Florida Keys Romantic Vacations

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Escape to paradise with a romantic getaway in the Florida Keys

Florida Keys, located in the southernmost part of the United States, offers a unique and romantic getaway. With its breathtaking sunsets, crystal-clear waters, and stunning beaches, it is a paradise for couples seeking a romantic vacation. Explore the vibrant marine life by swimming with dolphins or embark on an exciting fishing adventure. Enjoy live music and dancing at beachside bars, where you can indulge in delicious seafood and refreshing cocktails. Florida Keys is the perfect destination for couples looking to create unforgettable memories in a picturesque and enchanting setting.

Top Romantic vacation packages in Florida Keys

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

Hawks Cay Resort

$595
per person
Sep 14 - Sep 18
found 2 hours ago
Roundtrip flight included
New Haven (HVN) to Miami (MIA)
8.2/10 Very Good! (1,009 reviews)
The beauty of the resort takes you away, and reminds you that this is paradise.

Reviewed on Aug 13, 2026

Pier House Resort & Spa

Pier House Resort & Spa

Key West Historic District
$979
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Asheville (AVL) to Key West (EYW)
9/10 Wonderful! (1,258 reviews)
Beautiful beach, helpful staff

Reviewed on Aug 14, 2026

Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
$1,132
per person
Oct 15 - Oct 18
found 4 hours ago
Roundtrip non-stop flight included
Bismarck (BIS) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

Key West Historic District
$965
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (459 reviews)
Location is directly in old town area of Key West. Convenient walk to Mallory Square. Sunset Pier, Sloppy Joe's, Hogs Breath Salon and various other local hot spots and shops.

Reviewed on Aug 13, 2026

Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

$982
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Miami (MIA)
8.8/10 Excellent! (1,008 reviews)
staff very nice

Reviewed on Aug 14, 2026

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5* Romantic vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
$1,132
per person
Oct 15 - Oct 18
found 4 hours ago
Roundtrip non-stop flight included
Bismarck (BIS) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
Don't see what you're looking for?
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3 Night Romantic vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
$894
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Asheville (AVL) to Key West (EYW)
8.8/10 Excellent! (3,469 reviews)
Older resort but still nice, clean. The sargassum was in full force and the smell was very unpleasant but not the resorts fault. Amenities provided were nice. Pool area bars close way to early, adult only pool doesn’t have drinks available without walking. To neighboring pool. Close to sightseeing areas, shopping and dining options.

Reviewed on Aug 14, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
$1,064
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Asheville (AVL) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
The lodging itself was clean and the staff great! We enjoyed our stay. All the chickens, seagulls and pigeons outside on everything was a little gross.

Reviewed on Aug 12, 2026

Pier House Resort & Spa

Pier House Resort & Spa

Key West Historic District
$979
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Asheville (AVL) to Key West (EYW)
9/10 Wonderful! (1,258 reviews)
Beautiful beach, helpful staff

Reviewed on Aug 14, 2026

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4 Night Romantic vacations in Florida Keys

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

Hawks Cay Resort

Save 100% on your flight
$722
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
8.2/10 Very Good! (1,009 reviews)
The beauty of the resort takes you away, and reminds you that this is paradise.

Reviewed on Aug 13, 2026

Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
Save 100% on your flight
$923
per person
Oct 15 - Oct 19
just found
Roundtrip non-stop flight included
Memphis (MEM) to Miami (MIA)
9.2/10 Wonderful! (1,360 reviews)
Pier House Resort & Spa

Pier House Resort & Spa

Key West Historic District
Save 100% on your flight
$1,365
per person
Oct 15 - Oct 19
found 22 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Key West (EYW)
9/10 Wonderful! (1,258 reviews)
Beautiful beach, helpful staff

Reviewed on Aug 14, 2026

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Top reasons for your vacation to Florida Keys

  • Breathtaking Sunsets: Florida Keys offers stunning sunsets that create a romantic atmosphere for walks along the beach or running together.
  • Crystal-clear Waters: With its crystal-clear waters, Florida Keys is perfect for swimming with dolphins and enjoying water activities like boating, snorkeling, and swimming.
  • Delicious Seafood: Indulge in delicious seafood and refreshing cocktails at beachside bars while enjoying live music and dancing.
  • Enchanting Setting: Florida Keys provides a picturesque and enchanting setting, ideal for couples looking to create unforgettable memories.
  • Diverse Destinations: From Key West's vibrant nightlife to Islamorada's marinas and Marathon's beautiful beaches, Florida Keys offers a variety of romantic destinations for couples to explore.

Book a Package and Save Money on Your Florida Keys Vacation

A travel package combines flights and accommodations, or flights and car rental, making it convenient to book everything together. It saves time from searching for separate deals and can even help you save money. With customizable options, you can find the perfect package to suit your preferences and budget. Expedia's price and theme filters ensure you find a great deal for your romantic getaway in Florida Keys.

Escape to the Florida Keys for a romantic vacation like no other. Bask in breathtaking sunsets, enjoy exhilarating runs along the beach, and witness the beauty of dolphins playing in the sea. Dance the night away to live music at vibrant bars, indulge in delicious seafood, and create unforgettable memories together. Book a package now for the perfect romantic getaway.

