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Tonight
Check prices in Islamorada for tonight, Jul 11 - Jul 12
Jul 11 - Jul 12
Tomorrow night
Check prices in Islamorada for tomorrow night, Jul 12 - Jul 13
Jul 12 - Jul 13
Next weekend
Check prices in Islamorada for next weekend, Jul 17 - Jul 19
Jul 17 - Jul 19

Most frequently booked Islamorada hotels

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free cancellation
Reserve now, pay when you stay
1 km from city centre
The price is CA $237 per night
CA $237
CA $370 total
Jul 16 - Jul 17
includes taxes & fees
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Florida Keys Brewing Co. and Lorelei Restaurant & Cabana Bar are located nearby.
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Free cancellation
Reserve now, pay when you stay
1.98 km from city centre
The price is CA $241 per night
CA $241
CA $350 total
Aug 6 - Aug 7
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions History of Diving Museum and Windley Key Fossil Reef Geological State Park are located nearby.
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Free cancellation
Reserve now, pay when you stay
3.88 km from city centre
The price is CA $212 per night
CA $212
CA $342 total
Jul 22 - Jul 23
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Free cancellation
Reserve now, pay when you stay
0.52 km from city centre
The price is CA $284 per night
CA $284
CA $415 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Keys History & Discovery Center and Lorelei Restaurant & Cabana Bar are located nearby.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
Free cancellation
Reserve now, pay when you stay
2.93 km from city centre
The price is CA $360 per night
CA $360
CA $508 total
Aug 9 - Aug 10
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Windley Key Fossil Reef Geological State Park and Hog Heaven are located nearby.
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
Free cancellation
Reserve now, pay when you stay
3.31 km from city centre
The price is CA $247 per night
CA $247
CA $382 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious rooms in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Free cancellation
Reserve now, pay when you stay
3.79 km from city centre
The price is CA $140 per night
CA $140
CA $231 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
Free cancellation
Reserve now, pay when you stay
4.05 km from city centre
The price is CA $177 per night
CA $177
CA $246 total
Jul 13 - Jul 14
includes taxes & fees
Book a stay at this beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Windley Key Fossil Reef Geological State Park and Hog Heaven are located nearby.
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy Islamorada FL
3.22 km from city centre
The price is CA $330 per night
CA $330
CA $449 total
Jul 15 - Jul 16
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
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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.

Top family friendly Islamorada hotel deals

Islander Resort

Islander Resort

82100 Overseas Highway Islamorada FL
The price is CA $284 per night from Aug 2 to Aug 3
CA $284
CA $415 total
Aug 2 - Aug 3
includes taxes & fees
9.4/10 Exceptional! (1,078 reviews)

Top cheap Islamorada hotel deals

Conch On Inn Motel

Conch On Inn Motel

103 Caloosa Street Tavernier FL
Get rates

Top hotels in Islamorada for Extended Stay

Island Bay Resort

Island Bay Resort

92530 OVERSEAS HIGHWAY Tavernier FL
The price is CA $362 per night from Aug 6 to Aug 7
CA $362
CA $408 total
Aug 6 - Aug 7
includes taxes & fees
10/10 Exceptional! (173 reviews)
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
2,160 hotels
Lowest Price
CA $203
Highest Price
CA $508
Popular hotels
Cheeca Lodge & Spa, Chesapeake Beach Resort, Amara Cay Resort, Islander Resort, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, La Siesta Resort & Villas, Breezy Palms Resort, Fisher Inn Resort & Marina, Pines & Palms Resort

Frequently asked questions

What are the top kid-friendly hotels in Islamorada?
From well-thought-out amenities to bigger rooms, kid-friendly hotels are equipped with features that can help transform a routine family vacation into a sensational one. These Islamorada options make traveling with young ones child's play: Your crew will enjoy staying at Bayside: 1st Floor Apartment in Native Hammock on Florida Bay. A playground and a nearby theme park are among the things that help make this property a winner. Mitchells Keys Villa - private, secluded bayfront home is another excellent choice. After a big day of exploring, come back home to your comfortable room and amenities like a water park and a playground.
Where can I find cheap hotels in Islamorada?
At Travelocity you'll find really nice hotels in Islamorada at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Islamorada rather than in Islamorada. We may find you even better rates, too.
How do I find the best Islamorada hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Islamorada then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Islamorada?
The cheapest hotel in Islamorada is CA $203 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Islamorada?
There are 2,160 hotels in Islamorada on Travelocity.
What are the best hotels in Islamorada?
Islamorada has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Islamorada for you!
When is the best time to visit Islamorada?
If you want the joy of a fun-filled trip in peak season, visit Islamorada during November, December and January. If you'd prefer the peace of off-season, book a stay during quieter months, such as April, September and October.
When is the cheapest time to stay in Islamorada?
Based on historic data is usually the cheapest month to visit Islamorada. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Islamorada?
There are multiple hotels in Islamorada that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Islamorada. We have plenty of kid-friendly hotels in Islamorada to choose from on Travelocity!
Why book a hotel in Islamorada through Travelocity?
Because we have the top hotels in Islamorada! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Islamorada on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Islamorada hotel reviews by fellow wanderers

Chesapeake Beach Resort

Chesapeake Beach Resort

4 out of 5
Posted 6 hours ago
Travelocity Verified Review
"This was a nice place to get away from the urban Key West. The staff was very friendly and solved any issues regardless of the time (noisy neighbor, needed blanket) and the shore was close by. There was staff routinely monitoring the beach and property so it was very secure. The location has easy access to restaurants and shops if you have a car. The large pool had a bar / food and the property has a nice restaurant. The breakfast is cook to order pancakes and omelets, very nice! Pros Great staff everywhere! Ocean view is a real view if you select it We had a suite with a king bed and the teen had a separate fold out couch that was comfortable Microwave and mini-fridge were convenient Bathroom was very nice had a toilet in a separated section with a door A second pool was available with shade making it cooler in the summer Parking was easy and right outside, some covered by the buildings Elevator if you have the ocean view was very convenient Fresh omelet to order with a dozen ingredients, good yogurt options with toppings that were plentiful Balcony was very nice Reasonable price Cons - not much Next to a busy road. We could not hear it from outside the room door but there are two buildings and we were at the far building, so not bad at all for us Not much available without a car I recommend not going in June as the seaweed odor is unpleasant No one went to the beach but it was fine at the pool"
A verified traveller stayed at Chesapeake Beach Resort
Chesapeake Beach Resort