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

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Check availability on Islamorada Romantic Hotels

Tonight
7 Oct - 8 Oct
Tomorrow
8 Oct - 9 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Islamorada romantic hotels

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.
A tropical resort with a swimming pool, palm trees, and a waterfall.
A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Morgan
AED 604
AED 948 total
includes taxes & fees
19 Oct - 20 Oct
Cheeca Lodge & Spa
A beach with palm trees and lounge chairs.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Leihla
AED 532
AED 805 total
includes taxes & fees
8 Oct - 9 Oct
Chesapeake Beach 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.
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.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Danielle
AED 477
AED 805 total
includes taxes & fees
20 Oct - 21 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 beachside patio with wooden furniture, a thatched roof, and a view of the ocean.
A bar area with a wooden counter, bar stools, and potted plants.

4. Islander Resort

Islander Resort
Matecumbe
United States
Steven
AED 988
AED 1,380 total
includes taxes & fees
27 Oct - 28 Oct
Islander 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.
A hotel room with two beds, a TV, a desk with a chair, and a balcony with a view of greenery.
A man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.

5. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
United States
Siobhan
AED 582
AED 774 total
includes taxes & fees
1 Nov - 2 Nov
Fisher Inn Resort & Marina
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.
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.
A pool area with a view of the ocean, surrounded by palm trees and a clear sky.

6. Rock Reef Resort

Rock Reef Resort
Rock Harbor
United States
Tia
AED 320
AED 360 total
includes taxes & fees
13 Oct - 14 Oct
Rock Reef Resort
Terrace/patio
A resort with a swimming pool, lounge chairs, and palm trees.
A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.
A spacious living area with a large island, wooden furniture, and a ceiling fan.

7. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
United States
Michael
AED 447
AED 668 total
includes taxes & fees
8 Oct - 9 Oct
Lime Tree Bay Resort
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.
A beach with lounge chairs, kayaks, and a wooden pier.
A modern living room with a dark brown sofa, a coffee table, and a blue lamp. There is a kitchen area with a microwave and a coffee machine. A painting of a beach scene is on the wall.
A tree with string lights, a wooden bench, and a building in the background.

8. Drift Hotel

Drift Hotel
Key Largo
United States
kelly
AED 338
AED 421 total
includes taxes & fees
21 Oct - 22 Oct
Drift Hotel
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A beach with palm trees, a clear blue sky, and a calm sea.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.
A resort with a pool, beach, and ocean view.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
United States
Liosbel
AED 790
AED 1,158 total
includes taxes & fees
19 Oct - 20 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A beach with thatched umbrellas, wooden chairs, and a wooden pier 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.
A balcony with a view of the sea, a beach, and a thatched hut.
A garden with various trees and a gravel path.

10. Sunset Cove Beach Resort

Sunset Cove Beach Resort
Key Largo
United States
Payton
AED 430
AED 483 total
includes taxes & fees
12 Oct - 13 Oct
Sunset Cove Beach Resort
View all properties

Top Islamorada Hotel Reviews

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"Good stay"
Michael 1-night trip
Posted 19 hours ago
Fisher Inn Resort & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Absolutely beautiful property. The front desk staff is friendly and as helpful as you could ask for. The breakfast provided was excellent. We definitely took the opportunity to use all the activity options we could in a one-night stay. I will recommend this place to anyone and everyone."
Angie 1-night trip
Posted 20 hours ago
Chesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"Clean, comfortable rooms. On site amenities were fantastic!"
chris 3-night trip
Posted 1 day ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islander Resort

Islander Resort

10/10 Excellent
"We got the poolside cabana king and it was perfect! Resort was immaculate! Already want to go back!"
Cheyenne 4-night trip
Posted 1 day ago
Islander Resort
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Very clean resort. The pool was fabulous. The tiki bar was great. Stall friendly and helpful. Truly enjoyed my stay!"
Maureen 2-night trip
Posted 1 day ago
Amara Cay Resort
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Amazing gym, really cool pool with waterfall, beautiful view of the sunrise on a small beach. Overall was super nice."
Heidi 2-night trip
Posted 3 days ago
Coconut Cove Resort and Marina
Drop Anchor

Drop Anchor

10/10 Excellent
"Exceeded all my expectations, definitely going back. Highly recommend"
Payman 3-night trip
Posted 13 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.