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 Index
- Part 1 – Mexico (Cancun, Los Cabos, Mexico City, and Puerto Vallarta)
- Part 2 – The Caribbean (Aruba, The Bahamas, Dominican Republic, Jamaica, and Puerto Rico)
- Part 3 – Central America (Costa Rica and Belize)
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.
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.
Club Carlson
Radisson Aruba Resort, Casino & Spa – 50,000 points per nightChoice Hotels
La Cabana Beach Resort and Casino – 30,000 points per nightHyatt
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.
IHG
Holiday Inn Resort Aruba – Beach Resort & Casino – 25,000 points per nightMarriott / 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 night2. 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.Best Western
Best Western Bay View Suites – 36,000 points per nightChoice 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!
Hyatt
Grand Hyatt Baha Mar – 15,000 points per nightIHG
Holiday Inn Resort: Nassau – no points information as yetMarriott / 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 night3. 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.
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.
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.
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.Hilton
Hilton Rose Hall Resort and Spa (All-Inclusive) – ~125,000 points per nightHyatt
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 nightIHG
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!
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. 🙂
Best Western
Best Western Plus Condado Palm Inn & Suites – 24,000 points per nightClub Carlson
Radisson Ambassador Plaza Hotel & Casino San Juan – 38,000 points per nightChoice Hotels
Le Consulat, an Ascend Hotel Collection Member – 16,000 points per night Quality Inn El Portal – 16,000 points per nightComfort 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 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 nightHyatt
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 nightIHG
Holiday Inn Express: San Juan Condado – 15,000 points per night InterContinental: San Juan – 50,000 points per nightMarriott / 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!
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 nightStarwood
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 nightWyndham
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 nightCollecting Points for These Hotels
If you don’t have enough points, here are some ways to quickly increase your point balances!
Best Western
- Transfer American Express Membership Rewards points
- Buy Best Western points (call or email)
Club Carlson
- Sign-up bonus from the Club Carlson Premier Rewards Visa card (and you’ll get your last night free on award stays of 2 nights or longer)
- Buy Club Carlson points
Choice Hotels
- Transfer American Express Membership Rewards points
- Sign-up bonus from the Barclays Choice Privileges card (again, choose your Barclays cards wisely!)
- Buy Choice Hotel points
Hilton
- Transfer American Express Membership Rewards points
- Transfer Citi ThankYou points
- Sign-up bonuses from the Hilton Honors Card from American Express, Hilton Honors Surpass Card from American Express, Citi Hilton HHonors Reserve, or Citi Hilton HHonors Visa Signature cards
- Transfer airline miles like Hawaiian Airlines or Virgin Atlantic
- Buy Hilton points
Hyatt
- Transfer Chase Ultimate Rewards points
- Sign-up bonus from the Chase Hyatt card
- Buy Hyatt points
IHG
- IHG Cash & Points Trick (cheapest option)
- Transfer Chase Ultimate Rewards points
- Buy IHG points
- Sign-up bonus from the Chase IHG Rewards Club Select Credit Card
Marriott / Ritz-Carlton
- Transfer Chase Ultimate Rewards points
- Buy Marriott points
- Sign-up bonus from the Marriott Rewards® Premier Credit Card
- Sign-up bonus from the Chase Marriott Rewards Credit Card
- Sign-up bonus from the Chase Ritz-Carlton Rewards card
Starwood
- Transfer American Express Membership Rewards points
- Sign-up bonus from the American Express Starwood Preferred Guest card
- Buy Starwood points
Wyndham
- Sign-up bonus from Barclays Wyndham Rewards card (be careful, again!)
- Buy Wyndham points
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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