How I booked a Caribbean 5 star holiday for under £500.

You probably read the title of this post and thought “that price can only be for a few days”, “that price can only be bed and breakfast” or “that price can’t include flights, accommodation and transfers”, right?

Well, you’re wrong on all accounts: I’ve booked a week in a 5 star resort, all-inclusive, in the Dominican Republic, for the grand total of £492.90 each.

In just over a fortnight, my mum and I will be jetting off for some R&R and a much needed natural vitamin D boost. I cannot wait. We’ll be staying at the Lifestyle Tropical Beach Resort & Spa in Puerto Plata, which I’m sure you’ll agree, judging by the photos on its website, looks like paradise:

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This trip isn’t an “off the shelf” package holiday like Cuba was when I went in November last year, so I’ve had to do a bit of research and some careful planning (actually, a bit like the last trip mum and I went on to Puerto Rico in March 2016). But using my favourite travel websites, I’ve still kept the price of the whole holiday to below £500 each, proving that package holidays aren’t always cheapest, even to long haul destinations.

We’ll actually be on the Caribbean island for a total of nine nights. Two nights will be spent in Airbnbs in the country’s capital, Santo Domingo, and seven nights will be in the resort. The hotel stay didn’t include flights, so these were booked separately – but factoring in the cost of the flights, the Airbnb stays and the cost of transfers to and from the airports in both the UK and the Dominican Republic, it still works out cheaper than my Cuba holiday (which was only in a 4 star resort).

I’ll explain how I got such a cheap holiday in a bit, but first, here’s a little about the hotel and local area, so you can see what we’re getting for our money…

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Dominican Republic all-inclusive resort.

We’ll be staying at the Lifestyle Tropical Beach Resort & Spa hotel in Puerto Plata for seven nights out of the total nine in the Dominican Republic. Puerto Plata is the eighth biggest city in the country, serving as one of the most important trading ports on the island. Tourism is also big in the area, whic is most famous for the Playa Dorada and Costa Dorada resorts, located east of San Felipe de Puerto Plata.

Not far from San Felipe de Puerto Plata is Cofresi Beach, where the Lifestyle Tropical Beach Resort & Spa stretches along 1.5 miles of golden sand. The hotel has 212 “Tropical” rooms (most with ocean views) and 70 “Junior Suites”. As you’d expect, rooms all have private balconies and bathrooms, and either a king-size bed or two queen-size beds.

I’ve booked a Tropical room, which can cost up to £180 per night, according to Booking.com. This is the price based on two people sharing the room, on all-inclusive. The hotel doesn’t offer any other board options, but then there doesn’t seem to be much by way of eating and drinking options outside the resort. That doesn’t bother us in the slightest though, as this trip is very much about relaxing by the pool, sipping cocktails and doing very little.

My travel buddy to the Dominican Republic will be my mum – I’m treating her to the trip to say “thank you” for all she’s done for me since moving back down south after my ex-boyfriend and I split up earlier in the year. We’ve agreed that the time away is just what we both need – I can’t wait to be reading a book on the beach, preferably laying on one of these:

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The three-storey hotel buildings are decorated in a Mediterranean style with Caribbean influenced roofs and cobblestone paths. Looking on the website, the resort has everything you could ever want from an all-inclusive holiday: not one but seven sandy beaches to choose from, nightly entertainment, snorkeling and scuba diving, tennis courts, a spa, even a nine-hole golf course.

Food’s served 24 hours a day in 11 different restaurants, and there’s unlimited drinks available from 12 bars. Oh, and let’s not forget the 12 pools, all with fresh water. The Tropical Resort on the Cofresi Beach looks like the hotel of dreams. So how did all this luxury cost me so little? What’s the catch?

Here’s where I let you into my most money-saving travel secret: Holiday Pirates.

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How to find cheap holiday deals.

If you’ve never heard of Holiday Pirates before, essentially it’s a deals website specifically for travel. Similar to those  deal hunters who post on the HotUKDeals website and the MoneySavingExpert forum, a team of “Pirates” scour hundreds of travel sites to find cheap package holidays and discounts on flights, hotels, car hire, activities and experiences, both abroad and in the UK.

As I used to work at MoneySavingExpert, I’ve always loved finding deals, loopholes and hacks that either help me save money on travel (including getting the cheapest foreign currency), or help save me money on everyday costs, meaning I have more money for travel. That’s why Holiday Pirates is usually my go-to site when it comes to package holidays, rather than the tour operators themselves.

