Lower Keys Romantic Vacations 2026

Photo by Rick Tuers

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4 Night Romantic vacations in Lower Keys

Price found within the past 48 hours. Click for updated prices.

Looe Key Reef Resort

$567

per person

Sep 27 - Sep 30

found 21 hours ago

Roundtrip non-stop flight included

Denver (DEN) to Miami (MIA)

7.6/10 Good! (1,001 reviews)

Great clean place to stay with a great tiki bar/restaurant/pool and fabulous dive/snorkle center on site with a fabulous crew that takes you to the protected Looe Key Reef. Highly recommend the water trip over anything in Key West,

Reviewed on Aug 16, 2026

Parmer's Resort

$765

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (1,006 reviews)

We stayed at Parmer’s Resort for just one night and overall had a great experience. The room was clean and comfortable, and the staff was very helpful and friendly. They gave us excellent recommendations for places to visit in the area. Based on their recommendation, we decided to visit Kiki’s Sandbar, and we absolutely loved it! The food was delicious, the drinks were great, and the live music and atmosphere made it a really enjoyable experience. Everything about our stay was excellent, and we appreciated how helpful the staff was. I decided to give 4 stars instead of 5 only because we did not have hot water in the shower. Other than that, we had a wonderful stay and would definitely recommend Parmer’s Resort!

Reviewed on Aug 23, 2026

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How can I find the best Lower Keys 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 Lower Keys 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 Lower Keys?

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 Lower Keys?

Put a price on love with stunning deals for duos starting at just $567. Prices and availability are subject to change. Additional terms may apply.

Can I book Lower Keys 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 Lower Keys?

To book a loved-up break in Lower Keys, 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 Lower Keys 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 Lower Keys 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?

Top Romantic Lower Keys Hotels

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

Cudjoe Key FL

14 min drive from Florida Keys Beaches

Book a stay at this family-friendly vacation home in Summerland Key. Enjoy free WiFi, 2 outdoor pickleball courts, and laundry facilities. Popular attractions ...

9.8/10 Exceptional! (272 reviews)

"This house was great for our whole family! Easy to get to. Quick and easy check in process. Tons to do and the host provided a lot to use if wanted (bikes for kids/adults, kayaks..). Our kids loved the pool more than anything, which was great!! Our host had all the amenities. Full kitchen with all ..."

Reviewed on Jul 12, 2026

Parmer's Resort

565 Barry Avenue Summerland Key FL

27 min drive from Florida Keys Beaches

A garden and a private beach await at this romantic motel, which also offers a terrace and a waterfront location.

9/10 Wonderful! (1,007 reviews)

"We stayed at Parmer’s Resort for just one night and overall had a great experience. The room was clean and comfortable, and the staff was very helpful and friendly. They gave us excellent recommendations for places to visit in the area. Based on their recommendation, we decided to visit Kiki’s Sandbar, ..."

Reviewed on Aug 23, 2026

Looe Key Reef Resort

27340 Overseas Highway Summerland Key FL

23 min drive from Florida Keys Beaches

Poolside dining and happy hours await at this romantic hotel, which also offers an outdoor pool and a waterfront location.

7.6/10 Good! (1,002 reviews)

"Great clean place to stay with a great tiki bar/restaurant/pool and fabulous dive/snorkle center on site with a fabulous crew that takes you to the protected Looe Key Reef. Highly recommend the water trip over anything in Key West,"

Reviewed on Aug 16, 2026

See all 825 properties in Lower Keys

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.