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, 33036
    The price is $230 per night from Dec 12 to Dec 13
    $230
    per night
    Dec 12 - Dec 13
    4.6/5 Wonderful! (1,220 reviews)
    Postcard Inn Beach Resort & Marina

    Postcard Inn Beach Resort & Marina

    84001 Overseas Hwy, Islamorada, FL, 33036
    The price is $146 per night from Dec 13 to Dec 14
    $146
    per night
    Dec 13 - Dec 14
    4.2/5 Very Good! (1,247 reviews)
    Pelican Cove Resort & Marina

    Pelican Cove Resort & Marina

    84457 Overseas Highway, Islamorada, FL, 33036
    The price is $136 per night from Dec 18 to Dec 19
    $136
    per night
    Dec 18 - Dec 19
    4.1/5 Very Good! (1,001 reviews)
    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL, 33036
    The price is $155 per night from Dec 7 to Dec 8
    $155
    per night
    Dec 7 - Dec 8
    4.4/5 Excellent! (1,003 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL, 33036
    The price is $230 per night from Dec 25 to Dec 26
    $230
    per night
    Dec 25 - Dec 26
    4.4/5 Wonderful! (1,065 reviews)
    Creekside Inn Islamorada

    Creekside Inn Islamorada

    90611 Old Highway, Tavernier, FL, 33070
    The price is $106 per night from Dec 7 to Dec 8
    $106
    per night
    Dec 7 - Dec 8
    3.9/5 Good! (1,002 reviews)
    La Siesta Resort & Villas

    La Siesta Resort & Villas

    80241 Overseas Highway, Islamorada, FL, 33036
    The price is $219 per night from Dec 14 to Dec 15
    $219
    per night
    Dec 14 - Dec 15
    4.2/5 Very Good! (1,000 reviews)
    Drop Anchor

    Drop Anchor

    84959 Overseas Highway, 222, Islamorada, FL, 33036
    The price is $249 per night from Dec 6 to Dec 7
    $249
    per night
    Dec 6 - Dec 7
    4.4/5 Wonderful! (1,000 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL, 33036
    The price is $129 per night from Dec 11 to Dec 12
    $129
    per night
    Dec 11 - Dec 12
    3.9/5 Very Good! (1,004 reviews)

Hotel Options in Islamorada

    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL, 33036
    The price is $230 per night from Dec 25 to Dec 26
    $230
    per night
    Dec 25 - Dec 26
    4.4/5 Wonderful! (1,065 reviews)
    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL, 33036
    The price is $155 per night from Dec 7 to Dec 8
    $155
    per night
    Dec 7 - Dec 8
    4.4/5 Excellent! (1,003 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL, 33036
    The price is $129 per night from Dec 11 to Dec 12
    $129
    per night
    Dec 11 - Dec 12
    3.9/5 Very Good! (1,004 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.