5 Star Hotels Santorini Island Greece How to Choose One

Oh my god, I almost completely screwed up my honeymoon at one of the 5 star hotels Santorini Island Greece.

Picture this: it’s 2:30 AM, three days before we’re supposed to fly to Santorini, and I’m sitting in my kitchen in my pajamas, laptop open, having a full-on panic attack. Why? Because I just found out through a random TripAdvisor review that the hotel I’d booked nine months earlier – you know, the one that cost more than my car payment – was having their entire pool deck renovated.

My husband finds me there an hour later, surrounded by empty coffee mugs and printouts of different hotels, basically losing my mind. “Babe,” he says, “it’s just a hotel.” JUST A HOTEL? This was supposed to be our perfect romantic getaway! Those Instagram photos of infinity pools hanging over the Aegean Sea weren’t going to take themselves!

Anyway, I ended up canceling (thank god for refundable rates) and booking something completely different last minute. And you know what? That “panic booking” turned out to be the best decision I ever made. We ended up at this gorgeous family-run place in Imerovigli that wasn’t even on my original radar, and it was absolutely magical.

That disaster taught me that picking the right luxury hotel in Santorini is way more complicated than just scrolling through pretty pictures on booking websites. There’s so much stuff nobody tells you – like how some “private” terraces are basically fishbowls, or how the most expensive hotels sometimes have the worst service.

I’ve been back to Santorini four times now (my husband jokes that I’m obsessed, and honestly? He’s not wrong). I’ve stayed at eight different luxury properties, made some amazing discoveries, and had a few experiences I’d rather forget. Like the time I paid €850 a night for a room where I couldn’t use my terrace because tour groups kept walking by and taking photos. Fun times.

So if you’re planning a trip and feeling overwhelmed by all the choices, grab some wine and let me share everything I wish I’d known before my first visit.

The Truth About 5 Star Hotels Santorini Island Greece

OK, here’s something weird that I didn’t realize until my third visit: Santorini’s luxury hotels are basically making it up as they go along.

What I mean is, most of these places started as regular houses or small guesthouses and just kept adding rooms and upgrading over the years. So you’ll find hotels where one suite has a massive terrace with an infinity pool, and another “identical” suite has a tiny balcony overlooking a parking lot. Same price, completely different experience.

I learned this the hard way in 2019 when I booked what I thought was a “sea view suite” in Oia. The sea view was technically there, but I had to lean out over my balcony railing and crane my neck to see it. Meanwhile, the couple next door had this incredible panoramic view right from their bed. We paid the exact same rate.

The service thing is even weirder. Some of these hotels grew so fast that they never really figured out luxury hospitality. I’ve been to places that have Hermès toiletries but can’t manage to deliver room service without calling you three times to find your room. It’s like they know they’re supposed to be fancy but aren’t quite sure how to actually do it.

And don’t even get me started on the star ratings. I’m pretty sure there’s a 5-star hotel in Santorini that would barely qualify as a 3-star anywhere else. The standards are just… different here.

But here’s the thing – when these hotels get it right, they’re absolutely incredible. The best ones feel like staying at a friend’s gorgeous private villa, if your friend happened to be absurdly wealthy and have impeccable taste.

Where to Stay: The Real Talk on Santorini Locations

Let me break down each area based on actually staying there, not just reading about it online.

Oia: Instagram vs. Reality

Everyone wants to stay in Oia. I get it – those photos are insane. The blue domes, the windmills, the sunset that literally stops traffic. I was completely obsessed with staying there too.

So in July 2019, I booked five nights at one of those famous cliff-hanging hotels. The photos on their website were basically porn for travel addicts like me. Infinity pool? Check. Private terrace? Check. That iconic sunset view? Double check.

Reality check: I spent more time hiding in my room than enjoying my “private” terrace.

The problem nobody talks about is that Oia is basically Disneyland during sunset hours. As hundreds of people search for photo ops, many of them wind up directly outside your ostensibly secluded patio. I had tourists literally leaning over railings to get shots, with me clearly visible in my bikini in the background of their photos.

One evening, I was trying to have a romantic dinner on my terrace, and this group of influencers set up with a professional photographer right below us. They were there for two hours, posing and shouting directions at each other. So much for romance.

The restaurants in Oia are gorgeous but crazy expensive and usually booked solid. We ended up eating at our hotel restaurant more than I’d planned, which got old fast.

Would I stay in Oia again? Maybe for like two nights, just to get those bucket list photos. But not for a whole week.

Imerovigli: Where I Actually Want to Live

This is where I had my accidental honeymoon booking, and oh my god, I fell in love. Imerovigli sits at the highest point of the caldera, so the views are absolutely insane – you can see everything from up there.

But the best part? It’s QUIET. Like, actually peaceful quiet, not just “less busy than Oia” quiet.