How to Save Money on a Vacation to Florida Keys

  • Combine your flights with hotels or car rentals to save money on your romantic vacation package to the Florida Keys.
  • Take advantage of Expedia's OneKey program to earn points and save money on local transport, activities, and sightseeing in the Florida Keys.
  • Consider traveling during the off-peak season, typically from April to July, for more budget-friendly options in the Florida Keys.
  • Use the travel experience filter on Expedia to find the best romantic vacation package in the Florida Keys that fits your preferences.

Where to Stay in Florida Keys

When it comes to planning a romantic vacation in the Florida Keys, you'll be delighted with the diverse neighborhoods and areas that offer a variety of experiences. From the vibrant nightlife of Key West to the tranquil beaches of Islamorada, there is something for every couple to enjoy. Explore the stunning sunsets, indulge in live music and dancing, or embark on a fishing adventure - the Florida Keys has it all.

  • Key West: Experience breathtaking sunsets, lively bars, and vibrant live music while enjoying the beautiful sea views. Explore the exciting entertainment scene, join fun festivals, and indulge in boating and biking adventures.
  • Key Largo: Encounter playful dolphins, witness stunning sunsets, and dive into the crystal-clear waters to explore mesmerizing coral reefs. Relax at the marina, go snorkeling, and enjoy delicious seafood while taking in the serene atmosphere.
  • Miami: Immerse yourself in the urban charm of Miami's beaches and vibrant art scene. Enjoy shopping, lively music, and dancing by the sea. Marvel at the impressive skyscrapers, savor delectable dining experiences, and soak in the picturesque scenery.

Explore the best places to visit in Florida Keys

Florida Keys is a dream destination for a romantic package vacation. With its stunning sunsets, you can enjoy romantic walks on the beach or go running together along the shore. Experience the thrill of swimming with dolphins or simply relax by the sea. Dance the night away to live music at local bars and enjoy the vibrant entertainment scene. Don't miss the chance to go fishing and catch your own dinner. Florida Keys offers the perfect atmosphere for a romantic and unforgettable getaway.

  • Biscayne Bay: Immerse yourself in the beauty of this lagoon, surrounded by lush gardens and tropical landscapes. Explore the urban oasis, stroll along the beach, and marvel at the stunning sunsets over the sea. Discover the diverse flora and fauna, visit the zoo, and admire the vibrant art scene that showcases the local culture.
  • Fairchild Tropical Botanic Garden: Indulge in the tropical paradise of this botanical garden in Miami. Relax on the beach, wander through the stunning gardens, and witness the artistry of the urban landscape. Enjoy excursions and dining experiences amidst friendly people. Immerse yourself in the vibrant colors of exotic flowers and the calming presence of the sea.
  • Big Pine Key Flea Market: Experience the charm of this public market in Big Pine Key. Interact with friendly locals as you browse through a variety of stalls. Enjoy leisurely fishing and snorkeling excursions, witness breathtaking sunrises, and explore the nearby islands. Take a boat ride in the marina and immerse yourself in the relaxed atmosphere of this unique destination.

How to find a romantic Florida Keys vacation

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

Put a price on love with stunning deals for duos starting at just $595. Prices and availability are subject to change. Additional terms may apply.

Can I book Florida 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 Florida Keys?

To book a loved-up break in Florida 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 Florida 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 Florida 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 Florida Keys Hotels

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
  • 36 min drive from Florida Keys Beaches
A spa, in-room massages, and ocean-view dining await couples visiting this romantic hotel. The property also offers happy hours, premium mattresses, and a waterfront ...
8.8/10 Excellent! (3,522 reviews)

Couples like: full-service spa, couples spa treatments, beachfront dining

Travelers say...
"Older resort but still nice, clean. The sargassum was in full force and the smell was very unpleasant but not the resorts fault. Amenities provided were nice. Pool area bars close way to early, adult only pool doesn’t have drinks available without walking. To neighboring pool. Close to sightseeing ..."

Reviewed on Aug 14, 2026

Southernmost Beach Resort and Guesthouses
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL
  • 32 min drive from Florida Keys Beaches
In-room massages, a garden, and poolside dining await couples visiting this romantic hotel. The property also offers luxury bedding, a terrace, and a waterfront ...
9/10 Wonderful! (1,447 reviews)
"We love the ambiance and quiet adults only pool. The shuttle to and from downtown and the beach is also wonderful. The staff are friendly and accommodating."

Reviewed on Aug 14, 2026

Parrot Key Hotel & Villas
Pier House Resort & Spa

Pier House Resort & Spa

1 Duval St Key West FL
  • 37 min drive from Florida Keys Beaches
A spa, in-room massages, and ocean-view dining await couples visiting this romantic resort. The property also offers a garden, a hot tub, and a waterfront ...
9/10 Wonderful! (1,281 reviews)

Couples like: full-service spa, beachfront dining, hot tub, on the beach

Travelers say...
"Beautiful beach, helpful staff"

Reviewed on Aug 14, 2026

Pier House Resort & Spa
See all 8,271 properties in Florida 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

$45
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Florida 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.