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
    The price is $332 per night from May 12 to May 13
    $332
    includes taxes & fees
    $295 per night
    May 12 - May 13
    9/10 Wonderful! (1,005 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
    The price is $371 per night from May 4 to May 5
    $371
    includes taxes & fees
    $330 per night
    May 4 - May 5
    8.8/10 Excellent! (17 reviews)
    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
    The price is $373 per night from May 18 to May 19
    $373
    includes taxes & fees
    $331 per night
    May 18 - May 19
    9/10 Wonderful! (1,064 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    The price is $310 per night from May 4 to May 5
    $310
    includes taxes & fees
    $276 per night
    May 4 - May 5
    8.8/10 Excellent! (1,195 reviews)
    Creekside Inn Islamorada

    Creekside Inn Islamorada

    90611 Old Highway, Tavernier, FL
    The price is $188 per night from May 11 to May 12
    $188
    includes taxes & fees
    $167 per night
    May 11 - May 12
    7.8/10 Good! (1,000 reviews)
    La Siesta Resort & Villas

    La Siesta Resort & Villas

    80241 Overseas Highway, Islamorada, FL
    The price is $271 per night from May 14 to May 15
    $271
    includes taxes & fees
    $241 per night
    May 14 - May 15
    8.6/10 Excellent! (1,005 reviews)
    Drop Anchor

    Drop Anchor

    84959 Overseas Highway, 222, Islamorada, FL
    The price is $231 per night from May 4 to May 5
    $231
    includes taxes & fees
    $209 per night
    May 4 - May 5
    8.8/10 Excellent! (1,002 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    The price is $333 per night from May 11 to May 12
    $333
    includes taxes & fees
    $296 per night
    May 11 - May 12
    9/10 Wonderful! (1,430 reviews)
    Fisher Inn Resort & Marina

    Fisher Inn Resort & Marina

    84951 Overseas Hwy, Islamorada, FL
    The price is $213 per night from Jun 1 to Jun 2
    $213
    includes taxes & fees
    $190 per night
    Jun 1 - Jun 2
    7.8/10 Good! (1,002 reviews)

Hotel Options in Islamorada

    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    The price is $333 per night from May 11 to May 12
    $333
    includes taxes & fees
    $296 per night
    May 11 - May 12
    9/10 Wonderful! (1,430 reviews)
    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
    The price is $373 per night from May 18 to May 19
    $373
    includes taxes & fees
    $331 per night
    May 18 - May 19
    9/10 Wonderful! (1,064 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
    The price is $371 per night from May 4 to May 5
    $371
    includes taxes & fees
    $330 per night
    May 4 - May 5
    8.8/10 Excellent! (17 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
$188
Highest Price
$373
Popular accommodation
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