My favorite memory from our honeymoon was floating in our infinity pool at sunset (yes, a real infinity pool, not some tiny plunge pool masquerading as one), with a glass of local wine, watching the light change across the whole caldera. A couple of hikers passed by on the walking path below and one of them shouted up “Living the dream!” And you know what? I really was.

The hotels in Imerovigli tend to be smaller and more intimate. Ours only had 12 suites, so the service was incredibly personal. The manager knew our names by day two and would ask about our plans each morning.

Downside? You’re not walking distance to a ton of restaurants, so you’ll need to take taxis or buses if you want variety. But honestly, after busy days of exploring, I was happy to just chill at the hotel.

Fira: Convenience Central

I stayed in Firostefani (basically Fira’s quieter neighbor) during my March 2023 trip, and I have to admit, the convenience factor was pretty great.

You can walk to like 30 different restaurants, the main bus station, shops, everything. If you’re the type who likes having options right outside your door, this area is perfect.

The views are still gorgeous – you’re looking at the volcano and the other islands instead of the classic “sun into the sea” Oia view. Different but equally beautiful.

What surprised me was how much cheaper it was. My suite was about €250 less per night than similar places in Oia, even though the amenities were basically identical.

The trade-off is that some parts of Fira can get pretty rowdy, especially near the cruise ship port. But if you pick a hotel that’s positioned right, you get the convenience without the chaos.

Beach Areas: The Plot Twist

OK so I was skeptical about staying at a beach hotel because, come on, if I’m going to Santorini, I want those cliff views, right? But last year I decided to try it for the last three nights of my trip, and it was actually amazing.

Instead of tiny terraces carved into cliffs, I had this huge modern suite with an actual garden. The pool area was massive – like resort-style massive – with tons of loungers and no 6 AM towel wars.

It felt like being at a completely different kind of luxury. Less dramatic, maybe, but way more relaxing. And the value for money was incredible compared to caldera properties.

Let’s Talk About Private Pools (And Why They’re Complicated)

This is probably the question I get asked most: are private pools worth the extra €200-400 per night?

Short answer: sometimes.

Longer answer: I’ve had private pools that made my entire trip, and others that I literally never used.

The good: My Imerovigli infinity pool was heated, actually big enough to swim in, and positioned so I could float while watching the sunset. I spent hours in there every day. Worth every penny.

The bad: My Oia “plunge pool” was basically an expensive bathtub. So small I couldn’t even float – I had to sort of crouch in it like I was taking a bath. And despite it being July, the water was freezing because it never got direct sunlight.

The ugly: One hotel charged me €350 extra per night for a “private pool suite” where the pool was visible from three different public walking paths. I was more concerned with privacy than I was with enjoying it.

Questions I always ask now:

• What are the actual dimensions? (Don’t trust photos – they’re always taken with wide-angle lenses)
• Is it heated? (Essential unless you’re visiting in peak summer)
• How private is it really? (Ask specifically about sightlines from other rooms, public areas, walking paths)
• What hours does it get sun? (Cliff positions can mean shade most of the day)

My rule: If I’m staying less than 3 nights or planning to be out all day, I skip the private pool and just enjoy the hotel’s main pool area.

The Food Situation (It’s More Important Than You Think)

I used to be one of those travelers who barely ate at their hotel because I wanted to “experience local culture.” Santorini changed that perspective real quick.

After climbing up and down hundreds of stairs in 90-degree heat, sometimes the thought of getting dressed up and hiking to a restaurant feels impossible. There were nights when I gladly paid €45 for hotel room service just to avoid leaving my air conditioning.

Best hotel dining experience: This boutique place in Imerovigli where the chef would come out every morning and describe what looked good at the market. “The tomatoes today are incredible,” he told us one morning. “Let me make you something special.” Those tomato fritters with local cheese became my obsession.

Worst experience: A beach hotel that charged €32 for the most mediocre Greek salad I’ve ever had. It took 50 minutes to arrive. The server genuinely shrugged when I brought up the wait.

Now I always check:

• Are the restaurants popular with non-hotel guests? (Usually a good sign)
• What’s included with breakfast? (Some places are generous, others charge €8 for orange juice)
• Are all restaurants open during my stay dates? (Some close randomly in shoulder season)

The Service Lottery (And How to Win It)

Here’s something funny – the most expensive hotels don’t always have the best service. Actually, some of the worst service I’ve experienced was at the priciest places.

At a €950/night hotel in Oia, our bathroom flooded on day two. The front desk person suggested we “use the bath towels to soak it up” and said maintenance might get there the next day. For nearly a thousand euros a night!

Compare that to a family-owned hotel where the owner’s mother sent up homemade Greek mountain tea when she heard my husband had a cold. No charge, no big deal, just genuine hospitality.

I’ve noticed the best service comes from hotels that have been operating at the luxury level for years, not places that recently upgraded from budget accommodations. There’s a learning curve to high-end hospitality.

