Hotels in Islamorada

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Where to stay in Islamorada?

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 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
$151
$226 total
includes taxes & fees
Oct 18 - Oct 19
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 resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

2. Amara Cay Resort

Amara Cay Resort
Matecumbe
$172
$266 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay Resort
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.

3. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
$199
$297 total
includes taxes & fees
Oct 19 - Oct 20
Cheeca Lodge & Spa
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.
A beach with wooden lounge chairs, palm trees, and a clear view of the ocean.
A beachfront property with a staircase leading to a light blue building, palm trees, and a clear view of the ocean.
A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.

4. La Jolla Resort

La Jolla Resort
Matecumbe
$143
$189 total
includes taxes & fees
Oct 22 - Oct 23
La Jolla Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.
A beach with thatched umbrellas, palm trees, and lounge chairs.
A living room with a sofa, armchair, coffee table, and lamp. There is a dining area with a table and chairs. The room has a kitchen area with a stove and cabinets.
A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

5. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
$109
$139 total
includes taxes & fees
Oct 18 - Oct 19
Breezy Palms Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
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.
A wooden pier leading to a beach with palm trees and a row of beach huts.

6. Islander Resort

Islander Resort
Matecumbe
$208
$307 total
includes taxes & fees
Oct 18 - Oct 19
Islander Resort
A beachside patio with white furniture, palm trees, and a thatched umbrella.
A wooden boardwalk leading to a building with a brick wall and a white roof.
A pool area with lounge chairs and a sign indicating a drop-off zone.
A beach with palm trees, a thatched umbrella, and lounge chairs.

7. Drop Anchor

Drop Anchor
Islamorada
$123
$174 total
includes taxes & fees
Oct 18 - Oct 19
Drop Anchor
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.

8. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
$159
$212 total
includes taxes & fees
Oct 28 - Oct 29
Fisher Inn Resort & Marina
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 beach with palm trees, lounge chairs, and a view of the ocean.
A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.

9. Rock Reef Resort

Rock Reef Resort
Rock Harbor
$87
$98 total
includes taxes & fees
Oct 21 - Oct 22
Rock Reef Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.
A resort with thatched-roof structures, palm trees, and a sandy beach area.
A beach with palm trees, a thatched-roof hut, and lounge chairs.

10. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
$149
$168 total
includes taxes & fees
Oct 26 - Oct 27
Coconut Cove Resort and Marina
A beach with rows of sun loungers and palm trees.
A spacious room with a high ceiling, a ceiling fan, a dining table with chairs, a sofa, and a television mounted on the wall.
Three Adirondack chairs facing a sunset over a body of water.
A marina with a boat docked at a wooden pier, surrounded by palm trees and buildings.

11. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
Islamorada
$131
$147 total
includes taxes & fees
Oct 18 - Oct 19
Ragged Edge Resort & Marina
A balcony with a view of a beach, a pool, and a thatched-roof structure.
A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.
A beach scene with two yellow beach chairs and a person lying on one.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.

12. Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
$159
$212 total
includes taxes & fees
Nov 9 - Nov 10
Hadley Resort and Marina
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.
A resort with a pool, beach, and ocean view.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$239
$342 total
includes taxes & fees
Nov 3 - Nov 4
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.

14. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
$130
$192 total
includes taxes & fees
Oct 28 - Oct 29
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 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.

15. Drift Hotel

Drift Hotel
Key Largo
$111
$136 total
includes taxes & fees
Oct 21 - Oct 22
Drift Hotel
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A resort with a pool surrounded by palm trees and a view of the ocean.
A row of colorful beach huts with palm trees in the background.

16. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
$172
$266 total
includes taxes & fees
Nov 15 - Nov 16
La Siesta Resort & Villas
A beach with lounge chairs, palm trees, and a view of the water.
A paved pathway lined with palm trees leading to a beach area with lounge chairs and a view of the ocean.
A spacious bedroom with a bed, a dresser, a television, and a view of the sea through the window.
A beachside seating area with Adirondack chairs and a table, palm trees, and a view of the ocean.

