Pool's Island Romantic Vacations

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Top Romantic vacation packages in Pool's Island

Price found within the past 48 hours. Click for updated prices.
  • Aug 25 - Aug 29

    Cliffs Edge Retreat + Flight

    Tors Cove
    4 nights
    2.5 star property
    9.8/10 - Exceptional (279 reviews)
    "Beautiful location only a short drive from St. John’s. The rooms were spacious and charming overlooking the ocean . We watched puffins from our hotel room. Dinner at the hotel restaurant was steps away. The meal was excellent yet very casual environment. We returned to the café for breakfast. The baked goods were amazing. It was an extremely quiet place to sit enjoy the view and relax.."
    Reviewed July 20, 2026
    Roundtrip Hamilton (YHM) - St. John's (YYT)
    YHM - YYTNonstop YYT - YHM1 stop
    $924
    $808
    per traveler
    found 1 day ago
    Cliffs Edge Retreat
  • Aug 31 - Sep 3

    Dvele Inn + Flight

    Georgestown
    2 nights
    4.0 star property
    9.8/10 - Exceptional (37 reviews)
    Roundtrip Palm Springs (PSP) - St. John's (YYT)
    PSP - YYT1 stop YYT - PSP2 stops
    $1,112
    $990
    per traveler
    found 1 day ago
    Dvele Inn
  • Aug 22 - Aug 27

    Monastery Hotel + Flight

    Central
    5 nights
    5.0 star property
    8.8/10 - Excellent (1,019 reviews)
    Roundtrip Boston (BOS) - St. John's (YYT)
    BOS - YYT1 stop YYT - BOS1 stop
    $1,278
    $1,140
    per traveler
    found 1 day ago
    Monastery Hotel
  • Aug 22 - Aug 27

    Mallard Inn + Flight

    Quidi Vidi
    5 nights
    3.5 star property
    9.8/10 - Exceptional (9 reviews)
    "Absolutely AMAZING! What a great location and stunning place. Magical."
    Reviewed July 20, 2026
    Roundtrip Boston (BOS) - St. John's (YYT)
    BOS - YYT1 stop YYT - BOS1 stop
    $1,992
    $1,801
    per traveler
    found 1 day ago
    Mallard Inn
  • Aug 22 - Aug 27

    Ramada by Wyndham St. John's + Flight

    Kenmount East
    5 nights
    3.5 star property
    8.8/10 - Excellent (1,219 reviews)
    Roundtrip Boston (BOS) - St. John's (YYT)
    BOS - YYT1 stop YYT - BOS1 stop
    $1,256
    $1,172
    per traveler
    found 1 day ago
    Ramada by Wyndham St. John's

How to find a romantic Pool's Island vacation

How can I find the best Pool's Island 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 Pool's Island 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 Pool's Island?

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 Pool's Island?

Put a price on love with stunning deals for duos starting at just $808. Prices and availability are subject to change. Additional terms may apply.

Can I book Pool's Island 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 Pool's Island?

To book a loved-up break in Pool's Island, 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 Pool's Island 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 Pool's Island 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?