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 beach with palm trees and a clear view of the ocean.

1. Lime Tree Bay Resort

9.2 km from Sunset Drive Beach

Michael

￥19,608

￥29,183 total

includes taxes & fees

Oct 13 - Oct 14

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

Richard

￥21,960

￥33,611 total

includes taxes & fees

Oct 14 - Oct 15

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

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.

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

3. Matecumbe Resort

Matecumbe, 3.2 km from Sunset Drive Beach

angel

￥21,229

￥23,882 total

includes taxes & fees

Oct 12 - Oct 13

A beach with palm trees, thatched-roof huts, 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.

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

4. Breezy Palms Resort

Matecumbe, 9.2 km from Sunset Drive Beach

Gavin

￥16,076

￥20,610 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.

A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.

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

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

5. Amara Cay Resort

Matecumbe, 9.1 km from Sunset Drive Beach

Danielle

￥22,758

￥37,180 total

includes taxes & fees

Oct 20 - Oct 21

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 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.

6. Cheeca Lodge & Spa

Matecumbe, 11.9 km from Sunset Drive Beach

Morgan

￥26,331

￥41,199 total

includes taxes & fees

Oct 13 - Oct 14

A beach with rows of sun loungers and palm trees.

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.

A spacious room with a high ceiling, a ceiling fan, a dining table with chairs, a sofa, and a television mounted on the wall.

7. Ragged Edge Resort & Marina

19.5 km from Sunset Drive Beach

Nathalie

￥19,716

￥22,181 total

includes taxes & fees

Oct 12 - Oct 13

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

A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.

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

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

8. La Jolla Resort

Matecumbe, 12.9 km from Sunset Drive Beach

Brett

￥17,922

￥24,616 total

includes taxes & fees

Oct 18 - Oct 19

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 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.

9. Islander Resort

Matecumbe, 12.4 km from Sunset Drive Beach

Steven

￥37,600

￥53,876 total

includes taxes & fees

Oct 18 - Oct 19

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

A boat with a covered deck, metal railings, and a table with 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.

10. Treasure Harbor

19.6 km from Sunset Drive Beach

Laura

￥16,955

￥41,336 total

includes taxes & fees

Oct 12 - Oct 13

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

A resort with thatched-roof structures, palm trees, and a sandy beach area.

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.

11. Coconut Cove Resort and Marina

16.7 km from Sunset Drive Beach

Hailey Ritch and Patrick

￥23,588

￥26,537 total

includes taxes & fees

Oct 26 - Oct 27

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

An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

12. Casa Morada

Matecumbe, 12.7 km from Sunset Drive Beach

David

￥25,322

￥30,269 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 bedroom with a bed, a nightstand, a chair, and a door.

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

13. The Ocean View Inn & Pub

16.6 km from Sunset Drive Beach

Maria

￥29,493

￥33,180 total

includes taxes & fees

Oct 12 - Oct 13

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

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

A coastal resort with a marina, clear blue water, and lush greenery.

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

14. Pines & Palms Resort

Matecumbe, 9.7 km from Sunset Drive Beach

Colt

￥32,628

￥45,434 total

includes taxes & fees

Oct 15 - Oct 16

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

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

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

15.8 km from Sunset Drive Beach

Liosbel

￥36,197

￥52,299 total

includes taxes & fees

Oct 18 - Oct 19

A pier extending into clear blue water with boats docked.

An aerial view of a coastal hotel with a pool, multiple buildings, and a pier extending into the water.

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

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

16. Edgewater Lodge

13.1 km from Sunset Drive Beach

Leda

￥24,079

￥27,090 total

includes taxes & fees

Oct 12 - Oct 13

A beachside lounge with a wooden deck, thatched roof, and tropical plants.

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.

17. Bayside Villas by Islander Resort

Matecumbe, 11 km from Sunset Drive Beach

beata

￥41,034

￥57,739 total

includes taxes & fees

Oct 18 - Oct 19

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

A pool area with lounge chairs and a sign indicating a drop-off zone.

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

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

18. Drop Anchor

17.2 km from Sunset Drive Beach

Payman

￥18,458

￥26,306 total

includes taxes & fees

Oct 15 - Oct 16

A beachside lounge area with sun loungers, a thatched structure, and a view of the ocean.

A spacious living area with a round dining table, a sofa, and a TV mounted on the wall.

A two-story building with a balcony, surrounded by palm trees and a sandy ground.

A beach with an American flag, palm trees, and a barbecue area.

19. Sands of Islamorada

Matecumbe, 9.2 km from Sunset Drive Beach

Nicolas

￥30,396

￥36,332 total

includes taxes & fees

Oct 12 - Oct 13

A beachfront property with a white balcony, palm trees, and a sandy beach.

A beach with clear blue water, a palm tree, and rocky outcrops.

A pool area with lounge chairs, a wooden deck, and a view of the ocean.

A coastal hotel with a pool, parked cars, and a view of the ocean.

20. Conch Key Fishing Lodge and Marina

17.6 km from Sunset Drive Beach

Daniel

￥22,654

￥25,487 total

includes taxes & fees

Oct 12 - Oct 13

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Compare popular hotels close to Sunset Drive Beach

Property	Star rating	Guest rating
Lime Tree Bay Resort	9.4 Exceptional 1,536 reviews	View
Chesapeake Beach Resort	9.2 Wonderful 1,796 reviews	View
Matecumbe Resort	9.0 Wonderful 172 reviews	View
Breezy Palms Resort	9.0 Wonderful 763 reviews	View
Amara Cay Resort	8.8 Excellent 1,319 reviews	View

Top Sunset Drive Beach Hotel Reviews

Caloosa Cove Resort by CoolVacay

10/10 Excellent

"Caloosa Cove is well located for exploring both Islamorada as well as the lower keys. The room was clean and spacious and had a very usable kitchen. The balcony in the room offered unobstructed views of the ocean and pool area. The pool was large and also had a great view of the ocean. The only criticism I have is that they had few of the resort amenities I've seen at other properties such as kayaks, bicycles, or hammocks, but I knew that in advance. There's really no sunrise view from the property, but that's a geographic limitation they can't really do anything about."

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!"

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."

Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views

8/10 Good

"Great views and location. Pool was nice and clean. If your looking for beach access your out of luck but we sat at waters edge in chairs and it was great. Good value."

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 ￥20,610

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Sunset Drive Beach hotels

1. Lime Tree Bay Resort

2. Chesapeake Beach Resort

3. Matecumbe Resort

4. Breezy Palms Resort

5. Amara Cay Resort

6. Cheeca Lodge & Spa

7. Ragged Edge Resort & Marina

8. La Jolla Resort

9. Islander Resort

10. Treasure Harbor

11. Coconut Cove Resort and Marina

12. Casa Morada

13. The Ocean View Inn & Pub

14. Pines & Palms Resort

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

16. Edgewater Lodge

17. Bayside Villas by Islander Resort

18. Drop Anchor

19. Sands of Islamorada

20. Conch Key Fishing Lodge and Marina

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

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

Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views

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