17. Atlantic Bay Resort

Atlantic Bay Resort
Tavernier
$160
$202 total
includes taxes & fees
Oct 18 - Oct 19
Atlantic Bay Resort
A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.
A sign for Matecumbe Resort with a full kitchen and heated pool.
A compact kitchen with modern appliances, a dining area with a sofa, and a large window providing natural light.
A compact kitchen with wooden cabinets, a refrigerator, and a window with curtains.

18. Matecumbe Resort

Matecumbe Resort
Matecumbe
$144
$162 total
includes taxes & fees
Oct 18 - Oct 19
Matecumbe Resort
A wooden dock extending over calm turquoise water, lined with white railings and palm trees.
A swimming pool with a rock waterfall feature and a 3 ft depth marker.
A hallway with a tiled floor, a painting on the wall, a lamp, and a view of a pool area.
A waterfront patio with outdoor seating, a yellow umbrella, and a view of the water.

19. Creekside Inn

Creekside Inn
Tavernier
$143
$161 total
includes taxes & fees
Nov 15 - Nov 16
Creekside Inn
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
A resort with a pool, multiple buildings, and a waterfront view.
A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.
A hotel room with a bed, a TV, a sofa, and a balcony with a view.

20. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
$107
$152 total
includes taxes & fees
Oct 26 - Oct 27
Dove Creek Resort & Marina, Trademark Collection by Wyndham
View all properties

Get last-minute hotel deals in Islamorada and save more

Sign in to unlock great savings.
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 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.

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
$170
per night
$248 total
includes taxes & fees
Sign in for extra savings
Chesapeake Beach 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.

Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
$50 off
$116
per night
$175 total
includes taxes & fees
Lime Tree Bay 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 resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

Amara Cay Resort

Amara Cay Resort
Matecumbe
$181
per night
$277 total
includes taxes & fees
Amara Cay Resort
A beachside patio with white furniture, palm trees, and a thatched umbrella.
A wooden boardwalk leading to a building with a brick wall and a white roof.
A pool area with lounge chairs and a sign indicating a drop-off zone.
A beach with palm trees, a thatched umbrella, and lounge chairs.

Drop Anchor

Drop Anchor
Islamorada
$28 off
$113
per night
$162 total
includes taxes & fees
Drop Anchor
A beach with lounge chairs, palm trees, and a view of the water.
A paved pathway lined with palm trees leading to a beach area with lounge chairs and a view of the ocean.
A spacious bedroom with a bed, a dresser, a television, and a view of the sea through the window.
A beachside seating area with Adirondack chairs and a table, palm trees, and a view of the ocean.

Atlantic Bay Resort

Atlantic Bay Resort
Tavernier
$160
per night
$202 total
includes taxes & fees
Sign in for extra savings
Atlantic Bay Resort
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
A resort with a pool, multiple buildings, and a waterfront view.
A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.
A hotel room with a bed, a TV, a sofa, and a balcony with a view.

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
$13 off
$116
per night
$162 total
includes taxes & fees
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Two hands holding wine glasses with a beach and ocean view in the background.
A bed with white and turquoise pillows, a bottle of champagne, and two glasses on a round table.
A beach with palm trees, a sandy path, and a building with a balcony.
A hand holding a card with the Bayside Inn logo, palm trees, and a beach setting in the background.

Bayside Inn Key Largo

Bayside Inn Key Largo
Key Largo
$118
per night
$158 total
includes taxes & fees
Sign in for extra savings
Bayside Inn Key Largo
A poolside area with a water feature, a palm tree, and lounge chairs.
A marina with boats docked, a dock, and a building with a blue roof.
A beach with rows of sun loungers, a thatched hut, and a wooden walkway leading to the water.
A balcony with a view of the sea, a white chair, and two buckets with a red shovel.

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
Tavernier
$32 off
$129
per night
$167 total
includes taxes & fees
Ocean Pointe Suites at Key Largo
A beachside lounge with a wooden deck, thatched roof, and tropical plants.
A resort with a central swimming pool surrounded by palm trees and a view of the ocean.
A bar area with a counter, stools, and potted plants.
A waterfront property with a paved walkway, palm trees, and a white building with a dock.

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
$351
per night
$468 total
includes taxes & fees
Sign in for extra savings
Bayside Villas by Islander 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.

Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
$71 off
$165
per night
$231 total
includes taxes & fees
Lime Tree Bay 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 resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

Amara Cay Resort

Amara Cay Resort
Matecumbe
$27 off
$242
per night
$345 total
includes taxes & fees
Amara Cay Resort
A beachside patio with white furniture, palm trees, and a thatched umbrella.
A wooden boardwalk leading to a building with a brick wall and a white roof.
A pool area with lounge chairs and a sign indicating a drop-off zone.
A beach with palm trees, a thatched umbrella, and lounge chairs.

Drop Anchor

Drop Anchor
Islamorada
$47 off
$172
per night
$229 total
includes taxes & fees
Drop Anchor
Two hands holding wine glasses with a beach and ocean view in the background.
A bed with white and turquoise pillows, a bottle of champagne, and two glasses on a round table.
A beach with palm trees, a sandy path, and a building with a balcony.
A hand holding a card with the Bayside Inn logo, palm trees, and a beach setting in the background.

Bayside Inn Key Largo

Bayside Inn Key Largo
Key Largo
$146
per night
$189 total
includes taxes & fees
Sign in for extra savings
Bayside Inn Key Largo
A beach with lounge chairs, palm trees, and a view of the water.
A paved pathway lined with palm trees leading to a beach area with lounge chairs and a view of the ocean.
A spacious bedroom with a bed, a dresser, a television, and a view of the sea through the window.
A beachside seating area with Adirondack chairs and a table, palm trees, and a view of the ocean.

Atlantic Bay Resort

Atlantic Bay Resort
Tavernier
$240
per night
$292 total
includes taxes & fees
Sign in for extra savings
Atlantic Bay Resort
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
A resort with a pool, multiple buildings, and a waterfront view.
A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.
A hotel room with a bed, a TV, a sofa, and a balcony with a view.

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
$18 off
$161
per night
$213 total
includes taxes & fees
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A poolside area with a water feature, a palm tree, and lounge chairs.
A marina with boats docked, a dock, and a building with a blue roof.
A beach with rows of sun loungers, a thatched hut, and a wooden walkway leading to the water.
A balcony with a view of the sea, a white chair, and two buckets with a red shovel.

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
Tavernier
$45 off
$179
per night
$223 total
includes taxes & fees
Ocean Pointe Suites at Key Largo
A beachside lounge with a wooden deck, thatched roof, and tropical plants.
A resort with a central swimming pool surrounded by palm trees and a view of the ocean.
A bar area with a counter, stools, and potted plants.
A waterfront property with a paved walkway, palm trees, and a white building with a dock.

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
$441
per night
$569 total
includes taxes & fees
Sign in for extra savings
Bayside Villas by Islander Resort
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 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.

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
$74 off
$332
per night
$860 total
includes taxes & fees
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 resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

Amara Cay Resort

Amara Cay Resort
Matecumbe
$73 off
$327
per night
$881 total
includes taxes & fees
Amara Cay Resort
A beachside patio with white furniture, palm trees, and a thatched umbrella.
A wooden boardwalk leading to a building with a brick wall and a white roof.
A pool area with lounge chairs and a sign indicating a drop-off zone.
A beach with palm trees, a thatched umbrella, and lounge chairs.

Drop Anchor

Drop Anchor
Islamorada
$133 off
$231
per night
$590 total
includes taxes & fees
Drop Anchor
A beach with lounge chairs, palm trees, and a view of the water.
A paved pathway lined with palm trees leading to a beach area with lounge chairs and a view of the ocean.
A spacious bedroom with a bed, a dresser, a television, and a view of the sea through the window.
A beachside seating area with Adirondack chairs and a table, palm trees, and a view of the ocean.

Atlantic Bay Resort

Atlantic Bay Resort
Tavernier
$280
per night
$674 total
includes taxes & fees
Sign in for extra savings
Atlantic Bay Resort
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.
A resort with a pool, beach, and ocean view.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$481
per night
$1,228 total
includes taxes & fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.
A beachside resort with a pool area, lounge chairs, and palm trees.
A beach with palm trees, a wooden pier, and beach chairs.
A coastal resort with a marina, clear blue water, and lush greenery.

