Islamorada Holiday Rentals, Florida: Private House Rentals

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

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Our top choices for Islamorada hotels

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 garden with various trees and a gravel path.

1. Sunset Cove Beach Resort

Key Largo

Melissa

3.051.126 ₫

3.432.647 ₫ total

includes taxes & fees

1 Sept - 2 Sept

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.

2. Chesapeake Beach Resort

Matecumbe

Yeniaris

3.939.082 ₫

5.898.354 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A pool area with palm trees and a building with a white roof.

A coastal property with a grassy lawn, palm trees, and a white fence overlooking the sea.

A spacious interior with a central open area, a balcony with a railing, and a tiled floor.

A coastal scene with rocky shores, a wooden pier, and calm water.

3. Bahia Bay Resort

Rock Harbor

Ben

3.966.464 ₫

4.462.272 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A beach with palm trees, a dock, and a boat named "STYX".

A thatched-roof hut surrounded by lush greenery and vibrant red flowers.

Two purple Adirondack chairs on a sandy beach with palm trees and a clear blue sky.

A beach with a thatched-roof hut, lounge chairs, and a swimming area.

4. The Pelican Key Largo Cottages

Key Largo

Richard

2.571.291 ₫

2.892.703 ₫ total

includes taxes & fees

9 Sept - 10 Sept

A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

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.

A tree with string lights, a wooden bench, and a building in the background.

5. Drift Hotel

Key Largo

Sheily

3.033.755 ₫

3.706.352 ₫ total

includes taxes & fees

14 Sept - 15 Sept

Two hands holding wine glasses with a beach and ocean view in the background.

An aerial view of a resort with a swimming pool, beach area, and dock.

A beach with palm trees, a sandy path, and a building with a balcony.

A bed with white and turquoise pillows, a bottle of champagne, and two glasses on a round table.

6. Bayside Inn Key Largo

Key Largo

Karen

3.311.645 ₫

4.377.551 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.

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.

7. Cheeca Lodge & Spa

Matecumbe

John

3.885.622 ₫

6.278.409 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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.

A resort with a swimming pool, lounge chairs, and palm trees.

8. Lime Tree Bay Resort

Long Key

Chadwick

2.922.745 ₫

4.461.598 ₫ total

includes taxes & fees

1 Sept - 2 Sept

A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

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.

A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.

9. Rock Reef Resort

Rock Harbor

manuel

2.523.046 ₫

2.838.427 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

A hotel room with two beds, a TV, a desk with a chair, and a balcony with a view of greenery.

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.

10. Fisher Inn Resort & Marina

Islamorada

MARC

3.027.656 ₫

4.257.038 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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.

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

Key Largo

Mae L

2.558.252 ₫

3.704.966 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A tropical resort with a thatched-roof hut, palm trees, and a view of the ocean at sunset.

A tropical resort with a dock, clear water, palm trees, and a thatched-roof building.

An aerial view of a tropical resort with clear waters, a dock, and several kayaks.

A living room with a teal sofa, a coffee table, and a view of a garden through large windows.

12. Bay Harbor Lodge

Rock Harbor

3.781.310 ₫

4.254.104 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A beachside lounge with two blue umbrellas, a hammock, and lounge chairs.

A bakery display case with various muffins and frittatas labeled with flavors like blueberry, cranberry orange, banana walnut, chocolate, egg cheese vegetable fritta, egg sausage fritta, and egg cheese fritta.

A beach scene with colorful Adirondack chairs, a blue umbrella, and a view of the ocean.

A pathway lined with palm trees and a speed limit sign of 5 MPH.

13. Seafarer Key Largo

Rock Harbor

Susan

2.504.198 ₫

3.183.944 ₫ total

includes taxes & fees

10 Sept - 11 Sept

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 wooden sign with the name 'Creekside' above a white pergola entrance.

A waterfront patio with outdoor seating, a yellow umbrella, and a view of the water.

14. Creekside Inn

Tavernier

Cristy

3.238.879 ₫

3.643.739 ₫ total

includes taxes & fees

8 Sept - 9 Sept

A covered outdoor area with a pool, palm trees, and a wooden deck.

A pool area with lounge chairs and a pool, surrounded by a building with multiple balconies and a garden.

A building with a colorful fish mural on the wall, a door, and a window.

A building with a sign reading "C&C wood fired eats" and a menu board listing items like wood, fired, eats, drinks, salumi, and fromage.

15. Key Largo Inn

Key Largo

EDWARD

2.792.954 ₫

3.142.073 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.

A beachside resort with lounge chairs, a pool, and palm trees.

A tropical resort with a paved pathway leading to a building, surrounded by palm trees and lush greenery.

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a sign indicating no diving.

16. Kona Kai Resort and Gallery - Adults Only

Rock Harbor

Michelle

3.108.498 ₫

4.230.634 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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.

17. Coconut Cove Resort and Marina

Islamorada

Lisa C

3.885.622 ₫

4.371.325 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A house with a covered porch, surrounded by palm trees and lush greenery.