I’ve previously booked getaways to Cyprus, Mexico and last year’s trip to Cuba using the holiday deal finder tool on the website, and I’ve signed up for daily deals emails too. As the best offers often have limited availability, you have to act quickly to make sure you don’t miss out on a bargain.

How do the “Pirates” find these deals? Well, cheap prices are always available online somewhere – but before Holiday Pirates was set-up no one had taken the trouble to search through the internet to find and publish them. For example, there are often vouchers for last minute city breaks that can reduce the cost of travel by 80%, flight offers can include availability in last minute fare buckets or open jaw flights. Extremely low flight prices or hotel stays can also come about due to errors in the booking systems – these are known as “error fares” or misprices.

That’s what my stay at the Lifestyle Tropical Beach Resort & Spa was, a hotel misprice…

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Holiday Pirates recently launched a new Whatsapp service, which when subscribed to, pings you a message every time it finds a deal that fits your sign-up preferences.

The very first message I received from the service on Tuesday 18 July was a hotel misprice for an all inclusive resort in the Dominican Republic. This was what I received:


Clicking the link through to the Holiday Pirates site, it explained that instead of the hotel being reduced by £23/night, it had been reduced to £23/night. This misprice was a computer error and travellers wanting to take advantage of the deal were urged not to contact the resort to check the price until they’d received their booking confirmation. And as flights weren’t included, it was also advised not to book flights until the booking confirmation was received.

As soon as I saw the deal I thought “well Dominican Republic is somewhere I haven’t been yet”, and clicked over to TripAdvisor to read the hotel reviews – which were all pretty positive. According to Booking.com, a week at the resort should have cost £757, or £108 per night:

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Instead, for seven nights from Saturday 14 October to Saturday 21 October it was costing £158.90 for two people, the equivalent of £11.35 each per night. It seemed too good to be true, so I jumped on it, and booked straight away, without even checking if mum was free.

And without checking the price of the flights…

How to find cheap flights.

As I said, the super cheap hotel unfortunately didn’t include flights. So after I got my booking confirmation from ebookers, I went straight onto my second favourite travel website to look for flights: Skyscanner.

The closest airport to the resort is Puerto Plata, only 17 miles away. However flights from London to Puerto Plata were really expensive – over £1,000 each. I couldn’t justify paying that much for the trip, even though the hotel was cheap. So I had considered not going at all – this would have meant losing the £158.90 spent on the hotel, but I could have booked an all-inclusive break for mum and I somewhere else a lot cheaper, such as Turkey or Majorca.

Then I looked at other airports in Dominican Republic, and realised that flights from London to Punta Cana were significantly cheaper, at around £750 each. The flights were cheaper still if you flew on Friday 13 October, and returned on Sunday 22 October. A quick check on Google Maps told me that Punta Cana airport was a five-and-a-half hour drive from the resort though, and while I’ve driven abroad before, I didn’t really fancy doing it in the Dominican Republic. The total cost of the holiday was still averaging to about £650 each as well – which I still thought was a lot.

So I set-up a Skyscanner price alert and waited for the price to come down to less than £400. It was fluctuating for weeks, but then finally, just as I was about to give up hope and start looking at holidays to Marmaris, this happened:

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Again, I didn’t even check with mum, I just booked the flights straightaway before the price increased again. So that was that: we’re flying with Air France from Heathrow T2 for £372 each return. There’s a short stop over in Paris before the long flight to Punta Cana, which touches down at 4.30pm UTC. In-flight meals are included, as is 23kg of hold luggage each too – but I’m pretty sure I won’t need that much (I’ve done plenty of long haul flights with just carry on luggage before).

Anyway, I’m so glad I booked the flights when I did, because the very next day the price had risen to £407 each:

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And three days after that it had gone even higher to £605 each.

It definitely pays to use these tools if you know exactly when you want to go and have a set budget. Of course, it could have gone the other way; flights may have dropped even more after I’d booked them at £372 each, or they could have increased higher than £605 each and I wouldn’t have been going to the Dominican Republic at all. It’s a chance you’ve got to be prepared to take, and in this instance, it paid off.

But there was still the small issue of landing a day before the booking for the resort, and leaving a day after check out from the resort. Plus not wanting to do a five-and-a-half hour drive to and from the airport…

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Booking an Airbnb in Santo Domingo.