Pines & Palms Resort

Pines & Palms Resort
Matecumbe
$395
per night
$999 total
includes taxes & fees
Sign in for extra savings
Pines & Palms Resort
Two hands holding wine glasses with a beach and ocean view in the background.
A bed with white and turquoise pillows, a bottle of champagne, and two glasses on a round table.
A beach with palm trees, a sandy path, and a building with a balcony.
A hand holding a card with the Bayside Inn logo, palm trees, and a beach setting in the background.

Bayside Inn Key Largo

Bayside Inn Key Largo
Key Largo
$20 off
$204
per night
$508 total
includes taxes & fees
Bayside Inn Key Largo
A beachside lounge with a wooden deck, thatched roof, and tropical plants.
A resort with a central swimming pool surrounded by palm trees and a view of the ocean.
A bar area with a counter, stools, and potted plants.
A waterfront property with a paved walkway, palm trees, and a white building with a dock.

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
$397
per night
$1,039 total
includes taxes & fees
Sign in for extra savings
Bayside Villas by Islander Resort

Check out pet-friendly hotels in Islamorada

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
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.
A wooden pier leading to a beach with palm trees and a row of beach huts.

Islander Resort

Islander Resort
Matecumbe
$208
$307 total
includes taxes & fees
Oct 18 - Oct 19
Islander Resort
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 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.

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
$151
$226 total
includes taxes & fees
Oct 18 - Oct 19
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 resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

Amara Cay Resort

Amara Cay Resort
Matecumbe
$172
$266 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay Resort
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.
A resort with a pool, beach, and ocean view.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$239
$342 total
includes taxes & fees
Nov 3 - Nov 4
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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.

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
$159
$212 total
includes taxes & fees
Oct 28 - Oct 29
Fisher Inn Resort & Marina
A balcony with a view of a beach, a pool, and a thatched-roof structure.
A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.
A beach scene with two yellow beach chairs and a person lying on one.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
$159
$212 total
includes taxes & fees
Nov 9 - Nov 10
Hadley Resort and Marina
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A resort with a pool surrounded by palm trees and a view of the ocean.
A row of colorful beach huts with palm trees in the background.

La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
$172
$266 total
includes taxes & fees
Nov 15 - Nov 16
La Siesta Resort & Villas
A beachside patio with white furniture, palm trees, and a thatched umbrella.
A wooden boardwalk leading to a building with a brick wall and a white roof.
A pool area with lounge chairs and a sign indicating a drop-off zone.
A beach with palm trees, a thatched umbrella, and lounge chairs.

Drop Anchor

Drop Anchor
Islamorada
$123
$174 total
includes taxes & fees
Oct 18 - Oct 19
Drop Anchor
A beachside lounge with a wooden deck, thatched roof, and tropical plants.
A resort with a central swimming pool surrounded by palm trees and a view of the ocean.
A bar area with a counter, stools, and potted plants.
A waterfront property with a paved walkway, palm trees, and a white building with a dock.

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
$284
$392 total
includes taxes & fees
Oct 29 - Oct 30
Bayside Villas by Islander Resort
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.
A cozy living room with a pool table, a large bookshelf, and comfortable seating.
An aerial view of a resort with two large swimming pools surrounded by palm trees and lounge chairs.
A child sitting on a beach with sand toys and a green bucket nearby.

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
$294
$386 total
includes taxes & fees
Oct 28 - Oct 29
Baker's Cay Resort Key Largo, Curio Collection by Hilton
View all properties

You may also like resorts in Islamorada

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.

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
$199
$297 total
includes taxes & fees
Oct 19 - Oct 20
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.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

Amara Cay Resort

Amara Cay Resort
Matecumbe
$172
$266 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay Resort
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.
A resort with a pool, beach, and ocean view.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$239
$342 total
includes taxes & fees
Nov 3 - Nov 4
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A resort with a pool surrounded by palm trees and a view of the ocean.
A row of colorful beach huts with palm trees in the background.

La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
$172
$266 total
includes taxes & fees
Nov 15 - Nov 16
La Siesta Resort & Villas
A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.
A sign for Matecumbe Resort with a full kitchen and heated pool.
A compact kitchen with modern appliances, a dining area with a sofa, and a large window providing natural light.
A compact kitchen with wooden cabinets, a refrigerator, and a window with curtains.

