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

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

Creekside Inn
90611 Old Highway Tavernier FL
$433 nightly
The price is $487 total per night
$487 total
Apr 28 - Apr 29
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

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

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

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

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
$198 nightly
The price is $223 total per night
$223 total
Apr 28 - Apr 29
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

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
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 7 minutes by foot from Islamorada Brewery & Distillery.
On private beach
Pool

Angler's Reef Resort by KeysCaribbean
84977 Overseas Highway Islamorada FL
With a stay at Angler's Reef Resort by KeysCaribbean in Islamorada, you'll be within a 5-minute drive of Windley Key Fossil Reef Geological State Park and Rain Barrel Village.
Pool
Kitchen

Breezy Palms Resort
80015 Overseas Highway Islamorada FL
$165 nightly
The price is $185 total per night
$185 total
Apr 28 - Apr 29
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at Breezy Palms Resort in Islamorada (Matecumbe), you'll be within a 15-minute walk of Bud n' Mary's Dive Center and Indian Key Historic State Park.
Pool
Kitchen

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

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$364 nightly
The price is $410 total per night
$410 total
May 3 - May 4
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
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 | $185 |
Highest Price | $603 |
Popular hotels | La Siesta Resort & Villas, Creekside Inn, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Chesapeake Beach Resort, Drop Anchor, Fisher Inn Resort & Marina, Amara Cay Resort, Islander Resort, Angler's Reef Resort by KeysCaribbean, Breezy Palms Resort, Casa Morada, Cheeca Lodge & Spa |
Most Recent Islamorada Hotel Reviews

Chesapeake Beach Resort
5 out of 5
Posted 2 hours ago
CheapTickets Verified Review
"Amazing staff helped created an amazing stay. We arrived early. The front desk expedited cleaning of an open room to get us in four hours before the normal check-in time. We had an ocean view room that was spacious and indeed had a great view of the sunrise over the water each morning. The room had some plumbing issue and that was addressed by the maintenance staff within 5 minutes of calling the front desk.
The breakfast was included and provided made to order omelet each morning. The hotel staff was attentive and friendly. Many of them actively engaged us in conversation, including those whose English was clearly not their native language.
The grounds of the property is well maintained. You also get access to bikes, paddle board and kayaks for 2 hours each day as needed. We took advantage of the kayak and paddled to the famous Islamorada sandbar that was only 1 mile off shore, which probably was the most memorable activity of our trip.
The hotel is well situated and put us half way between Key West and Miami. Everything from great restaurants to activity hubs were just easy drive away.
Would definitely stay here again if we return to the keys."
A verified traveler stayed at Chesapeake Beach Resort
More to Explore in Islamorada
Top Picks
- Hotels with Room Service in Key Largo
- 4 Star Hotels in Key Largo
- Anglers Park Hotels
- Cross Key Waterways Hotels
- 3 Star Hotels in Key Largo
- Hotels with Childcare in Duck Key
- Fishing Resorts & in Islamorada
- Kid Friendly Hotels in Duck Key
- Key Largo Hotels
- Hotels with Restaurants in Tavernier
- Islamorada Hotels
- Hotels near Everglades National Park
- Green Hotels in Key Largo
- Inns in Duck Key
- Pet Friendly Hotels in Key Colony Beach
- Indian Waterways Hotels
- Rv Parks in Duck Key
- Apartments in Duck Key
- Business Hotels in Tavernier
- Holiday Park Resorts in Key Largo
- Hotels with Childcare in Key Largo
- 4 Star Hotels in Islamorada
- Arcade Hotels in Duck Key
- Hotels on the Lake in Duck Key
- Beach Resorts & in Duck Key
- 4 Star Hotels in Key Colony Beach
- Kid Friendly Hotels in Islamorada
- Rv Parks in Key Colony Beach
- 3 Star Hotels in Tavernier
- Pet Friendly Hotels in Islamorada
- Spa Resorts & in Tavernier
- 5 Star Hotels in Islamorada
- Hotels with Restaurants in Key Largo
- Motels in Key Colony Beach
- Fishing Resorts & in Tavernier
- Hotels near Harry Harris Park
- Hotels near Anne's Beach
- 5 Star Hotels in Key Largo
- Vacation Rentals in Tavernier
- Beach Resorts & in Key Colony Beach
- Historic Hotels in Tavernier
- 5 Star Hotels in Tavernier
- Beach Resorts & in Key Largo
- Hotels with a Wedding Venue in Duck Key
- Oceanfront Hotels in Grassy Key
- 4 Star Hotels in Tavernier
- Golf Resorts & in Islamorada
- Gay Friendly Hotels in Islamorada
- 4 Star Hotels in Duck Key
- Romantic Getaways & Hotels in Key Colony Beach
- Villas in Tavernier
- Resorts in Key Colony Beach
- Oceanfront Hotels in Tavernier
- Hotels with a Wedding Venue in Key Largo
- Green Hotels in Islamorada
- Kid Friendly Hotels in Key Colony Beach
- 4 Star Hotels in Marathon
- Condo Rentals in Tavernier
- 3 Star Hotels in Key Colony Beach
- Hotels near Long Key State Park
- Condo Rentals in Islamorada
- Tavernier Hotels
- Hotels with Hot Tubs in Tavernier
- Flights from Nashville to Marathon
- Flights from Las Vegas to Marathon
- Flights from Rochester to Marathon
- Flights from Princeton to Marathon
- Flights from Pittsburgh to Marathon
- Flights from San Juan to Marathon
- Flights from Cairo to Marathon
- Flights from Tampa to Marathon
- Flights from Atlanta to Marathon
- Flights from Madrid to Marathon
- Flights from Asuncion to Marathon
- Flights from Raleigh to Marathon
- Flights from Charlotte to Marathon
- Flights from Florida Keys Marathon
- Flights from Kingston to Marathon
- Flights from Seattle to Marathon
- Flights to Florida Keys Marathon
- Flights from Indianapolis to Marathon
- Flights from San Francisco to Marathon
- Flights from Minneapolis - St. Paul to Marathon
- Flights from Spokane to Marathon
- Flights to Key Largo
- Flights from Newark to Marathon
- Flights from Düsseldorf to Marathon
- Flights from Detroit to Marathon
- Flights from Chicago to Marathon





