Compare Islamorada Cottage Rentals

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Featured Islamorada Cottages

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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.

Islamorada Beach Accommodation

    Islander Resort

    Islander Resort

    82100 Overseas Highway, Islamorada, FL
    $265 nightly
    The price is $298 total per night from Jun 2 to Jun 3
    $298 total
    Jun 2 - Jun 3
    Total includes taxes and fees
    9/10 Wonderful! (1,010 reviews)
    Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

    84001 Overseas Hwy, Islamorada, FL
    $313 nightly
    The price is $352 total per night from Jun 1 to Jun 2
    $352 total
    Jun 1 - Jun 2
    Total includes taxes and fees
    9/10 Wonderful! (24 reviews)
    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
    $259 nightly
    The price is $291 total per night from May 22 to May 23
    $291 total
    May 22 - May 23
    Total includes taxes and fees
    9/10 Wonderful! (1,077 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    $276 nightly
    The price is $310 total per night from May 26 to May 27
    $310 total
    May 26 - May 27
    Total includes taxes and fees
    8.8/10 Excellent! (1,201 reviews)
    Creekside Inn Islamorada

    Creekside Inn Islamorada

    90611 Old Highway, Tavernier, FL
    $160 nightly
    The price is $180 total per night from Jun 3 to Jun 4
    $180 total
    Jun 3 - Jun 4
    Total includes taxes and fees
    7.8/10 Good! (1,003 reviews)
    La Siesta Resort & Villas

    La Siesta Resort & Villas

    80241 Overseas Highway, Islamorada, FL
    $261 nightly
    The price is $293 total per night from Jun 3 to Jun 4
    $293 total
    Jun 3 - Jun 4
    Total includes taxes and fees
    8.6/10 Excellent! (1,006 reviews)
    Drop Anchor

    Drop Anchor

    84959 Overseas Highway, 222, Islamorada, FL
    $194 nightly
    The price is $214 total per night from May 22 to May 23
    $214 total
    May 22 - May 23
    Total includes taxes and fees
    8.8/10 Excellent! (1,001 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    $220 nightly
    The price is $248 total per night from May 26 to May 27
    $248 total
    May 26 - May 27
    Total includes taxes and fees
    9/10 Wonderful! (1,465 reviews)
    Fisher Inn Resort & Marina

    Fisher Inn Resort & Marina

    84951 Overseas Hwy, Islamorada, FL
    $159 nightly
    The price is $178 total per night from May 22 to May 23
    $178 total
    May 22 - May 23
    Total includes taxes and fees
    7.8/10 Good! (1,009 reviews)

Hotel Options in Islamorada

    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    $220 nightly
    The price is $248 total per night from May 26 to May 27
    $248 total
    May 26 - May 27
    Total includes taxes and fees
    9/10 Wonderful! (1,465 reviews)
    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
    $259 nightly
    The price is $291 total per night from May 22 to May 23
    $291 total
    May 22 - May 23
    Total includes taxes and fees
    9/10 Wonderful! (1,077 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    $276 nightly
    The price is $310 total per night from May 26 to May 27
    $310 total
    May 26 - May 27
    Total includes taxes and fees
    8.8/10 Excellent! (1,201 reviews)

Cottages

Book a cottage in Islamorada
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Islamorada. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Islamorada better.

Cottage apartments in Islamorada range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Islamorada
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Islamorada and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Islamorada cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Islamorada. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Islamorada Cottages essential information

Accommodation
29 Cottages
Lowest Price
$178 total
Highest Price
$352 total
Popular accommodation
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