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 balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

1. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (83 reviews)
"We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back."
United States
Catherine
The price is AED 2,437
AED 3,010 total
includes taxes & fees
30 Nov - 1 Dec
The Islands of Islamorada
A beach with palm trees and lounge chairs.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,810 reviews)
"Location is amazing make sure to book a balcony with a view"
United States
Olga Vasiliy
The price is AED 538
AED 812 total
includes taxes & fees
10 Nov - 11 Nov
Chesapeake Beach Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,162 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
The price is AED 658
AED 1,009 total
includes taxes & fees
15 Nov - 16 Nov
Islander Resort
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, (1,511 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 wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

5. 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 409
AED 563 total
includes taxes & fees
10 Nov - 11 Nov
La Jolla Resort
Exterior

6. 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 balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

7. 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, (309 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.

8. 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 919
AED 1,303 total
includes taxes & fees
9 Nov - 10 Nov
Bayside Villas by Islander Resort
A balcony with a view of a beach, a pool, and a thatched-roof structure.

9. 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.

10. 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
A wooden deck with a picnic table, surrounded by palm trees and tropical plants.

11. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (278 reviews)
"Incredible place, ample room and everything you need to cook and to bbq."
United States
Nathalie
The price is AED 472
AED 531 total
includes taxes & fees
18 Nov - 19 Nov
Ragged Edge Resort & Marina
A wooden deck with white railings, outdoor seating, and a view of the sea with palm trees.

12. Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.6 out of 10, Exceptional, (561 reviews)
"Beautiful place hidden in Tavenier Great staff and the best sunset in the keys"
United States
ED
The price is AED 856
AED 1,108 total
includes taxes & fees
10 Nov - 11 Nov
Coconut Palm Inn
A beach with lounge chairs, palm trees, and a view of the water.

13. Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (836 reviews)
"Excellent Stay!"
United States
Annette
The price is AED 547
AED 698 total
includes taxes & fees
1 Dec - 2 Dec
Atlantic Bay Resort
Terrace/patio

14. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,585 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
18 Nov - 19 Nov
Lime Tree Bay Resort
A beachside lounge with two blue umbrellas, a hammock, and lounge chairs.

15. Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor
9.2 out of 10, Wonderful, (266 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 316
AED 408 total
includes taxes & fees
19 Nov - 20 Nov
Seafarer Key Largo
A covered outdoor area with a view of a beach and palm trees.

16. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,206 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 beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

17. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,002 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 bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.

18. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.2 out of 10, Wonderful, (34 reviews)
"Very friendly staff"
United States
Maria
The price is AED 684
AED 770 total
includes taxes & fees
16 Nov - 17 Nov
The Ocean View Inn & Pub
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

19. 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 palm trees, a dock, and a boat named "STYX".

20. 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
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Perfect halfway stop off for trip to The Keys . Staff exceptionally helpful.. particularly ‘Fran’ I think that was her name on Front Desk. Great pools and loved the bikes ! Rooms were spacious and comfy beds. Recommend Lorelei Restaurant for something to eat off site ..! Great stay, definitely recommend."
Claire 1-night trip
Posted 13 hours ago
Cheeca Lodge & Spa

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.