Top 5 Starwood Hotels in Hawaii to Redeem Points for Free Stays

By Guillermo Rodriguez (Award Travel Points)

Sheraton Maui Resort & Spa

Hawaii is an awesome vaca­tion destination with the per­fect mix of beach, scenery and adven­ture but accom­mo­da­tions are not cheap. I have selected five amazing Hawaii hotels that we can stay for Free by redeeming Star­wood Pre­ferred Guest points that we can easily earn with the Amex SPG Credit Card. I am going to focus on the afford­able des­ti­na­tions where a cou­ple can get a 5 night vaca­tion for a rea­son­able amount of points in a 4-5 star Hotel.

Whether you want to visit Maui, Kauai, the Big Island or Oahu, every island has an afford­able hotel where we can use our Star­wood Pre­ferred Guest points. 

Earn­ing Star­wood Pre­ferred Guest Points for a Hawai­ian Vacation

Star­wood Pre­ferred Guest points can be earned either through Star­wood hotel stays or the Starwood Preferred Guest Card from American Express. This card cur­rently comes with a 25,000 point bonus after spend­ing $5,000 in 6 months. You receive 10,000 points after your first pur­chase and another 15,000 after meet­ing the $5,000 spend­ing require­ment. The annual fee of $65 is waived the first year.

If $5,000 seems on the high side for a spend­ing require­ment, don’t for­get we can earn miles pay­ing bills by sign­ing up for the Bluebird Card, which is free and has no hard credit pull. You can earn miles for your rent, mort­gage, tuition, insur­ance, you name it. I never have prob­lems meet­ing min­i­mum spend­ing require­ments this way.

Star­wood mem­bers with the same address for at least 30 days are permitted to combine their points into one account. This means that a cou­ple apply­ing for one Star­wood Pre­ferred Guest card each will have 60,000 points total after meet­ing the min­i­mum spend­ing require­ments. That’s enough for 6 nights in low sea­son at each of the 5 hotels I’ve selected. It’s also enough for five nights in high season.

For each hotel, I am going to go over the points rates in high and low sea­son as all but one hotel has high and low sea­son rates. We’ll also look at the hotel rates so we can see exactly how much value we’d get per point.

1. Sher­a­ton Maui Resort & Spa

Sheraton Maui Resort & Spa

Sher­a­ton Maui Resort & Spa

Maui is def­i­nitely an expen­sive island for hotels and food and you can def­i­nitely reduce your bill by get­ting a free hotel. The Sher­a­ton Maui Resort & Spa is a great choice to use Star­wood Pre­ferred Guest points in Hawaii.

The first two hotels on my list are right next to each other on Ka’anapali beach. Ka’anapali is the long stretch of beach in Maui fac­ing south and is about a 15 min­utes drive from Lahaina, the main town where you can find plenty of restau­rants and luaus.

The one rea­son I put the Sher­a­ton first is that it’s sit­u­ated by the black rock for some inter­est­ing scenery and good snor­kel­ing.  As an island, Maui tends to be roman­tic, yet adven­tur­ous. Be sure to take a drive to road to Hana for water­falls, a black sand beach, a red sand beach and nat­ural pools. The scenery is unbeatable.

Points and Rates for 5 nights:

The Sher­a­ton Maui Resort & Spa is a Cat­e­gory 5 Star­wood Hotel. This year, peak sea­son rates will be charged the fol­low­ing dates:

  • 12/25/2014 — 12/31/2014
  • 11/21/2014 — 11/27/2014
  • 6/27/2014 — 8/7/2014
  • 2/7/2014 — 2/20/2014
  • 12/25/2013 — 12/31/2013
  • 11/22/2013 — 11/28/2013

There is a $31.25 a night resort charge on all rates includ­ing points rates.

Peak Sea­son: 

  • Peak sea­son rates are 16,000 points a night or 64,000 points for 5 nights using the Fifth Night Free option.
  • Room rates in high sea­son June start at $419 a night + tax.

Low Sea­son:

  • Low sea­son rates are 12,000 points a night or 48,000 points for 5 nights using the Fifth Night Free option.
  • Room rates in low sea­son March start at $389 a night + tax.

2. The Westin Maui Resort & Spa, Ka’anapali

Westin Maui Resort & Spa

Westin Maui Resort & Spa

The Westin Maui Resort & Spa, Ka’anapali is the other Star­wood hotel sit­u­ated on Ka’anapali beach in Maui. While both hotels occupy the same beach, the Westin has a far more expan­sive aquatic cen­ter. There are five sep­a­rate pools and pool decks, a 120 ft. super water­slide, a smaller slide for the younger keiki, a swim-through grotto with twin water­falls and a hid­den whirlpool. There are also adults-only pools and jacuzzi with a pool bar. Though with Maui being such an excit­ing island, there is plenty to do out­side the hotel.

Points and Rates for 5 nights:

The Westin Maui Resort & Spa is a Cat­e­gory 5 Star­wood Hotel. This year, peak sea­son rates will be charged the fol­low­ing dates:

  • 11/21/2014 — 11/27/2014
  • 6/27/2014 — 8/16/2014
  • 2/8/2014 — 2/22/2014
  • 12/24/2013 — 12/31/2013
  • 11/22/2013 — 11/28/2013
  • 6/28/2013 — 8/17/2013
  • 2/8/2013 — 2/23/2013
  • 12/24/2014 — 12/31/2014

There is a $31.25 a night resort charge on all rates includ­ing points rates.

