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

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Update: One or more card offers in this post are no longer available. Check our Hot Deals for the latest offers. 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 Baha Mar – 15,000 points per night
IHG
Holiday Inn Resort:  Nassau – 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 World Elite Mastercard 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?

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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