Southwest’s New Destinations – Where to Stay Using Points in the Caribbean

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Update:   Thanks to Million Mile Secrets readers for sharing their thoughts about hotels in the Caribbean.  Emily and I haven’t been to many of these destinations, so it’s helpful when our readers add their experiences!  We hope these guides can save folks time when searching for hotels, and that our readers continue sharing their feedback and advice.

In response to the news that Southwest will start flying to Belize, Million Mile Secrets reader Julianna commented:

Someone should do a post on points and rewards hotels in Belize…just sayin’.

I’m taking this a step further and checking out which hotels are available using points in all of Southwest’s new international destinations!

We’ll continue by looking at Southwest’s new destinations in the Caribbean:

  • Aruba (Oranjestad)
  • Bahamas (Nassau)
  • Dominican Republic (Punta Cana)
  • Jamaica (Montego Bay)
  • Puerto Rico (San Juan)
Southwest's New Destinations Where To Stay Using Points In The Caribbean

Flying Southwest to the Caribbean and Not Sure Where to Stay? I’ll Help!

Southwest’s New Destinations – Where to Stay Using Points Index

Southwest Flies to the Caribbean – Here’s Where to Stay!

Link:   Hotel Award Charts

With some help from AwardMapper, I searched for hotels in each Southwest city.  It’s a tool that displays major chain hotels (and the points required per night) on a map.

Southwest's New Destinations Where To Stay Using Points In The Caribbean

AwardMapper Is Handy for Finding Hotel Award Nights in Unfamiliar Destinations

Note:   Some of these hotels are away from the main tourist areas, for example near the airport or downtown instead of the beach.  So check the location before you book!

1.   Oranjestad, Aruba

Part of the Kingdom of the Netherlands, Aruba is an island located just north of Venezuela.  The capital, Oranjestad, is known for its Dutch Colonial architecture and festive Carnival.

Southwest's New Destinations Where To Stay Using Points In The Caribbean

Colorful Dutch Caribbean Style Architecture in Oranjestad, Aruba

Club Carlson

Radisson Aruba Resort, Casino & Spa – 50,000 points per night

Choice Hotels

La Cabana Beach Resort and Casino – 30,000 points per night

Hyatt

Hyatt Regency Aruba Resort and Casino – 25,000 points per night (Top Pick!)

Folks on TripAdvisor love this hotel for its central location and beautiful grounds.  If you’re transferring Chase Ultimate Rewards points for your stay, you’ll need fewer at this Hyatt than you would at similar Marriott hotels in Aruba.

Southwest's New Destinations Where To Stay Using Points In The Caribbean

The Hyatt Regency Aruba Resort and Casino Is Right on the Beach With Beautiful Landscaping

IHG

Holiday Inn Resort Aruba – Beach Resort & Casino – 25,000 points per night

Marriott / Ritz-Carlton

Renaissance Aruba Resort & Casino – 35,000 points per night

Aruba Marriott Resort & Stellaris Casino – 40,000 points per night

Marriott’s Aruba Surf Club – 45,000 points per night

The Ritz-Carlton, Aruba – 60,000 points per night

2.   Nassau, Bahamas

Nassau is the largest city and capital of the Bahamas.  Tourists come for the beaches, diving, nightlife, and golf.  And it’s a popular destination for weddings.

Southwest's New Destinations Where To Stay Using Points In The Caribbean

Dive With the Dolphins in Nassau, Bahamas

Best Western

Best Western Bay View Suites – 36,000 points per night

Choice Hotels

Comfort Suites Paradise Island – 35,000 points per night

Hilton

British Colonial Hilton Nassau – 40,000 points per night (Top Pick!)

Opened in 1923, this historic hotel gets top reviews on TripAdvisor and was a shooting location for 2 James Bond movies!  I like old hotels with lots of character!

Southwest's New Destinations Where To Stay Using Points In The Caribbean

The British Colonial Hilton Is a Nassau Landmark

Hyatt

Grand Hyatt at Baha Mar (Opening June 1, 2015) – 15,000 points per night

IHG

Holiday Inn Resort:  Nassau (Opening Summer 2015) – no points information as yet

Marriott / Ritz-Carlton

Atlantis, Beach Tower, Autograph Collection – 35,000 points per night

Atlantis, Coral Towers, Autograph Collection – 35,000 points per night

The Cove Atlantis, Autograph Collection – 45,000 points per night

Atlantis, Royal Towers, Autograph Collection – 40,000 points per night

3.   Punta Cana, Dominican Republic

On the east coast of the Dominican Republic, Punta Cana is a golfer’s dream destination.  With courses right on the ocean (and lots of white sand beaches), it attracts so many tourists that it’s now got the 2nd busiest airport in the Caribbean.

