Deals on vacations and trips to Islamorada

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Islamorada flight + hotel vacation packages

Kimpton Hotel Palomar South Beach, an IHG Hotel

Kimpton Hotel Palomar South Beach, an IHG Hotel

4 out of 5
South Beach
Save 100% on your flightPrice was $1,389, price is now $793 per person
per person
Apr 10 - Apr 15
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a poolside bar. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Enjoy the 24-hour gym and perks like a free beach shuttle.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Save 100% on your flightPrice was $14,774, price is now $8,885 per person
per person
Apr 17 - Apr 22
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This condo resort features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free self parking and free WiFi.
Private Ocean Condos at Marenas Beach

Private Ocean Condos at Marenas Beach

4 out of 5
Save 100% on your flightPrice was $2,595, price is now $1,583 per person
per person
Apr 5 - Apr 12
Roundtrip non-stop flight included
New York (NYC) to Miami (MIA)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this hotel. Enjoy the outdoor pool and perks like free WiFi. Enjoy the gym and unwind at the bar/lounge and poolside bar.
Kimpton Angler's Hotel, an IHG Hotel

Kimpton Angler's Hotel, an IHG Hotel

4 out of 5
South Beach
Save 100% on your flightPrice was $2,823, price is now $1,760 per person
per person
Mar 3 - Mar 10
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Save 100% on your flightPrice was $1,349, price is now $845 per person
per person
Mar 3 - Mar 8
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Enjoy the sauna and unwind at the bar/lounge and beach bar.

Top Islamorada hotels deals

Amara Cay Resort

Amara Cay Resort

3.5 out of 5
80001 Overseas Hwy, Islamorada, FL, 33036
Free Cancellation
Reserve now, pay when you stay
The price is $347 per night
$347
per night
Feb 6 - Feb 7
A private beach, 2 restaurants, and an outdoor pool are all featured at this smoke-free resort. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking. You'll appreciate the gym, poolside bar, and laundry facilities.
On private beach
Pool
Postcard Inn Beach Resort & Marina

Postcard Inn Beach Resort & Marina

3 out of 5
84001 Overseas Hwy, Islamorada, FL, 33036
The price is $336 per night
$336
per night
Feb 28 - Mar 1
A private beach, a marina, and 2 outdoor pools are all featured at this Art Deco resort. Dine at the beachfront restaurant and relax with sun loungers. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
On private beach
Pool
Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5
83409 Overseas Hwy, Islamorada, FL, 33036
Free Cancellation
Reserve now, pay when you stay
The price is $259 per night
$259
per night
Feb 5 - Feb 6
This smoke-free hotel's private beach and 2 outdoor pools are some of the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the spa tub and free perks like on-the-go breakfast and WiFi in public areas.
On private beach
Pool
Cheeca Lodge & Spa

Cheeca Lodge & Spa

4 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL, 33036
Free Cancellation
Reserve now, pay when you stay
The price is $410 per night
$410
per night
Feb 3 - Feb 4
This smoke-free resort features a private beach, a golf course, and a full-service spa. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. Families will appreciate the arcade/game room, onsite laundry facilities, and babysitting.
On private beach
Pool
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy, Islamorada, FL, 33036-3637
The price is $249 per night
$249
per night
Feb 2 - Feb 3
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also on offer.
Pool
Free WiFi
La Siesta Resort & Villas

La Siesta Resort & Villas

2.5 out of 5
80241 Overseas Highway, Islamorada, FL, 33036
The price is $242 per night
$242
per night
Feb 2 - Feb 3
This smoke-free resort's private beach and marina are among the highlights. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.
On private beach
Pool
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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.

Popular places to visit

Image for Theater of the Sea

Theater of the Sea

4.5/5(215 reviews)

Take the kids to visit the sea life you'll find at Theater of the Sea during your trip to Islamorada. Take in the entertainment choices and beautiful sunsets in this family-friendly area.

Theater of the Sea
Image for Anne's Beach

Anne's Beach

3.5/5(139 reviews)

If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada. Wander the seaside or discover the beautiful sunsets in this relaxing area.

Anne's Beach
Image for Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada. Amble around this relaxing area's seaside or experience its entertainment choices.

Florida Keys Brewing Co.

Frequently asked questions

How much are vacation packages to Islamorada?
Epic adventures await in Islamorada, with Travelocity vacation packages starting as low as $793. Including flights and hotels, these incredible deals are an easy way to see all corners of the globe.
How long should my Islamorada vacation be?
Many visitors pack their suitcase and vacation in Islamorada for an average of 3 nights. That gives you some guidance, but don’t be restricted by it. Whether you stay a few nights to see the top attractions or hang around to experience this place like a local, an unforgettable journey awaits.
Where can I get the best vacation package deals for Islamorada?
There are exciting Islamorada package deals to be snapped up with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties worldwide? Keep this in mind when you’re ready to check another destination off the old bucket list.
Why should I purchase my Islamorada vacation package via Travelocity?
The three S’s — savings, support and a stress-free booking — are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on 24/7 customer support. With the Travelocity Price Match Guarantee, you know you’re getting the best deal available.
Can I save on my Islamorada car rental if I bundle it with my hotel or flight?
You sure can — bundle your hotel, car and flight into an Islamorada vacation package and you can save a handsome sum. With so many places to explore in the Islamorada area, that rental car will make exploring easy. Once you’ve slid into the driver’s seat, crank up the tunes and make your way to PortMiami, a top sight approximately 65 mi from Islamorada.
What is the best time of year to go to Islamorada?
If you’re watching your pennies, is an ideal month to explore Islamorada, whereas is the dearest time of year. is regarded as the peak season. If you’d prefer to avoid big crowds, tend to be quieter.
What is there to do in Islamorada?
While venturing off the beaten track can be rewarding, you really shouldn’t miss the popular attractions that make a destination famous. Theater of the Sea and Bud n’ Mary’s Dive Center are just two of them in Islamorada.
Where should I stay when visiting Islamorada?
Many visitors spend their nights at the Postcard Inn Beach Resort & Marina. It’s the perfect base for your Islamorada escape.
Can I go on vacation to Islamorada at this time?
Don’t fly off to Islamorada without the facts about travel restrictions and quarantine policies. Travelocity’s Covid-19 Travel Advisor can fill you in. It has all the information you need to make your getaway as stress-free as possible.