Matecumbe Resort

Matecumbe Resort
Matecumbe
$144
$162 total
includes taxes & fees
Oct 18 - Oct 19
Matecumbe Resort
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.
A cozy living room with a pool table, a large bookshelf, and comfortable seating.
An aerial view of a resort with two large swimming pools surrounded by palm trees and lounge chairs.
A child sitting on a beach with sand toys and a green bucket nearby.

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
$294
$386 total
includes taxes & fees
Oct 28 - Oct 29
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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.

Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
$130
$192 total
includes taxes & fees
Oct 28 - Oct 29
Lime Tree Bay Resort
An aerial view of a resort with a large pool, palm trees, and a beach.
A beach with clear water, a wooden pier, and lounge chairs under a tree.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
$279
$369 total
includes taxes & fees
Oct 29 - Oct 30
Playa Largo Resort & Spa, Autograph Collection
View all properties

You can also stay at hotels with a pool in Islamorada

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.

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
$199
$297 total
includes taxes & fees
Oct 19 - Oct 20
Cheeca Lodge & Spa
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
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.
A wooden pier leading to a beach with palm trees and a row of beach huts.

Islander Resort

Islander Resort
Matecumbe
$208
$307 total
includes taxes & fees
Oct 18 - Oct 19
Islander Resort
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 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.

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
$151
$226 total
includes taxes & fees
Oct 18 - Oct 19
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 resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

Amara Cay Resort

Amara Cay Resort
Matecumbe
$172
$266 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.
A beach with wooden lounge chairs, palm trees, and a clear view of the ocean.
A beachfront property with a staircase leading to a light blue building, palm trees, and a clear view of the ocean.
A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.

La Jolla Resort

La Jolla Resort
Matecumbe
$143
$189 total
includes taxes & fees
Oct 22 - Oct 23
La Jolla Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.
A resort with thatched-roof structures, palm trees, and a sandy beach area.
A beach with palm trees, a thatched-roof hut, and lounge chairs.

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
$149
$168 total
includes taxes & fees
Oct 26 - Oct 27
Coconut Cove Resort and Marina
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.
A resort with a pool, beach, and ocean view.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$239
$342 total
includes taxes & fees
Nov 3 - Nov 4
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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.

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
$159
$212 total
includes taxes & fees
Oct 28 - Oct 29
Fisher Inn Resort & Marina
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A pool area with clear blue water, white lounge chairs, and palm trees.
A gated entrance to a resort with palm trees and a clear sky.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.

The Islands of Islamorada

The Islands of Islamorada
Matecumbe
$580
$719 total
includes taxes & fees
Oct 18 - Oct 19
The Islands of Islamorada
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A resort with a pool surrounded by palm trees and a view of the ocean.
A row of colorful beach huts with palm trees in the background.

La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
$172
$266 total
includes taxes & fees
Nov 15 - Nov 16
La Siesta Resort & Villas
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
Our prices for hotels in Islamorada are cheapest in September
Price trends for hotels in Islamorada
Pricing is based on two traveler single night rates
View properties in October
Typical weather for Islamorada
October
High 28°C / low 26°C. Sunny most days.
View properties in October
28°
26°
26°
23°
24°
21°
23°
19°
23°
21°
24°
21°
26°
24°
27°
25°
29°
27°
30°
28°
30°
28°
29°
28°
Monthly weather averages (˚C)

Top neighborhoods in Islamorada

A shark sculpture with a sign above it that reads "Islamorada Florida Keys".
A marina with boats docked, a motel, and a cafe.
A calm lake with a reflection of trees and a cloudy sky.
Photo by Joel Rosenblatt
A beachside café with colorful chairs and tables, palm trees, and a view of the ocean.
A beach with white lounge chairs, a covered pavilion, and palm trees.