Southwest's New Destinations Where To Stay Using Points In The Caribbean

Like Golf? You’ll Love Punta Cana’s Oceanside Courses

Note:   There are almost NO international chain hotels in Punta Cana.  So folks traveling there on Southwest should be prepared to pay cash for their stay.

Starwood

Four Points by Sheraton Puntacana Village – 3,000 points per night

The Westin Puntacana Resort and Club – 12,000 points per night (Top Pick!)

This new hotel gets good reviews for its amazing views, white sand beaches, and customer service.

Southwest's New Destinations Where To Stay Using Points In The Caribbean

The Westin Puntacana Features a White Sand Beach and Has a Top Golf Course Nearby

That’s it!  (See, I wasn’t kidding!) 😉

But there are options.  You could use Chase Ultimate Rewards points through the Chase Travel portal to save 20% on hotels.  I compared their prices to Kayak and they’re competitive.

Southwest's New Destinations Where To Stay Using Points In The Caribbean

Your Chase Ultimate Rewards Points Are Worth 1.25 Cents Each When You Book Through the Chase Travel Portal

If you do pay cash, remember to use a card like the Chase Sapphire Preferred (which earns 2 points per $1 on travel, or 3 points per $1 on travel booked through the Chase Travel Portal).

Or pay with your Barclaycard Arrival Plus to earn 2.1% back on travel purchases.  Neither of these cards have foreign transaction fees.

It’s also worth checking sites like TravelPony.  They sometimes (not always) list hotels in Caribbean cities.

4.   Montego Bay, Jamaica

Montego Bay is a popular destination for foreign tourists and for Jamaicans.  It’s common for folks from Kingston to vacation there, and it’s known for its old sugar plantations, golf courses, and shopping.

Southwest's New Destinations Where To Stay Using Points In The Caribbean

Montego Bay Was Once a Busy Port, Mainly Exporting Sugar

Hilton

Hilton Rose Hall Resort and Spa (All-Inclusive) – ~125,000 points per night

Hyatt

Hyatt Zilara Rose Hall (All-Inclusive) – 25,000 points plus 12,500 points per additional person, per night

Hyatt Ziva Rose Hall (All-Inclusive) – 25,000 points plus 12,500 points per additional person, per night

IHG

Holiday Inn Sunspree Resort (All-Inclusive) – 35,000 points (up to 2 adults and 2 children under 12) (Top Pick!)

I think 35,000 points for 2 adults and 2 kids (per night) for an all-inclusive stay is great value!

Southwest's New Destinations Where To Stay Using Points In The Caribbean

Using Points for an All-Inclusive Stay Can Be a Great Deal!

5.   San Juan, Puerto Rico

Did you know that San Juan, Puerto Rico is 1 of the oldest cities in the Americas?  It’s popular with tourists because of its history, culture, and eco-tourism.  And perhaps because of the Bacardi rum factory tour.  🙂

Southwest's New Destinations Where To Stay Using Points In The Caribbean

If You’re an Outdoorsy Type, You’ll Love Puerto Rico

Best Western

Best Western Plus Condado Palm Inn & Suites – 24,000 points per night

Club Carlson

Radisson Ambassador Plaza Hotel & Casino San Juan – 38,000 points per night

Choice Hotels

Le Consulat, an Ascend Hotel Collection Member – 16,000 points per night

Quality Inn El Portal – 16,000 points per night

Comfort Inn – 20,000 points per night

Comfort Inn and Suites – 20,000 points per night

Hilton

Caribe Hilton – 40,000 points per night

Condado Lagoon Villas at Caribe Hilton – 40,000 points per night

The Condado Plaza Hilton – 40,000 points per night

DoubleTree by Hilton Hotel San Juan – 40,000 points per night

Southwest's New Destinations Where To Stay Using Points In The Caribbean

Yes, You Can Take the Famous DoubleTree Cookie to the Beach in San Juan!