Now, if you’ve read the post about my first Airbnb experience, you’ll know that despite booking the cutest Airbnb in Berlin, my stay in the German capital was somewhat soured by my host’s lack of understanding when it came to collecting my bag before flying to Budapest. While not negative, her feedback on my profile wasn’t particularly descriptive or generous, and the whole experience had me questioning whether I’d use the accommodation booking service ever again.

However, I was determined to keep the cost of my trip to Dominican Republic as low as possible, so thought I’d give it another shot – it would only be for a maximum of one or two nights anyway. I’d discovered that the country’s capital, Santo Domingo, is about half way between Punta Cana and Puerto Plata, so a stay in the city would split up the journey from the airport to the resort, and I’d get to see a bit more of the island.

Plus, someone called Helen had very kindly signed up to the service through my Airbnb referral link (which gives newbies £25 off their first booking, if you haven’t used the service before), so I had a free £15 credit to use on my next stay. Well, I thought I did, but when I checked it had gone down to £14. I contacted the company via Twitter to find out if credit had an expiry date, and received a reply from a really helpful Airbnb rep called Bartosz. He explained that there had been a problem with the conversion of my credit from US dollars to British pounds, resulting in less credit than I should have had.

To apologise for the error he gave me an additional £25 credit. I couldn’t believe it, I now had £40 credit to use on the site. So I scoured the available homes and rooms, looking for something that was within budget, pretty central and not too shabby.

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Described as “just like home”, I found the perfect place to stay in Santo Domingo, only a short walk from the colonial old town area. Miguel rents out a private room in his home for £12.90 per night. Even with the extra £6.83 cleaning charge and £2.95 Airbnb booking fee, this still only came to £22.68 (or £11.34 each) for a one night stay. But using my credit, it was completely free.

Next, I had to find somewhere for the return stay from Puerto Plata to Punta Cana. Again, I booked somewhere in Santo Domingo, though this time I pushed the boat out (a bit) and used actual money to pay for part of the stay. The room cost £24.33 per night, plus a £3.80 cleaning fee and the £4.39 Airbnb booking fee, totalling £32.52. But with my remaining £15 credit I paid just £17.52 for the night (£8.76 each). More on this Airbnb stay in another post, as it looks like it’s going to be a little different than usual Airbnb stays…

Cheapest transport to and from the airport.

Finally, I had to work out the cost of getting to and from the airports and the accommodation.

Getting from Reading to Heathrow wasn’t going to be a problem – as the outbound flight is early morning, my brother has kindly offered to drive mum and I to the terminal before he goes to work. Because there are two of us, this works out a lot cheaper (and quicker) than travelling by public transport or taxi. Heathrow is 22.3 miles from my house, so doing the journey there and back twice is 89.2 miles. Using the average mpg for my brother’s car (39 mpg) and the average petrol price for the area of 115.9p per litre, this works out to £12.05 in petrol for all four journeys.

The transport in Dominican Republic proved a little more difficult. Most of the articles I’d read online said that public transport wasn’t great on the island, so I’d looked into hiring a car. This would be out about £100 for the nine days, but obviously didn’t include the cost of petrol for the 516 mile round-trip. But then, after trawling through the TripAdvisor forum, I found a thread about buses from Punta Cana to Santo Domingo and Santo Domingo to Puerto Plata. It would cost $10 each from the airport to the first Airbnb, then just $8 each from the Airbnb to the resort. Doing this both ways works out to $72 overall, the equivalent of £26.66 each.

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So, I figured that the total cost of this trip adds up to £985.79, or £492.90 each. Obviously this doesn’t include any spending money, but as we’re all-inclusive for the most part, I doubt we’ll need a lot. It did take a bit of time to hunt around and find the cheapest options for transport, flights and accommodation outside of the resort, but I’m pretty sure it’ll be worth it once we’re there. Only 19 sleeps to go…

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Have you ever managed to get a super cheap break away like this through Holiday Pirates? Or do you have any go-to travel deals sites that you’d recommend? I’d love to hear from you, so drop your suggestions in the comments below.

169 thoughts on “How I booked a Caribbean 5 star holiday for under £500.”

  2. I loved every part of this post. Such brilliant tips here and although I’d heard of holiday pirates I forgot all about it. Really brilliant tips. Hope you and your mum have a great trip!