Matecumbe

Matecumbe gives you the full Florida Keys experience without trying too hard. Snorkel crystal waters at Anne's Beach, grab a cold one at Florida Keys Brewing Co, or watch fishermen haul in their catch at Bud n' Mary's. The Hurricane Monument and Indian Key Historic State Park tell stories of this laid-back paradise, while the MoradaWay Arts District adds cultural flair. Waterfront tiki bars serve fresh mahi-mahi as the sun sets over Florida Bay. Most visitors stay in charming resorts with private beaches and pools, though vacation rentals offer more space. You'll need a car to explore properly, but many resort areas are perfectly walkable.

A clear blue sea with a sandy beach and a distant horizon.

Lower Matecumbe Beach

Lower Matecumbe Beach offers pristine Atlantic shorelines where powder-soft sand meets crystal-clear turquoise waters. Sunset Drive Beach and nearby Anne's Beach provide perfect spots for swimming and sunbathing in the shallow, calm waters. You'll discover scenic overlooks at mile markers, historic fishing piers extending into Florida Bay, and the popular Founder's Park with its recreational facilities. Waterfront seafood restaurants serve fresh mahi-mahi and key lime pie with stunning ocean views. Accommodations range from luxury beachfront resorts to intimate bed-and-breakfasts. Getting around requires a rental car, though the beachfront areas are highly walkable with bike-friendly roads.

A sunset over a palm tree-lined pier extending into calm waters.

Venetian Shores

Venetian Shores offers the Keys dream—canal-front homes with private docks where dolphins practically introduce themselves at breakfast. Spend your days boating from your backyard to snorkeling spots or fishing the flats between the Atlantic and Florida Bay. This upscale residential enclave lets you live like a local without the tourist crowds. You'll need wheels to explore nearby attractions like Founders Park and the History of Diving Museum. The neighborhood itself has no restaurants or shops—just peaceful streets lined with luxury vacation rentals featuring pools and tropical gardens. For dining out, a quick 5-10 minute drive takes you to Islamorada's waterfront eateries.

A beach with palm trees, lounge chairs, and a building with balconies.

Seabreeze Trailer Park

Seabreeze Trailer Park offers a laid-back slice of Florida Keys paradise without the resort price tag. You'll get direct beach access for swimming and snorkeling in crystal-clear waters. Nearby Founders Park and Windley Key Fossil Reef Geological State Park provide perfect day trips. Rain Barrel Village offers local shopping when you need a break from all that sunshine. Seafood restaurants and waterfront dining options are just a short drive away in Islamorada. While public transit is limited, having a rental car or golf cart makes exploring the surrounding Keys a breeze. The peaceful, no-frills atmosphere makes this spot ideal for travelers seeking an authentic Keys experience on a budget.

Top landmarks in Islamorada

A wooden deck with benches overlooking a clear blue sea.

Anne's Beach

7.8/10 (597 reviews)
If you can't wait to get to the beach, you might enjoy a trip to Anne's Beach located 8.8 mi (14.1 km) from central Islamorada. If you want to continue walking by the waves, head to Sunset Drive Beach located nearby.
See properties
A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
You can stroll along Bud n' Mary's Dive Center for relaxing water views when you're in Matecumbe. Hotels.com travelers also say the area is relaxing and has lots of nice beaches.
See properties
An aerial view of a coastal area with a marina, tennis courts, a baseball field, and surrounding greenery.

Founders Park

8.8/10 (450 reviews)
Founders Park is 4.6 mi (7.4 km) from central Islamorada, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here? Want to stretch your legs some more? Head to Islamorada County Park, just a short walk away.
See properties
A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Florida Keys Brewing Co.

9.2/10 (520 reviews)
Matecumbe is home to Florida Keys Brewing Co., so why not stop by during your stay in Islamorada.
See properties
An archaeological site with stone structures and metal machinery.

