Hot Islamorada Cottage Rates

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Featured Cottages in Islamorada

Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise

Tavernier
With a stay at this cottage in Tavernier (Plantation Key Colony), you'll be within a 15-minute drive of Jimmy Johnson's Big Chill and Florida Keys Dive ...
Mercy’s waterfront piece of paradise
Sunny Tavernier Key Cottage!

Sunny Tavernier Key Cottage!

Tavernier
With a stay at this cottage in Tavernier, you'll be within a 15-minute drive of Jimmy Johnson's Big Chill and Harry Harris Park.
Sunny Tavernier Key Cottage!
Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`

Key Largo
When you stay at this cottage in Key Largo, you'll be on the beach, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral Reef ...
Cottage w/ Bay View FREE Kayaks, Snorkel`
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Canal-front Florida Keys Home w/ Dock!

Canal-front Florida Keys Home w/ Dock!

3 out of 5
Tavernier
With a stay at this cottage in Tavernier, you'll be within a 5-minute drive of Florida Keys Dive Center and Old Road Gallery.
Canal-front Florida Keys Home w/ Dock!
Waterfront Cottage at Tavernier, Florida Keys

Waterfront Cottage at Tavernier, Florida Keys

Tavernier
With a stay at this cottage in Tavernier (Blue Waters), you'll be within a 15-minute drive of Jimmy Johnson's Big Chill and Harry Harris Park.
Waterfront Cottage at Tavernier, Florida Keys
Luxury Key Largo Home w/ Guest House & Pool!

Luxury Key Largo Home w/ Guest House & Pool!

3 out of 5
Key Largo
With a stay at this cottage in Key Largo (Buccaneer Point), you'll be within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State ...
Luxury Key Largo Home w/ Guest House & Pool!
Lush tropical plantings in a gated compound located directly on the Florida Bay

Lush tropical plantings in a gated compound located directly on the Florida Bay

Islamorada
With a stay at this cottage in Islamorada (Matecumbe), you'll be steps from Islamorada Brewery & Distillery and 11 minutes by foot from Keys History & Discovery ...
Lush tropical plantings in a gated compound located directly on the Florida Bay
Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Key Largo
With a stay at this cottage in Key Largo, you'll be within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill.
Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use
Cosy Cottage in Islamorada with private garden & pool - 6 pers.

Cosy Cottage in Islamorada with private garden & pool - 6 pers.

Islamorada
With a stay at this cottage in Islamorada, you'll be within a 10-minute walk of Founders Park and Islamorada County Park.
Cosy Cottage in Islamorada with private garden & pool - 6 pers.
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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 Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Islamorada will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Islamorada definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Islamorada, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Islamorada Cottages essential information

Accommodation
20 Cottages
Lowest Price
AU$322
Highest Price
AU$490
Popular accommodation
Mercy’s waterfront piece of paradise, Sunny Tavernier Key Cottage!, Cottage w/ Bay View FREE Kayaks, Snorkel`, Canal-front Florida Keys Home w/ Dock!, Waterfront Cottage at Tavernier, Florida Keys, Luxury Key Largo Home w/ Guest House & Pool!, Lush tropical plantings in a gated compound located directly on the Florida Bay, Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use, Cosy Cottage in Islamorada with private garden & pool - 6 pers.

Top trending hotels in Islamorada

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is AU$480 per night from 27 Nov to 28 Nov
AU$480
includes taxes & fees
27 Nov - 28 Nov
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 5 minutes by foot from Florida ...
Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$387 per night from 2 Dec to 3 Dec
AU$387
includes taxes & fees
2 Dec - 3 Dec
With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and 13 minutes by foot from Indian Key Historic ...
Amara Cay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$322 per night from 8 Dec to 9 Dec
AU$322
includes taxes & fees
8 Dec - 9 Dec
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State ...
Chesapeake Beach Resort
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La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$490 per night from 30 Nov to 1 Dec
AU$490
includes taxes & fees
30 Nov - 1 Dec
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive ...
La Siesta Resort & Villas
Don't see what you're looking for?
See all available properties in Islamorada
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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.

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^Subject to availability and chosen travel dates.