Embassy Suites San Juan – Hotel & Casino – 40,000 points per night

El San Juan Resort & Casino, a Hilton Hotel – 50,000 points per night

Hampton Inn & Suites San Juan – 40,000 points per night

Embassy Suites Dorado del Mar Beach Resort – 40,000 points per night

El Conquistador, A Waldorf Astoria Resort – 50,000 points per night

Las Casitas, A Waldorf Astoria Resort – ~75,000 points per night

Hilton Ponce Golf & Casino Resort – 40,000 points per night

Hyatt

Hyatt House San Juan – 8,000 points per night

Hyatt Place San Juan / Bayamon – 8,000 points per night

Hyatt Hacienda del Mar, A Hyatt Residence Club – 25,000 points per night

Hyatt Place Manati – 8,000 points per night

IHG

Holiday Inn Express:  San Juan Condado – 15,000 points per night

InterContinental:  San Juan – 50,000 points per night

Marriott / Ritz-Carlton

San Juan Marriott Resort & Stellaris Casino – 40,000 points per night (Top Pick!)

Ranked the #3 hotel in San Juan by TripAdvisor, this Marriott resort gets high scores from families.  And the casino is apparently excellent!

Southwest's New Destinations Where To Stay Using Points In The Caribbean

Stay Right on the Beach at the San Juan Marriott Resort and Stellaris Casino

La Concha Renaissance San Juan Resort – 40,000 points per night

Courtyard San Juan Miramar – 25,000 points per night

The Ritz-Carlton, San Juan – 60,000 points per night

Courtyard Isla Verde Beach Resort – 35,000 points per night

Starwood

Sheraton Old San Juan Hotel & Casino – 7,000 points per night

Sheraton Puerto Rico Hotel & Casino – 10,000 points per night

Four Points by Sheraton Caguas Real Hotel & Casino – 7,000 points per night

The St. Regis Bahia Beach Resort, Puerto Rico – 30,000 points per night

W Retreat & Spa – Vieques Island – 20,000 points per night

Wyndham

Wyndham Grand Rio Mar Beach Resort & Spa – 25,000 points per night

Wyndham Garden at Palmas del Mar – 20,000 points per night

Howard Johnson Hotel – Carolina San Juan PR – 16,000 points per night

Howard Johnson Centro Cardiovascular San Juan – 16,000 points per night

Collecting Points for These Hotels

If you don’t have enough points, here are some ways to quickly increase your point balances!

Best Western

Club Carlson

Choice Hotels

Hilton

Hyatt

IHG

Marriott / Ritz-Carlton

Starwood

Wyndham

Bottom Line

Southwest now flies to the Caribbean, including Aruba, the Bahamas, Dominican Republic, Jamaica, and Puerto Rico.

Some of these destinations have very few large hotel chains where you can get award stays.  So you might need to pay cash!

Stay tuned for where to stay Southwest’s Central American destinations!

Have you used points for award stays in the Caribbean?  Which hotel is your favorite?

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7 responses to “Southwest’s New Destinations – Where to Stay Using Points in the Caribbean

  1. One thing to keep in mind is that some of these international destinations have a LOT of airport taxes and fees. I did a post comparing the fees of the various places in the Caribbean. From the Dominican Republic where you have to pay over $100 / person for your “free” flight down to Puerto Rico which is just the regular TSA fees of $11.20 roundtrip.

    We chose to go to San Juan and we’re staying at the Hyatt House San Juan this weekend.

  2. A fantastic post, Thanks!

  3. I know it’s only January. However, this is the Post of the Year, and it will be very hard to beat! 🙂

  4. Can you use the annual free night you get for having the IHG card at the Holiday Inn Resort in Aruba OR the Holiday Inn Sunspree (All inclusive) in Jamaica? Or does it have to be specifically an InterContinental hotel? I guess I’m a little confused on where I can use the free nights my husband and I will be getting next month. Thanks!!!

  5. Also, when I read the fine print for Jamaica’s Holiday Inn Sunspree All Inclusive I don’t see where it says that the 35,000 points include the All Inclusive. Are you sure this is correct? Thanks again!

  6. I also have the same questions as Tammy Horvath.

  7. We just got back from the Holiday Inn Sunspree, and YES, the 35,000 points includes the all-inclusive. Make sure you book theKing Oceanview Suite when you book using points, you can book any room, so why not go with their nicest. Great family resort, we went for a week with our 3 children all on points!! If its just a couple, I may go somewhere else.