Luxury Vacations in Naxos and Lesser Cyclades 2026

Photo by William Keller

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Flight and Luxury hotel deals in Naxos and Lesser Cyclades

Price found within the past 48 hours. Click for updated prices.

Grand Ambassador Santorini Hotel

CA $2,044

per person

Oct 19 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

9.4/10 Exceptional! (261 reviews)

Phōs The Boutique Luxury Hotel & Villas

CA $3,227

per person

Oct 22 - Oct 26

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Thira (JTR)

9.6/10 Exceptional! (40 reviews)

The hotel is amazing and views are spectacular. But it is the staff who made our stay exceptional!!

Reviewed on Sep 17, 2026

Art Maisons Aspaki Exclusive Suites

CA $2,919

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Thira (JTR)

9.8/10 Exceptional! (145 reviews)

Art Maisons Oia Castle

CA $3,587

per person

Oct 26 - Oct 30

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Thira (JTR)

9.6/10 Exceptional! (124 reviews)

Everything was amazing!

Reviewed on Jul 27, 2026

Santorini Secret Premium

CA $2,607

per person

Oct 22 - Oct 26

found 7 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Thira (JTR)

9.6/10 Exceptional! (58 reviews)

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5* Luxury holidays in Naxos and Lesser Cyclades

Price found within the past 48 hours. Click for updated prices.

Grand Ambassador Santorini Hotel

CA $2,044

per person

Oct 19 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

9.4/10 Exceptional! (261 reviews)

Phōs The Boutique Luxury Hotel & Villas

CA $3,227

per person

Oct 22 - Oct 26

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Thira (JTR)

9.6/10 Exceptional! (40 reviews)

The hotel is amazing and views are spectacular. But it is the staff who made our stay exceptional!!

Reviewed on Sep 17, 2026

Art Maisons Aspaki Exclusive Suites

CA $2,919

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Thira (JTR)

9.8/10 Exceptional! (145 reviews)

Don't see what you're looking for?

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3 Night Luxury holidays in Naxos and Lesser Cyclades

Price found within the past 48 hours. Click for updated prices.

Delion View Hotel

CA $1,442

per person

Oct 19 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

9.4/10 Exceptional! (307 reviews)

Accommodating staff, great location in town, picturesque view from restaurant and room balcony.

Reviewed on Sep 18, 2026

Grand Ambassador Santorini Hotel

CA $2,044

per person

Oct 19 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

9.4/10 Exceptional! (261 reviews)

Santorini Princess Spa Hotel

CA $1,590

per person

Oct 19 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

10/10 Exceptional! (1,002 reviews)

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See all available trips from Columbus to Naxos and Lesser Cyclades

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4 Night Luxury holidays in Naxos and Lesser Cyclades

Price found within the past 48 hours. Click for updated prices.

Rocabella Mykonos Hotel, a member of Design Hotels

CA $1,502

per person

Oct 24 - Oct 27

found 1 hour ago

Roundtrip non-stop flight included

Toronto (YTO) to Mykonos (JMK)

9.4/10 Exceptional! (403 reviews)

We had a wonderful stay at Rocabella Mykonos. It’s stylish, luxurious and the pool area is lovely. One thing I really appreciated was that there was none of the usual sunbed-saving nonsense. There always seemed to be loungers available, which made it feel much more relaxed. The hotel is on a hill, so it’s worth knowing the nearest shop is around a 10–15 minute walk away, downhill going there and uphill coming back, with no proper footpath. A taxi into Mykonos Town is also around €60 return, so you can feel quite dependent on the hotel. There is a small hotel shop, but it’s mainly spa-style items. I really wish they sold a few basic holiday essentials like sunscreen, snacks, crisps, chocolate and canned soft drinks. At the moment, if you want a drink or nibble, you’re generally buying it from the bar or restaurant. That’s honestly my only real criticism. The hotel itself is fabulous. And a very funny bonus: there’s a two-way mirror near the villas, so watching people take selfies in it without realising villa guests can see them perfectly clearly has been hilarious. 😂

Reviewed on Sep 9, 2026

Art Maisons Aspaki Exclusive Suites

Save 100% on your flight

CA $2,643

per person

Oct 24 - Oct 27

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

9.8/10 Exceptional! (145 reviews)

Santorini Princess Spa Hotel

CA $1,702

per person

Oct 24 - Oct 27

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

10/10 Exceptional! (1,002 reviews)

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What are some benefits when booking luxury Naxos and Lesser Cyclades vacations?

When you book a luxury Naxos and Lesser Cyclades vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Naxos and Lesser Cyclades?

If you're looking for something luxurious in Naxos and Lesser Cyclades, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,442, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 32. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Naxos and Lesser Cyclades. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Naxos and Lesser Cyclades?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Naxos and Lesser Cyclades.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Naxos and Lesser Cyclades. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Naxos and Lesser Cyclades?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Naxos and Lesser Cyclades or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Naxos and Lesser Cyclades. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.