Fleming Key Romantic Vacations

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Top Romantic vacation packages in Fleming Key

Price found within the past 48 hours. Click for updated prices.
  • A modern living room with a sofa set, a coffee table, and a view of the cityscape through large windows.
    Jan 10 - Jan 14

    District 225 - Rooftop Pool - Gym - Parking - Downtown Miami + Flight

    Downtown Miami
    4 nights
    4.0 star property
    Roundtrip • Philadelphia (PHL) - Miami (MIA)
    TTN - FLL • Nonstop MIA - PHL • Nonstop
    $1,126
    $572
    per traveler
    found 1 day ago
    District 225 - Rooftop Pool - Gym - Parking - Downtown Miami
  • A poolside area with lounge chairs, a table with a beverage, and a view of the ocean.
    Jan 14 - Jan 17

    The Retreat Collection at 1 Hotel & Homes South Beach + Flight

    South Beach
    3 nights
    5.0 star property
    8.0/10 - Very good (1 review)
    "Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay...."
    Reviewed June 22, 2016
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop FLL - BOS • Nonstop
    $16,135
    $7,820
    per traveler
    found 1 day ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • A modern living room with a large window, a flat-screen TV, a potted plant, a candle, and a view of a city skyline.
    Jan 16 - Jan 21

    501 First Studio Balcony by Palermo Home + Flight

    Downtown Miami
    5 nights
    2.0 star property
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop FLL - BOS • Nonstop
    $1,545
    $765
    per traveler
    found 18 hours ago
    501 First Studio Balcony by Palermo Home
  • A modern hotel room with a sofa, a small table with a telephone, a desk with a lamp, a bed with patterned bedding, a TV on the wall, and a large window with a city view.
    Dec 16 - Dec 19

    Avi Lux Stay + Flight

    East Fort Lauderdale
    3 nights
    4.5 star property
    7.6/10 - Good (10 reviews)
    "If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE. "
    Reviewed August 28, 2025
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • 1 stop FLL - BOS • Nonstop
    $1,183
    $620
    per traveler
    found 17 hours ago
    Avi Lux Stay
  • A spacious living area with a large window overlooking the sea, a sofa set, a dining table, and a potted plant.
    Jan 28 - Feb 3

    72 Park Miami Beach Boutique Residences by IliosRentals + Flight

    North Beach
    6 nights
    4.5 star property
    8.2/10 - Very good (19 reviews)
    "We had a wonderful stay with our group of three adults and three children! Everything was very comfortable, and the apartment was beautiful, clean, and well-maintained. There is a convenient shuttle service to the beach, but the 10-minute walk is also perfectly fine, even with children. Communication was excellent, and any questions we had were answered quickly. Overall, a very pleasant experience for the whole family. We would definitely recommend this place and would happily stay here again!"
    Reviewed October 17, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop MIA - BOS • Nonstop
    $2,594
    $1,391
    per traveler
    found 14 hours ago
    72 Park Miami Beach Boutique Residences by IliosRentals

How to find a romantic Fleming Key vacation

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

Put a price on love with stunning deals for duos starting at just $572. Prices and availability are subject to change. Additional terms may apply.

Can I book Fleming 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 Fleming Key?

To book a loved-up break in Fleming 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 Fleming 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 Fleming 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?