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

Greek Islands Romantic Vacations

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Top Romantic vacation packages in Greek Islands

Price found within the past 48 hours. Click for updated prices.
  • Outdoor pool, free cabanas, pool umbrellas
    Sep 5 - Sep 11

    Desiterra Resort & Spa + Flight

    Santorini
    5 nights
    5.0 star property
    9.6/10 - Exceptional (238 reviews)
    "We had a great stay. Staff were very attentive, driver was lovely and cheaper than using island taxi. Would highly recommend for a quiet stay, not too far from Fira."
    Reviewed July 21, 2026
    Roundtrip • Boston (BOS) - Santorini (JTR)
    BOS - JTR • 1 stop JTR - BOS • 1 stop
    $2,486
    $1,805
    per traveler
    found 2 days ago
    Desiterra Resort & Spa
  • Beach/ocean view
    Sep 13 - Sep 19

    Amirandes, A Resort to Live + Flight

    Hersonissos
    5 nights
    5.0 star property
    9.4/10 - Exceptional (230 reviews)
    Roundtrip • New York (EWR) - Heraklion (HER)
    EWR - HER • 2 stops HER - EWR • 2 stops
    $3,168
    $2,280
    per traveler
    found 2 days ago
    Amirandes, A Resort to Live
  • Superior Honeymoon Plunge Pool Suite with Sunset View | Terrace/patio
    Oct 9 - Oct 14

    Esperas Santorini + Flight

    Santorini
    4 nights
    4.0 star property
    9.6/10 - Exceptional (343 reviews)
    Roundtrip • Boston (BOS) - Santorini (JTR)
    BOS - JTR • 1 stop JTR - BOS • 1 stop
    $2,647
    $1,934
    per traveler
    found 2 days ago
    Esperas Santorini
  • Villa, 2 Bedrooms, Private Pool, Sea View (Sapphire) | Premium bedding, minibar, in-room safe, desk
    Sep 5 - Sep 11

    Volcano View Hotel Santorini + Flight

    Santorini
    5 nights
    5.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    "Wonderful staff who were friendly and welcoming. They do everything to make you happy. Clean and spacious rooms. Generous breakfast and good selection of lunch and dinner options on the menu. Breathtaking caldera view!"
    Reviewed July 24, 2026
    Roundtrip • Boston (BOS) - Santorini (JTR)
    BOS - JTR • 1 stop JTR - BOS • 1 stop
    $3,031
    $2,240
    per traveler
    found 2 days ago
    Volcano View Hotel Santorini
  • Premium Studio Suite, 1 King Bed, Private Pool, Sea View | Terrace/patio
    Sep 13 - Sep 19

    Castello Boutique Resort & Spa - Adults Only + Flight

    Agios Nikolaos
    5 nights
    5.0 star property
    9.0/10 - Wonderful (91 reviews)
    Roundtrip • New York (EWR) - Heraklion (HER)
    EWR - HER • 1 stop HER - EWR • 1 stop
    $2,921
    $2,255
    per traveler
    found 2 days ago
    Castello Boutique Resort & Spa - Adults Only

Discover the most popular places to visit in Greek Islands

A coastal beach with clear turquoise waters, a sandy shore, and rocky cliffs.

Balos Beach

9.4/10 (336 reviews)
Nothing says vacation like spending a lazy day at Balos Beach, a popular beach in Kissamos. Wander the seaside in this relaxing area.

Top Romantic Greek Islands Hotels

Cave Suite with Hot Tub Caldera & Sea View | Premium bedding, pillowtop beds, in-room safe, WiFi (free)

Caldera Premium Villas - Adults Only

Caldera Premium Villas - Adults Only
39.1 mi from Greek Islands
9.0 out of 10, Wonderful, (734 reviews)
$201 nightly
The price is $231
Aug 18 - Aug 19
Total with taxes and fees
Caldera Premium Villas - Adults Only
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.
See all properties in Greek Islands

How to find a romantic Greek Islands vacation

How can I find the best Greek Islands vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Greek Islands romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Greek Islands?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Greek Islands?

Put a price on love with stunning deals for duos starting at just $1,805. Prices and availability are subject to change. Additional terms may apply.

Can I book Greek Islands spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Greek Islands?

To book a loved-up break in Greek Islands, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Greek Islands with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Greek Islands romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?