Hot Islamorada Cottage Rates

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Featured Cottages in Islamorada

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

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

Key Largo FL
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.
Opens in a new windowBayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach
Oceanfront Private Cottage!

Oceanfront Private Cottage!

Islamorada FL
Located in Islamorada (Matecumbe), this cottage is within a 15-minute walk of Islamorada Brewery & Distillery and History of Diving Museum.
Opens in a new windowOceanfront Private Cottage!
Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`

Key Largo FL
With a stay at this cottage in Key Largo, you'll be on the beach, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's Big ...
Opens in a new windowCottage w/ Bay View FREE Kayaks, Snorkel`
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Cottage w/ FREE Sailboat, Kayak, Bikes & More

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Key Largo FL
With a stay at this cottage in Key Largo, you'll be near the beach, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's Big ...
Opens in a new windowCottage w/ FREE Sailboat, Kayak, Bikes & More
Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Key Largo FL
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.
Opens in a new windowBungalow w/ FREE Kayaks, Sailboat, Bicycle Use
Kayaking, sailing, snorkeling Free w/ Cottage

Kayaking, sailing, snorkeling Free w/ Cottage

Key Largo FL
With a stay at this cottage in Key Largo, you'll be near the beach, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's Big ...
Opens in a new windowKayaking, sailing, snorkeling Free w/ Cottage
Bayside view Cottage , Free kayaks and sailboat

Bayside view Cottage , Free kayaks and sailboat

Key Largo FL
With a stay at this cottage in Key Largo, you'll be on the beach, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's Big ...
Opens in a new windowBayside view Cottage , Free kayaks and sailboat
Cottage w/ Full Kitchen FREE sailboats and kayaks

Cottage w/ Full Kitchen FREE sailboats and kayaks

Key Largo FL
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.
Opens in a new windowCottage w/ Full Kitchen FREE sailboats and kayaks
Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

Key Largo FL
With a stay at this cottage in Key Largo, you'll be near the beach, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's Big ...
Opens in a new windowLarge House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear
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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
32 Cottages
Lowest Price
AU$484
Highest Price
AU$593
Popular accommodation
Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach, Oceanfront Private Cottage!, Cottage w/ Bay View FREE Kayaks, Snorkel`, Cottage w/ FREE Sailboat, Kayak, Bikes & More, Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use, Kayaking, sailing, snorkeling Free w/ Cottage, Bayside view Cottage , Free kayaks and sailboat, Cottage w/ Full Kitchen FREE sailboats and kayaks, Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

Top trending hotels in Islamorada

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$550 per night from 29 Apr to 30 Apr
AU$550
29 Apr - 30 Apr
includes taxes & fees
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be steps from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing ...
Opens in a new windowCheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$484 per night from 14 Apr to 15 Apr
AU$484
14 Apr - 15 Apr
includes taxes & fees
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 ...
Opens in a new windowChesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is AU$503 per night from 21 Apr to 22 Apr
AU$503
21 Apr - 22 Apr
includes taxes & fees
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 a 2-minute drive from Florida Keys Brewing ...
Opens in a new windowAmara Cay Resort
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Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is AU$593 per night from 22 Apr to 23 Apr
AU$593
22 Apr - 23 Apr
includes taxes & fees
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 7 minutes by foot from Islamorada Brewery ...
Opens in a new windowIslander Resort
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.

Top Picks

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^Subject to availability and chosen travel dates.