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A tropical island with clear blue waters, palm trees, and a thatched-roof hut.

Cudjoe Key Romantic Vacations

Book a Hotel + Flight or Car together to unlock savings

Top Romantic vacation packages in Cudjoe Key

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Sep 8 - Sep 12

    Atlantic View Luxury Villa with Pool + Flight

    Summerland Key
    4 nights
    3.5 star property
    7.4/10 - Good (3 reviews)
    "Everything the description states is inaccurate. The Host was not available at any time, it plain as day states to contact host for gate code and I notified 24hrs before, I called at 1pm the next day, no response, I called at 3pm and texted that i would arrive at house by 5pm like check in states with no response, I stopped for lunch and my new arrival was at 6pm, which is the time I arrived at the house, I called several times to host for gate code, and no success again, It was frustrating I..."
    Reviewed June 8, 2026
    Roundtrip • New York (NYC) - Miami (MIA)
    EWR - EYW • 1 stop EYW - EWR • 1 stop
    $1,809
    $1,695
    per traveler
    found 21 hours ago
    Atlantic View Luxury Villa with Pool

What to do in Cudjoe Key

Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

$667
per traveler
60% of travelers recommend
Marathon Backcountry Fishing Charter
See all activities in Cudjoe Key

Top Romantic Cudjoe Key Hotels

Exterior

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
0.6 mi from Cudjoe Key
7.4 out of 10, Good, (3 reviews)
"Everything the description states is inaccurate. The Host was not available at any time, it plain as day states to contact host for gate code and I notified 24hrs before, I called at 1pm the next day, no response, I called at 3pm and texted that i would arrive at house by 5pm like check in states with no response, I stopped for lunch and my new arrival was at 6pm, which is the time I arrived at the house, I called several times to host for gate code, and no success again, It was frustrating I...
$1,075 nightly
The price is $1,209
Aug 11 - Aug 12
Total with taxes and fees
Atlantic View Luxury Villa with Pool
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 Cudjoe Key

How to find a romantic Cudjoe Key vacation

How can I find the best Cudjoe Key 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 Cudjoe Key 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 Cudjoe Key?

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 Cudjoe Key?

Put a price on love with stunning deals for duos starting at just $1,695. Prices and availability are subject to change. Additional terms may apply.

Can I book Cudjoe Key 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 Cudjoe Key?

To book a loved-up break in Cudjoe Key, 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 Cudjoe Key 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 Cudjoe Key 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?