Compare Luxury Hotels in Islamorada
Secret Bargains - Save an extra 10% or more on select Luxury Hotels
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Featured Islamorada Luxury Hotels

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$304 nightly
The price is $342 total per night
$342 total
Jul 13 - Jul 14
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be steps from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing Co..
On private beach
Pool

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$274 nightly
The price is $309 total per night
$309 total
Jul 6 - Jul 7
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and a 2-minute drive from Florida Keys Brewing Co..
On private beach
Pool

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$186 nightly
The price is $205 total per night
$205 total
Jun 28 - Jun 29
Total with taxes and fees
With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, just a 4-minute walk from Windley Key Fossil Reef Geological State Park and 7 minutes by foot from Hog Heaven.
Pool
Pet friendly

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
$336 nightly
The price is $378 total per night
$378 total
Jul 15 - Jul 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
Located in Islamorada, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort is by the ocean, within a 5-minute drive of Windley Key Fossil Reef Geological State Park and History of Diving Museum.
On private beach
Pool

Creekside Inn
90611 Old Highway Tavernier FL
$127 nightly
The price is $143 total per night
$143 total
Jul 6 - Jul 7
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Creekside Inn, you'll be centrally located in Tavernier, within a 15-minute drive of Jimmy Johnson's Big Chill and Florida Keys Dive Center.
Pool
Pet friendly

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$249 nightly
The price is $280 total per night
$280 total
Jun 22 - Jun 23
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State Park.
On private beach
Pool

Conch On Inn Motel
103 Caloosa Street Tavernier FL
Located in Tavernier (Indian Waterways), Conch On Inn Motel is within a 5-minute drive of Old Road Gallery and Florida Keys Dive Center.
Pet friendly
Parking included

Casa Morada
136 Madeira Road Islamorada FL
$345 nightly
The price is $388 total per night
$388 total
Jun 22 - Jun 23
Total with taxes and fees
With a stay at Casa Morada in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 6 minutes by foot from Lorelei Restaurant & Cabana Bar.
Pool
Breakfast included

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
$188 nightly
The price is $212 total per night
$212 total
Jun 22 - Jun 23
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Fisher Inn Resort & Marina, you'll be centrally located in Islamorada, just a 3-minute walk from Windley Key Fossil Reef Geological State Park and 9 minutes by foot from Hog Heaven.
On private beach
Pool

Islander Resort
82100 Overseas Highway Islamorada FL
$305 nightly
The price is $343 total per night
$343 total
Jul 19 - Jul 20
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 4 minutes by foot from Lorelei Restaurant & Cabana Bar.
On private beach
Pool

Pines & Palms Resort
80401 Old Hwy Islamorada FL
$308 nightly
The price is $347 total per night
$347 total
Jun 30 - Jul 1
Total with taxes and fees
With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 5-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center.
On private beach
Pool

La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
$260 nightly
The price is $293 total per night
$293 total
Jul 6 - Jul 7
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center.
On private beach
Pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Islamorada hotels essential information
Accommodation | 2,173 hotels |
|---|---|
Lowest Price | $143 |
Highest Price | $388 |
Popular hotels | Cheeca Lodge & Spa, Amara Cay Resort, Drop Anchor, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Creekside Inn, Chesapeake Beach Resort, Conch On Inn Motel, Casa Morada, Fisher Inn Resort & Marina, Islander Resort, Pines & Palms Resort, La Siesta Resort & Villas |
Most Recent Islamorada Hotel Reviews

Chesapeake Beach Resort
5 out of 5
Posted 2 hours ago
CheapTickets Verified Review
"Great resort with friendly staff. Very clean!"
A verified traveler stayed at Chesapeake Beach Resort
More to Explore in Islamorada
Top Picks
- Hotels with Suites in Key Colony Beach
- Green Hotels in Islamorada
- Oceanfront Hotels in Tavernier
- Hotels with Hot Tubs in Tavernier
- 4 Star Hotels in Duck Key
- Motels in Key Colony Beach
- 5 Star Hotels in Tavernier
- 5 Star Hotels in Islamorada
- Key Largo Hotels
- Hotels near Harry Harris Park
- Indian Waterways Hotels
- Hotels near Everglades National Park
- 4 Star Hotels in Key Largo
- Cross Key Waterways Hotels
- Hotels with Restaurants in Key Largo
- Green Hotels in Key Largo
- Kid Friendly Hotels in Islamorada
- 4 Star Hotels in Key Colony Beach
- 3 Star Hotels in Key Largo
- 4 Star Hotels in Islamorada
- Inns in Duck Key
- Hotels with Restaurants in Tavernier
- Hotels with Air Conditioning in Islamorada
- Beach Resorts & in Duck Key
- 3 Star Hotels in Tavernier
- Kid Friendly Hotels in Duck Key
- Hotels near Long Key State Park
- Rv Parks in Duck Key
- Hotels with Childcare in Key Largo
- 5 Star Hotels in Key Largo
- Fishing Resorts & in Islamorada
- Business Hotels in Tavernier
- Vacation Rentals in Tavernier
- Spa Resorts & in Tavernier
- Resorts in Key Colony Beach
- Rv Parks in Key Colony Beach
- Pet Friendly Hotels in Islamorada
- Villas in Tavernier
- Hotels near Anne's Beach
- Apartments in Duck Key
- Tavernier Hotels
- Islamorada Hotels
- Fishing Resorts & in Tavernier
- Hotels with Room Service in Key Largo
- Oceanfront Hotels in Grassy Key
- Beach Resorts & in Key Largo
- Hotels with Childcare in Duck Key
- Anglers Park Hotels
- Pet Friendly Hotels in Key Colony Beach
- Gay Friendly Hotels in Islamorada
- Hotels with a Wedding Venue in Key Largo
- Arcade Hotels in Duck Key
- 4 Star Hotels in Tavernier
- Holiday Park Resorts in Key Largo
- Luxury Hotels in Key Colony Beach
- Condo Rentals in Islamorada
- Condo Rentals in Tavernier
- Golf Resorts & in Islamorada
- 3 Star Hotels in Key Colony Beach
- Historic Hotels in Tavernier
- 4 Star Hotels in Marathon
- Hotels with a Wedding Venue in Duck Key
- Hotels on the Lake in Duck Key
- Flights from Cairo to Marathon
- Flights from Greenville - Spartanburg to Marathon
- Flights to Key Largo
- Flights from Florida Keys Marathon
- Flights to Florida Keys Marathon
- Flights from Phoenix to Marathon
- Flights from Columbus to Marathon
- Flights from Milwaukee to Marathon
- Flights from Hamburg to Marathon
- Flights from Atlanta to Marathon
- Flights from New Orleans to Marathon
- Flights from Casablanca to Marathon
- Flights from Buffalo to Marathon
- Flights from Curitiba to Marathon
- Flights from Barcelona to Marathon
- Flights from Mexico City to Marathon
- Flights from Rochester to Marathon
- Flights from Fort Wayne to Marathon
- Flights from Madrid to Marathon
- Flights from Tampa to Marathon
- Flights from Asuncion to Marathon
- Flights from Detroit to Marathon
- Flights from Istanbul to Marathon
- Flights from Frankfurt to Marathon
- Flights from Santo Domingo to Marathon
- Flights from Montreal to Marathon





