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
    $250 nightly
    The price is $281 total per night from Oct 6 to Oct 7
    $281 total
    Oct 6 - Oct 7
    Total with taxes and fees
    9/10 Wonderful! (1,022 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
    $245 nightly
    The price is $276 total per night from Oct 6 to Oct 7
    $276 total
    Oct 6 - Oct 7
    Total with taxes and fees
    8.8/10 Excellent! (87 reviews)
    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
    $159 nightly
    The price is $179 total per night from Oct 5 to Oct 6
    $179 total
    Oct 5 - Oct 6
    Total with taxes and fees
    9/10 Wonderful! (1,221 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    $208 nightly
    The price is $234 total per night from Oct 6 to Oct 7
    $234 total
    Oct 6 - Oct 7
    Total with taxes and fees
    8.8/10 Excellent! (1,260 reviews)
    Creekside Inn Islamorada

    Creekside Inn Islamorada

    90611 Old Highway, Tavernier, FL
    $114 nightly
    The price is $128 total per night from Oct 5 to Oct 6
    $128 total
    Oct 5 - Oct 6
    Total with taxes and fees
    7.8/10 Good! (1,013 reviews)
    La Siesta Resort & Villas

    La Siesta Resort & Villas

    80241 Overseas Highway, Islamorada, FL
    $193 nightly
    The price is $217 total per night from Oct 21 to Oct 22
    $217 total
    Oct 21 - Oct 22
    Total with taxes and fees
    8.6/10 Excellent! (1,006 reviews)
    Drop Anchor

    Drop Anchor

    84959 Overseas Highway, 222, Islamorada, FL
    $134 nightly
    The price is $147 total per night from Oct 6 to Oct 7
    $147 total
    Oct 6 - Oct 7
    Total with taxes and fees
    8.6/10 Excellent! (1,000 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    $182 nightly
    The price is $205 total per night from Oct 6 to Oct 7
    $205 total
    Oct 6 - Oct 7
    Total with taxes and fees
    9.2/10 Wonderful! (1,529 reviews)
    Fisher Inn Resort & Marina

    Fisher Inn Resort & Marina

    84951 Overseas Hwy, Islamorada, FL
    $147 nightly
    The price is $166 total per night from Oct 5 to Oct 6
    $166 total
    Oct 5 - Oct 6
    Total with taxes and fees
    8/10 Very Good! (1,003 reviews)

Hotel Options in Islamorada

    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
    $159 nightly
    The price is $179 total per night from Oct 5 to Oct 6
    $179 total
    Oct 5 - Oct 6
    Total with taxes and fees
    9/10 Wonderful! (1,221 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    $182 nightly
    The price is $205 total per night from Oct 6 to Oct 7
    $205 total
    Oct 6 - Oct 7
    Total with taxes and fees
    9.2/10 Wonderful! (1,529 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    $208 nightly
    The price is $234 total per night from Oct 6 to Oct 7
    $234 total
    Oct 6 - Oct 7
    Total with taxes and fees
    8.8/10 Excellent! (1,260 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
30 Cottages
Lowest Price
$128
Highest Price
$281
Popular accommodation
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