16 deals from our U.S. site*
* Taxes and fees may be additional.
Source: TripMasters.com

Includes hotels, flight transfer between islands and breakfast

Priced for September; more dates available
 
Source: TripMasters.com

Includes flight transfer, daily breakfast and taxes

Priced for September; more dates available
 
Source: Olavine Spa

Experience Wailea's Olavine Spa -- a new boutique day spa praised by The Maui News -- with a massage and facial for more than $120 off.

Through Nov. 4, 2015
 
Source: Airbnb

Soak up ocean views from this open-plan home set in a tropical garden setting

May-August, October-December; 5 nts minimum
 
Priced for September; more dates available
TripMasters.com
 
Priced for September; more dates available
TripMasters.com
 
Priced for September; more dates available
TripMasters.com
 
Priced for September; more dates available
TripMasters.com
 
Depart Oct. 19; other departures available
Pleasant Holidays
 
Priced for September; more dates available
TripMasters.com
 
Priced for September; more dates available
TripMasters.com
 
Priced for September; more dates available
TripMasters.com
 
Priced for September; more dates available
TripMasters.com
 
 
 
Many dates through December
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Travelzoo Tips

Anna Heinemann — Travel, Entertainment and Local Deal Expert
Anna Heinemann
Deal Expert, Chicago
So get your travel dates set and start planning early for the best opportunities. More