A balcony with wicker chairs, a glass table, and a vase with red flowers.

A covered outdoor area with a table and chairs, a wooden deck, and a view of palm trees and the ocean.

18. Coconut Bay Resort Key Largo

Rock Harbor

Cody

4.302.870 ₫

4.840.859 ₫ total

includes taxes & fees

2 Sept - 3 Sept

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.

An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Islamorada

Ana

4.568.866 ₫

7.047.059 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A beachfront property with a pool, palm trees, and a thatched-roof structure.

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the water.

A wooden pier leading to docked boats, with a covered area and a calm water body in the background.

A pathway leading to a beach with tropical plants and flowers.

20. Coconut Palm Inn

Tavernier

judith

4.905.272 ₫

6.545.383 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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Where to stay in Islamorada

Find the best Islamorada areas for the activities you enjoy most.

A beachside café with colorful chairs and tables, palm trees, and a view of the ocean.

A marina with several yachts docked, palm trees, and a clear blue sky.

A stone monument with a relief sculpture, surrounded by palm trees and a clear blue sky.

A marina with several yachts docked, surrounded by lush greenery and palm trees.

Matecumbe

Matecumbe captures the essence of the Florida Keys with its laid-back charm and coastal beauty. Anne's Beach and Sunset Drive Beach offer pristine shorelines perfect for relaxing or swimming. Visitors can explore marine life at Bud n' Mary's Dive Centre or feed tarpon at Robbie's of Islamorada. This resort community balances tourism with authentic Keys lifestyle. Florida Keys Brewing Co. provides local craft beers after a day of snorkelling crystal-clear waters. The Hurricane Monument and MoradaWay Arts District showcase the area's rich history and creative spirit. Waterfront paths offer stunning views of both Atlantic Ocean and Florida Bay.

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

Lower Matecumbe Beach

Lower Matecumbe Beach offers a serene Florida Keys escape where powder-soft sand meets crystal-clear turquoise waters. The pristine Atlantic shoreline invites visitors to unwind while scenic overlooks provide spectacular coastal vistas. Sunset Drive Beach and Anne's Beach showcase the area's natural beauty. This tranquil area balances tourism with authentic Keys living. Waterfront seafood restaurants serve fresh catches while boutique shops sell tropical souvenirs. Luxury resorts and intimate bed-and-breakfasts provide comfortable bases for exploring nearby mangrove preserves by kayak or snorkelling the calm, shallow waters.

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

Venetian Shores

Venetian Shores in Islamorada offers a luxurious waterfront escape with direct access to the Atlantic Ocean and Florida Bay. Private canal-front properties feature personal docks where you can launch your boat for a day of fishing or island exploration. This upscale residential area provides the perfect base for travellers seeking exclusive waterfront holiday rentals. The peaceful area streets lead to high-end homes with private pools and tropical landscaping. Though lacking shops or restaurants within its boundaries, Venetian Shores sits just minutes from Founders Park and local attractions like the History of Diving Museum. Water activities dominate the experience in this serene Keys community.

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

Seabreeze Trailer Park

This affordable Keys hideaway puts you right on the beautiful shores of Islamorada. Seabreeze Caravan Park offers a laid-back alternative to pricey resorts while still delivering stunning ocean views. Fish, swim, or snorkel just steps from your door. The nearby Founders Park and Florida Keys Dive Centre provide plenty of outdoor recreation options. Windley Key Fossil Reef Geological State Park offers fascinating natural history just a short drive away. Palm-lined paths and gentle waves create the perfect backdrop for authentic Florida Keys living.

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Stay near popular Islamorada attractions

A sandy beach with green vegetation and a calm sea.

Anne's Beach

7.8/10 (597 reviews)

Anne's Beach offers shallow, calm waters and a scenic boardwalk winding through mangroves. Enjoy the covered pavilions for picnicking or launch your paddleboard into the crystal-clear waters of the Florida Keys.

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Florida Keys Brewing Co.

9.2/10 (520 reviews)

The Upper Keys' first microbrewery infuses local flavours like Key lime and honey into its craft beers. Sip seasonal brews in the vibrant taproom or lush beer garden while enjoying local art and live music.

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A small green leaf growing on a rough, textured surface.

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)

Walk through ancient coral walls rising eight feet high in this former limestone quarry turned state park. Ranger-guided tours reveal the fascinating geological history preserved in the fossilised reef.

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A building with a blue facade, a large mural of a diving scene, and a statue of a diver.

History of Diving Museum

9.0/10 (177 reviews)

Discover 4,000 years of underwater exploration at this unique museum featuring diving helmets from around the world. Explore exhibits showcasing the evolution of diving technology from ancient to modern times.

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Robbie’s of Islamorada

8.4/10 (15 reviews)

Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.

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Islamorada County Park

8.8/10 (198 reviews)

This 40-acre waterfront retreat offers a bayfront beach, marina, and scenic trails for active relaxation. Enjoy a refreshing swim in the pool or bring your four-legged friend to the specialised dog parks.

