Islamorada stretches along US 1, so the first decision is location: which key, and which side of the highway. The Village says it sits between Mile Marker 90.0 and Mile Marker 72.6, and it is no more than one mile wide at its widest point. Bayside is the Florida Bay side of US 1 and oceanside is the Atlantic side. Below, we name a side only when the property names it. The list includes only places whose own site loaded on October 21, 2026 with an Islamorada address. We publish no ratings, prices or rankings.
- The Village says Islamorada sits in the middle of the Florida Keys, between Mile Marker 90.0 and Mile Marker 72.6 on U.S. Highway 1. Islamorada, Village of Islands: Why Islamorada Matters
- The Village says Islamorada is no more than one mile wide at its widest point, with an average elevation of about five feet above sea level. Islamorada, Village of Islands: Why Islamorada Matters
Windley Key
Three Waters Resort & Marina, 84001 Overseas Hwy, is the former Holiday Isle and later Postcard Inn. Its history page traces the property to Holiday Isle Resort & Marina in the 1950s, says it was badly damaged by Hurricane Irma in 2017, and describes it today as 15 oceanfront acres with 214 rooms, suites and cottages. It belongs to the Islamorada Resort Collection along with Amara Cay and La Siesta. Kindler Wood-Fired Fare, which is open to the public, is on site.
Drop Anchor Resort, 84959 Overseas Highway, calls itself “a Florida Keys vacation lodge located at MM85 on Windley Key” and offers oceanfront rooms and kitchen suites. Theater of the Sea (MM 84.5) and Windley Key Fossil Reef Geological State Park (MM 84.9) are on the same key.
Upper Matecumbe Key, from Whale Harbor south
Chesapeake Beach Resort, 83409 Overseas Hwy, calls itself “Islamorada’s legendary beach and fishing destination” and an oceanfront venue for weddings and events.
Casa Morada, 82200 Overseas Hwy, is a small boutique hotel. It offers “barefoot luxury, ocean breezes, boat tours, and dreamy suites,” and lets guests choose between “Garden Peace or Bayside Breeze” rooms.
Islander Resort, 82100 Overseas Highway, gives Mile Marker 82.1 in its site footer and has oceanfront bungalows and suites. The separate Bayside Villas by Islander are two-bedroom townhouses on the bay whose guests can use the oceanside resort’s amenities. The Florida Keys History & Discovery Center, open Tuesday to Sunday from 10 a.m. to 5 p.m., is on the Islander’s property, and the Fish for Holly Sailfish Tournament (January 8 to 9, 2027) is based there.
- Fish for Holly says its 9th Annual Fish for Holly Sailfish Tournament is January 8 to 9, 2027 at Islander Resort, Islamorada. Fish for Holly Sailfish Tournament: Tournament page
Cheeca Lodge & Spa, 81801 Overseas Highway, describes itself as a 27-acre oceanfront resort with a golf course, a spa and several restaurants, one of them Atlantic’s Edge. The Gold Cup series site lists the Cheeca Lodge Presidential Sailfish Tournament for January 23 and 24, 2027, a date we could not confirm on the host’s own page.
La Siesta Resort & Villas, 80241 Overseas Hwy, calls itself “a lush oasis of stunning sunrises” but does not say which side of the highway it is on. Amara Cay Resort, 80001 Overseas Hwy, mentions views of the Alligator Reef Lighthouse, a beach and a pool, and gives guests access to the sister resorts’ restaurants and water taxi.
The Moorings Village, 123 Beach Rd, is a family-owned cottage resort. Its beachfront homes sit under the tree canopy, and the site says the present owner bought the property in 1987. It posts no mile marker.
Our list has no lodging on Plantation Key or Lower Matecumbe Key. That reflects the limits of our list, not proof that none exists. On Lower Matecumbe Key, the stops on our list are Robbie’s of Islamorada (MM 77.5 bayside) and Anne’s Beach (MM 73.5 oceanside).
Taxes on a short stay
The Monroe County Tax Collector says the Tourist Development Tax is 5% of the total rental amount for stays of 6 months or less in hotels, motels, condominiums, RV parks and similar lodging. We found no Village page listing an extra local lodging tax, and we did not research state sales tax. Some properties post their own resort fees, so ask about the full nightly total before you book. Source: Monroe County Tax Collector.
- The Monroe County Tax Collector says the Tourist Development Tax is 5% of the total rental amount for stays of 6 months or less in hotels, motels, condominiums, RV parks and similar lodging. Monroe County Tax Collector: Tourist Development Tax
- The Monroe County Tax Collector lists a 5% tourist development tax; we did not find a Village page stating any additional local lodging tax when we checked on October 21, 2026. Monroe County Tax Collector: Tourist Development Tax
Founders Park when you are staying in Islamorada
Village residents and their guests get into Founders Park free, and non-residents pay the posted fee. The Village says non-rental guests staying at an Islamorada residence can get a free Guest Pass from their host, good for up to 30 days. That covers non-rental guests only, so ask the park office before you count on one.
