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Book Exclusive Islamorada Vacation Packages

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Islamorada flight + hotel packages

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Florida Center
$1,423

$1,039

per person
Dec 27 - Jan 3
Roundtrip flight included
Minneapolis (MSP) to Key West (EYW)

This hotel features an outdoor pool and a rooftop terrace. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the spa tub and perks like free self parking.…

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
$1,346

$1,041

per person
Dec 27 - Jan 3
Roundtrip flight included
Minneapolis (MSP) to Key West (EYW)

This smoke-free resort features a full-service spa, a marina, and 3 restaurants. There's fun for all ages with a children's club and a bowling alley, and barbecue grills are available on site. Enjoy the 7 outdoor pools and perks like free valet parking and free WiFi.…

Fairfield Inn & Suites Key West at The Keys Collection

Fairfield Inn & Suites Key West at The Keys Collection

3.5 out of 5
New Town
$880

$714

per person
Jan 26 - Jan 31
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

This hotel features a poolside bar, a bar/lounge, and an outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the fitness center and conveniences like a 24-hour front desk and laundry facilities.…

Fantasy World Resort

Fantasy World Resort

3.5 out of 5
$1,164

$965

per person
Dec 27 - Jan 3
Roundtrip flight included
Minneapolis (MSP) to Key West (EYW)

This condo resort's water park, 2 outdoor pools, and 2 spa tubs are some of the highlights. Bring the family and enjoy the lazy river, mini golf, and free theme park shuttle. Enjoy the outdoor tennis court and perks like free WiFi and a free area shuttle.…

Crowne Plaza Key West-La Concha

Crowne Plaza Key West-La Concha

4 out of 5
Historic Seaport
$1,212

$1,008

per person
Jan 26 - Jan 31
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

This romantic hotel includes 2 restaurants, an outdoor pool, and a health club. Traveling on business? Take advantage of the business center and free WiFi in public areas. A poolside bar, a 24-hour front desk, and a coffee shop are also provided.…

2021 Islamorada vacations

Kimpton Fitch Lodge

Kimpton Fitch Lodge

3.5 out of 5
Historic Seaport
Save 100% on your flight$1,400

$1,002

per person
Feb 13 - Feb 20
Roundtrip flight included
Detroit (DTW) to Key West (EYW)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and a terrace. A picnic area, luggage storage, and concierge services are also on offer.…

The Gates Hotel Key West

The Gates Hotel Key West

4 out of 5
Save 100% on your flight$1,191

$861

per person
Feb 24 - Mar 1
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

This hotel features a restaurant, an outdoor pool, and a poolside bar. Enjoy the fitness center and perks like free self parking and free WiFi. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.…

Casa Marina Key West, A Waldorf Astoria Resort

Casa Marina Key West, A Waldorf Astoria Resort

4 out of 5
Old Town
$1,121

$936

per person
Feb 7 - Feb 10
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this romantic resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Families will appreciate supervised childcare, along with kayaking.…

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

3.5 out of 5
Uptown - Upper Duval
$1,045

$878

per person
Feb 7 - Feb 10
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

This romantic resort features a private beach, a full-service spa, and a restaurant. Families will appreciate the onsite laundry facilities and supervised childcare. Traveling on business? Take advantage of the 17 conference rooms, express check-out, and valet parking.…

The Gardens Hotel

The Gardens Hotel

4 out of 5
Downtown
$1,554

$1,316

per person
Feb 24 - Mar 1
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

This romantic bed & breakfast features 2 outdoor pools and 2 bars/lounges. Business travelers can take advantage of the free WiFi in public areas. A restaurant and a poolside bar offer onsite options for dining and drinks, and laundry facilities are provided.…

Top Islamorada hotels deals

Islander Resort
Islander Resort
3 out of 5
82100 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $146 per night
This resort features a private beach, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the spa ...
Amara Cay Resort
Amara Cay Resort
3.5 out of 5
80001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $169 per night
A private beach, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and ...
Postcard Inn Beach Resort & Marina
Postcard Inn Beach Resort & Marina
3 out of 5
84001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $174 per night
This Art Deco resort features a private beach, a marina, and 3 restaurants. Dine at the beachfront restaurant and relax with sun loungers. Enjoy the 2 outdoor ...
Cheeca Lodge & Spa
Cheeca Lodge & Spa
4 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $169 per night
This romantic 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 ...
Sunset Inn
Sunset Inn
3 out of 5
82200 Overseas Hwy, Islamorada, FL
The price is $99 per night
An outdoor pool, free self parking, and barbecue grills are featured at this inn. WiFi in public areas is free. A garden, a picnic area, and luggage storage ...
Chesapeake Beach Resort
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $137 per night
This smoke-free resort's private beach and 2 outdoor pools are some of the highlights. Traveling on business? Take advantage of the 24-hour business center and ...
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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 in Islamorada

Image for Theater of the Sea

Theater of the Sea

4.5/5(215 reviews)

Take in a show or just stop by for a photo at Theater of the Sea, one of the favorite theaters in Islamorada. Take in the entertainment choices and beautiful sunsets in this family-friendly area.

