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

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

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

Topsider Resort
75500 Overseas Hwy Islamorada FL
Located in Islamorada (Matecumbe), this condo is within a 5-minute drive of Robbie’s of Islamorada and Indian Key Historic State Park.
Pool
Hot Tub

Islander Resort
82100 Overseas Highway Islamorada FL
$316 nightly
The price is $356 total per night
$356 total
Jun 29 - Jun 30
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

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
Jun 30 - Jul 1
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
$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
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

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

Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$174 nightly
The price is $192 total per night
$192 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

Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$239 nightly
The price is $269 total per night
$269 total
Jun 18 - Jun 19
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

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

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
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 | 2,169 hotels |
|---|---|
Lowest Price | $143 |
Highest Price | $388 |
Popular hotels | Creekside Inn, Casa Morada, Topsider Resort, Islander Resort, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Cheeca Lodge & Spa, Amara Cay Resort, La Siesta Resort & Villas, Drop Anchor, Chesapeake Beach Resort, Fisher Inn Resort & Marina, Pines & Palms Resort |
Most Recent Islamorada Hotel Reviews

Chesapeake Beach Resort
4 out of 5
Posted 4 hours ago
CheapTickets Verified Review
"Breakfast selection each day was excellent. Room was clean, just a little noisy from upstairs kids footsteps in the morning. 2 pools were great although main pool in need of resurfacing and a bit too warm, understandable due to 90+ temps. Love the free kayaks and paddle boards. Staff was very friendly and accommodating. Beautiful views and convenient location."
A verified traveler stayed at Chesapeake Beach Resort
More to Explore in Islamorada
Top Picks
- Inns in Duck Key
- Islamorada Hotels
- Fishing Resorts & in Islamorada
- Motels in Key Colony Beach
- Spa Resorts & in Tavernier
- Hotels with Air Conditioning in Islamorada
- Golf Resorts & in Islamorada
- 5 Star Hotels in Key Largo
- Apartments in Duck Key
- 4 Star Hotels in Duck Key
- Condo Rentals in Tavernier
- Hotels near Harry Harris Park
- Vacation Rentals in Tavernier
- 4 Star Hotels in Tavernier
- 4 Star Hotels in Key Largo
- Beach Resorts & in Key Largo
- Business Hotels in Tavernier
- Hotels with Room Service in Key Largo
- Key Largo Hotels
- Rv Parks in Duck Key
- 3 Star Hotels in Key Colony Beach
- Green Hotels in Key Largo
- Hotels with Restaurants in Key Largo
- Kid Friendly Hotels in Duck Key
- Hotels with Childcare in Key Largo
- Historic Hotels in Key Colony Beach
- 5 Star Hotels in Tavernier
- Rv Parks in Key Colony Beach
- Historic Hotels in Tavernier
- Resorts in Key Colony Beach
- Hotels near Anne's Beach
- Anglers Park Hotels
- Pet Friendly Hotels in Islamorada
- Kid Friendly Hotels in Key Colony Beach
- Beach Resorts & in Duck Key
- Hotels with a Wedding Venue in Key Largo
- Oceanfront Hotels in Grassy Key
- Hotels with Restaurants in Tavernier
- Green Hotels in Islamorada
- Condo Rentals in Islamorada
- Gay Friendly Hotels in Islamorada
- Hotels near Everglades National Park
- 3 Star Hotels in Tavernier
- 4 Star Hotels in Islamorada
- Fishing Resorts & in Tavernier
- 3 Star Hotels in Key Largo
- Kid Friendly Hotels in Islamorada
- Hotels with a Wedding Venue in Duck Key
- Hotels with Childcare in Duck Key
- Hotels with Hot Tubs in Tavernier
- Holiday Park Resorts in Key Largo
- Oceanfront Hotels in Tavernier
- Indian Waterways Hotels
- Arcade Hotels in Duck Key
- Cross Key Waterways Hotels
- 4 Star Hotels in Key Colony Beach
- Tavernier Hotels
- Hotels on the Lake in Duck Key
- 5 Star Hotels in Islamorada
- Villas in Tavernier
- Hotels near Long Key State Park
- Beach Resorts & in Key Colony Beach
- Flights from Chicago to Marathon
- Flights from Kingston to Marathon
- Flights from Rochester to Marathon
- Flights from Boston to Marathon
- Flights from Milwaukee to Marathon
- Flights from Las Vegas to Marathon
- Flights to Florida Keys Marathon
- Flights from New Orleans to Marathon
- Flights from Madrid to Marathon
- Flights from Salt Lake City to Marathon
- Flights from San Francisco to Marathon
- Flights to Key Largo
- Flights from Stuttgart to Marathon
- Flights from Richmond to Marathon
- Flights from Princeton to Marathon
- Flights from Orlando to Marathon
- Flights from Detroit to Marathon
- Flights from Buffalo to Marathon
- Flights from Fort Wayne to Marathon
- Flights from Incheon to Marathon
- Flights from Hamburg to Marathon
- Flights from Minneapolis - St. Paul to Marathon
- Flights from Cairo to Marathon
- Flights from Washington to Marathon
- Flights from Oklahoma City to Marathon
- Flights from Florida Keys Marathon
- Flights from Berlin to Marathon





