Hotels in Islamorada

October 2026
November 2026

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This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Where to stay in Islamorada?

1. La Jolla Resort

La Jolla Resort
Matecumbe
$97
$137 total
includes taxes & fees
Sep 28 - Sep 29
La Jolla Resort

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
$149
$241 total
includes taxes & fees
Sep 29 - Sep 30
Cheeca Lodge & Spa

3. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
$151
$226 total
includes taxes & fees
Sep 29 - Sep 30
Chesapeake Beach Resort

4. Amara Cay Resort

Amara Cay Resort
Matecumbe
$172
$266 total
includes taxes & fees
Sep 27 - Sep 28
Amara Cay Resort

5. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
$93
$120 total
includes taxes & fees
Oct 1 - Oct 2
Breezy Palms Resort

6. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
$127
$175 total
includes taxes & fees
Sep 28 - Sep 29
Fisher Inn Resort & Marina

7. Islander Resort

Islander Resort
Matecumbe
$212
$312 total
includes taxes & fees
Oct 1 - Oct 2
Islander Resort

8. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
$149
$168 total
includes taxes & fees
Sep 27 - Sep 28
Coconut Cove Resort and Marina

9. Rock Reef Resort

Rock Reef Resort
Rock Harbor
$93
$104 total
includes taxes & fees
Sep 27 - Sep 28
Rock Reef Resort

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$207
$306 total
includes taxes & fees
Oct 15 - Oct 16
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

11. Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
$118
$166 total
includes taxes & fees
Sep 28 - Sep 29
Hadley Resort and Marina

12. Drop Anchor

Drop Anchor
Islamorada
$131
$182 total
includes taxes & fees
Sep 27 - Sep 28
Drop Anchor

13. Drift Hotel

Drift Hotel
Key Largo
$82
$104 total
includes taxes & fees
Sep 28 - Sep 29
Drift Hotel

14. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
$127
$188 total
includes taxes & fees
Oct 8 - Oct 9
Lime Tree Bay Resort

15. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
Islamorada
$140
$157 total
includes taxes & fees
Sep 27 - Sep 28
Ragged Edge Resort & Marina

16. Treasure Harbor

Treasure Harbor
Islamorada
$119
$275 total
includes taxes & fees
Sep 28 - Sep 29
Treasure Harbor

17. Matecumbe Resort

Matecumbe Resort
Matecumbe
$143
$161 total
includes taxes & fees
Sep 27 - Sep 28
Matecumbe Resort

18. Atlantic Bay Resort

Atlantic Bay Resort
Tavernier
$151
$192 total
includes taxes & fees
Sep 28 - Sep 29
Atlantic Bay Resort

19. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
Key Largo
$97
$110 total
includes taxes & fees
Sep 27 - Sep 28
The Pelican Key Largo Cottages

20. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
$219
$302 total
includes taxes & fees
Oct 1 - Oct 2
Pines & Palms Resort
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Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
$134
per night
$196 total
includes taxes & fees
Sign in for extra savings
Lime Tree Bay Resort

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
$152
per night
$204 total
includes taxes & fees
Fisher Inn Resort & Marina

Drop Anchor

Drop Anchor
Islamorada
$132
per night
$183 total
includes taxes & fees
Drop Anchor

Amara Cay Resort

Amara Cay Resort
Matecumbe
$223
per night
$324 total
includes taxes & fees
Amara Cay Resort

Bayside Inn Key Largo

Bayside Inn Key Largo
Key Largo
$118
per night
$158 total
includes taxes & fees
Sign in for extra savings
Bayside Inn Key Largo

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
$178
per night
$232 total
includes taxes & fees
Hadley Resort and Marina

Islander Resort

Islander Resort
Matecumbe
$293
per night
$402 total
includes taxes & fees
Islander Resort

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
Tavernier
$169
per night
$212 total
includes taxes & fees
Ocean Pointe Suites at Key Largo

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
$346
per night
$462 total
includes taxes & fees
Sign in for extra savings
Bayside Villas by Islander Resort

Atlantic Bay Resort

Atlantic Bay Resort
Tavernier
$386
per night
$457 total
includes taxes & fees
Sign in for extra savings
Atlantic Bay Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
$218
per night
$301 total
includes taxes & fees
Sign in for extra savings
Chesapeake Beach Resort

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
$178
per night
$232 total
includes taxes & fees
Fisher Inn Resort & Marina

Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
$51 off
$172
per night
$239 total
includes taxes & fees
Lime Tree Bay Resort

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
$178
per night
$232 total
includes taxes & fees
Hadley Resort and Marina

