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 22 - Aug 26

    Monastery Hotel + Flight

    Central
    4 nights
    5.0 star property
    8.8/10 - Excellent (1,005 reviews)
    "I thought I booked a hotel room, but when I checked in it was outside the hotel, more like a motel room. That is not what I wanted. It had an outside door and again that’s not what I wanted or booked, l booked a hotel room. I didn’t sleep as I was nervous all night with being in a room that opened up to outside. We did enjoy the complimentary breakfast and staff were great."
    Reviewed July 22, 2026
    Roundtrip New York (NYC) - St. John's (YYT)
    LGA - YYT1 stop YYT - EWR1 stop
    $1,188
    $1,072
    per traveler
    found 13 hours ago
    Monastery Hotel
  • Aug 22 - Aug 26

    Mallard Inn + Flight

    Quidi Vidi
    4 nights
    3.5 star property
    9.8/10 - Exceptional (10 reviews)
    "Absolutely AMAZING! What a great location and stunning place. Magical."
    Reviewed July 20, 2026
    Roundtrip New York (NYC) - St. John's (YYT)
    LGA - YYT1 stop YYT - EWR1 stop
    $1,756
    $1,586
    per traveler
    found 13 hours ago
    Mallard Inn
  • Aug 22 - Aug 26

    Leaside Manor by The Leaside Group + Flight

    West End
    4 nights
    4.5 star property
    9.2/10 - Wonderful (591 reviews)
    "Close to the downtown. Parking and a space to unload the vehicle close to our unit. Ice for water bottles. Breakfasts were delicious and staff very helpful."
    Reviewed July 20, 2026
    Roundtrip New York (NYC) - St. John's (YYT)
    LGA - YYT1 stop YYT - EWR1 stop
    $1,225
    $1,141
    per traveler
    found 13 hours ago
    Leaside Manor by The Leaside Group
  • Aug 22 - Aug 26

    Ramada by Wyndham St. John's + Flight

    Kenmount East
    4 nights
    3.5 star property
    8.8/10 - Excellent (1,219 reviews)
    Roundtrip New York (NYC) - St. John's (YYT)
    LGA - YYT1 stop YYT - EWR1 stop
    $1,160
    $1,090
    per traveler
    found 13 hours ago
    Ramada by Wyndham St. John's
  • Sep 30 - Oct 4

    Castle Landing + Flight

    Placentia
    4 nights
    3.0 star property
    9.6/10 - Exceptional (61 reviews)
    "super endroit"
    Reviewed July 20, 2026
    Roundtrip Cincinnati (CVG) - St. John's (YYT)
    CVG - YYT2 stops YYT - CVG1 stop
    $1,231
    $1,162
    per traveler
    found 14 hours ago
    Castle Landing

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 $1,072. 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?