- The Village says Village residents and their guests get free admission to Founders Park; park fees apply to non-Islamorada residents. Islamorada, Village of Islands: Founders Park Rules
Dates that fill the calendar
When you choose your dates, check the events page. The Chamber’s Holiday Fest is Friday, December 4, 2026, and the Islamorada Sailfish Tournament fishes December 5 and 6. Island Fest is April 10 and 11, 2027, and FWC’s lobster sport season is July 28 and 29, 2027. The Atlantic hurricane season runs June 1 to November 30.
- The Chamber says the 22nd Annual Islamorada Holiday Fest is Friday, December 4, 2026, 4 to 10 p.m. on the Great Lawn at Founders Park, with the Holiday Parade at 7:30 p.m. Islamorada Chamber of Commerce: Holiday Fest 2026
- The Islamorada Sailfish Tournament says its 63rd annual event fishes December 5 and 6, 2026, with festivities starting Friday, December 4; it is the primary fundraiser of the Islamorada Charter Boat Association. Islamorada Sailfish Tournament: home page
- The Chamber says the 35th Annual Island Fest is Saturday and Sunday, April 10 and 11, 2027, 10am to 5pm at Founders Park, mile marker 87 bayside. Islamorada Chamber of Commerce: Island Fest
- FWC lists the 2027 spiny lobster sport season as July 28 to 29, 2027 (the last consecutive Wednesday and Thursday of July), for residents and non-residents. FWC: Spiny Lobster recreational regulations
- For the Keys, the season to plan around is the Atlantic hurricane season: June 1 through November 30 every year, as NOAA's National Hurricane Center defines it. NOAA National Hurricane Center: Tropical Cyclone Climatology
Every property on our list
Cheeca Lodge & Spa
Oceanfront resort
81801 Overseas Highway, Islamorada, Florida 33036
The resort calls itself a '27-acre oceanfront Islamorada resort' with a golf course, spa and several restaurants on site (Atlantic's Edge, Mia Cucina, Nikai Sushi Bar & Restaurant among them). Key inferred from the OSM pin position.
Source: Cheeca Lodge & Spa: The Best Islamorada Resort, checked 2026-10-21
Islander Resort
Oceanfront resort
82100 Overseas Highway, Islamorada, FL 33036
Oceanfront bungalows and suites on the 'oceanside resort'; the separate Bayside Villas by Islander (81450 Overseas Highway in OSM) are two-bedroom townhouses on the bay with full access to the oceanside resort's amenities.
Source: Islander Resort: Luxury Florida Keys Resort in Islamorada, checked 2026-10-21
Three Waters Resort & Marina
Oceanfront resort and marina
84001 Overseas Hwy, Islamorada, FL 33036
The former Holiday Isle and later Postcard Inn Beach Resort & Marina: its history page says the property traces its roots to the 1950s as Holiday Isle Resort & Marina, was rebranded Postcard Inn, was badly damaged by Hurricane Irma in 2017 and is now Three Waters Resort & Marina. '15 oceanfront acres' with '214 rooms, suites, and cottages'. holidayisle.com redirects here. Part of the Islamorada Resort Collection with Amara Cay and La Siesta.
Source: Islamorada Resort Collection: The History of Three Waters Resort in Islamorada, checked 2026-10-21
Amara Cay Resort
Boutique resort
80001 Overseas Hwy, Islamorada, FL 33036
Boutique resort in the Islamorada Resort Collection; the site mentions 'captivating views of the Alligator Reef Lighthouse', a beach and pool, and guest access to the sister resorts' restaurants and water taxi.
Source: Islamorada Resort Collection: Amara Cay Resort, checked 2026-10-21
La Siesta Resort & Villas
Resort and villas
80241 Overseas Hwy, Islamorada, FL 33036
Islamorada Resort Collection property described as 'a lush oasis of stunning sunrises'. The site does not state ocean or bay side.
Source: Islamorada Resort Collection: La Siesta Resort & Villas, checked 2026-10-21
Casa Morada
Boutique hotel
82200 Overseas Hwy. Islamorada, FL 33036
Small boutique hotel offering 'barefoot luxury, ocean breezes, boat tours, and dreamy suites'; its rooms section invites guests to choose 'Garden Peace or Bayside Breeze'.
Source: Casa Morada, checked 2026-10-21
Chesapeake Beach Resort
Oceanfront resort
83409 Overseas Hwy, Islamorada, FL 33036
Calls itself 'Islamorada's legendary beach and fishing destination' and 'an oceanfront venue' for weddings and events.
Source: Chesapeake Beach Resort, checked 2026-10-21
Drop Anchor Resort
Oceanfront lodge
84959 Overseas Highway Islamorada, Florida, 33036
'A Florida Keys vacation lodge located at MM85 on Windley Key in Islamorada' with oceanfront rooms and kitchen suites. dropanchorresort.com redirects to dropanchorislamorada.com.