    Holly x

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  7. Oh, I love Holiday Pirates! Because of them I went to Peru paying less than 400 euros for the return flight! I am one of their first followers, since they were really small and I even won their first ever competition so they sent me on a free 21 days trip to India. 🙂

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  9. If I need to book a holiday I should definitely come to you for help because I can never find bargains like this! I definitely agree that you and your mum deserve some time away from everything and I can imagine she must be very grateful to you for finding an all inclusive holiday under 500! That is almost unheard of x

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  17. I am blown away by your savvy skills girl, I am looking to travel to Hawaii or Mexico soon and not tried these holiday pirates yet only use skyscanner for flights but what an incredible deal you got. Have fun on your R&R

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  22. I am glad I came across your post! It’s really helpful to be able to cut down the prices wherever possible. I aggregate homestays back in India and provide the travelers a feel of real indian culture by enrolling them in Indian cookery classes or Indian classical dance classes. I am glad you had a good experience with Airbnb and i hope you keep saving and writing for me to learn!

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  23. wow..this was such a great and informative post..signing up to holiday pirates right away 🙂
    also sky scanner price alert..this is insane but so awesome and so happy to know you are taking your mum to such gorgeous place..your mum will have a blast. loved ur post so so much .

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    1. unfortunately there’s no easy way of booking it, and the price of the hotel is back up to the normal price! But sign up for the alerts and hopefully you’ll bag yourself an equally good bargain x

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  26. You sound like me, I am obsessed with getting a good holiday bargain. I’ve not heard of Holiday Pirates before but I am bookmarking them now along with a few other sites you mentioned. Great resources. Enjoy your holiday.

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  28. It’s so expensive to travel anymore so finding a great deal is absolutely amazing! The last time I traveled, I booked my flight way in advance so it was a bit cheaper and didn’t take a flight on a popular day. Of course, it wasn’t to the Carribean lol but it was fun just the same!

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  29. Awesome deals you got! I will have to check on Skyscanner next time we travel. That would really save us a lot of money. I also read the benefits of renting a place through AirBnB instead of paying for hotel stays. If I could save this much everytime, I will be able to tick off a lot from my travel bucket list

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  30. Wow. Holiday Pirates. Skyscanner and AirBnB! Combine these three and you’ll get the best vacation package ever. I am downloading the apps and see what they can offer me.

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  31. This looks like a great vacation. The resort is pretty. Your mom is very lucky and it’s a very thoughtful gesture to take her on the trip. Have a great time and with all that savings I guess you’ll have more cocktails or souvenirs.

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  33. Holiday Pirates is just what my husband and I need! I know there are deals to be had, but it’s overwhelming looking for them online, then wondering if they’re legit, etc. If I could log into a clearinghouse of sorts and simply have them presented to me, I know we’d travel much more often. Thank-you .. bookmarking and I know we’ll be putting it to very good use! x

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  35. This seems like a brilliant find !! I am going to sign up right away and start looking at saving money at amazing resorts. Thanks for sharing this Becca, I cannot believe you’ve had such cheap vacations at such superb destinations.

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  38. Love this! Dominican Republic is so beautiful and tropical! We spent just a short day there but had an amazing time! Thank you for these great budget/discount travel tips and sites!

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    1. Also I am Going to add that it is so nice and thoughtful of you to take your mother, the women that supported you during your stughles and tough times, on such a wonderful trip to such a wonderful place. She must be lucky to have such a thoughtful and travel savvy daughter who would take the time to think about her and thank her with this trip.

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  40. What the… I need that vacation right now! It cost me phenomenally more just to go to San Francisco for 5 nights with my Husband!! That’s such a great deal and what a fabulous vacation to be able to take to just relax and enjoy yourself!!

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  42. I’ve never heard of Holiday Pirates, but it seems like a good one to sign up to! I love how you booked everything even if you didn’t know whether your mum would be free! That’s spontaneous travel right there. Have a lovely time in La Republica Dominicana, be sure to take plenty of great photos, and above all, relax!

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  44. Ah it was me who signed up using your code! So thank you for my bonus 🙂 we stayed in a gorgeous Airbnb cottage in Northumberland using it.
    What an amazing deal you’ve got! The hotel and flights are both such bargains. I’d not heard of Holiday Pirates before so I’m definitely off to look at that now.

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  45. wow, these are very well-detailed travel tips. it’s great you could find such a bargain on your flight. it looks amazing, and i have heard such good things about sky scanner too. great to know about this place too. it looks amazing.

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  46. Amazing work!! I love travelling and this is what i yearn for. i had never heard of Holiday Pirates. Thanks for telling about it and hooray there is a US version of it as well. Already bookmarked it.
    Hope you guys have a wonderful and relaxing vacation.

