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

Find Romantic Hotels in Islamorada, FL

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Check availability on Islamorada Romantic Hotels

Tonight
19 Oct - 20 Oct
Tomorrow
20 Oct - 21 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Islamorada romantic hotels

A beach with palm trees and lounge chairs.
A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Dianne
AED 521
AED 793 total
includes taxes & fees
20 Oct - 21 Oct
Chesapeake Beach Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A bar area with a wooden counter, bar stools, and potted plants.
A paved pathway leading to a beach with palm trees and a view of the ocean.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

2. Islander Resort

Islander Resort
Matecumbe
United States
Bryan
AED 717
AED 1,075 total
includes taxes & fees
15 Nov - 16 Nov
Islander Resort
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
A beach with palm trees, a dock, and lounge chairs.
A resort pool with palm trees, beach chairs, and umbrellas.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Ronald
AED 519
AED 852 total
includes taxes & fees
16 Nov - 17 Nov
Amara Cay Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A tropical resort with a swimming pool, palm trees, and a waterfall.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.

4. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
James
AED 651
AED 1,000 total
includes taxes & fees
21 Oct - 22 Oct
Cheeca Lodge & Spa
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.
A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.
A wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.
A beach with palm trees, lounge chairs, and a view of the ocean.

5. Rock Reef Resort

Rock Reef Resort
Rock Harbor
United States
Jared
AED 280
AED 315 total
includes taxes & fees
27 Oct - 28 Oct
Rock Reef Resort
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.
A balcony with a view of the sea, a beach, and a thatched hut.
A waterfront pier with wooden posts and a wooden walkway extending into the water.
A view through a door of a tropical outdoor area with a pathway leading to a beach, palm trees, and a clear sky.

6. Sunset Cove Beach Resort

Sunset Cove Beach Resort
Key Largo
Canada
Alexey
AED 404
AED 454 total
includes taxes & fees
20 Oct - 21 Oct
Sunset Cove Beach Resort
Terrace/patio
A resort with a swimming pool, lounge chairs, and palm trees.
A beach with palm trees and a clear view of the ocean.
A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.

7. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
United States
Christopher Michael
AED 424
AED 643 total
includes taxes & fees
20 Oct - 21 Oct
Lime Tree Bay Resort
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.
Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.
A hotel room with two beds, a TV, a desk with a chair, and a balcony with a view of greenery.

8. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
United States
Robyn
AED 545
AED 733 total
includes taxes & fees
25 Oct - 26 Oct
Fisher Inn Resort & Marina
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.
A tree with string lights, a wooden bench, and a building in the background.
A beach with lounge chairs, kayaks, and a wooden pier.
A modern living room with a sofa, a glass coffee table, a TV, and a sliding door leading to a bedroom.

9. Drift Hotel

Drift Hotel
Key Largo
United States
kelly
AED 406
AED 498 total
includes taxes & fees
21 Oct - 22 Oct
Drift Hotel
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.
A row of floating cottages with balconies and outdoor seating, docked along a waterway.
A pool area with a white fence, a lifebuoy, and palm trees in the background.
A kitchen with white cabinets, a microwave, a stove, and a refrigerator.

10. Treasure Harbor

Treasure Harbor
Islamorada
United States
Laura
AED 393
AED 959 total
includes taxes & fees
20 Oct - 21 Oct
Treasure Harbor
View all properties

Top Islamorada Hotel Reviews

Amara Cay Resort

Amara Cay Resort

8/10 Good
"Clean room and nice amenities. Parking was good. Common areas very well designed."
Alfonso 1-night trip
Posted 7 hours ago
Amara Cay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Very professional reception, room clean staff very polite"
Rene 1-night trip
Posted 12 hours ago
Chesapeake Beach Resort
Islander Resort

Islander Resort

10/10 Excellent
"We had an incredible stay here. Great views, delicious food, and the staff went above and beyond to make our stay exceptional. We already can’t wait to come back!"
Michaela 1-night trip
Posted 13 hours ago
Islander Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"Room wash clean, bed and pillows very comfortable and staff was friendly. Lots of little ants on the outdoor walkway and stairs but none in the room."
Janell 1-night trip
Posted 15 hours ago
Fisher Inn Resort & Marina
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"We have stayed here multiple times and always have a good stay."
Michael 1-night trip
Posted 1 day ago
Pines & Palms 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.