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

1. Lime Tree Bay Resort

9.2 km from Sunset Drive Beach

milayda

HK$906

HK$1,373 total

includes taxes & fees

28 Sept - 29 Sept

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

2. Breezy Palms Resort

Matecumbe, 9.2 km from Sunset Drive Beach

Debra

HK$641

HK$846 total

includes taxes & fees

1 Oct - 2 Oct

A beach with palm trees and lounge chairs.

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.

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

3. Chesapeake Beach Resort

Matecumbe, 14.9 km from Sunset Drive Beach

Suresh

HK$1,185

HK$1,774 total

includes taxes & fees

28 Sept - 29 Sept

A beach with rows of sun loungers and palm trees.

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

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

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

4. Ragged Edge Resort & Marina

19.5 km from Sunset Drive Beach

Nathalie

HK$977

HK$1,099 total

includes taxes & fees

27 Sept - 28 Sept

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

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.

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

5. La Jolla Resort

Matecumbe, 12.9 km from Sunset Drive Beach

Leslie

HK$759

HK$1,074 total

includes taxes & fees

28 Sept - 29 Sept

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

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

6. Treasure Harbor

19.6 km from Sunset Drive Beach

Molly

HK$840

HK$2,048 total

includes taxes & fees

28 Sept - 29 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 bathroom with a sink, toilet, and shower. There is a mirror above the sink and a shelf with towels.

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.

7. The Ocean View Inn & Pub

16.6 km from Sunset Drive Beach

Maria

HK$1,461

HK$1,644 total

includes taxes & fees

27 Sept - 28 Sept

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

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

8. Pines & Palms Resort

Matecumbe, 9.7 km from Sunset Drive Beach

Colt

HK$1,546

HK$2,171 total

includes taxes & fees

1 Oct - 2 Oct

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

A compact, well-lit room with a bed, bedside table, and a small seating area.

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.

9. Sands of Islamorada

Matecumbe, 9.2 km from Sunset Drive Beach

Nicolas

HK$1,506

HK$1,800 total

includes taxes & fees

1 Oct - 2 Oct

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

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

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.

10. Drop Anchor

17.2 km from Sunset Drive Beach

Payman

HK$1,031

HK$1,435 total

includes taxes & fees

28 Sept - 29 Sept

A pier extending into clear blue water with boats docked.

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

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.

11. Edgewater Lodge

13.1 km from Sunset Drive Beach

Yudisley

HK$1,171

HK$1,317 total

includes taxes & fees

27 Sept - 28 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 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.

12. Cheeca Lodge & Spa

Matecumbe, 11.9 km from Sunset Drive Beach

RAIBEL

HK$1,169

HK$1,888 total

includes taxes & fees

29 Sept - 30 Sept

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

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

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.

13. Conch Key Fishing Lodge and Marina

17.6 km from Sunset Drive Beach

Eduardo

HK$774

HK$871 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 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.

A paved pathway leading to a beach with palm trees and a view of the ocean.

14. Islander Resort

Matecumbe, 12.4 km from Sunset Drive Beach

John

HK$1,662

HK$2,443 total

includes taxes & fees

1 Oct - 2 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.

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

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

15.8 km from Sunset Drive Beach

Eslita

HK$1,625

HK$2,402 total

includes taxes & fees

6 Oct - 7 Oct

A coastal property with multiple buildings, a wooden dock, and a clear view of the turquoise water.

A waterfront property with a dock, a boat, and a row of houses with a view of the water.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden countertop.

A covered outdoor deck with a table and chairs, overlooking a body of water and trees.

16. Village at Hawks Cay Villas by KeysCaribbean

20.4 km from Sunset Drive Beach

APRIL

HK$1,553

HK$4,350 total

includes taxes & fees

27 Sept - 28 Sept

A pool area with lounge chairs and umbrellas, surrounded by palm trees.

A pathway leading to a pool area with palm trees and a sunset view.

An aerial view of a coastal resort with multiple white buildings, a clear turquoise sea, and lush greenery.

A spacious lobby with high ceilings, large windows, and a central coffee table surrounded by sofas and chairs.

17. Hawks Cay Resort

20.1 km from Sunset Drive Beach

Katherine

HK$1,455

HK$2,240 total

includes taxes & fees

4 Oct - 5 Oct

A resort pool with palm trees and lounge chairs, surrounded by a beachfront.

An aerial view of a resort island with a large building, a swimming pool, and a boat docked nearby.

A modern kitchen with white cabinetry, a stainless steel oven, and a large island with a bowl of fruit.

A resort with a large pool surrounded by lounge chairs, a beach area, and a building with multiple floors.

18. Villas At Hawks Cay Resort

20.1 km from Sunset Drive Beach

Gabriela

HK$2,972

HK$3,829 total

includes taxes & fees

27 Sept - 28 Sept

View all properties

Compare popular hotels close to Sunset Drive Beach

Property	Property class	Guest rating
Lime Tree Bay Resort	9.4 Exceptional 1,517 reviews	View
Breezy Palms Resort	9.0 Wonderful 753 reviews	View
Chesapeake Beach Resort	9.2 Wonderful 1,783 reviews	View
Ragged Edge Resort & Marina	9.6 Exceptional 273 reviews	View
La Jolla Resort	9.2 Wonderful 1,004 reviews	View

Top Sunset Drive Beach Hotel Reviews

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

10/10 Excellent

"Perfect for our weekend trip"

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!"

Private Beachfront Paradise

8/10 Good

"Was missing a bed that was pictured."

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."

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

10/10 Excellent

"Pool and beach area were great. Great value for our family of six. I would stay here again. It was wonderful being able to book 6 nights as opposed to 7 given the Easter holiday and needing to return home. "

Other attractions near Sunset Drive Beach

A beach with a wooden structure, clear blue sky, and dense green foliage.

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 157 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 157 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. Breezy Palms Resort

3. Chesapeake Beach Resort

4. Ragged Edge Resort & Marina

5. La Jolla Resort

6. Treasure Harbor

7. The Ocean View Inn & Pub

8. Pines & Palms Resort

9. Sands of Islamorada

10. Drop Anchor

11. Edgewater Lodge

12. Cheeca Lodge & Spa

13. Conch Key Fishing Lodge and Marina

14. Islander Resort

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

16. Village at Hawks Cay Villas by KeysCaribbean

17. Hawks Cay Resort

18. Villas At Hawks Cay Resort

Compare popular hotels close to Sunset Drive Beach

Top Sunset Drive Beach Hotel Reviews

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

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

Private Beachfront Paradise

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

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

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