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Cleared for Takeoff: Booking an overwater villa dream vacation with points and miles

June 29, 2021
14 min read
The Westin Maldives
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Cleared for Takeoff is a weekly series showing readers like you the best ways to book post-pandemic adventures using points and miles.

Staying in an overwater villa is the pinnacle of aspirational travel. Although the Maldives is home to the most overwater villas, you can find these unique accommodations across the world, including in other exotic destinations like Bora Bora, Tahiti, Moorea and Fiji, as well as some closer to home, like Mexico and Belize.

Cash rates for overwater villas can easily exceed $1,000 per night. However, if you strategize correctly, you can book these stays on points, potentially even for the price of a standard room. TPG readers Ray Saylor and Nicole Saylor reached out to us recently for advice on how to do exactly this.

We would love for the TPG team to help us book our dream vacation through the Cleared for Take-off Series! In summer 2020 my wife and I had United Polaris lie-flat business class seats booked (never flew this before) out of IAD to Heathrow, from Heathrow to Athens, and Athens back to RIC, but unfortunately had to cancel (pandemic :/). We had transferred Chase UR points to United for this trip, and luckily we did get the miles back (unfortunately, still with United).
We have dreamed of visiting the Maldives, Moorea, Bora Bora, or one of the French Polynesian islands (really, we would love to book an overwater bungalow). Ideally, we would like to fly business class lie-flat seats, if possible with points (we had been saving and building up our points so we could fly business class with the life flat seats and still hope to be able to experience it on a long-haul flight). We would be traveling from Richmond, VA (RIC), but could fly from DC if needed/better itinerary and product (last international trip was from IAD). Trip would be for two people both with global entry. Below is a list of our current points and miles:
Marriott points: 372,962 (Marriott Bonvoy Boundless Credit Card) - currently have Boundless free night award - 35,000 night e-certificate
Chase Ultimate Rewards: 112,760 (Chase Sapphire Reserve)
United Miles (Joe): 283,290
United Miles (Jessica): 5,879
AA Miles (Joe): 13,698
AA Miles (Jessica): 10,695
Delta Miles (Joe): 7,319 ($356.20 e-credit from another cancelled trip)
Delta Miles (Jessica): 14,557 (70,000 pending with Delta SkyMiles® Gold American Express Card SUB) ( $356.20 e-credit from another cancelled trip)
Jetblue (Jessica): 6,672
Jetblue (Joe): 6,318
We are also open to other locations if there are better bang-for-your buck itineraries that we may be overlooking, maybe Africa (Giraffe Manor), Croatia, or somewhere tropical. We do currently have a 5070 EUR credit with Mediterra Holidays that is held from our 2020 trip to Athens where we were going to visit Mykonos and Santorini (could not be refunded until the end of 2022 or could be used before then). We are also open to opening up additional credit cards for the SUB if it helps (neither of us are able to get Chase bonuses at this time).
We have not set a timeframe on this particular trip but what we do want to do is maximize the use of our points. We cannot do it Labor Day week or first week of June. October and beyond would be ok or even the week of July 4th if that was an option. In light of Covid we do prefer to stay away from Christmas and Thanksgiving so we can now spend it with family.
We did just open the United Quest Card in Jessica's name and will be getting the 80,000 bonus within the next month.
Thank you for helping us plan our dream vacation!
Ray Saylor and Nicole Saylor

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Current points stash

Ray and Nicole have a healthy mix of Marriott Bonvoy, United MileagePlus and Chase Ultimate Rewards points, as well as some additional miles with American Airlines AAdvantage, Delta SkyMiles and JetBlue TrueBlue. They also have a credit with a European travel agency but will need to save it since the company focuses on travel to Europe and the Middle East.

  • 112,760 Chase Ultimate Rewards points
  • 372,962 Marriott Bonvoy points
  • Marriott Bonvoy 35,000-point free night certificate
  • 283,290 United MileagePlus miles (Joe)
  • 5,879 United MileagePlus miles (Jessica)
  • 13,698 American Airlines AAdvantage miles (Joe)
  • 10,695 American Airlines AAdvantage miles (Jessica)
  • 7,319 Delta SkyMiles (Joe)
  • 14,557 Delta SkyMiles (Jessica)
  • $356.20 Delta e-credit
  • 6,318 JetBlue TrueBlue points (Joe)
  • 6,672 JetBlue TrueBlue points (Jessica)

Related: How points and miles helped my family book a dream vacation to Bora Bora

Airfare to the Maldives


Miles needed: 160,000 miles + $146.85 per person

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Joe and Jessica are flexible with their destination so long as they can book an overwater bungalow. That said, based on their balances, the Maldives seems to be the best fit. Marriott Bonvoy offers a whopping seven hotels in the Maldives and they can get there with any major airline alliance.