Bayside Inn Key Largo

Bayside Inn Key Largo
Key Largo
$129
per night
$170 total
includes taxes & fees
Sign in for extra savings
Bayside Inn Key Largo

Drop Anchor

Drop Anchor
Islamorada
$177
per night
$235 total
includes taxes & fees
Sign in for extra savings
Drop Anchor

Amara Cay Resort

Amara Cay Resort
Matecumbe
$32 off
$287
per night
$396 total
includes taxes & fees
Amara Cay Resort

Islander Resort

Islander Resort
Matecumbe
$330
per night
$444 total
includes taxes & fees
Islander Resort

Atlantic Bay Resort

Atlantic Bay Resort
Tavernier
$226
per night
$277 total
includes taxes & fees
Sign in for extra savings
Atlantic Bay Resort

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
Tavernier
$169
per night
$212 total
includes taxes & fees
Ocean Pointe Suites at Key Largo

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
$361
per night
$480 total
includes taxes & fees
Sign in for extra savings
Bayside Villas by Islander Resort

Amara Cay Resort

Amara Cay Resort
Matecumbe
$40 off
$182
per night
$555 total
includes taxes & fees
Amara Cay Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
$74 off
$332
per night
$860 total
includes taxes & fees
Chesapeake Beach Resort

Islander Resort

Islander Resort
Matecumbe
$350
per night
$933 total
includes taxes & fees
Sign in for extra savings
Islander Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
$135 off
$225
per night
$597 total
includes taxes & fees
Lime Tree Bay Resort

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
$220
per night
$561 total
includes taxes & fees
Hadley Resort and Marina

Drop Anchor

Drop Anchor
Islamorada
$201
per night
$522 total
includes taxes & fees
Drop Anchor

Bayside Inn Key Largo

Bayside Inn Key Largo
Key Largo
$154
per night
$396 total
includes taxes & fees
Sign in for extra savings
Bayside Inn Key Largo

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$350
per night
$934 total
includes taxes & fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Atlantic Bay Resort

Atlantic Bay Resort
Tavernier
$260
per night
$630 total
includes taxes & fees
Sign in for extra savings
Atlantic Bay Resort

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
Matecumbe
$36 off
$219
per night
$560 total
includes taxes & fees
Caloosa Cove Resort by CoolVacay

Coconut Palm Inn

Coconut Palm Inn
Tavernier
$330
per night
$820 total
includes taxes & fees
Sign in for extra savings
Coconut Palm Inn

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
$474
per night
$1,212 total
includes taxes & fees
Sign in for extra savings
Bayside Villas by Islander Resort

Check out pet-friendly hotels in Islamorada

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
$151
$226 total
includes taxes & fees
Sep 29 - Sep 30
Chesapeake Beach Resort

Amara Cay Resort

Amara Cay Resort
Matecumbe
$172
$266 total
includes taxes & fees
Sep 27 - Sep 28
Amara Cay Resort

Islander Resort

Islander Resort
Matecumbe
$212
$312 total
includes taxes & fees
Oct 1 - Oct 2
Islander Resort

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
$127
$175 total
includes taxes & fees
Sep 28 - Sep 29
Fisher Inn Resort & Marina

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$207
$306 total
includes taxes & fees
Oct 15 - Oct 16
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Drop Anchor

Drop Anchor
Islamorada
$131
$182 total
includes taxes & fees
Sep 27 - Sep 28
Drop Anchor

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
$118
$166 total
includes taxes & fees
Sep 28 - Sep 29
Hadley Resort and Marina

Creekside Inn

Creekside Inn
Tavernier
$143
$161 total
includes taxes & fees
Oct 8 - Oct 9
Creekside Inn

Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
$127
$188 total
includes taxes & fees
Oct 8 - Oct 9
Lime Tree Bay Resort

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
$247
$350 total
includes taxes & fees
Sep 28 - Sep 29
Bayside Villas by Islander Resort
View all properties

You may also like resorts in Islamorada

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
$149
$241 total
includes taxes & fees
Sep 29 - Sep 30
Cheeca Lodge & Spa

Amara Cay Resort

Amara Cay Resort
Matecumbe
$172
$266 total
includes taxes & fees
Sep 27 - Sep 28
Amara Cay Resort

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$207
$306 total
includes taxes & fees
Oct 15 - Oct 16
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
$127
$188 total
includes taxes & fees
Oct 8 - Oct 9
Lime Tree Bay Resort

Matecumbe Resort

Matecumbe Resort
Matecumbe
$143
$161 total
includes taxes & fees
Sep 27 - Sep 28
Matecumbe Resort

