Hot Islamorada Cottage Rates

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Featured Cottages in Islamorada

RELAX in your PRIVATE Oceanfront Cottage!

RELAX in your PRIVATE Oceanfront Cottage!

Islamorada
Located in Islamorada (Matecumbe), this cottage is within a 15-minute walk of Islamorada Brewery & Distillery and History of Diving Museum.
RELAX in your PRIVATE Oceanfront Cottage!
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
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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Kayaking, sailing, snorkeling Free w/ Cottage

Kayaking, sailing, snorkeling Free w/ Cottage

Key Largo
When you stay at this cottage in Key Largo, you'll be near the beach, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral ...
Kayaking, sailing, snorkeling Free w/ Cottage
Cottage w/ FREE Sailboat, Kayak, Bikes & More

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Key Largo
When you stay at this cottage in Key Largo, you'll be near the beach, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral ...
Cottage w/ FREE Sailboat, Kayak, Bikes & More
Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

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

Key Largo
When you stay at this cottage in Key Largo, you'll be near the beach, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral ...
Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear
Bayside view Cottage , Free kayaks and sailboat

Bayside view Cottage , Free kayaks and sailboat

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 ...
Bayside view Cottage , Free kayaks and sailboat
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 a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral Reef State Park.
Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use
Free sailing, kayaking, water toys etc w/ Cottage

Free sailing, kayaking, water toys etc w/ Cottage

Key Largo
When you stay at this cottage in Key Largo, you'll be near the beach, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral ...
Free sailing, kayaking, water toys etc w/ Cottage
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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
29 Cottages
Lowest Price
AU$420
Highest Price
AU$582
Popular accommodation
RELAX in your PRIVATE Oceanfront Cottage!, Mercy’s waterfront piece of paradise, Cottage w/ Bay View FREE Kayaks, Snorkel`, Kayaking, sailing, snorkeling Free w/ Cottage, Cottage w/ FREE Sailboat, Kayak, Bikes & More, Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear, Bayside view Cottage , Free kayaks and sailboat, Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use, Free sailing, kayaking, water toys etc w/ Cottage

Top trending hotels in Islamorada

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$449 per night from 28 Apr to 29 Apr
AU$449
includes taxes & fees
28 Apr - 29 Apr
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
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$582 per night from 12 May to 13 May
AU$582
includes taxes & fees
12 May - 13 May
Located in Islamorada, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort is by the ocean, within a 5-minute drive of Windley Key Fossil ...
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$420 per night from 12 May to 13 May
AU$420
includes taxes & fees
12 May - 13 May
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
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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$463 per night from 4 May to 5 May
AU$463
includes taxes & fees
4 May - 5 May
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
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.