Pro tip: Email hotels directly with specific questions before booking. How they respond tells you everything about what service will be like. Quick, personal, helpful replies = good sign. Slow, generic responses = maybe look elsewhere.

Timing Your Trip (The Expensive Truth)

My first trip was in August because, you know, that’s when everyone goes to Greece. Big mistake.

Peak season (June-September) has perfect weather but also:

• Maximum prices (my August room would’ve cost 40% less in October)
• Crowds everywhere
• Stressed-out staff
• Impossible restaurant reservations
• Minimum stay requirements

I went back in late September the next year and it was like visiting a different island. Fewer crowds, relaxed atmosphere, and significantly cheaper rates. The weather was still great – warm days, perfect for swimming, just needed a light jacket for evenings.

My March 2023 trip was an experiment. Many hotels were closed, but the ones that stayed open offered incredible deals. I paid €285/night for a suite that goes for €750+ in summer. The weather was hit or miss – some gorgeous days, some windy ones – but having sunset spots almost to myself was magical.

My Booking Strategy (After Many Expensive Mistakes)

1. Research on booking sites, I almost always get something extra – free transfers, room upgrades, welcome amenities – that aren’t available through third parties.
2. Always book refundable rates, even if it costs more. Santorini weather can be unpredictable, ferries get cancelled, plans change. That flexibility has saved me multiple times.
3. Email about construction before arrival. Hotels often do renovations during off-season, but sometimes work runs late. Nothing ruins luxury like jackhammers at 8 AM.
4. Be specific about your needs. Before my last trip, I wrote: “We value privacy highly and would prefer a room where our terrace isn’t visible from public walkways.” They actually moved us to a better-positioned suite.
5. Ask about your specific room location. Lower floors might have better views but more foot traffic. Higher floors more privacy but potentially more stairs. There’s no right answer, but knowing helps set expectations.

My Biggest Santorini Regret

I wish someone had told me it’s OK to split your stay between different areas. My first trip was six nights all in Oia, and by day four I was getting cabin fever. I kept thinking about other parts of the island I wasn’t experiencing.

Now I always split: maybe 2-3 nights for the “bucket list” experience in Oia or Imerovigli, then 2-3 nights at a beach property for actual relaxation. Yes, packing and moving is slightly annoying, but Santorini is tiny – transfers are never more than 20 minutes.

Experiencing different parts of the island gives you a much richer sense of what Santorini actually offers beyond the postcard views.

How to Actually Choose (My Personal Framework)

After helping friends plan their trips (and talking my sister out of a €1,100/night booking that would’ve been all wrong for her), here’s what I suggest:

Be brutally honest about your travel style:

• Do crowds make you anxious? (Skip Oia in summer)
• Are you planning to explore all day? (Don’t splurge on hotel amenities you won’t use)
• Do you need constant stimulation or prefer peace? (This determines everything)

Calculate your REAL budget: Santorini is expensive beyond just hotels. Cocktails are €20+, dinners easily €80-100 per person, taxi rides €30-50. If you max out your budget on accommodation, you might be too stressed about money to enjoy the experience.

Think about the memories you want: When I picture my perfect Santorini day, it involves a peaceful breakfast on my terrace, some exploration mid-day, then returning to watch sunset with a glass of wine. Your perfect day might be completely different – adventure, nightlife, beach time. Book accordingly.

So… Is Luxury Santorini Worth the Money?

After spending embarrassing amounts of money on various fancy hotels across the island, here’s my honest take: sometimes absolutely, sometimes hell no.

Worth every penny moments:

• Floating in my heated infinity pool watching the most incredible sunset of my life
• The boutique hotel manager who remembered I liked my coffee “Greek style” every morning
• Having a gorgeous private space to retreat to after dealing with summer crowds

Total waste of money moments:

• The “luxury” hotel where I hid in my room because of privacy issues
• Any time I booked amenities I didn’t actually have time to use
• Paying premium rates during peak season for a stressed, overwhelmed experience

Here’s the truth: Santorini’s natural beauty is accessible to everyone. You can see those famous sunsets from public viewpoints, swim at gorgeous beaches for free, and eat incredible food at family tavernas for reasonable prices.

What you’re paying for at luxury hotels isn’t just the view – it’s privacy to enjoy that view on your own terms, personalized service that makes you feel special, and a beautiful retreat from what can be a pretty hectic island during busy periods.

Is that worth the premium? Depends entirely on what you value and what your budget can handle without causing stress.

The most important thing I’ve learned: the “best” hotel for you depends completely on your personality, travel style, and what kind of experience you’re actually looking for. Don’t just book the most Instagrammable option – book the one that fits how you actually want to spend your time.

What do you think? Have you been to Santorini? Are you planning a trip? I’d love to hear about your experiences or help with any specific questions just drop a comment below!