Lower Keys Romantic Vacations

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4 Night Romantic vacations in Lower Keys

Price found within the past 48 hours. Click for updated prices.
Parmer's Resort

Parmer's Resort

$925
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Miami (MIA)
9/10 Wonderful! (1,004 reviews)
The staff at Parmer’s is excellent from the check-in person to everyone that works on the grounds. However, this place had to grow on me because my initial reaction was one of disappointment. I think the pictures look much better than what’s actually there. The beach that’s advertised and looks like a sandy oasis with a clean shoreline is actually about sandy to mid calf and then algae and seaweed. A nice place to catch some rays with nice loungers but sitting on the waters edge but not for swimming or wading. The furniture is straight out of the 60’s or 70’s, but is clean and well kept. The A/C is enough to keep the cottage type bungalow cool but too far from the bathroom to keep that area cool. The pool is super clean and well maintained but water too hot during summer and would benefit from the pump keeping water flowing longer. Having said all this I found Parmer’s growing on us because of the staff, the light breakfast, eagerness of staff to please providing a fan to keep the bath cooler, the boat ramp, kayaks, shaded sitting areas by the water, fishing on property and the overall laid back feeling made me forget what wasn’t perfect and remember what hotel stays were like when I was young. No fancy Marriott’s or Sheraton, but just a place where you felt you hadn’t left home, but gained a water view with a summer breeze.

Reviewed on Aug 29, 2026

Looe Key Reef Resort

Looe Key Reef Resort

$981
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Miami (MIA)
7.6/10 Good! (1,002 reviews)
Everything was great! Staff was very friendly! Easy check in and check out.

Reviewed on Aug 27, 2026

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How to find a romantic Lower Keys vacation

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 and visiting outside busy months of .

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 $925. Stay during the quiet season, in , for breaks to make your bank balance smile. 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.

What’s the best time of year for a romantic vacation in Lower Keys?

Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience.

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

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

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

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! (1,002 reviews)
"The staff at Parmer’s is excellent from the check-in person to everyone that works on the grounds. However, this place had to grow on me because my initial reaction was one of disappointment. I think the pictures look much better than what’s actually there. The beach that’s advertised and looks like ..."

Reviewed on Aug 29, 2026

Parmer's Resort
Looe Key Reef Resort

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! (1,001 reviews)
"Everything was great! Staff was very friendly! Easy check in and check out."

Reviewed on Aug 27, 2026

Looe Key Reef Resort
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.

Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$69
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Lower Keys

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.