Given the large number of United miles Joe has, I suggest he try to redeem those first. Although United doesn't fly directly to the Maldives, it has Star Alliance partners like Turkish Airlines and Lufthansa that will help get them there.

Ideally, Joe and Jessica will find award availability from Washington Dulles (IAD) to Malé (MLE) with just one stop in a city like Frankfurt (FRA) or Instanbul (IST). However, based on some searches we did for this fall, they'll likely need two stops if they want to fly business class.

Related: The best ways to get to the Maldives on points and miles

For instance, for the outbound, Joe and Jessica could fly from IAD to FRA on United and then to IST and onward to MLE on Turkish Airlines. Then, for the return, they could fly Turkish via Instanbul again and then from Brussels (BRU) to IAD on United.

For the flights operated by United, Joe and Jessica will experience the airline's latest and greatest Polaris business class seats. On Turkish, they'll be treated to a unique inflight experience that includes an onboard chef.

(Photo by Zach Griff/The Points Guy)

Although United no longer publishes award charts, you can still find business class awards from the U.S. to the Maldives from 160,000 miles round-trip. That's worth $2,080 based on TPG valuations, which is not bad at all considering these Joe and Jessica will be flying for over 24 hours in each direction and the cash fares on these tickets are usually well over $4,000.

Since seaplane transfers within the Maldives are set up directly through the resorts, you, unfortunately, won't be able to redeem miles for them.

How to book this award with points

The best thing about using United miles for this award is how straightforward the booking process is. Simply go to and enter your route (IAD-MLE). Be sure to check the boxes that say "Book with miles" and "Flexible dates."

(Screenshot courtesy of

On the next page, you'll be shown a two-month calendar showing saver award availability. Dates with saver availability (low-priced awards) in premium cabins have five dots.

(Screenshot courtesy of

Once you selected your dates, you'll need to pick the flights you want to book. You can sort by total travel time and price. When flying on a combination of United and partner airlines, be sure to check both "Business saver awards" and "Business everyday awards" as the latter might be cheaper.

(Screenshot courtesy of

It's also important to review the details of your itinerary to make sure you're not booking a mixed cabin itinerary.

(Screenshot courtesy of

After selecting your return flight, you'll be directed to a page displaying your itinerary and the total cost of miles and cash for the award. As I mentioned, I managed to find an all-business-class itinerary for 160,000 miles per person, with the segments to and from the U.S. operated by United and the others by Turkish Airlines. The taxes and fees came out to a reasonable $146.85.

Related: How to get maximum value from the United MileagePlus program

(Screenshot courtesy of

How to earn enough miles for this award

Although Joe currently only has about 283,000 United miles, which is just short of the 320,000 he needs to book his and Jessica's flights, they're expecting 80,000 bonus miles to post soon for meeting the sign-up bonus requirement of the United Quest Card.

If they don't want to wait, they can transfer some of their Chase Ultimate Rewards points to United instantly at a 1:1 ratio.

If you’re looking to replicate this itinerary and starting with a zero balance, the best option would be to pick up a cobranded United card or an Ultimate Rewards-earning card and then transfer your points to United. Here are some of the top offers available:

  • Chase Sapphire Preferred Card: Earn 60,000 bonus points after you spend $4,000 on purchases in the first three months from account opening.
  • Chase Sapphire Reserve: Earn 60,000 bonus points after you spend $4,000 on purchases in the first three months from account opening.
  • United Quest Card: Earn 80,000 bonus miles after you spend $5,000 on purchases in the first three months your account is open.
  • United Explorer Card: Earn 50,000 bonus miles after you spend $3,000 on purchases in the first three months your account is open.
  • United Club Infinite Card: Earn 80,000 bonus miles after you spend $5,000 on purchases in the first three months from account opening.
  • United Gateway Card: Earn 20,000 bonus miles after you spend $1,000 on purchases in the first three months your account is open.