    Safarnama

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  47. Wow, you got an incredible deal! I’d never heard of Holiday Pirates but I love the idea so I’ll be sure to check them out when I’m going to book my next trip – thanks!

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  49. My go to website is always Wotif but I’ve not seen prices this good! The hotel looks absolutely amazing, I would love to stay there for a week! I wonder if Holiday Pirates will work in Australia?

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        1. Oh my apology, because when i read CARIBBEAN my mind automatically equats cruising.
          Anyway, glad that you save a lot of $$$ for your travel and accommodation. Would you know the best months to grab those deals? Would buying some ticks 6months before would such a good idea?

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          1. It’s not about best months to go or booking six months in advance – as I’ve shown in the article, Holiday Pirates has a deal finder alert system that you can sign up for with Whatsapp, and it will message you every time it has a great deal.

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  50. My husband and I are always on the lookout for cheap travel deals and packages but we have never done it as good as you, you just hit a jackpot in my opinion! That is such a gorgeous property! I can’t wait to read more about this holiday on your blog. 🙂

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  51. I have never heard of Holiday Pirates before. But those deals do look absolutely incredible. I will have to check them out to see what’s available and out there. I know my daughter and I would love to do some more traveling.

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  52. Becca I have to stand and applaud at this haha, it’s brilliant. Sooo the next time I’m booking one of my budget destination, I’m gonna come get some tips from you on if you’ve got the inside scoop on a luxury resort I can do for cheap haha. I love how you how you scoped out sky-scanner and got the alerts on for the price drops (you can get some killer bargains with that) Can’t wait to hear your stories from the Dominican republic 😀

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  61. I have never heard of Holiday Pirates before but this looks like an awesome place to find great bargains. You have shared some amazing tips, I am going to use them in my next vacation.

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  62. Because I love traveling, thanks for sharing these tips! I’ve never been into Carribean but this post makes me want to visit this place next year.

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  63. My word, this is such an amazing breakdown. Thank you for showing us how you did what you did to get such amazing deals. I’m going to look over this with my wife so that, we as well, can start taking the vacation of our dreams

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  64. Wow! I’m very jealous!! I spent more than this on my holiday to Malia, in a 2* hotel! I’ll definitely be taking on these tips to find these cheap deals. Have a lovely time!

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  66. Well after reading, I felt the urge to go ot Carribean. Maybe in future. But by that time, I hope rates won’t go up. Our system is little different. But hey thanks for the heads up, I know where I should go.

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    1. What system do you have Aditya? How is it different? This was a hotel mis-price, so “rates going up” is inevitable, it was an error with their systems that made it this cheap in the first place – I just took advantage of that error! ☺️

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  67. Holiday Pirates here I come…. going to register now! I can’t believe the price you got the hotel for! I went to Dominican Republic when I was pregnant 13 years ago and had the worst morning sickness so really didn’t get to explore as much as I wanted. Can’t wait to see your posts about it.

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  74. Great post! This will be an ideal options for travel / trip because of its amazing deal. By the way with all those lovely pictures I can’t wait to check your tips. Thank you

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  79. I’ve used Airbnb before to save a fortune on holiday accommodation, but I’ve never heard of Holiday Pirates before!! Literally clicking over right this very second to check them out. Summer holiday here I come!

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  81. What?!? You got an amazing deals! I have never heard of Holiday Pirates before, but I will be checking them out! I’m also excited to look into your other suggestions. Traveling and saving money are my two favorite hobbies!

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  87. Oh wow, This sounds really great. I’ve been wishing to stay at this kinds of hotel. This is truly a bucket lists material. Such a brilliant tips. Will try this for sure.

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  88. How exciting for you and your mum to enjoy this holiday together, it really does look like paradise. I am really impressed at the low price you paid too. I hope you have a great time.

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  91. That is so beautiful resort, everything looks so magnificent and perfect for a relaxing holiday. I am so glad you had a great time there. You got a great deal and the price is really good.

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  92. OMG my family is from the Dominican Republic! Not sure if you heard of it, but it’s a little mountain town called San Jose de Ocoa. I love it so much and it’s so cool you got to go!

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  93. Oh my gosh this is an amazing price for that amazing trip! And I just checked that site also works in the US. 😀 I’m going to buy allll the vacations!

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  96. I like the helpful information you provide in your articles.
    I will bookmark your blog and check again here frequently.
    I’m quite sure I’ll learn many new stuff right here! Good luck for the next!

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