The Best Hotels Closest to Sunset Drive Beach in Islamorada for 2026

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Our top choices for Sunset Drive Beach hotels

A spacious living area with a large island, wooden furniture, and a ceiling fan.

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.

1. Lime Tree Bay Resort

9.2 km from Sunset Drive Beach

Christopher Michael

￥19,572

￥29,129 total

includes taxes & fees

Oct 19 - Oct 20

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, 14.9 km from Sunset Drive Beach

Dianne

￥21,921

￥33,550 total

includes taxes & fees

Oct 20 - Oct 21

A beach with rows of sun loungers and palm trees.

A clear blue swimming pool with a metal railing, surrounded by palm trees and a view of the ocean.

A marina with a boat docked at a wooden pier, surrounded by palm trees and buildings.

Three Adirondack chairs facing a sunset over a body of water.

3. Ragged Edge Resort & Marina

19.5 km from Sunset Drive Beach

Nathalie

￥24,800

￥27,900 total

includes taxes & fees

Oct 29 - Oct 30

A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

A beach view with palm trees and a thatched-roof structure.

A compact kitchen with modern appliances, a dining area with a sofa, and a large window providing natural light.

A sign for Matecumbe Resort with a full kitchen and heated pool.

4. Matecumbe Resort

Matecumbe, 3.2 km from Sunset Drive Beach

angel

￥22,755

￥25,600 total

includes taxes & fees

Oct 19 - Oct 20

A beach with palm trees, thatched-roof huts, and lounge chairs.

A building facade with the text "Buzzy Plims" and a website address. There are two potted plants and a staircase leading up to the entrance.

A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

A beach with thatched umbrellas, palm trees, and lounge chairs.

5. Breezy Palms Resort

Matecumbe, 9.2 km from Sunset Drive Beach

Gavin

￥15,502

￥19,961 total

includes taxes & fees

Oct 19 - Oct 20

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

A tropical resort with a swimming pool, palm trees, and a waterfall.

A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

A bar area with a thatched roof, wooden chairs, and a view of the ocean.

6. Cheeca Lodge & Spa

Matecumbe, 11.9 km from Sunset Drive Beach

James

￥29,245

￥44,456 total

includes taxes & fees

Oct 21 - Oct 22

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.

An aerial view of a resort with a swimming pool, palm trees, and a dock.

A resort pool with palm trees, beach chairs, and umbrellas.

A beach with palm trees, a dock, and lounge chairs.

7. Amara Cay Resort

Matecumbe, 9.1 km from Sunset Drive Beach

Danielle

￥23,937

￥38,485 total

includes taxes & fees

Oct 21 - Oct 22

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

A paved pathway leading to a beach with palm trees 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.

8. Islander Resort

Matecumbe, 12.4 km from Sunset Drive Beach

Clara

￥30,846

￥46,256 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

A pool area with a white fence, a lifebuoy, and palm trees in the background.

A kitchen with white cabinets, a microwave, a stove, and a refrigerator.

A row of floating cottages with balconies and outdoor seating, docked along a waterway.

9. Treasure Harbor

19.6 km from Sunset Drive Beach

Laura

￥16,924

￥41,262 total

includes taxes & fees

Oct 19 - Oct 20

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 beach with palm trees, a thatched-roof hut, and lounge chairs.

A wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.

10. Coconut Cove Resort and Marina

16.7 km from Sunset Drive Beach

Hailey Ritch and Patrick

￥23,545

￥26,488 total

includes taxes & fees

Oct 26 - Oct 27

An aerial view of a resort with a swimming pool, lounge chairs, and palm trees.

A view from a window overlooking a beach with palm trees and a wooden pier.

11. Casa Morada

Matecumbe, 12.7 km from Sunset Drive Beach

David

￥24,745

￥29,616 total

includes taxes & fees

Oct 19 - Oct 20

A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.

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.

12. The Islands of Islamorada

Matecumbe, 13.6 km from Sunset Drive Beach

Christian

￥75,888

￥95,603 total

includes taxes & fees

Oct 20 - Oct 21

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 waterfront property with a paved walkway, palm trees, and a white building with a dock.

13. Bayside Villas by Islander Resort

Matecumbe, 11 km from Sunset Drive Beach

Brian

￥33,859

￥49,646 total

includes taxes & fees

Oct 28 - Oct 29

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 bathroom with a sink, toilet, and shower. There is a mirror above the sink and a shelf with towels.

