Islamorada Romantic Holidays

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How to find romantic Islamorada holiday packages on Expedia?

How can I book a romantic getaway in Islamorada?

Find your dream romantic Islamorada getaway on Expedia. From secluded hideaways to blissful spa treatments and charming country escapes, we’ve got it all. Just activate our “romantic” filters to uncover your ideal couple’s retreat in Islamorada.

How can I find cheap Islamorada romantic holidays?

Unveil the perfect and budget-friendly romantic getaways in Islamorada with Expedia. Our filters unlock countless options, ensuring a heart-pounding experience. Set budget filters to match your spending limits and sort by price to prioritise the most affordable options in your search results.

How can I select a romantic couple’s package for Islamorada?

In your search, you can apply search filters for Islamorada trip packages and sort your results to see the romantic getaway options first. With those standards, you could find amazing romantic holiday options in Islamorada, from winter getaways to secluded country or budget beach holidays with your loved one.

How can I find excellent romantic Islamorada holiday deals?

Plan your ultimate couple’s getaway in Islamorada with our user-friendly search tools. Opt for a hotel suite with a view worth sharing on Instagram. Cruise with the top down and feel the warm breeze in your hair with a luxury car hire. Decide on a romantic couple’s spa treatment, a beachfront candle-lit dinner, or a glamorous night out on the town.

How can I find last-minute romantic holiday deals to Islamorada using Expedia?

For last-minute romantic holiday package deals in Islamorada, enter your travel dates into the search and discover available deals. Customise your search with filters, covering amenities, price, star rating, and more to find your ideal romantic package for couples.

How can I find pet-friendly romantic getaway packages in Islamorada?

Refine your search with the “pet-friendly” filter to discover top pet-welcoming hotels and resorts in Islamorada. Experience a couple’s treatment, bask in beautiful surroundings, and revel in a pampering romantic getaway, knowing your pet is either by your side or well cared for in doggy day care.

How can I find great weekend couple’s holiday packages Islamorada?

Escape the weekly grind with fantastic couple’s weekend getaways in Islamorada. Enter your location and date preferences in your Expedia search and let us reveal hidden gems to leave you refreshed and love-struck for the week ahead.

Where can I find the most luxurious couple’s holiday packages in Islamorada?

Discover the ultimate luxury romantic packages in Islamorada with ease. Use the site’s or app’s search function to explore a range of lavish options, as well as to refine your choices by star rating and price.

Why should book I my romantic Islamorada holiday with Expedia?

Choose from our latest incredible deals or customise your trip in just a few clicks, with simple search and filter functions that make finding your next romantic Islamorada getaway easy. Plus, booking a package with Expedia could save you money, too, making a Islamorada holiday for couples all the more attractive.

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! (1,198 reviews)
Very Nice Resort and AMAZING STAFF!
"Honestly, we started with a pretty bad experience with some issues pertaining to our room. However, we mentioned it to Natalia at the concierge and she was SUPER accommodating! Needless to say that the issues were resolved immediately. Definitely recommend Cheeca Lodge & Spa to anyone looking for ..."

Reviewed on 16 Sept 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 WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,530 reviews)
Relaxation 😌
"Such a relaxing and fun spot. Enjoyed snorkeling every day at sunrise and sunset 😍 Can't wait for my next stay 🤗"

Reviewed on 15 Sept 2025

Chesapeake Beach Resort
Large Screened Porch, Professional Cleaning, Wifi

Large Screened Porch, Professional Cleaning, Wifi

Tavernier
  • 13 min drive from Theater of the Sea
Book a 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 ...
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.