Hot Islamorada Cottage Rates

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Featured Cottages in Islamorada

Oceanfront Private Cottage!

Oceanfront Private Cottage!

Islamorada
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!
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 ...
Opens in a new windowMercy’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 ...
Opens in a new windowCottage 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 15-minute drive of Jimmy Johnson's Big Chill and Florida Keys Dive Center.
Opens in a new windowCanal-front Florida Keys Home w/ Dock!
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 ...
Opens in a new windowLuxury Key Largo Home w/ Guest House & Pool!
Waterfront Gem w/ Decks, Views & More in Key Largo

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

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 ...
Opens in a new windowWaterfront Gem w/ Decks, Views & More in Key Largo
Walk to Beach: Home 8 Mi to Key Largo!

Walk to Beach: Home 8 Mi to Key Largo!

3 out of 5
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.
Opens in a new windowWalk to Beach: Home 8 Mi to Key Largo!
Close to Beach: Canal-front Home in Islamorada

Close to Beach: Canal-front Home in Islamorada

3 out of 5
Islamorada
Located in Islamorada (Matecumbe), this cottage is within a 5-minute drive of Sunset Drive Beach and Anne's Beach.
Opens in a new windowClose to Beach: Canal-front Home in Islamorada
Half-mi to Boat Ramp: Canal-front Florida Keys Gem

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

3 out of 5
Tavernier
With a stay at this cottage in Tavernier (Indian Waterways), you'll be within a 5-minute drive of Old Road Gallery and Florida Keys Dive Center.
Opens in a new windowHalf-mi to Boat Ramp: Canal-front Florida Keys Gem
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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
30 Cottages
Lowest Price
AU$259
Highest Price
AU$375
Popular accommodation
Oceanfront Private Cottage!, Mercy’s waterfront piece of paradise, Cottage w/ Bay View FREE Kayaks, Snorkel`, Canal-front Florida Keys Home w/ Dock!, Luxury Key Largo Home w/ Guest House & Pool!, Waterfront Gem w/ Decks, Views & More in Key Largo, Walk to Beach: Home 8 Mi to Key Largo!, Close to Beach: Canal-front Home in Islamorada, Half-mi to Boat Ramp: Canal-front Florida Keys Gem

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
Fully refundableReserve now, pay when you stay
The price is AU$259 per night from 30 Sept to 1 Oct
AU$259
30 Sept - 1 Oct
includes taxes & fees
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 ...
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$283 per night from 24 Sept to 25 Sept
AU$283
24 Sept - 25 Sept
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
Fully refundableReserve now, pay when you stay
The price is AU$375 per night from 29 Sept to 30 Sept
AU$375
29 Sept - 30 Sept
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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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$371 per night from 1 Oct to 2 Oct
AU$371
1 Oct - 2 Oct
includes taxes & fees
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 ...
Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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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.