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Islamorada Brewery & Distillery

9.4/10 (8 reviews)

The Florida Keys' first distillery crafts award-winning spirits and beers capturing the island's essence. Enjoy tastings in their relaxed taproom or pet-friendly garden with pub-style food available.

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Sunset Drive Beach

9.0/10 (91 reviews)

This secluded stretch of Islamorada shoreline offers a peaceful retreat from Florida's busier beaches. Watch the sky transform into a canvas of colours as the sun sinks into the Atlantic Ocean.

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Learn more about Islamorada

The turquoise waters between the Keys offer world-class fishing that even beginners can enjoy with knowledgeable local guides. Spend mornings snorkelling coral reefs teeming with tropical fish, then unwind at waterfront restaurants where chefs cook your fresh catch.

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A wooden pier extending into calm waters with a covered seating area and a boat docked at the end.

Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

10/10 Excellent

"Everything was fabulous. We stayed in a newer building on the beach. The room, service, and staff were all 10/10. Shout out to Dee at the atlantics edge restaurant for her great dinner service. Our room was clean and replenished daily. The pool and poolside service also excellent. The only downside of our stay was the seaweed. The smell was bad at times. We would've liked to spend more time on the beach and look forward to coming back for that."

Islander Resort

10/10 Excellent

"It’s a beautiful property right on the water with very nice pool area and right near everything in Islamorada"

Casa Morada

8/10 Good

"The room was updated, clean, and comfortable. The bed and pillows were nice. The location was perfect for us. When it’s all completed it’s going to be a really cool spot for sunsets. Overall worth the money for a one nighter on our way home from the lower keys."

The Caribbean Resort

10/10 Excellent

"Excellent place to stay!"

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

10/10 Excellent

"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."

Caloosa Cove Resort by CoolVacay

10/10 Excellent

"."

Pines & Palms Resort

8/10 Good

"Lovely location, beautifully renovated, clean room, close to everything including great restaurants. If you want peace and quiet this is the spot for you. If your idea of the keys includes loud activities this is not for you. The small beach was not accessible due to rotting sargassum. You could not even spend much time at the pool due to the smell. Not the hotels fault obviously but affected our stay negatively."

Treasure Harbor

10/10 Excellent

"Great air conditioning. Very cozy quaint get away. I would return. Great pit stop heading down to Key West."

More cheap stays in Islamorada

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

2.389.788 ₫

2.688.511 ₫ total

1 Sept - 2 Sept

includes taxes & fees

9/10 Wonderful! (1,003 reviews)

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

2.523.046 ₫

2.838.427 ₫ total

31 Aug - 1 Sept

includes taxes & fees

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

3.051.126 ₫

3.432.647 ₫ total

1 Sept - 2 Sept

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

3.238.879 ₫

3.643.739 ₫ total

8 Sept - 9 Sept

includes taxes & fees

Drift Hotel

95320 Overseas Hwy Key Largo FL

3.033.755 ₫

3.706.352 ₫ total

14 Sept - 15 Sept

includes taxes & fees

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

2.447.942 ₫

4.105.981 ₫ total

6 Sept - 7 Sept

includes taxes & fees

Hotels in Islamorada with star rating

Frequently asked questions

What's the weather like in Islamorada?

The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 22°C. Average annual precipitation for Islamorada is 1122 mm.

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Book Hotels in Islamorada on Expedia.com

Find hotels in Islamorada, FL from 2.688.511 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Islamorada

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Islamorada hotels

1. Sunset Cove Beach Resort

2. Chesapeake Beach Resort

3. Bahia Bay Resort

4. The Pelican Key Largo Cottages

5. Drift Hotel

6. Bayside Inn Key Largo

7. Cheeca Lodge & Spa

8. Lime Tree Bay Resort

9. Rock Reef Resort

10. Fisher Inn Resort & Marina

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

12. Bay Harbor Lodge

13. Seafarer Key Largo

14. Creekside Inn

15. Key Largo Inn

16. Kona Kai Resort and Gallery - Adults Only

17. Coconut Cove Resort and Marina

18. Coconut Bay Resort Key Largo

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

20. Coconut Palm Inn

Where to stay in Islamorada

Matecumbe

Lower Matecumbe Beach

Venetian Shores

Seabreeze Trailer Park

Stay near popular Islamorada attractions

Anne's Beach

Florida Keys Brewing Co.

Windley Key Fossil Reef Geological State Park

History of Diving Museum

Robbie’s of Islamorada

Islamorada County Park

Islamorada Brewery & Distillery

Sunset Drive Beach

Learn more about Islamorada

Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

Islander Resort

Casa Morada

The Caribbean Resort

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

Caloosa Cove Resort by CoolVacay

Pines & Palms Resort

Treasure Harbor

More cheap stays in Islamorada

The Pelican Key Largo Cottages

Rock Reef Resort

Sunset Cove Beach Resort

Creekside Inn

Drift Hotel

Breezy Palms Resort

Hotels in Islamorada with star rating

Frequently asked questions

Explore a world of travel with Expedia

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