Maldives hotels you can book with points

There are more ways than ever to stay in the Maldives on points. Marriott Bonvoy alone has seven hotels to choose from. Since Joe has a stockpile of Marriott points, that's the program we're going to focus on.

Marriott has options ranging from Category 5 through 8, or about 30,000 – 100,000 points per night, such as the Westin Maldives Miriandhoo Resort and the St. Regis Maldives. They all offer overwater bungalows. However, Joe will want to book one of the following resorts as they consider overwater villas as the “base” rooms and don't charge extra points or cash copay to book them.

  • Le Méridien Maldives Resort & Spa (Category 5): 30,000 - 40,000 points per night
  • The Ritz-Carlton Maldives, Fari Islands (Category 8): 70,000 - 100,000 points per night
  • W Maldives (Category 8): 70,000 - 100,000 points per night

Related: Where to stay in the Maldives using points and miles

Le Méridien Maldives
(Screenshot courtesy of

The Le Méridien is Marriott's newest property in the island nation, expected to open this September, and will be the lowest-priced. One bedroom Sunrise Overwater Villas start at just 30,000 points per night on off-peak nights. That's the equivalent of $240 per night based on TPG valuations, which is a steal considering cash rates will usually be double or triple that.

More excitingly, Joe and Jessica will be able to redeem their Marriott Bonvoy 35,000-point free night certificate that comes with Marriott credit cards like Marriott Bonvoy Boundless Credit Card here on standard and off-peak nights.

Related: 10 private-island resorts you can book with points

(Photo courtesy of Marriott)

Unfortunately, Marriott’s other Maldives properties are much more expensive when redeeming points. The Ritz-Carlton and W both cost 70,000 - 100,000 points per night. The Ritz-Carlton is a brand-new property and is a bit more luxurious, though you may find it easier to find award availability at the W. Also, the W offers a healthier house reef and better marine life. Overwater villas at both properties feature private pools.

Related: 6 reasons to pick the W Maldives over The St. Regis

(Photo by Ethan Steinberg/The Points Guy)

Regardless of which Marriott property Joe and Jessica decide to book, they'll be able to save even more on their stay by taking advantage of Marriott Bonvoy's fifth-night free perk. Plain and simple, whenever you book five or more consecutive nights on points, you'll get the fifth night free. This means that they can book the Le Meridien for as little as 24,000 points per night.

(Screenshot courtesy of Marriott)

Joe and Jessica will also need to factor in transfer costs. Although they'll be booking their stay on points, they'll need to pay a couple of hundreds of dollars for a seaplane or speedboat transfer from the capital of Malé (MLE) to their hotel. The Le Meridien charges $420 per person, the W $505 and the Ritz-Carlton $900.

Related: Do you earn points on seaplane transfers in the Maldives?

(Photo by Ethan Steinberg/The Points Guy)

How to earn Marriott Bonvoy points

Although you could transfer American Express Membership Rewards and Chase Ultimate Rewards points to Marriott Bonvoy, you can likely get better value from these transferable currencies on other redemptions. So, if you need Marriott Bonvoy points, you may want to consider adding a new Marriott Bonvoy card to your wallet instead.

Several of the cards are currently offering welcome offers. Also, keep in mind that all cards offer some degree of automatic elite status.

  • Marriott Bonvoy Brilliant® American Express® Card: Earn 150,000 Marriott Bonvoy bonus points after you use your new card to make $5,000 in eligible purchases within the first three months of card membership.
  • Marriott Bonvoy Boundless Credit Card: Earn 100,000 bonus points after you spend $3,000 on purchases in the first three months of account opening.
  • Marriott Bonvoy Business® American Express® Card: Earn 100,000 Marriott Bonvoy bonus points after you use your new card to make $4,000 in eligible purchases within the first three months of card membership.
  • Marriott Bonvoy Bold Credit Card: Earn 30,000 bonus points after you spend $1,000 on purchases in the first three months from account opening

Related: 5 ways to maximize Marriott Bonvoy award night redemptions

Bottom line

Staying in an overwater villa seems to be on every award traveler’s bucket list — and for a good reason. We showed a couple how they could book their dream trip to the Maldives, including business class flights, all with points and miles they already had. But if you wanted to replicate their itinerary, you could do so fairly easily.

If you have a destination in mind and need help figuring out your points strategy, send us an email to be featured in the next installment of Cleared for Takeoff.

Related video:

Featured image by The Westin Maldives (Photo courtesy of Marriott)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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