Source: Drop Anchor: Tropical Paradise Vacation Resort in Islamorada, FL, checked 2026-10-21
The Moorings Village
Beachfront cottage resort
123 Beach Rd, Islamorada, FL 33036
Family-owned and operated cottage resort; the site describes 'beachfront homes' kept under the tree canopy 'to be as discrete as possible from a boating or ocean approach', and says the present owner, Hubert Baudoin, bought it in 1987. The site lists a daily resort fee of $35.00 plus 12.5% tax.
Source: The Moorings Village, checked 2026-10-21
Planning your stay: FAQ
Where is the Village office and what is the phone number?
The Village lists 86800 Overseas Highway, Islamorada, FL 33036, phone 305-664-6400.
How much is admission to the History of Diving Museum?
The museum lists $15 adults, $13 seniors 62+, $7 children 6 to 11, free for children 5 and under, $12 US veterans and $11 college students with ID. US active military are free.
Can I bring my dog to the History of Diving Museum?
The museum says it is pet-friendly for well-behaved, leashed domestic animals under 50 lbs.
What are Theater of the Sea hours?
Park hours are 9:15 a.m. to 5:00 p.m. The last set of shows starts at 2:00 and the last program at 4:25. Parking is free.
How much is Theater of the Sea general admission?
Theater of the Sea lists $49.95 for ages 11+, $32.95 for ages 3 to 10, and free for ages 2 and under.
Source: Theater of the Sea: home page
Can I bring food into Theater of the Sea?
No. The park does not permit outside food or drink, glass, straws and lids, drones, snorkels or smoking. Leashed dogs are allowed if you clean up after them.
What are Windley Key state park hours and fees?
Florida State Parks lists 8 a.m. to 5 p.m., Thursday through Monday, closed Tuesday and Wednesday. Admission is $2.50 per person.
Source: Florida State Parks: Windley Key Fossil Reef Geological State Park, Hours & Fees
Is Indian Key open?
Florida State Parks posted that effective April 2026 Indian Key is completely closed to the public while its dock is rebuilt, a project slated to take up to six months. Check the park page before going.
What is the fee at Indian Key?
When open, Florida State Parks lists $2.50 per person, paid in cash at the iron ranger near the kayak launch or online. Hours are 8 a.m. to sunset.
What are Lignumvitae Key hours and fees?
Florida State Parks lists 8 a.m. to 4 p.m., Thursday through Monday, closed Tuesday and Wednesday. The visitor fee is $2.50 per person and the tour fee $2 per person.
Source: Florida State Parks: Lignumvitae Key Botanical State Park, Hours & Fees
Are there ranger tours at Lignumvitae Key?
Florida State Parks gives two answers: the main page says ranger-guided tours are currently unavailable, while the Hours & Fees page lists tours Friday to Sunday at 10 a.m. and 2 p.m. Call 305-664-2540 to confirm.
Source: Florida State Parks: Lignumvitae Key Botanical State Park
How much is a non-resident saltwater fishing license?
FWC lists $47.00 annual, $17.00 for 3 days and $30.00 for 7 days.
Do I need a license to fish from shore or a bridge?
FWC says you need a license if you cast a line, even for catch and release. Its no-cost shoreline-only license is listed as a resident license.
Do I need my own license on a fishing charter?
FWC exempts anglers fishing from a for-hire vessel (guide, charter, party boat) with a valid charter license.
Do kids need a fishing license?
FWC exempts youth under 16 from recreational fishing licenses and snook and lobster permits.
When is hurricane season?
Islamorada sits in the Atlantic hurricane basin, and NOAA's National Hurricane Center puts the season at June 1 through November 30 each year.
Source: NOAA National Hurricane Center: Tropical Cyclone Climatology
Can I drink alcohol at Founders Park?
No. The Village has zero tolerance for alcohol at Founders Park, and no glass, smoking or fishing.
Can visitors use Founders Park?
Yes. The Village says park fees apply to non-Islamorada residents; residents and their guests get free admission.
Is there public transportation in Islamorada?
The Village runs Freebee, an on-demand electric rideshare across Islamorada at $2 per rider, a fare that began in July 2026.
Source: Islamorada, Village of Islands: Ridesharing Services (Freebee)
What is the hotel tax in the Florida Keys?
The Monroe County Tax Collector says the Tourist Development Tax is 5% of the total rental amount for stays of 6 months or less.
Source: Monroe County Tax Collector: Tourist Development Tax
Where is the Islamorada visitor center?
The Chamber of Commerce & Visitors Center is at 87100 Overseas Hwy, Mile Marker 87 bayside. Phone 305-664-4503.
Dates, rules and hours can change. The organisers have the final word: Village of Islamorada (official site)