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.
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight
$700
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
8.8/10 Excellent! (1,009 reviews)
Recommend

Reviewed on Sep 9, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
$1,349
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Hawks Cay Resort

Hawks Cay Resort

Save 100% on your flight
$804
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
8.2/10 Very Good! (1,006 reviews)
The unit I got when checked in was very badly maintained and dirty. The couches were dirty and the pillows had blood stains on them. The bathroom would not lock and would not close completely…it stayed a qtr inch open. The TVs would not work with subscription expired. The kids room shades were busted. Outside patio, in both upstairs and downstairs, the ceiling fans were very rusted, the upstairs lounge chairs were torn and you couldn’t sit on them, the small round tables had white dirty stuff on it and the floors were dirty. When you step outside, it smelled like rotten fish on account of the dumpster being near by. There is no in unit phone so you have to call their general phone number and go through prompts to get to the front desk. When I explained the problems, they said they will send someone to fix the bathroom door… told them I need to talk to manager and was told that she is busy and will call me back… 1/2 hr later, no call back… went through the process again and same story… third time same story and I said if I should come to front desk and ultimately had to go front desk and ask the manager for different unit. The new room was better but there was a water leak upstairs floor puddled with water… back to front desk…they offered engineering to come and fix… I refused and they said they didn’t have another rm but after complaining a lot, gave another room. 12 hr travel to hotel, with kids, and 3hrs after getting to resort, got an ok room. 1st day ruined.

Reviewed on Sep 9, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
$975
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (3,560 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
$804
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
This was our first time at the Garden House and we LOVED it! Everything about the place was outstanding. So much, that we booked again to stay there in October, 2026. The staff, drinks, food, grounds....Everything is just wonderful.l

Reviewed on Sep 8, 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
Save 100% on your flight
$2,326
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Richmond (RIC) to Miami (MIA)
9.2/10 Wonderful! (1,422 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.
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight
$700
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
8.8/10 Excellent! (1,009 reviews)
Recommend

Reviewed on Sep 9, 2026

Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
Save 100% on your flight
$1,020
per person
Nov 14 - Nov 17
just found
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
9.2/10 Wonderful! (1,422 reviews)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
$1,349
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
View all trips

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
$832
per person
Nov 11 - Nov 15
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.2/10 Very Good! (1,006 reviews)
The unit I got when checked in was very badly maintained and dirty. The couches were dirty and the pillows had blood stains on them. The bathroom would not lock and would not close completely…it stayed a qtr inch open. The TVs would not work with subscription expired. The kids room shades were busted. Outside patio, in both upstairs and downstairs, the ceiling fans were very rusted, the upstairs lounge chairs were torn and you couldn’t sit on them, the small round tables had white dirty stuff on it and the floors were dirty. When you step outside, it smelled like rotten fish on account of the dumpster being near by. There is no in unit phone so you have to call their general phone number and go through prompts to get to the front desk. When I explained the problems, they said they will send someone to fix the bathroom door… told them I need to talk to manager and was told that she is busy and will call me back… 1/2 hr later, no call back… went through the process again and same story… third time same story and I said if I should come to front desk and ultimately had to go front desk and ask the manager for different unit. The new room was better but there was a water leak upstairs floor puddled with water… back to front desk…they offered engineering to come and fix… I refused and they said they didn’t have another rm but after complaining a lot, gave another room. 12 hr travel to hotel, with kids, and 3hrs after getting to resort, got an ok room. 1st day ruined.

Reviewed on Sep 9, 2026

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
$1,175
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
9/10 Wonderful! (1,460 reviews)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
$1,887
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Florida Keys
View all trips

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 and visiting outside busy months of .

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 $700. 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 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.

What’s the best time of year for a romantic vacation in Florida 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 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
  • 10 min walk from Duval Street
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 ...
Southernmost Beach Resort and Guesthouses
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL
  • 5 min drive from Duval Street
In-room massages, al fresco dining, and a garden await couples visiting this romantic hotel. The property also offers luxury bedding, a terrace, and a waterfront ...
Parrot Key Hotel & Villas
Pier House Resort & Spa

Pier House Resort & Spa

1 Duval St Key West FL
  • 11 min walk from Duval Street
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! (1,317 reviews)

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

Travelers say...
"need in room slippers. rooms need to be cleaned of dust, especially beds. rust spots on lamps and furniture. one lamp had exposed wires"

Reviewed on Sep 9, 2026

Pier House Resort & Spa
See all 8,253 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

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

$42
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
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
Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!

Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!

$45
per adult
92% of travellers recommend
Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!
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.