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

14. The Ocean View Inn & Pub

16.6 km from Sunset Drive Beach

Maria

￥29,439

￥33,118 total

includes taxes & fees

Oct 19 - Oct 20

A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

A beach with palm trees, a wooden pier, and beach chairs.

A modern two-story beachfront property with balconies, a pool, and a sandy beach area.

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

15. Pines & Palms Resort

Matecumbe, 9.7 km from Sunset Drive Beach

Colt

￥32,568

￥45,351 total

includes taxes & fees

Oct 21 - Oct 22

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

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

A resort with a pool, beach, and ocean view.

A beach with palm trees, a clear blue sky, and a calm sea.

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

15.8 km from Sunset Drive Beach

Liosbel

￥37,798

￥54,078 total

includes taxes & fees

Nov 2 - Nov 3

A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

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.

A beachfront property with a white building, a balcony with a white railing, and palm trees.

17. La Jolla Resort

Matecumbe, 12.9 km from Sunset Drive Beach

Brett

￥22,612

￥29,884 total

includes taxes & fees

Oct 22 - Oct 23

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 beach with colorful buildings, kayaks, and lounge chairs.

A resort with a pool surrounded by palm trees and a view of the ocean.

18. La Siesta Resort & Villas

Matecumbe, 9.7 km from Sunset Drive Beach

Brianne

￥20,274

￥34,364 total

includes taxes & fees

Nov 16 - Nov 17

A pier extending into clear blue water with boats docked.

A beachside area with thatched umbrellas, picnic tables, and a pool.

A beach with a thatched umbrella, lounge chairs, and a pool.

An aerial view of a coastal resort with multiple buildings, a dock with boats, and a clear view of the ocean.

19. Edgewater Lodge

13.1 km from Sunset Drive Beach

Leda

￥31,446

￥35,378 total

includes taxes & fees

Oct 19 - Oct 20

A beachside patio with white furniture, palm trees, and a thatched umbrella.

A deck with white lounge chairs and a bench, overlooking a beach with palm trees and a thatched roof structure.

A beach with palm trees, a thatched umbrella, and lounge chairs.

A wooden boardwalk leading to a building with a brick wall and a white roof.

20. Drop Anchor

17.2 km from Sunset Drive Beach

Payman

￥17,605

￥25,337 total

includes taxes & fees

Oct 19 - Oct 20

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Compare popular hotels close to Sunset Drive Beach

Property	Star rating	Guest rating
Lime Tree Bay Resort	9.4 Exceptional 1,542 reviews	View
Chesapeake Beach Resort	9.4 Exceptional 1,799 reviews	View
Ragged Edge Resort & Marina	9.6 Exceptional 275 reviews	View
Matecumbe Resort	9.0 Wonderful 176 reviews	View
Breezy Palms Resort	9.0 Wonderful 771 reviews	View

Top Sunset Drive Beach Hotel Reviews

Caloosa Cove Resort by CoolVacay

10/10 Excellent

"Very clean efficiency with a full fridge, stove and oven. Grills by the water to cook your own catch or from the market down the road. Large pool, well maintained."

Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two

10/10 Excellent

"A beautiful property with excellent customer service."

Private Beachfront Paradise

8/10 Good

"When we arrived the upstairs of the house did not have air conditioning it was 94 degrees in the house. And when I reached out the host said it would be fixed on Friday. We arrived on Wednesday. Our guest arrived on Thursday. The host was able to find a place for 3 couple to sleep for 1 night. One couple had air conditioning in the lower level. Wish we would have had a heads up on this issue."

AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!!

10/10 Excellent

"A true gem set for relaxing and enjoying Islamorada with Key West within reach to visit for the day. Comunication was excellent as well!!"

ISLAMORADA WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CONTACT OWNER

10/10 Excellent

"The house was exactly as described and was an awesome home base location for our family’s Florida Keys vacation! We brought our boat and the dock was perfect with lights, power, and water located right on the dock. The home was very spacious and we really enjoyed the huge screened porch with string lights in the evening to gather and unwind after a busy day. The beds were comfortable and the home was very clean and definitely had a Florida keys vibe. We enjoyed many species of fish and manatee sightings from the dock. Chis was very accommodating and easily reachable with any questions. Our family really enjoyed this rental and would recommend it for anyone seeking a low key Florida Keys getaway!"

Gulf View Retreat @ Bay Harbor

10/10 Excellent

"Excellent choice!"

Islamorada Boaters Paradise with 70' Dock and private beach access..

