Islamorada Sunset Drive Beach Hotels: 2026 Limited-Time Hotel Deals @Expedia

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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 bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.

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

1. Lime Tree Bay Resort

9.2 km from Sunset Drive Beach

Christopher Michael

HK$907

HK$1,373 total

includes taxes & fees

20 Oct - 21 Oct

A beach with palm trees and lounge chairs.

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

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.

2. Chesapeake Beach Resort

Matecumbe, 14.9 km from Sunset Drive Beach

Dianne

HK$1,185

HK$1,775 total

includes taxes & fees

20 Oct - 21 Oct

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

A beach with thatched umbrellas, palm trees, 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 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.

3. Breezy Palms Resort

Matecumbe, 9.2 km from Sunset Drive Beach

Gavin

HK$770

HK$991 total

includes taxes & fees

21 Oct - 22 Oct

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 compact kitchen with wooden cabinets, a refrigerator, and a window with curtains.

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

4. Matecumbe Resort

Matecumbe, 3.2 km from Sunset Drive Beach

angel

HK$1,130

HK$1,271 total

includes taxes & fees

20 Oct - 21 Oct

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

5. Cheeca Lodge & Spa

Matecumbe, 11.9 km from Sunset Drive Beach

James

HK$1,326

HK$2,066 total

includes taxes & fees

22 Oct - 23 Oct

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 beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

6. Islander Resort

Matecumbe, 12.4 km from Sunset Drive Beach

Bryan

HK$1,532

HK$2,297 total

includes taxes & fees

15 Nov - 16 Nov

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

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

7. Amara Cay Resort

Matecumbe, 9.1 km from Sunset Drive Beach

Ronald

HK$1,319

HK$2,058 total

includes taxes & fees

15 Nov - 16 Nov

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.

8. Ragged Edge Resort & Marina

19.5 km from Sunset Drive Beach

Nathalie

HK$1,200

HK$1,350 total

includes taxes & fees

29 Oct - 30 Oct

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

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

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.

9. Treasure Harbor

19.6 km from Sunset Drive Beach

Laura

HK$770

HK$1,970 total

includes taxes & fees

20 Oct - 21 Oct

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

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

10. Casa Morada

Matecumbe, 12.7 km from Sunset Drive Beach

David

HK$1,229

HK$1,471 total

includes taxes & fees

26 Oct - 27 Oct

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 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.

11. The Islands of Islamorada

Matecumbe, 13.6 km from Sunset Drive Beach

Christian

HK$4,097

HK$5,123 total

includes taxes & fees

20 Oct - 21 Oct

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

12. Coconut Cove Resort and Marina

16.7 km from Sunset Drive Beach

Hailey Ritch and Patrick

HK$1,169

HK$1,316 total

includes taxes & fees

26 Oct - 27 Oct

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.

13. Pines & Palms Resort

Matecumbe, 9.7 km from Sunset Drive Beach

Michael

HK$1,067

HK$1,633 total

includes taxes & fees

20 Oct - 21 Oct

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 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.

14. The Ocean View Inn & Pub

16.6 km from Sunset Drive Beach

Maria

HK$1,462

HK$1,645 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

15.8 km from Sunset Drive Beach

Liosbel

HK$1,877

HK$2,686 total

includes taxes & fees

2 Nov - 3 Nov

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 beachfront property with a staircase leading to a light blue building, 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.

16. La Jolla Resort

Matecumbe, 12.9 km from Sunset Drive Beach

Brett

HK$1,123

HK$1,484 total

includes taxes & fees

22 Oct - 23 Oct

A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

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

A beach with colorful buildings, kayaks, and lounge chairs.

A row of colorful beach huts with palm trees in the background.

17. La Siesta Resort & Villas

Matecumbe, 9.7 km from Sunset Drive Beach

Brianne

HK$1,213

HK$1,939 total

includes taxes & fees

15 Nov - 16 Nov

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.

18. Bayside Villas by Islander Resort

Matecumbe, 11 km from Sunset Drive Beach

Brian

HK$1,808

HK$2,608 total

includes taxes & fees

25 Oct - 26 Oct

A pier extending into clear blue water with boats docked.

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

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

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

19. Edgewater Lodge

13.1 km from Sunset Drive Beach

Leda

HK$1,562

HK$1,757 total

includes taxes & fees

20 Oct - 21 Oct

A hotel room with a bed, a nightstand with a lamp, a microwave, and a refrigerator.

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

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.

20. Conch Key Fishing Lodge and Marina

17.6 km from Sunset Drive Beach

Daniel

HK$672

HK$756 total

includes taxes & fees

29 Oct - 30 Oct

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Compare popular hotels close to Sunset Drive Beach

Property	Property class	Guest rating
Lime Tree Bay Resort	9.4 Exceptional 1,544 reviews	View
Chesapeake Beach Resort	9.4 Exceptional 1,802 reviews	View
Breezy Palms Resort	9.0 Wonderful 771 reviews	View
Matecumbe Resort	9.0 Wonderful 177 reviews	View
Cheeca Lodge & Spa	9.2 Wonderful 1,490 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 “FLASH SALE 5/1-5/10/25+DOCK+POOL+GYM+”150” 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 holiday is part of your travel plans, Anne's Beach might be the perfect place to visit 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, take a look at the 158 hotels and other accommodation options you'll find within a mile.

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

Caloosa Cove Resort by CoolVacay is one of the top choices for your stay based on our traveller 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 will I find near Sunset Drive Beach?

Expedia has 158 hotels and other accommodation options 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 that most hotel bookings are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you have a reservation that's non-refundable, you may still be able to cancel and be given a refund within 24 hours of your booking. Enter your dates, click on "Search", then use the filter option "fully refundable" to get the top deals on offer near Sunset Drive Beach.

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 from Sunset Drive Beach, or make a stop by Long Key State Park, located 6.4 mi away.

Islamorada Sunset Drive Beach Hotels

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Sunset Drive Beach hotels

1. Lime Tree Bay Resort

2. Chesapeake Beach Resort

3. Breezy Palms Resort

4. Matecumbe Resort

5. Cheeca Lodge & Spa

6. Islander Resort

7. Amara Cay Resort

8. Ragged Edge Resort & Marina

9. Treasure Harbor

10. Casa Morada

11. The Islands of Islamorada

12. Coconut Cove Resort and Marina

13. Pines & Palms Resort

14. The Ocean View Inn & Pub

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

16. La Jolla Resort

17. La Siesta Resort & Villas

18. Bayside Villas by Islander Resort

19. Edgewater Lodge

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 “FLASH SALE 5/1-5/10/25+DOCK+POOL+GYM+”150” 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