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
    $279 nightly
    The price is $314 total per night from Aug 3 to Aug 4
    $314 total
    Aug 3 - Aug 4
    Total includes taxes and fees
    9/10 Wonderful! (1,000 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
    $339 nightly
    The price is $381 total per night from Jul 7 to Jul 8
    $381 total
    Jul 7 - Jul 8
    Total includes taxes and fees
    9/10 Wonderful! (46 reviews)
    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
    $229 nightly
    The price is $258 total per night from Jul 7 to Jul 8
    $258 total
    Jul 7 - Jul 8
    Total includes taxes and fees
    9/10 Wonderful! (1,116 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    $238 nightly
    The price is $268 total per night from Jul 6 to Jul 7
    $268 total
    Jul 6 - Jul 7
    Total includes taxes and fees
    8.8/10 Excellent! (1,219 reviews)
    Creekside Inn Islamorada

    Creekside Inn Islamorada

    90611 Old Highway, Tavernier, FL
    $139 nightly
    The price is $156 total per night from Jul 7 to Jul 8
    $156 total
    Jul 7 - Jul 8
    Total includes taxes and fees
    7.8/10 Good! (1,000 reviews)
    La Siesta Resort & Villas

    La Siesta Resort & Villas

    80241 Overseas Highway, Islamorada, FL
    $214 nightly
    The price is $240 total per night from Jul 8 to Jul 9
    $240 total
    Jul 8 - Jul 9
    Total includes taxes and fees
    8.6/10 Excellent! (1,004 reviews)
    Drop Anchor

    Drop Anchor

    84959 Overseas Highway, 222, Islamorada, FL
    $163 nightly
    The price is $179 total per night from Jul 6 to Jul 7
    $179 total
    Jul 6 - Jul 7
    Total includes taxes and fees
    8.8/10 Excellent! (1,000 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    $199 nightly
    The price is $224 total per night from Aug 3 to Aug 4
    $224 total
    Aug 3 - Aug 4
    Total includes taxes and fees
    9/10 Wonderful! (1,485 reviews)
    Fisher Inn Resort & Marina

    Fisher Inn Resort & Marina

    84951 Overseas Hwy, Islamorada, FL
    $143 nightly
    The price is $161 total per night from Jul 23 to Jul 24
    $161 total
    Jul 23 - Jul 24
    Total includes taxes and fees
    7.8/10 Good! (1,001 reviews)

Hotel Options in Islamorada

    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    $199 nightly
    The price is $224 total per night from Aug 3 to Aug 4
    $224 total
    Aug 3 - Aug 4
    Total includes taxes and fees
    9/10 Wonderful! (1,485 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    $238 nightly
    The price is $268 total per night from Jul 6 to Jul 7
    $268 total
    Jul 6 - Jul 7
    Total includes taxes and fees
    8.8/10 Excellent! (1,219 reviews)
    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
    $229 nightly
    The price is $258 total per night from Jul 7 to Jul 8
    $258 total
    Jul 7 - Jul 8
    Total includes taxes and fees
    9/10 Wonderful! (1,116 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
32 Cottages
Lowest Price
$156
Highest Price
$381
Popular accommodation
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