8/10 Good

"The 70’ dock is not all accessible because of owners 27’ sea hunt and a broken jet ski lift had 2 boats a 22’ pontoon and an 18’ flats boat had to tie the flats to the pontoon no big deal just don’t plan on 2 24’ bay boats would be very tight other then that everything was great"

Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One

10/10 Excellent

"Really nice place, a few maintenance issues but nothing major."

Flip-Flops & Sunshine: Islamorada Studio Escape

10/10 Excellent

"Super friendly and helpful staff. Located on the waterfront with an amazing pool. Check in was a breeze and the staff was amazing. We'll definitely stay here again in the future."

Other attractions near Sunset Drive Beach

A wooden deck with benches overlooking a clear blue sea.

Anne's Beach

7.8/10 (597 reviews)

If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.

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A mangrove tree with roots in shallow water.

Indian Key Historic State Park

8.4/10 (55 reviews)

You can take time to visit Indian Key Historic State Park during your travels to Islamorada. Stroll along the seaside or discover the beautiful sunsets in this relaxing area.

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A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.

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A coastal landscape with dense green vegetation and trees framing a calm sea.

Long Key State Park

8.6/10 (376 reviews)

You can take time to visit Long Key State Park during your travels to Long Key. Wander the beautiful beaches or discover the beautiful sunsets in this relaxing area.

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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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Frequently asked questions

What's the area like around Sunset Drive Beach?

Sunset Drive Beach is located in Islamorada. If you're looking for a convenient place to stay, check out the 158 hotels and other accommodations you'll find within a mile.

What's the best place to stay near Sunset Drive Beach?

Caloosa Cove Resort by CoolVacay is one of the top choices for your stay based on our traveler data, and this condo offers a marina and a restaurant. It's located 0.5 mi (0.8 km) from Sunset Drive Beach.

How many hotels are there near Sunset Drive Beach?

Expedia has 158 hotels and other accommodations within a mile from Sunset Drive Beach.

If I need to cancel the hotel reservation for my stay near Sunset Drive Beach, will I receive a refund?

Yes, you'll find most hotel reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you have a reservation that's non-refundable, it might still be possible to cancel it and get a refund within 24 hours of your booking. Add your dates and click on "Search", then filter by "fully refundable" to review the top deals on offer near Sunset Drive Beach.

Where can I learn more about changing or cancelling my trip in the area near Sunset Drive Beach?

For more details about updating your stay near Sunset Drive Beach or cancelling it, head over to our customer service page.

What can I see and do near Sunset Drive Beach?

Explore nature at Anne's Beach and Fiesta Key. If you're looking for something to do, plan a visit to Robbie's of Islamorada, San Pedro Underwater Archaeological Preserve State Park, and Indian Key Historic State Park while you're in the area. Spend some time checking out Bud n' Mary's Dive Center, which is 5.4 mi (8.8 km) from Sunset Drive Beach, or make a stop by Long Key State Park, located 6.4 mi (10.3 km) away.

Find hotels near Sunset Drive Beach, Islamorada from ￥19,961

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Treat yourself

Be picky

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Our top choices for Sunset Drive Beach hotels

1. Lime Tree Bay Resort

2. Chesapeake Beach Resort

3. Ragged Edge Resort & Marina

4. Matecumbe Resort

5. Breezy Palms Resort

6. Cheeca Lodge & Spa

7. Amara Cay Resort

8. Islander Resort

9. Treasure Harbor

10. Coconut Cove Resort and Marina

11. Casa Morada

12. The Islands of Islamorada

13. Bayside Villas by Islander Resort

14. The Ocean View Inn & Pub

15. Pines & Palms Resort

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

17. La Jolla Resort

18. La Siesta Resort & Villas

19. Edgewater Lodge

20. Drop Anchor

Compare popular hotels close to Sunset Drive Beach

Top Sunset Drive Beach Hotel Reviews

Caloosa Cove Resort by CoolVacay

Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two

Private Beachfront Paradise

AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!!

ISLAMORADA WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CONTACT OWNER

Gulf View Retreat @ Bay Harbor

Islamorada Boaters Paradise with 70' Dock and private beach access..

Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One

Flip-Flops & Sunshine: Islamorada Studio Escape

Other attractions near Sunset Drive Beach

Anne's Beach

Indian Key Historic State Park

Bud n' Mary's Dive Center

Long Key State Park

Robbie’s of Islamorada

Frequently asked questions