Theater of the Sea
Image for Bud n' Mary's Dive Center

Bud n' Mary's Dive Center

4.5/5(141 reviews)

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.

Bud n' Mary's Dive Center
Image for Founders Park

Founders Park

4.5/5(137 reviews)

Play soccer, baseball and volleyball just meters from the Atlantic Ocean before you dive into the water at this family-friendly beach park.

Founders Park

Islamorada Vacations

How much are vacation packages to Islamorada?

Prepare to be surprised — you can vacation in Islamorada for a paltry $714. Allow Travelocity to save you time and money with our excellent vacation packages. With flights, hotels and experiences all available at our one-stop shop, what's stopping you?

How long should my Islamorada vacation be?

There's no rule when it comes to how long you should spend in Islamorada, but many people decide to stay around 3 nights. Got some wiggle room in your travel dates? Extend your vacation by a few more nights. That way, you'll have loads of time to explore the area's off-the-beaten-path gems as well.

Where can I get the best vacation package deals for Islamorada?

No matter how you like to travel, Travelocity can help you get your hands on an unbeatable Islamorada package deal. The only thing you need to do is pick and choose between our 400 air carriers and 665,000 properties across the globe.

Why should I purchase my Islamorada vacation bundle via Travelocity?

We've got 24/7 support, excellent service and a Price Match Guarantee. Life is one big journey — and we have enticing destinations for you to journey to in all four corners of the globe. Explore with us and your bank balance will thank you for it.

Can I save on my Islamorada car rental if I combine it with a hotel or flight?

Absolutely — combine your hotel, car and flight into an Islamorada vacation package and you'll save a tidy sum. With so much to discover in and around Islamorada, that rental car will come in handy. Once you've buckled up, turn up the tunes and head to PortMiami, a well-known sight about 62 mi from Islamorada.

What is the best time of year to go to Islamorada?

Visiting in the least busy months, , comes with a few upsides — think cheaper hotels and flights and less pushing past hordes of strangers. But there's magic in the destination in the peak season. More events are likely to be on and more attractions will be open in . If you're on a tight budget, typically has the cheapest hotel rates. You can expect to pay more for a room in .

What is there to do in Islamorada?

Theater of the Sea should be at the top of your must-see list. Once you've crossed off this top attraction, simply wander the streets of Islamorada and find out what makes this vibrant city tick.

Where should I stay when visiting Islamorada?

The Hadley House Islamorada (2.0 stars) and the Coconut Cove Resort and Marina (2.0 stars) are ideal options if you're visiting Islamorada on a tight budget.

Frequently asked questions

How much are vacation packages to Islamorada?
You might be pleasantly surprised — you can find yourself in Islamorada for a mere $714. Allow Travelocity to save you time and money with our vacation packages. With hotels, flights and tours all ready to be snapped up, what’s holding you back?
How long should my Islamorada vacation be?
If you need some guidance, most travelers spend an average of 3 nights vacationing in Islamorada. But to discover the true essence of this destination, stay a little longer. That way you can check off more attractions and really immerse yourself in the local vibe.
Where can I get the best vacation package deals for Islamorada?
For the best Islamorada package deal, turn to Travelocity. Take your pick from as many as 400 partner airlines and 665,000 properties worldwide to create the ultimate escape — simple as that.
Why should I book my Islamorada vacation package with Travelocity?
Travel is all about making fantastic new memories and forgetting all your worries — which is why we have a friendly team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you’ll always get the best price available on our huge range of package deals. So what are you waiting for? There’s no time like the present to secure that vacation you’ve always wanted.
Can I save money on my Islamorada car rental if I combine it with a hotel or flight?
With an Islamorada vacation package, you can combine your flight, hotel and car bookings and save a whole lot. When you’re ready to uncover the best of this exciting destination, why not head to PortMiami? This famous attraction is 62 mi from Islamorada. With your own wheels, you’ll be there in a jiffy.
What is the best time of year to go to Islamorada?
Go in if you want to see this place at its most exciting. Even though they’re the most crowded months, the buzzing atmosphere that comes with peak season is part of its charm. If you’re after a more chilled pace, may fit your plans better. Don’t want to fork out for a place to sleep? Hold off on booking in , when rates generally skyrocket. Search for something cozy and affordable in instead.
What is there to do in Islamorada?
Theater of the Sea is just one of the superb sights that make Islamorada a popular place to visit. But leave some extra time to discover its lesser-known attractions too. This is sometimes where the best memories are made.
Where should I stay when visiting Islamorada?
Those traveling on a tight budget will enjoy spending their evenings at the Hadley House Islamorada (2.0 stars) or the Coconut Cove Resort and Marina (2.0 stars). These inexpensive Islamorada hotels have all you need for a great night’s snooze.

^Savings based on all package bookings with Flight + Hotel made on Travelocity.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.