel in Funchal. Enjoy 2 outdoor pools, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Funchal Marina and Ponta Gorda Bathing Complex are located nearby.

Studios by Aqua Natura Hotels

Studios by Aqua Natura Hotels

4 out of 5
Price was $1,775, price is now $1,439 per person
$1,439
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Stay at this aparthotel in Porto Moniz. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Porto Moniz Natural Pools and Lava Pools are located nearby.

Santa Cruz Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Studios by Aqua Natura Hotels

Studios by Aqua Natura Hotels

4 out of 5
Price was $1,380, price is now $1,277 per person
$1,277
per person
Dec 31 - Jan 3
found 2 hours ago
Roundtrip flight included
Amsterdam (AMS) to Funchal (FNC)
Aqua Natura Bay

Aqua Natura Bay

4 out of 5
Price was $1,452, price is now $1,330 per person
$1,330
per person
Dec 31 - Jan 3
found 2 hours ago
Roundtrip flight included
Amsterdam (AMS) to Funchal (FNC)
Zarco Bed&Breakfast

Zarco Bed&Breakfast

3 out of 5
Price was $2,502, price is now $2,310 per person
$2,310
per person
Dec 31 - Jan 3
found 2 hours ago
Roundtrip flight included
Amsterdam (AMS) to Funchal (FNC)
BIO Hotel - Hotel Quinta da Serra

BIO Hotel - Hotel Quinta da Serra

5 out of 5
Price was $1,497, price is now $1,387 per person
$1,387
per person
Dec 31 - Jan 3
found 2 hours ago
Roundtrip flight included
Amsterdam (AMS) to Funchal (FNC)

Santa Cruz Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pestana Grand Premium Ocean Resort

Pestana Grand Premium Ocean Resort

5 out of 5
Price was $2,013, price is now $1,344 per person
$1,344
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Pestana Casino Park Ocean and SPA Hotel

Pestana Casino Park Ocean and SPA Hotel

5 out of 5
Price was $5,469, price is now $3,723 per person
$3,723
per person
Dec 28 - Jan 2
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Pestana Carlton Madeira Ocean Resort Hotel

Pestana Carlton Madeira Ocean Resort Hotel

5 out of 5
Price was $1,946, price is now $1,358 per person
$1,358
per person
Nov 29 - Dec 5
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Pestana Churchill Bay

Pestana Churchill Bay

4 out of 5
Price was $4,240, price is now $3,249 per person
$3,249
per person
Dec 28 - Jan 2
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

easyJet
Mon, Nov 30 - Fri, Dec 11
LIS
Humberto Delgado
FNC
Cristiano Ronaldo
$91 Roundtrip, found 17 hours ago
$91
Roundtrip
found 17 hours ago
Select easyJet flight, departing Mon, Nov 30 from Humberto Delgado to Cristiano Ronaldo, returning Fri, Dec 11, priced at $91 found 17 hours ago
TAP Portugal
Sat, Jul 17 - Sun, Jul 25
MAN
Manchester
FNC
Cristiano Ronaldo
$398 Roundtrip, found 1 hour ago
$398
Roundtrip
found 1 hour ago
Select TAP Portugal flight, departing Sat, Jul 17 from Manchester to Cristiano Ronaldo, returning Sun, Jul 25, priced at $398 found 1 hour ago
TAP Portugal
Wed, Nov 18 - Wed, Nov 25
EWR
Newark Liberty Intl. Airport
FNC
Cristiano Ronaldo
$632 Roundtrip, just found
$632
Roundtrip
just found
Select TAP Portugal flight, departing Wed, Nov 18 from Newark Liberty Intl. Airport to Cristiano Ronaldo, returning Wed, Nov 25, priced at $632 just found
TAP Portugal
Wed, May 5 - Wed, May 12
JFK
John F. Kennedy Intl.
FNC
Cristiano Ronaldo
$668 Roundtrip, found 12 hours ago
$668
Roundtrip
found 12 hours ago
Select TAP Portugal flight, departing Wed, May 5 from John F. Kennedy Intl. to Cristiano Ronaldo, returning Wed, May 12, priced at $668 found 12 hours ago