A beach with white lounge chairs, a covered pavilion, and palm trees.

Find Romantic Hotels in Islamorada, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Islamorada Romantic Hotels

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Our top choices for Islamorada romantic hotels

A beach with palm trees and lounge chairs.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,808 reviews)
"Location is amazing make sure to book a balcony with a view"
United States
Olga Vasiliy
The price is AED 532
AED 805 total
includes taxes & fees
10 Nov - 11 Nov
Chesapeake Beach Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

2. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
United States
Jane
The price is AED 460
AED 621 total
includes taxes & fees
18 Nov - 19 Nov
La Jolla Resort
A hammock tied between two poles with a person sitting in it, overlooking a body of water and boats in the background during sunset.

3. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (467 reviews)
"Very helpful staff and great location"
United States
David
The price is AED 674
AED 800 total
includes taxes & fees
16 Nov - 17 Nov
Casa Morada
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

4. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,509 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is AED 666
AED 1,018 total
includes taxes & fees
19 Nov - 20 Nov
Cheeca Lodge & Spa
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (308 reviews)
"Great place to stay!"
United States
Liosbel
The price is AED 761
AED 1,125 total
includes taxes & fees
29 Nov - 30 Nov
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

6. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (468 reviews)
"Had a blast in the keys! This property gave us every reason to stay on property! Fishing provided! Bait provided! Games, bikes, excellent staff and the vibes are worth every booking moment! Definitely coming back! FYI: we stay in the townhomes and still had access to all of the amenities! Book your stay! Let’s go!"
United States
Brian
The price is AED 930
AED 1,314 total
includes taxes & fees
8 Nov - 9 Nov
Bayside Villas by Islander Resort
A balcony with a view of a beach, a pool, and a thatched-roof structure.

7. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,002 reviews)
"Can’t wait to stay again in the spring. Amazing property."
United States
Jason
The price is AED 493
AED 674 total
includes taxes & fees
29 Nov - 30 Nov
Hadley Resort and Marina
A beach with palm trees, a thatched-roof structure, and kayaks.

8. Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
2.5 star property
Rock Harbor
9.8 out of 10, Exceptional, (368 reviews)
"We had a great stay. Nice, cosy, and clean. Very quiet, which we loved. Great views from the dock. We will be back!"
Canada
Daniel
The price is AED 691
AED 881 total
includes taxes & fees
10 Nov - 11 Nov
Kona Kai Resort and Gallery - Adults Only
Three Adirondack chairs facing a sunset over a body of water.

9. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (277 reviews)
"Incredible place, ample room and everything you need to cook and to bbq."
United States
Nathalie
The price is AED 480
AED 540 total
includes taxes & fees
18 Nov - 19 Nov
Ragged Edge Resort & Marina
Terrace/patio

10. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,580 reviews)
"We truly enjoyed our stay at Lime Tree Bay. The room was nice and clean and I loved being able to relax in the chairs/hammocks close to the water."
United States
Jessica
The price is AED 455
AED 677 total
includes taxes & fees
17 Nov - 18 Nov
Lime Tree Bay Resort
A covered outdoor area with a view of a beach and palm trees.

11. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,205 reviews)
"cute nice place in an incredible spot. Will visit there again for sure."
United States
keith
The price is AED 332
AED 373 total
includes taxes & fees
15 Nov - 16 Nov
Rock Reef Resort
A beachside lounge with two blue umbrellas, a hammock, and lounge chairs.

12. Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor
9.2 out of 10, Wonderful, (265 reviews)
"This may be my favorite place I've stayed in the Keys! So quaint and the location and breakfast were amazing. We kayaked to the mangroves, ate at the wonderful restaurant across the street (Ballyhoos), and thoroughly enjoyed the beach area"
United States
Brittany
The price is AED 450
AED 558 total
includes taxes & fees
9 Nov - 10 Nov
Seafarer Key Largo
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

13. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,001 reviews)
"Very nice clean hotel with friendly staff."
Canada
Alexey
The price is AED 446
AED 502 total
includes taxes & fees
29 Nov - 30 Nov
Sunset Cove Beach Resort
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

14. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"We have stayed here multiple times and always have a good stay."
United States
Michael
The price is AED 702
AED 993 total
includes taxes & fees
15 Nov - 16 Nov
Pines & Palms Resort
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

15. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,002 reviews)
"Excellent location"
United States
kelly
The price is AED 383
AED 472 total
includes taxes & fees
9 Nov - 10 Nov
Drift Hotel
A beach with palm trees, a dock, and a boat named "STYX".

16. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1,007 reviews)
"Loved the location and the staff were very friendly"
United States
SUSAN
The price is AED 367
AED 413 total
includes taxes & fees
29 Nov - 30 Nov
The Pelican Key Largo Cottages
A pool area with palm trees and a building with a white roof.

17. Bahia Bay Resort

Bahia Bay Resort
2.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (206 reviews)
"This is our best kept secret! We love it here! We have stayed multiple times and will be back!!"
United States
Patricia
The price is AED 1,093
AED 1,229 total
includes taxes & fees
19 Nov - 20 Nov
Bahia Bay Resort
An aerial view of a resort with a large pool, palm trees, and a beach.

18. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,003 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
The price is AED 966
AED 1,289 total
includes taxes & fees
29 Nov - 30 Nov
Playa Largo Resort & Spa, Autograph Collection
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

19. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (181 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is AED 393
AED 959 total
includes taxes & fees
8 Nov - 9 Nov
Treasure Harbor
A beach with palm trees, thatched-roof huts, and lounge chairs.

20. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (780 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is AED 254
AED 476 total
includes taxes & fees
10 Nov - 11 Nov
Breezy Palms Resort
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.
View all properties

Top Islamorada Hotel Reviews

Amara Cay Resort

Amara Cay Resort

8/10 Good
"Have been staying here for years. The restaurant is excellent. Staff is nice. Unfortunately, the resort has become dog friendly. For this reason I will no longer stay here."
Robert 2-night trip
Posted less than an hour ago
Amara Cay Resort

Frequently asked questions

Searching for romantic hotels in Islamorada?
If you and your partner need a romantic escape, we've got just the ticket. Our guests also love Islamorada for its top seafood restaurants, fishing, and beautiful ocean views. You might consider checking out some of the nearby sights and attractions such as Bud n' Mary's Dive Center, Robbie's of Islamorada, or Anne's Beach. If you'd like to stay close to a particular destination, you can sort by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Islamorada?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Islamorada: The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.
What is there to do in Islamorada?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in Islamorada. Couples looking for a little of everything will enjoy Islamorada for its opera houses, theater scene, and fishing. If you want to spend a day exploring, you might consider a stop at Bud n' Mary's Dive Center, Robbie's of Islamorada, or Anne's Beach.
What's the best way to get to Islamorada and around town during my romantic getaway?
This information about transportation options in Islamorada might help your romantic trip get off to a smooth start: Make your way to Islamorada with a flight to Marathon, FL (MTH-Florida Keys Marathon), which is the closest major airport located 30 mi (48.2 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.