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
$262
$350 total
includes taxes & fees
Sep 28 - Sep 29
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
$263
$351 total
includes taxes & fees
Oct 8 - Oct 9
Playa Largo Resort & Spa, Autograph Collection
View all properties

You can also stay at hotels with a pool in Islamorada

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
$151
$226 total
includes taxes & fees
Sep 29 - Sep 30
Chesapeake Beach Resort

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
$149
$241 total
includes taxes & fees
Sep 29 - Sep 30
Cheeca Lodge & Spa

Amara Cay Resort

Amara Cay Resort
Matecumbe
$172
$266 total
includes taxes & fees
Sep 27 - Sep 28
Amara Cay Resort

Islander Resort

Islander Resort
Matecumbe
$212
$312 total
includes taxes & fees
Oct 1 - Oct 2
Islander Resort

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$207
$306 total
includes taxes & fees
Oct 15 - Oct 16
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
$149
$168 total
includes taxes & fees
Sep 27 - Sep 28
Coconut Cove Resort and Marina

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
$127
$175 total
includes taxes & fees
Sep 28 - Sep 29
Fisher Inn Resort & Marina

Pines & Palms Resort

Pines & Palms Resort
Matecumbe
$219
$302 total
includes taxes & fees
Oct 1 - Oct 2
Pines & Palms Resort

La Jolla Resort

La Jolla Resort
Matecumbe
$97
$137 total
includes taxes & fees
Sep 28 - Sep 29
La Jolla Resort

Drop Anchor

Drop Anchor
Islamorada
$131
$182 total
includes taxes & fees
Sep 27 - Sep 28
Drop Anchor
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Go beyond your typical stay in Islamorada

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Our prices for hotels in Islamorada are cheapest in September

Price trends for hotels in Islamorada

Pricing is based on two traveler single night rates
View properties in September

September

High 29°C / low 28°C. Sunny most days.
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Monthly weather averages (˚C)

Top neighborhoods in Islamorada

Matecumbe

Matecumbe gives you the full Florida Keys experience without trying too hard. Snorkel crystal waters at Anne's Beach, grab a cold one at Florida Keys Brewing Co, or watch fishermen haul in their catch at Bud n' Mary's. The Hurricane Monument and Indian Key Historic State Park tell stories of this laid-back paradise, while the MoradaWay Arts District adds cultural flair. Waterfront tiki bars serve fresh mahi-mahi as the sun sets over Florida Bay. Most visitors stay in charming resorts with private beaches and pools, though vacation rentals offer more space. You'll need a car to explore properly, but many resort areas are perfectly walkable.

Lower Matecumbe Beach

Lower Matecumbe Beach offers pristine Atlantic shorelines where powder-soft sand meets crystal-clear turquoise waters. Sunset Drive Beach and nearby Anne's Beach provide perfect spots for swimming and sunbathing in the shallow, calm waters. You'll discover scenic overlooks at mile markers, historic fishing piers extending into Florida Bay, and the popular Founder's Park with its recreational facilities. Waterfront seafood restaurants serve fresh mahi-mahi and key lime pie with stunning ocean views. Accommodations range from luxury beachfront resorts to intimate bed-and-breakfasts. Getting around requires a rental car, though the beachfront areas are highly walkable with bike-friendly roads.

Venetian Shores

Venetian Shores offers the Keys dream—canal-front homes with private docks where dolphins practically introduce themselves at breakfast. Spend your days boating from your backyard to snorkeling spots or fishing the flats between the Atlantic and Florida Bay. This upscale residential enclave lets you live like a local without the tourist crowds. You'll need wheels to explore nearby attractions like Founders Park and the History of Diving Museum. The neighborhood itself has no restaurants or shops—just peaceful streets lined with luxury vacation rentals featuring pools and tropical gardens. For dining out, a quick 5-10 minute drive takes you to Islamorada's waterfront eateries.

Seabreeze Trailer Park

Seabreeze Trailer Park offers a laid-back slice of Florida Keys paradise without the resort price tag. You'll get direct beach access for swimming and snorkeling in crystal-clear waters. Nearby Founders Park and Windley Key Fossil Reef Geological State Park provide perfect day trips. Rain Barrel Village offers local shopping when you need a break from all that sunshine. Seafood restaurants and waterfront dining options are just a short drive away in Islamorada. While public transit is limited, having a rental car or golf cart makes exploring the surrounding Keys a breeze. The peaceful, no-frills atmosphere makes this spot ideal for travelers seeking an authentic Keys experience on a budget.

