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

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Check availability on Islamorada Romantic Hotels

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Islamorada romantic hotels

A beach with palm trees and lounge chairs.
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Leihla
AED 527
AED 799 total
includes taxes & fees
8 Oct - 9 Oct
Chesapeake Beach 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.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
RAIBEL
AED 604
AED 948 total
includes taxes & fees
12 Oct - 13 Oct
Cheeca Lodge & Spa
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.
A resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Danielle
AED 551
AED 888 total
includes taxes & fees
18 Oct - 19 Oct
Amara Cay Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A wooden pier leading to a beach with palm trees and a row of beach huts.
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.

4. Islander Resort

Islander Resort
Matecumbe
United States
Steven
AED 918
AED 1,302 total
includes taxes & fees
21 Oct - 22 Oct
Islander Resort
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.
A pool area with a view of the ocean, surrounded by palm trees and a clear sky.
A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.
A beach with palm trees, lounge chairs, and a view of the ocean.

5. Rock Reef Resort

Rock Reef Resort
Rock Harbor
United States
Tia
AED 403
AED 453 total
includes taxes & fees
6 Oct - 7 Oct
Rock Reef Resort
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.
A man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.
Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.
A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.

6. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
United States
Siobhan
AED 465
AED 643 total
includes taxes & fees
12 Oct - 13 Oct
Fisher Inn Resort & Marina
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A resort with a pool, beach, and ocean view.
A coastal resort with a beach, a swimming pool, and multiple buildings.
A beach with palm trees, a clear blue sky, and a calm sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Canada
Eslita
AED 790
AED 1,158 total
includes taxes & fees
18 Oct - 19 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Terrace/patio
A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.
A resort with a swimming pool, lounge chairs, and palm trees.
A beach with palm trees and a clear view of the ocean.

8. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
United States
Michael
AED 424
AED 643 total
includes taxes & fees
5 Oct - 6 Oct
Lime Tree Bay Resort
A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.
A beach with kayaks lined up near the water's edge, palm trees, and lounge chairs.
A beachside resort with lounge chairs, a pool, and palm trees.
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.

9. Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor
United States
Karen
AED 590
AED 767 total
includes taxes & fees
6 Oct - 7 Oct
Kona Kai Resort and Gallery - Adults Only
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 modern living room with a sofa, a glass coffee table, a TV, and a sliding door leading to a bedroom.
A beach with lounge chairs, kayaks, and a wooden pier.

10. Drift Hotel

Drift Hotel
Key Largo
United States
kelly
AED 341
AED 425 total
includes taxes & fees
7 Oct - 8 Oct
Drift Hotel
View all properties

Top Islamorada Hotel Reviews

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Super clean resort."
Danielle 3-night trip
Posted 1 day ago
Amara Cay Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"Great place. Friendly staff overall really wonderful."
Siobhan 1-night trip
Posted 2 days ago
Fisher Inn Resort & Marina
Drop Anchor

Drop Anchor

10/10 Excellent
"Exceeded all my expectations, definitely going back. Highly recommend"
Payman 3-night trip
Posted 9 days ago
Drop Anchor

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.