Top Romantic vacation packages in Islamorada

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

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$638

per person

Feb 2 - Feb 6

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Great stay and beautiful space

Reviewed on Dec 1, 2025

Amara Cay Resort

Matecumbe

$652

per person

Feb 2 - Feb 6

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (1,252 reviews)

This resort was beautiful, clean and fantastic. The staff was friendly and helpful. We had a wonderful day and will be back.

Reviewed on Nov 20, 2025

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$937

per person

Feb 2 - Feb 6

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Property is beautiful with tons of amenities. The room was very nice and overall we were very happy. Here are a few of the issues we had though for full transparency. The beach is sand, but it's hard in a way that's a bit unnatural and doesn't flow into the water. There were weddings on two nights we were there and the noise from the afterparty was loud in the rooms even with the doors shut. The noise went fairly late into the evening past when most places would have a noise curfew of sorts for the respect of other guests. The water temperature in the shower was either hard to control or broken as sometimes it was extremely hot and sometimes barely warm. The roof mounted fill for the outside tub was a neat feature, but it was very loud. When we checked in our room was not available. We were promised a call when it was ready, but never got one. We finally asked at the check in time and they said it was ready and we were supposed to have been given a call some time ago. We also noticed that every time we overheard the check-in information being given to a new guest, we heard information that had not been given to us. Parking was limited later in the evening and we struggled to find a spot. The alternative is to use valet, but I rarely opt for that unless it is required.

Reviewed on Dec 3, 2025

Islander Resort

Matecumbe

$746

per person

Jan 2 - Jan 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,005 reviews)

This resort is beautiful and the rooms are decorated so tastefully. I highly recommend The Islander Resort for family fun and couples get aways alike.

Reviewed on Dec 3, 2025

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5* Romantic vacations in Islamorada

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

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$937

per person

Feb 2 - Feb 6

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Property is beautiful with tons of amenities. The room was very nice and overall we were very happy. Here are a few of the issues we had though for full transparency. The beach is sand, but it's hard in a way that's a bit unnatural and doesn't flow into the water. There were weddings on two nights we were there and the noise from the afterparty was loud in the rooms even with the doors shut. The noise went fairly late into the evening past when most places would have a noise curfew of sorts for the respect of other guests. The water temperature in the shower was either hard to control or broken as sometimes it was extremely hot and sometimes barely warm. The roof mounted fill for the outside tub was a neat feature, but it was very loud. When we checked in our room was not available. We were promised a call when it was ready, but never got one. We finally asked at the check in time and they said it was ready and we were supposed to have been given a call some time ago. We also noticed that every time we overheard the check-in information being given to a new guest, we heard information that had not been given to us. Parking was limited later in the evening and we struggled to find a spot. The alternative is to use valet, but I rarely opt for that unless it is required.

Reviewed on Dec 3, 2025

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3 Night Romantic vacations in Islamorada

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

Amara Cay Resort

Matecumbe

Save 100% on your flight

$583

per person

Feb 4 - Feb 7

found 10 hours ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Miami (MIA)

8.8/10 Excellent! (1,252 reviews)

This resort was beautiful, clean and fantastic. The staff was friendly and helpful. We had a wonderful day and will be back.

Reviewed on Nov 20, 2025

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$896

per person

Feb 4 - Feb 7

found 10 hours ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Property is beautiful with tons of amenities. The room was very nice and overall we were very happy. Here are a few of the issues we had though for full transparency. The beach is sand, but it's hard in a way that's a bit unnatural and doesn't flow into the water. There were weddings on two nights we were there and the noise from the afterparty was loud in the rooms even with the doors shut. The noise went fairly late into the evening past when most places would have a noise curfew of sorts for the respect of other guests. The water temperature in the shower was either hard to control or broken as sometimes it was extremely hot and sometimes barely warm. The roof mounted fill for the outside tub was a neat feature, but it was very loud. When we checked in our room was not available. We were promised a call when it was ready, but never got one. We finally asked at the check in time and they said it was ready and we were supposed to have been given a call some time ago. We also noticed that every time we overheard the check-in information being given to a new guest, we heard information that had not been given to us. Parking was limited later in the evening and we struggled to find a spot. The alternative is to use valet, but I rarely opt for that unless it is required.

Reviewed on Dec 3, 2025

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$863

per person

Feb 6 - Feb 9

found 4 hours ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

Great stay and beautiful space

Reviewed on Dec 1, 2025

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4 Night Romantic vacations in Islamorada

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

Creekside Inn

$507

per person

Jan 2 - Jan 6

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8/10 Very Good! (1,004 reviews)

Very basic amenities. Comfortable bed. Friendly staff. Pool clean. Able to use Freebie app to have rides around to restaurants and bars. Right on creek.

Reviewed on Dec 2, 2025

Amara Cay Resort

Matecumbe

$652

per person

Feb 2 - Feb 6

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (1,252 reviews)

This resort was beautiful, clean and fantastic. The staff was friendly and helpful. We had a wonderful day and will be back.

Reviewed on Nov 20, 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

$754

per person

Jan 2 - Jan 6

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9/10 Wonderful! (108 reviews)

Beautiful room, stunning views

Reviewed on Nov 19, 2025

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How can I find the best Islamorada 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 Islamorada 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 Islamorada?

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 Islamorada?

Put a price on love with stunning deals for duos starting at just $507. 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 Islamorada 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 Islamorada?

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 Islamorada?

To book a loved-up break in Islamorada, 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 Islamorada 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 Islamorada 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 Islamorada Hotels

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

8 min drive from Theater of the Sea

Fall in love again at this upscale resort. You and your special someone are sure to love the hot tub, spa, and in-room massages. You'll also appreciate the ocean-view ...

9/10 Wonderful! (1,277 reviews)

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

Travelers say...

We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David ...

Reviewed on Nov 26, 2025

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

22 min walk from Theater of the Sea

A private beach and premium mattresses await at this romantic hotel, which also offers 2 outdoor pools and a white sand beach.

9.2/10 Wonderful! (1,591 reviews)

Couples like: bar, on the beach

Travelers say...

Great place

Reviewed on Nov 28, 2025

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

12 min drive from Theater of the Sea

Ocean-view dining, a garden, and a private beach await visiting couples at this romantic resort. The property also offers romance packages and premium ...

8.8/10 Excellent! (1,269 reviews)

Couples like: restaurant with ocean view, on the beach, romance packages available

Travelers say...

Loved the resort

Reviewed on Nov 21, 2025

See all 2,241 properties in Islamorada

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.