Compare Islamorada Cottage Rentals

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Featured Islamorada Cottages

Oceanfront Private Cottage!

Oceanfront Private Cottage!

At this cottage, guests have access to barbecue grills.
Kitchen
Washer
Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach

Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`

At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
Luxury Key Largo Home w/ Guest House & Pool!

Luxury Key Largo Home w/ Guest House & Pool!

3 out of 5
Guests staying at this cottage enjoy an outdoor pool, free WiFi in public areas, and barbecue grills. A stay here includes free parking.
Pool
Kitchen
Canal-front Florida Keys Home w/ Dock!

Canal-front Florida Keys Home w/ Dock!

3 out of 5
This cottage features free WiFi in public areas and barbecue grills. There's free parking if you drive.
Kitchen
Parking included
Close to Beach: Canal-front Home in Islamorada

Close to Beach: Canal-front Home in Islamorada

3 out of 5
This cottage features free WiFi in public areas and barbecue grills. If you decide to drive, there's free parking.
Kitchen
Parking included
Waterfront Gem w/ Decks, Views & More in Key Largo

Waterfront Gem w/ Decks, Views & More in Key Largo

3 out of 5
Guests staying at this cottage enjoy free WiFi in public areas, an arcade/game room, and barbecue grills. If you drive, take advantage of free offsite parking.
Kitchen
Free WiFi
Half-mi to Boat Ramp: Canal-front Florida Keys Gem

Half-mi to Boat Ramp: Canal-front Florida Keys Gem

3 out of 5
This cottage features free WiFi in public areas and barbecue grills. You can take advantage of free parking if you drive.
Kitchen
Washer
Walk to Beach: Home 8 Mi to Key Largo!

Walk to Beach: Home 8 Mi to Key Largo!

3 out of 5
Guests staying at this cottage enjoy free WiFi in public areas, a terrace, and barbecue grills. If you plan to drive, free parking is available.
Kitchen
Washer
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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
    $239 nightly
    The price is $269 total per night from Nov 9 to Nov 10
    $269 total
    Nov 9 - Nov 10
    Total with taxes and fees
    9/10 Wonderful! (1,009 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
    $262 nightly
    The price is $295 total per night from Nov 19 to Nov 20
    $295 total
    Nov 19 - Nov 20
    Total with taxes and fees
    8.8/10 Excellent! (99 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 Nov 20 to Nov 21
    $291 total
    Nov 20 - Nov 21
    Total with taxes and fees
    9/10 Wonderful! (1,263 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    $205 nightly
    The price is $231 total per night from Nov 30 to Dec 1
    $231 total
    Nov 30 - Dec 1
    Total with taxes and fees
    8.8/10 Excellent! (1,272 reviews)
    Creekside Inn

    Creekside Inn

    90611 Old Highway, Tavernier, FL
    $179 nightly
    The price is $201 total per night from Nov 3 to Nov 4
    $201 total
    Nov 3 - Nov 4
    Total with taxes and fees
    7.8/10 Good! (1,002 reviews)
    La Siesta Resort & Villas

    La Siesta Resort & Villas

    80241 Overseas Highway, Islamorada, FL
    $203 nightly
    The price is $229 total per night from Nov 12 to Nov 13
    $229 total
    Nov 12 - Nov 13
    Total with taxes and fees
    8.6/10 Excellent! (1,006 reviews)
    Drop Anchor

    Drop Anchor

    84959 Overseas Highway, 222, Islamorada, FL
    $121 nightly
    The price is $132 total per night from Nov 11 to Nov 12
    $132 total
    Nov 11 - Nov 12
    Total with taxes and fees
    8.6/10 Excellent! (1,001 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    $165 nightly
    The price is $186 total per night from Nov 5 to Nov 6
    $186 total
    Nov 5 - Nov 6
    Total with taxes and fees
    9.2/10 Wonderful! (1,548 reviews)
    Fisher Inn Resort & Marina

    Fisher Inn Resort & Marina

    84951 Overseas Hwy, Islamorada, FL
    $153 nightly
    The price is $172 total per night from Nov 3 to Nov 4
    $172 total
    Nov 3 - Nov 4
    Total with taxes and fees
    8/10 Very Good! (1,004 reviews)

Hotel Options in Islamorada

    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 Nov 20 to Nov 21
    $291 total
    Nov 20 - Nov 21
    Total with taxes and fees
    9/10 Wonderful! (1,263 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    $205 nightly
    The price is $231 total per night from Nov 30 to Dec 1
    $231 total
    Nov 30 - Dec 1
    Total with taxes and fees
    8.8/10 Excellent! (1,272 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    $165 nightly
    The price is $186 total per night from Nov 5 to Nov 6
    $186 total
    Nov 5 - Nov 6
    Total with taxes and fees
    9.2/10 Wonderful! (1,548 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
$132
Highest Price
$295
Popular accommodation
Oceanfront Private Cottage!, Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach, Cottage w/ Bay View FREE Kayaks, Snorkel`, Luxury Key Largo Home w/ Guest House & Pool!, Canal-front Florida Keys Home w/ Dock!, Close to Beach: Canal-front Home in Islamorada, Waterfront Gem w/ Decks, Views & More in Key Largo, Half-mi to Boat Ramp: Canal-front Florida Keys Gem, Walk to Beach: Home 8 Mi to Key Largo!

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