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 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 waterfront pier with wooden posts and a wooden walkway extending into the water.

1. Sunset Cove Beach Resort

Key Largo

Douglas

2.542.752 ₫

2.860.790 ₫ total

includes taxes & fees

17 Sept - 18 Sept

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 sofa, a glass coffee table, a TV, and a sliding door leading to a bedroom.

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

2. Drift Hotel

Key Largo

Sheily

2.430.000 ₫

3.025.350 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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 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.

3. Chesapeake Beach Resort

Matecumbe

Suresh

3.915.216 ₫

5.862.618 ₫ total

includes taxes & fees

16 Sept - 17 Sept

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

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

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

A pathway leading to a building surrounded by lush tropical vegetation and a view of the sea.

4. The Pelican Key Largo Cottages

Key Largo

Kim

2.434.692 ₫

2.739.029 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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

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

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.

5. Seafarer Key Largo

Rock Harbor

Susan

2.599.776 ₫

3.289.248 ₫ total

includes taxes & fees

16 Sept - 17 Sept

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

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.

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

6. Cheeca Lodge & Spa

Matecumbe

Mian

3.862.080 ₫

6.240.500 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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

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.

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

7. Bayside Inn Key Largo

Key Largo

luis

2.990.390 ₫

4.012.190 ₫ total

includes taxes & fees

15 Sept - 16 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 man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.

8. Fisher Inn Resort & Marina

Islamorada

Alexandra

3.062.448 ₫

4.291.023 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

A hotel room with a large bed, a desk with a television, a chair, a desk lamp, and a window with curtains.

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.

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

9. Key Largo Inn

Key Largo

EDWARD

1.842.912 ₫

2.073.276 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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

A wooden deck overlooking clear turquoise water with a backdrop of dense green foliage and a clear blue sky.

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

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

10. Bahia Bay Resort

Rock Harbor

Ben

3.942.432 ₫

4.435.237 ₫ total

includes taxes & fees

15 Sept - 16 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 spacious living area with a large island, wooden furniture, and a ceiling fan.

11. Lime Tree Bay Resort

Long Key

Chadwick

2.780.930 ₫

5.331.747 ₫ total

includes taxes & fees

17 Sept - 18 Sept

A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

A hotel room with a bed, a TV, a sofa, and a balcony with a view.

A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.

A resort with a pool, multiple buildings, and a waterfront view.

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

Key Largo

Omar Ahmad

2.542.752 ₫

3.682.518 ₫ total

includes taxes & fees

20 Sept - 21 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.

13. Kona Kai Resort and Gallery - Adults Only

Rock Harbor

Laura

3.475.872 ₫

4.639.486 ₫ total

includes taxes & fees

21 Sept - 22 Sept

A beachside lounge with wooden lounge chairs and blue umbrellas, overlooking a calm sea and docked boats.

A beach with wooden lounge chairs and umbrellas, palm trees, and a clear view of the ocean.

A bedroom with a bed, a ceiling fan, a mirror, and a lamp.

A tropical resort with a wooden deck leading to a blue door, surrounded by lush greenery and palm trees.

14. Island Bay Resort

Tavernier

Katie Lyn

5.196.182 ₫

5.845.737 ₫ total

includes taxes & fees

29 Sept - 30 Sept

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.

15. Amara Cay Resort

Matecumbe

Amy

4.006.584 ₫

6.402.936 ₫ total

includes taxes & fees

16 Sept - 17 Sept

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 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.

16. Rock Reef Resort

Rock Harbor

charlotte

2.614.825 ₫

2.941.678 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A wooden dock extending over calm turquoise water, lined with white railings and palm trees.

A hallway with a tiled floor, a painting on the wall, a lamp, and a view of a pool area.

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.

17. Creekside Inn

Tavernier

Terry

3.412.368 ₫

3.838.752 ₫ total

includes taxes & fees

22 Sept - 23 Sept

A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.

A swimming pool with a 5 ft depth marker, surrounded by palm trees and a white picket fence.

A hotel room with two beds, each with a different patterned bedspread, a nightstand with a lamp, framed artwork on the wall, and an air conditioning unit.

A bedroom with a bed, a nightstand, a chair, and a door.

