A boat docked at a turquoise harbor surrounded by rocky cliffs and lush greenery.

Greek Islands Gay friendly Vacations

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    Save up to CA $4,200 when you book a flight and hotel together*
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Top Gay friendly vacation packages in Greek Islands

Price found within the past 48 hours. Click for updated prices.
  • Jan 16 - Jan 23

    Ethereal White Resort Hotel & Spa - Adults Only + Flight

    Heraklion
    6 nights
    5.0 star property
    9.6/10 - Exceptional (101 reviews)
    "The room was spotlessly clean and the front desk staff were all incredibly helpful"
    Reviewed November 5, 2026
    Roundtrip • Montreal (YUL) - Heraklion (HER)
    YUL - HER • 2 stops HER - YUL • 2 stops
    CA $2,238
    CA $2,003
    per traveller
    found 18 hours ago
    Ethereal White Resort Hotel & Spa - Adults Only
  • Jan 21 - Jan 28

    Delion View Hotel + Flight

    Santorini
    6 nights
    4.0 star property
    9.4/10 - Exceptional (342 reviews)
    "Excellent view, well priced"
    Reviewed October 30, 2026
    Roundtrip • Montreal (YUL) - Santorini (JTR)
    YUL - JTR • 2 stops JTR - YUL • 2 stops
    CA $3,020
    CA $2,162
    per traveller
    found 1 day ago
    Delion View Hotel
  • Dec 18 - Dec 23

    Aqua Luxury Suites + Flight

    Santorini
    4 nights
    5.0 star property
    9.4/10 - Exceptional (238 reviews)
    "This is a beautiful property but as with most places in Santorini, it comes with lots of stairs to get to your room and most of the stairs are uneven and some quite steep. Not all sections have handrails. Luckily this property is right by the road, so taxis can drop you right outside the reception. I saw others dragging and carrying their suitcases up the steep, uneven stairs around Santorini to get to their hotels… We stayed in the Grand Mare Suite which was really nice with a heated plunge..."
    Reviewed October 26, 2026
    Roundtrip • Montreal (YUL) - Santorini (JTR)
    YUL - JTR • 2 stops JTR - YUL • 1 stop
    CA $3,428
    CA $2,997
    per traveller
    found 1 day ago
    Aqua Luxury Suites
  • Dec 20 - Dec 27

    Creteco Hotel & Suites + Flight

    Hersonissos
    6 nights
    4.0 star property
    8.4/10 - Very good (49 reviews)
    "This a beautiful hotel right at the Mediterranean Sea. The prices are very good and the staff are friendly. Breakfast and WiFi is included. The rooms are spacious and clean. Wish we would have been able to stay more than one night. We highly recommend this hotel."
    Reviewed October 9, 2026
    Roundtrip • Winnipeg (YWG) - Heraklion (HER)
    YWG - HER • 2 stops HER - YWG • 2 stops
    CA $3,767
    CA $3,460
    per traveller
    found 12 hours ago
    Creteco Hotel & Suites
  • Dec 18 - Dec 23

    Rocabella Santorini Hotel & SPA + Flight

    Santorini
    4 nights
    4.0 star property
    9.4/10 - Exceptional (703 reviews)
    "."
    Reviewed November 8, 2026
    Roundtrip • Montreal (YUL) - Santorini (JTR)
    YUL - JTR • 2 stops JTR - YUL • 1 stop
    CA $2,733
    CA $2,617
    per traveller
    found 1 day ago
    Rocabella Santorini Hotel & SPA

Discover the most popular places to visit in Greek Islands

Top Gay friendly Greek Islands Hotels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a Greek Islands vacation package cost?

Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Greek Islands from just CA $2,003. And the more you bundle, the more you save. Your dream vacation has never been more affordable.

How do I get a cheap travel package to Greek Islands?

If you love bargains, combine your bookings into a Greek Islands vacation package. Whether you need flights, hotels, rental cars or activities, you can book them all in one place. You'll have endless choice at your fingertips as well. Expedia has over 550 air carriers and 1,000,000 hotels throughout the world to select from. Fly with who you prefer, book a room where you like and save precious dollars — now that's the ideal vacation!

Where should I stay in Greek Islands?

To explore popular sights like Museum of Prehistoric Thira and Archaeological Museum of Thera, Fira is where you need to be. Plenty of travelers also adore Mykonos Town, home to Windmills of Mykonos and Church of Panagia Paraportiani. If time is on your side, why not check out both cities?

What are the top hotels in Greek Islands?

When it comes to hotels in Chania, Samaria Hotel and Kydon, The Heart City Hotel are two fantastic options. If you're visiting Rethymno, Aquila Porto Rethymno and Veneto Boutique Hotel will make you feel at home.

How far in advance should I book my Greek Islands vacation?

Savvy travelers book early. Air carriers typically release flight tickets up to 12 months ahead of departure, and this is when you can pick up some of the lowest prices. Boss just told you to take your vacation time next month? No need to worry. Expedia are never short on fantastic bargains to send you on the getaway of your dreams, at a price you can afford.

What does an Expedia Greek Islands travel package include?

Rental cars, hotels and flights, or any combination of them — the choice is all yours! Whether you're exploring Greek Islands with the entire family or traveling by yourself, there's a package to match every style and budget. Once you've made your booking, why not add on one or two activities?

What should I know before booking a Greek Islands travel package?

When you book your hotels, flights and car rentals together, you'll pick up terrific discounts. Whether you're planning a rural escape in a cottage or prefer to stay in a luxurious city hotel, Expedia will help make it happen.

If I'm not able to travel, can I cancel my Greek Islands vacation package?

Yes, you can. We understand that life doesn't always go to plan, so we're here to help if you need to make changes to your Greek Islands vacation package. You may be able to cancel or amend your itinerary at no cost if you've booked within 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.