Compare Hotels with Bars in Islamorada
Secret Bargains - Save an extra 10% or more on select Hotels with Bars
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 Hotels with Bars

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$289 nightly
The price is $325 total per night
$325 total
May 3 - May 4
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

Islander Resort
82100 Overseas Highway Islamorada FL
$276 nightly
The price is $311 total per night
$311 total
May 19 - May 20
Total with taxes and fees
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 7 minutes by foot from Islamorada Brewery & Distillery.
On private beach
Pool

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
$322 nightly
The price is $362 total per night
$362 total
May 25 - May 26
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

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$364 nightly
The price is $410 total per night
$410 total
Apr 29 - Apr 30
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

Pines & Palms Resort
80401 Old Hwy Islamorada FL
$299 nightly
The price is $336 total per night
$336 total
Apr 29 - Apr 30
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

Casa Morada
136 Madeira Road Islamorada FL
$536 nightly
The price is $603 total per night
$603 total
Apr 29 - Apr 30
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 9 minutes by foot from Keys History & Discovery Center.
Pool
Breakfast included

Creekside Inn
90611 Old Highway Tavernier FL
$433 nightly
The price is $487 total per night
$487 total
Apr 29 - Apr 30
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
A stay at Creekside Inn places you in the heart of Tavernier, a short 3-minute walk from Florida Keys Dive Center and within 2 minutes by car from Mariners Hospital.
Pool
Pet friendly

La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
$253 nightly
The price is $285 total per night
$285 total
May 12 - May 13
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

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
$198 nightly
The price is $223 total per night
$223 total
Apr 29 - Apr 30
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
A stay at Fisher Inn Resort & Marina places you in the heart of Islamorada, a short 3-minute walk from Windley Key Fossil Reef Geological State Park and within 3 minutes by car from Rain Barrel Village.
On private beach
Pool

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$210 nightly
The price is $232 total per night
$232 total
Apr 30 - May 1
Total with taxes and fees
With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, a 4-minute walk from Windley Key Fossil Reef Geological State Park and a 3-minute drive from Rain Barrel Village.
Pool
Pet friendly

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$249 nightly
The price is $280 total per night
$280 total
May 10 - May 11
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
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 | 2,215 hotels |
|---|---|
Lowest Price | $223 |
Highest Price | $603 |
Popular hotels | Amara Cay Resort, Islander Resort, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Cheeca Lodge & Spa, Pines & Palms Resort, Casa Morada, Creekside Inn, La Siesta Resort & Villas, Fisher Inn Resort & Marina, Drop Anchor, Chesapeake Beach Resort, The Caribbean Resort |
Most Recent Islamorada Hotel Reviews

Chesapeake Beach Resort
5 out of 5
Posted 6 hours ago
CheapTickets Verified Review
"Breakfast area too small. Was chilly for Florida - no seating indoor or outdoor to eat your breakfast. "
A verified traveler stayed at Chesapeake Beach Resort
More to Explore in Islamorada
Top Picks
- 4 Star Hotels in Tavernier
- 4 Star Hotels in Marathon
- Hotels near Everglades National Park
- 4 Star Hotels in Duck Key
- Hotels with Restaurants in Tavernier
- Resorts in Key Colony Beach
- 4 Star Hotels in Key Colony Beach
- Anglers Park Hotels
- Rv Parks in Key Colony Beach
- Spa Resorts & in Tavernier
- Kid Friendly Hotels in Key Colony Beach
- Hotels near Anne's Beach
- Inns in Duck Key
- Hotels with a Wedding Venue in Key Largo
- Green Hotels in Islamorada
- Apartments in Duck Key
- Hotels with Air Conditioning in Islamorada
- Oceanfront Hotels in Tavernier
- Historic Hotels in Tavernier
- 3 Star Hotels in Key Largo
- Vacation Rentals in Tavernier
- 5 Star Hotels in Tavernier
- Cross Key Waterways Hotels
- Luxury Hotels in Key Colony Beach
- 4 Star Hotels in Islamorada
- Pet Friendly Hotels in Islamorada
- Rv Parks in Duck Key
- Hotels with Childcare in Duck Key
- 4 Star Hotels in Key Largo
- 5 Star Hotels in Key Largo
- Fishing Resorts & in Tavernier
- Kid Friendly Hotels in Islamorada
- Condo Rentals in Tavernier
- Motels in Key Colony Beach
- Islamorada Hotels
- Golf Resorts & in Islamorada
- Green Hotels in Key Largo
- Hotels with Room Service in Key Largo
- 3 Star Hotels in Key Colony Beach
- Hotels with Restaurants in Key Largo
- Hotels with a Wedding Venue in Duck Key
- Condo Rentals in Islamorada
- Hotels on the Lake in Duck Key
- Gay Friendly Hotels in Islamorada
- Key Largo Hotels
- Beach Resorts & in Key Largo
- Villas in Tavernier
- Indian Waterways Hotels
- Oceanfront Hotels in Grassy Key
- Kid Friendly Hotels in Duck Key
- Fishing Resorts & in Islamorada
- Arcade Hotels in Duck Key
- Hotels with Childcare in Key Largo
- Hotels with Hot Tubs in Tavernier
- Romantic Getaways & Hotels in Key Colony Beach
- Tavernier Hotels
- Beach Resorts & in Duck Key
- 3 Star Hotels in Tavernier
- Holiday Park Resorts in Key Largo
- 5 Star Hotels in Islamorada
- Business Hotels in Tavernier
- Hotels near Harry Harris Park
- Hotels near Long Key State Park
- Flights from Milwaukee to Marathon
- Flights from Atlanta to Marathon
- Flights from Tampa to Marathon
- Flights from Kingston to Marathon
- Flights from Incheon to Marathon
- Flights from Richmond to Marathon
- Flights from Hamburg to Marathon
- Flights from Philadelphia to Marathon
- Flights from Chicago to Marathon
- Flights from Buffalo to Marathon
- Flights from Houston to Marathon
- Flights from Oklahoma City to Marathon
- Flights from Istanbul to Marathon
- Flights from Guatemala City to Marathon
- Flights from Las Vegas to Marathon
- Flights from Florida Keys Marathon
- Flights to Florida Keys Marathon
- Flights from Madrid to Marathon
- Flights to Key Largo
- Flights from Salt Lake City to Marathon
- Flights from Barcelona to Marathon
- Flights from Sao Paulo to Marathon
- Flights from Salvador to Marathon
- Flights from Washington to Marathon
- Flights from Casablanca to Marathon
- Flights from Newark to Marathon
- Flights from Cleveland to Marathon






