Islamorada Romantic Holidays

Book a Romantic Hotel + Flight or Car together to unlock savings

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    Save up to £335 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Packages with flights are ATOL protected

How to find a romantic Islamorada holiday

How can I find the best Islamorada vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Islamorada. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Islamorada romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Islamorada that start from . Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Islamorada romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Islamorada?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Islamorada?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Islamorada that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Islamorada with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Islamorada romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

Top Romantic Islamorada Hotels

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
  • 8 min drive from Theater of the Sea
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,149 reviews)

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

Travellers say...
"Great place. Best way to relax and enjoy the keys."

Reviewed on 17 Aug 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
  • 22 min walk from Theater of the Sea
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their ...
9/10 Wonderful! (1,501 reviews)

Couples like: bar, on the beach

Travellers say...
"Excellent location on the ocean and everything was really perfect. will stay there again"

Reviewed on 17 Aug 2025

Chesapeake Beach Resort
Large Screened Porch, Professional Cleaning, Wifi

Large Screened Porch, Professional Cleaning, Wifi

Tavernier, FL
  • 13 min drive from Theater of the Sea
Stay at this beach condo in Tavernier. Enjoy private pools, a beach locale and a sauna. Popular attractions Florida Keys Dive Center and Old Road Gallery are ...
9.2/10 Wonderful! (63 reviews)
Awesome condo
"AMAZING! This condo has EVERYTHING that you are looking for in a short or extended stay! The property amenities are great and the balcony view is beautiful. The owner was extremely helpful with any questions we had and was very responsive. Will stay here again in the future."

Reviewed on 2 Feb 2025

Large Screened Porch, Professional Cleaning, Wifi
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.