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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.
Pestana Casino Park Ocean and SPA Hotel

Pestana Casino Park Ocean and SPA Hotel

5 out of 5
Price was $1,412, price is now $1,137 per person
$1,137
per person
Nov 22 - Nov 26
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, 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 Grand Premium Ocean Resort

Pestana Grand Premium Ocean Resort

5 out of 5
Price was $1,756, price is now $1,303 per person
$1,303
per person
Nov 21 - Nov 26
found 12 hours 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 Carlton Madeira Ocean Resort Hotel

Pestana Carlton Madeira Ocean Resort Hotel

5 out of 5
Price was $1,798, price is now $1,348 per person
$1,348
per person
Nov 21 - Nov 26
found 12 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.

Hotel Riu Madeira - All Inclusive

Hotel Riu Madeira - All Inclusive

4 out of 5
Price was $1,859, price is now $1,430 per person
$1,430
per person
Nov 21 - Nov 26
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Book a stay at this beach hotel in Santa Cruz. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Funchal Marina and Reis Magos Beach are located nearby.

Pestana Vila Lido Madeira Ocean Hotel

Pestana Vila Lido Madeira Ocean Hotel

5 out of 5
Price was $1,830, price is now $1,432 per person
$1,432
per person
Nov 21 - Nov 26
found 12 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 sauna, and parking (surcharge). Popular attractions Funchal Marina and Lido Bathing Complex are located nearby.

Pestana CR7 Funchal

Pestana CR7 Funchal

4 out of 5
Price was $1,582, price is now $1,288 per person
$1,288
per person
Nov 21 - Nov 26
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Stay at this hotel in Funchal. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Funchal Marina and CR7 Museum are located nearby.
Awesome location, we enjoyed spending time at the pool with a great view on the city.

Reviewed on Sep 20, 2026

Moon & Sun Funchal

Moon & Sun Funchal

4 out of 5
Price was $1,457, price is now $1,192 per person
$1,192
per person
Nov 21 - Nov 26
found 12 hours 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.
Loved this hotel! Staff were amazing so welcoming and helpful! Rooms were quiet and air conditioned , loved the rooftop pool. Great location. Highly recommend !

Reviewed on Sep 26, 2026

Pestana Churchill Bay

Pestana Churchill Bay

4 out of 5
Price was $1,482, price is now $1,218 per person
$1,218
per person
Nov 21 - Nov 26
found 12 hours 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

Santa Cruz Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pestana Casino Park Ocean and SPA Hotel

Pestana Casino Park Ocean and SPA Hotel

5 out of 5
Price was $1,412, price is now $1,137 per person
$1,137
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Pestana Grand Premium Ocean Resort

Pestana Grand Premium Ocean Resort

5 out of 5
Price was $1,753, price is now $1,403 per person
$1,403
per person
Nov 22 - Nov 26
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Pestana Vila Lido Madeira Ocean Hotel

Pestana Vila Lido Madeira Ocean Hotel

5 out of 5
Price was $1,814, price is now $1,509 per person
$1,509
per person
Nov 22 - Nov 26
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Pestana CR7 Funchal

Pestana CR7 Funchal

4 out of 5
Price was $1,613, price is now $1,344 per person
$1,344
per person
Nov 22 - Nov 26
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)

Santa Cruz Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pestana Casino Park Ocean and SPA Hotel

Pestana Casino Park Ocean and SPA Hotel

5 out of 5
Price was $1,565, price is now $1,211 per person
$1,211
per person
Nov 21 - Nov 26
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Pestana Grand Premium Ocean Resort

Pestana Grand Premium Ocean Resort

5 out of 5
Price was $1,756, price is now $1,303 per person
$1,303
per person
Nov 21 - Nov 26
found 12 hours 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 $1,798, price is now $1,348 per person
$1,348
per person
Nov 21 - Nov 26
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Hotel Riu Madeira - All Inclusive

Hotel Riu Madeira - All Inclusive

4 out of 5
Price was $1,859, price is now $1,430 per person
$1,430
per person
Nov 21 - Nov 26
found 12 hours 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
Fri, Nov 27 - Sun, Dec 13
LIS
Humberto Delgado
FNC
Cristiano Ronaldo
$122 Roundtrip, found 6 days ago
$122
Roundtrip
found 6 days ago
Select easyJet flight, departing Fri, Nov 27 from Humberto Delgado to Cristiano Ronaldo, returning Sun, Dec 13, priced at $122 found 6 days ago
TAP Portugal
Sat, Jul 17 - Sun, Jul 25
MAN
Manchester
FNC
Cristiano Ronaldo
$293 Roundtrip, found 3 days ago
$293
Roundtrip
found 3 days ago
Select TAP Portugal flight, departing Sat, Jul 17 from Manchester to Cristiano Ronaldo, returning Sun, Jul 25, priced at $293 found 3 days ago
TAP Portugal
Tue, Nov 17 - Thu, Nov 26
EWR
Newark Liberty Intl. Airport
FNC
Cristiano Ronaldo
$632 Roundtrip, found 1 day ago
$632
Roundtrip
found 1 day ago
Select TAP Portugal flight, departing Tue, Nov 17 from Newark Liberty Intl. Airport to Cristiano Ronaldo, returning Thu, Nov 26, priced at $632 found 1 day ago
TAP Portugal
Wed, May 5 - Wed, May 12
JFK
John F. Kennedy Intl.
FNC
Cristiano Ronaldo
$669 Roundtrip, found 5 days ago
$669
Roundtrip
found 5 days ago
Select TAP Portugal flight, departing Wed, May 5 from John F. Kennedy Intl. to Cristiano Ronaldo, returning Wed, May 12, priced at $669 found 5 days ago