Top landmarks in Islamorada

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

Anne's Beach

7.8/10 (597 reviews)
If you can't wait to get to the beach, you might enjoy a trip to Anne's Beach located 8.8 mi (14.1 km) from central Islamorada. If you want to continue walking by the waves, head to Sunset Drive Beach located nearby.
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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)
You can stroll along Bud n' Mary's Dive Center for relaxing water views when you're in Matecumbe. Hotels.com travelers also say the area is relaxing and has lots of nice beaches.
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A white tower with a dome, surrounded by palm trees and greenery.

Founders Park

8.8/10 (450 reviews)
Founders Park is 4.6 mi (7.4 km) from central Islamorada, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here? Want to stretch your legs some more? Head to Islamorada County Park, just a short walk away.
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A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Florida Keys Brewing Co.

9.2/10 (520 reviews)
Matecumbe is home to Florida Keys Brewing Co., so why not stop by during your stay in Islamorada.
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An archaeological site with stone structures and metal machinery.

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)
Windley Key Fossil Reef Geological State Park is 2.4 mi (3.8 km) from central Islamorada, why not stop by during your stay. Hotels.com travelers also say the area is family-friendly and has lots of nice beaches.
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Robbie’s of Islamorada

8.4/10 (15 reviews)
You can stroll along Robbie’s of Islamorada for relaxing water views when you're in Matecumbe.
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Islamorada County Park

8.8/10 (198 reviews)
Islamorada County Park is 4.5 mi (7.2 km) from central Islamorada, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here? Want to stretch your legs some more? Head to Founders Park, just a short walk away.
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Islamorada Brewery & Distillery

9.4/10 (8 reviews)
Matecumbe is home to Islamorada Brewery & Distillery, so why not stop by during your stay in Islamorada.
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Learn more about Islamorada

Dubbed the 'Sportfishing Capital of the World,' this Florida Keys paradise invites you to battle trophy tarpon and marlin in azure waters. Dive beneath the surface where coral reefs burst with marine life, or paddle through mysterious mangrove tunnels where herons stalk the shallows. The History of Diving Museum chronicles humanity's underwater exploration, while MoradaWay Arts District showcases island-inspired creativity. Anne's Beach offers shallow wading perfect for families, with picnic tables near the gentle surf. After a day on the water, sample fresh-caught seafood at dockside restaurants. For a wilder adventure, take a day trip to nearby Everglades National Park, where alligators sun themselves amid saw grass prairies.

See all hotels in Islamorada
A white two-story house with blue accents, surrounded by palm trees and a sandy area.

Check out reviews of Islamorada hotels guests love

Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
Rock Harbor

10/10 Exceptional

United States
Audrey
Kona Kai Resort and Gallery - Adults Only

Island Bay Resort

Island Bay Resort
Tavernier

10/10 Exceptional

United States
Michael
Island Bay Resort

Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
Islamorada

10/10 Exceptional

United States
Alejandro
Ragged Edge Resort & Marina

Coconut Palm Inn

Coconut Palm Inn
Tavernier

10/10 Exceptional

United States
K
Coconut Palm Inn

Islander Resort

Islander Resort
Matecumbe

10/10 Exceptional

United States
Patrick
Islander Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key

10/10 Exceptional

United States
Jack
Lime Tree Bay Resort

Atlantic Bay Resort

Atlantic Bay Resort
Tavernier

10/10 Exceptional

United States
Emily
Atlantic Bay Resort

Casa Morada

Casa Morada
Matecumbe

10/10 Exceptional

United States
Peggy
Casa Morada

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe

10/10 Exceptional

United States
David
Cheeca Lodge & Spa

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe

10/10 Exceptional

United States
Paco
Chesapeake Beach Resort

Pines & Palms Resort

Pines & Palms Resort
Matecumbe

10/10 Exceptional

United States
Ralph
Pines & Palms Resort

La Jolla Resort

La Jolla Resort
Matecumbe

10/10 Exceptional

United States
Kathleen
La Jolla Resort

Rock Reef Resort

Rock Reef Resort
Rock Harbor

10/10 Exceptional

United States
Jackson
Rock Reef Resort

The Ocean View Inn & Pub

The Ocean View Inn & Pub
Islamorada

10/10 Exceptional

United States
Heather
The Ocean View Inn & Pub

Sunset Cove Beach Resort

Sunset Cove Beach Resort
Key Largo

10/10 Exceptional

United States
Maricel
Sunset Cove Beach Resort

Seafarer Key Largo

Seafarer Key Largo
Rock Harbor

10/10 Exceptional

United States
Alejandra
Seafarer Key Largo

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada

10/10 Exceptional

United States
Mark
Coconut Cove Resort and Marina

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe

10/10 Exceptional

United States
Miami Resident
Bayside Villas by Islander Resort