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)
Windley Key Fossil Reef Geological State Park is 2.4 mi (3.8 km) from central Islamorada, why not stop by during your stay. Hotels.com travelers also say the area is family-friendly and has lots of nice beaches.
See properties

Robbie’s of Islamorada

8.4/10 (15 reviews)
You can stroll along Robbie’s of Islamorada for relaxing water views when you're in Matecumbe.
See properties

Islamorada County Park

8.8/10 (198 reviews)
Islamorada County Park is 4.5 mi (7.2 km) from central Islamorada, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here? Want to stretch your legs some more? Head to Founders Park, just a short walk away.
See properties

Islamorada Brewery & Distillery

9.4/10 (8 reviews)
Matecumbe is home to Islamorada Brewery & Distillery, so why not stop by during your stay in Islamorada.
See properties

Learn more about Islamorada

Dubbed the 'Sportfishing Capital of the World,' this Florida Keys paradise invites you to battle trophy tarpon and marlin in azure waters. Dive beneath the surface where coral reefs burst with marine life, or paddle through mysterious mangrove tunnels where herons stalk the shallows. The History of Diving Museum chronicles humanity's underwater exploration, while MoradaWay Arts District showcases island-inspired creativity. Anne's Beach offers shallow wading perfect for families, with picnic tables near the gentle surf. After a day on the water, sample fresh-caught seafood at dockside restaurants. For a wilder adventure, take a day trip to nearby Everglades National Park, where alligators sun themselves amid saw grass prairies.

See all hotels in Islamorada
An aerial view of a coastal town with a marina, surrounded by clear blue waters and green islands.

Check out reviews of Islamorada hotels guests love

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Desayuno muy bueno.Todo muy limpio"
YUDIANYS 2-night trip
Posted 19 hours ago
Chesapeake Beach Resort
Breezy Palms Resort

Breezy Palms Resort

8/10 Good
"The property was clean and extremely well lit. The parking was great. The room had a full kitchen which was a huge plus. The layout of the room and the furnishings were beautiful and up to date. The room was spacious and comfortable. The staff were friendly and hospitable. I didnt pay much attention when booking but free kayaks or bikes would have been a great additional amenity. I thought it was extra convenient to have boats for rent on property. This was also an added benefit. I will definitely stay here again in the future."
JODI 2-night trip
Posted 2 days ago
Breezy Palms Resort
La Jolla Resort

La Jolla Resort

10/10 Excellent
"It was quaint and right on the water"
Julie 1-night trip
Posted 2 days ago
La Jolla Resort
Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay

10/10 Excellent
"Great room and property amenities. Every room has a spectacular ocean view. Pool was awesome with plenty of chairs around it. Restaurants were very good."
Anonymous traveler 3-night trip
Posted 3 days ago
Caloosa Cove Resort by CoolVacay
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"It was EXACTLY what I was looking for. Thank you! I wish I had more time to enjoy the super adorable room."
Lynille 1-night trip
Posted 3 days ago
Fisher Inn Resort & Marina
Treasure Harbor

Treasure Harbor

10/10 Excellent
"They bent over backwards for us, we enjoyed the stay. Everyone should try it."
Anonymous traveler 3-night trip
Posted 5 days ago
Treasure Harbor
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"This was an absolute dream vacation for my husband and I. The amenities were fantastic and the property was immaculate. The staff were exceedingly concerned about our comfort and asking if we needed anything. The location couldn’t have been better. We will be back."
Steven Allen 3-night trip
Posted 5 days ago
Pines & Palms Resort
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Great place for the money!"
Nicholas 2-night trip
Posted 12 days ago
Hadley Resort and Marina
The Caribbean Resort

The Caribbean Resort

10/10 Excellent
"Muy bien todo excelente servicio"
Rodolfo 4-night trip
Posted 13 days ago
The Caribbean Resort

Frequently asked questions

What accommodations do travelers recommend in Islamorada?
Guests like Cheeca Lodge & Spa, Chesapeake Beach Resort and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort.
Can I book refundable hotels in Islamorada?
If you're looking for the flexibility to change your plans to Islamorada, most hotels provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
Where should I stay in Islamorada if I want an affordable accommodation?
Coconut Cove Resort and Marina is an accommodation you might want to consider that'll save you money.
Where can I stay in Islamorada if I want a vacation rental instead of a traditional hotel?
If you want to find a good alternative to a hotel, review our selection of 403 vacation homes. In addition, there are 89 apartments and 122 condos.
What will the weather in Islamorada be like during my trip?
With an average temperature of 72°F during the coldest months, Islamorada is a great place to visit any time of year.
Why should I book my Islamorada hotel with Hotels.com?
There are lots of reasons to book your Islamorada trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Keep exploring