Peak Sea­son: 

  • Peak sea­son rates are 16,000 points a night or 64,000 points for 5 nights using the Fifth Night Free option.
  • Room rates in high sea­son June start at $419 a night + tax.

Low Sea­son:

  • Low sea­son rates are 12,000 points a night or 48,000 points for 5 nights using the Fifth Night Free option.
  • Room rates in low sea­son March start at $389 a night + tax.

3. Sher­a­ton Kauai Resort

Sheraton Kauai Resort

Sher­a­ton Kauai Resort

Kauai is an extremely beau­ti­ful island, but with beauty always comes a price. Cer­tain parts of the island are rainy at dif­fer­ent times of the year. The Sher­a­ton Kauai Resort is located in Koloa tends to be rainy Octo­ber through March and drier in sum­mer. Its located on Poipu beach which is excel­lent.

Kauai has an amaz­ing nat­ural beauty. The Na Pali coast, Waimea canyon and numer­ous water­falls are def­i­nitely worth a visit. This is where Juras­sic Park and other movies have been filmed!

Points and Rates for 5 nights:

The Sher­a­ton Kauai Resort is a Cat­e­gory 5 Star­wood Hotel. This year, peak sea­son rates will be charged the fol­low­ing dates:

  • 12/25/2014 — 12/31/2014
  • 4/14/2014 — 4/20/2014
  • 2/13/2014 — 2/19/2014
  • 12/25/2013 — 12/31/2013

There is a $31.25 a night resort charge on all rates includ­ing points rates.

Peak Sea­son: 

  • Peak sea­son rates are 16,000 points a night or 64,000 points for 5 nights using the Fifth Night Free option.
  • Room rates in high sea­son June start at $299 a night + tax.

Low Sea­son:

  • Low sea­son rates are 12,000 points a night or 48,000 points for 5 nights using the Fifth Night Free option.
  • Room rates in low sea­son March start at $239 a night + tax.

4. Sher­a­ton Kona Resort & Spa on Big Island of Hawaii

Sheraton Kona Resort & Spa

Sher­a­ton Kona Resort & Spa

The Sher­a­ton Kona Resort & Spa at Keauhou Bay is the hotel that costs the least num­ber of points on all of Hawaii. The Big Island of Hawaii is home to the largest vol­cano and high­est point in Hawaii, Mauna Kea. This moun­tain stands at 13,796 feet and a visit to the sum­mit is one of the island’s top attrac­tions. Other attrac­tions include Akaka FallsMauna Kea BeachHawaii Trop­i­cal Botan­i­cal Gar­den and Kealakekua Bay.

Points and Rates for 5 nights:

The Sher­a­ton Kona Resort & Spa is a Cat­e­gory 4 Star­wood Hotel. This year, peak sea­son rates will be charged the fol­low­ing dates:

There is a $31.25 a night resort charge on all rates includ­ing points rates.

Peak sea­son rates are 10,000 points a night or 40,000 points for 5 nights using the Fifth Night Free option.

  • Room rates in high sea­son June start at $279 a night + tax.
  • Room rates in low sea­son March start at $239 a night + tax.

The Cash & Points rate is also read­ily avail­able at 5,000 points a night + $75. That’s 25,000 points + $375 for 5 nights (exclud­ing resort charge).

5. Sher­a­ton Waikiki on Oahu

Sheraton Waikiki

Sher­a­ton Waikiki

The Sher­a­ton Waikiki sits on the busiest beach on all of Hawaii right in Hon­olulu, Hawaii’s most pop­u­lous city. Waikiki is a pop­u­lar surf­ing des­ti­na­tion. Other than relax­ing by the hotel’s infin­ity pool, pop­u­lar attrac­tions in Oahu include a visit to Pearl Har­bor Memo­r­ial, Dia­mond Head vol­cano hik­ing trail and enjoy­ing numer­ous other beach around the island.

Points and Rates for 5 nights:

The Sher­a­ton Waikiki is a Cat­e­gory 5 Star­wood Hotel. This year, peak sea­son rates will be charged the fol­low­ing dates:

There is a $31.25 a night resort charge on all rates includ­ing points rates.

Peak Sea­son: 

  • Peak sea­son rates are 16,000 points a night or 64,000 points for 5 nights using the Fifth Night Free option.
  • Room rates in high sea­son June start at $385 a night + tax.

Low Sea­son:

  • Low sea­son rates are 12,000 points a night or 48,000 points for 5 nights using the Fifth Night Free option.
  • Room rates in low sea­son March start at $285 a night + tax.

Bottom line:

  • My picks for the five best value Star­wood Hotels in Hawaii include four Cat­e­gory 5 hotels and one Cat­e­gory 4 hotel with at least one hotel on every major island in Hawaii. A five night stay at these hotels can range from 40,000 to 64,000 Star­wood Pre­ferred Guest points.
  • A cou­ple can sign-up for the Starwood Preferred Guest Card from American Express and each earn 25,000 points after spend­ing $5,000 within 6 months. They will then have 60,000 points after meet­ing the spend­ing requirement.
  • 64,000 points is enough for a five night stay at any Cat­e­gory 5 hotel dur­ing peak sea­son. Non-peak sea­son is only 48,000 points. This can save thou­sands of dol­lars in vacation costs!

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