18. The Ocean View Inn & Pub

Islamorada

Maria

4.828.896 ₫

5.432.573 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

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.

A coastal resort with a beach, a swimming pool, and multiple buildings.

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

Islamorada

Eslita

4.748.544 ₫

7.237.642 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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 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.

20. Islander Resort

Matecumbe

Sonia

5.750.352 ₫

8.218.746 ₫ total

includes taxes & fees

20 Sept - 21 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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Lorelei Restaurant & Cabana Bar

After visiting Lorelei Restaurant & Cabana Bar, make a plan to see the other sights and activities in Islamorada.

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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

Chesapeake Beach Resort

10/10 Excellent

"/"

Amara Cay Resort

10/10 Excellent

"Beautiful lobby, nice outdoor area, room is clean, the elevator is a bit old though. Pool is very big, kids love it."

Coconut Cove Resort and Marina

10/10 Excellent

"This was a beautiful place to stay. The scenery was just absolutely breathtaking. Loved the bedroom and amenities. Staff were all sweet and treated you like family. I will definitely be going back!"

Breezy Palms Resort

10/10 Excellent

"Have stayed here for the past 5 years which includes over 20 nights. Spacious rooms and clean. Like all the recent upgrades to the rooms."

La Jolla Resort

10/10 Excellent

"This is like an oasis along US 1 on the way down to Key West. We only stayed one night, but, in retrospect, I wish we had stayed a night or two more to take advantage of the amenities like the paddleboards and kayaks. It’s immaculately clean, everyone was so friendly, and the room was great. I can’t recommend this place more. It’s like a throwback to an earlier time, but completely updated. Plenty of restaurants to pick from nearby and the Islamorada Brewery across the street is great, and has a wonderful beer garden out back."

Pines & Palms Resort

10/10 Excellent

"Loved staying here and would stay again. Staff were so friendly and nice - made you feel like you knew them for years."

Treasure Harbor

10/10 Excellent

"Amazing location and well equipped. Loved the local vibe, didn't see a manatee but plenty of green iguanas. Property was comfortable with great AC."

The Caribbean Resort

10/10 Excellent

"Excellent place to stay!"

More cheap stays in Islamorada

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

2.434.692 ₫

2.739.029 ₫ total

15 Sept - 16 Sept

includes taxes & fees

9/10 Wonderful! (1,003 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

2.141.510 ₫

2.822.688 ₫ total

15 Sept - 16 Sept

includes taxes & fees

8.8/10 Excellent! (746 reviews)

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

2.542.752 ₫

2.860.790 ₫ total

17 Sept - 18 Sept

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

2.614.825 ₫

2.941.678 ₫ total

27 Sept - 28 Sept

includes taxes & fees

9.2/10 Wonderful! (1,185 reviews)

Drift Hotel

95320 Overseas Hwy Key Largo FL

2.430.000 ₫

3.025.350 ₫ total

15 Sept - 16 Sept

includes taxes & fees

Creekside Inn

90611 Old Highway Tavernier FL

3.412.368 ₫

3.838.752 ₫ total

22 Sept - 23 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 2.739.029 ₫

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. Drift Hotel

3. Chesapeake Beach Resort

4. The Pelican Key Largo Cottages

5. Seafarer Key Largo

6. Cheeca Lodge & Spa

7. Bayside Inn Key Largo

8. Fisher Inn Resort & Marina

9. Key Largo Inn

10. Bahia Bay Resort

11. Lime Tree Bay Resort

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

13. Kona Kai Resort and Gallery - Adults Only

14. Island Bay Resort

15. Amara Cay Resort

16. Rock Reef Resort

17. Creekside Inn

18. The Ocean View Inn & Pub

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

20. Islander Resort

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

Lorelei Restaurant & Cabana Bar

Learn more about Islamorada

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Amara Cay Resort

Coconut Cove Resort and Marina

Breezy Palms Resort

La Jolla Resort

Pines & Palms Resort

Treasure Harbor

The Caribbean Resort

More cheap stays in Islamorada

The Pelican Key Largo Cottages

Breezy Palms Resort

Sunset Cove Beach Resort

Rock Reef Resort

Drift Hotel

Creekside Inn

Hotels in Islamorada with star rating

Frequently asked questions

Explore a world of travel with Expedia

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